Travel

City Guide: Chicago

City Guide: Chicago

We are huge fans of Chicago-native Tim Mazurek, whose delightful, random-in-the-best-way lifestyle blog, Lottie + Doof, covers everything from travel to books to limited edition Oreos. For our city guide series (it’s back!), we knew he’d have great ideas of where to eat, shop, stay and hang in his hometown, and please add your recommendations, too…

City Guide: Chicago

Chicago has been home for most of my life, and my love for it is deep and unwavering. I feel the love driving west through the city at dusk on a summer night, windows down and radio up. When I am swimming in Lake Michigan in the shadows of skyscrapers. Or trudging through the snow on my way to a cozy dinner with friends on a dark January night. I love the architecture, the art scene and the incredible food. But really I love the people and neighborhoods that make this the place it is — the urban heart of the glorious Midwest.

It is also impossible to ignore Chicago’s challenges and struggles: the segregation that divides the city, the violence that plagues parts of it, and the corrupt systems that too often work against the people they should be protecting. Chicago has long been a center of progressive activism and that work continues to this day with new generations of Chicagoans fighting to build a better, more just city.

City Guide: Chicago

Pastries at Loba

WHERE TO EAT

Head to Loba Pastry in Lakeview for the most exciting pastries in town (plus, great coffee) and see what chef Valeria Taylor is pulling out of the oven. It might be a mole croissant or a fruit danish dusted with violet sugar. But my truest love will always be the pineapple sourdough muffin (a staple on the otherwise constantly changing menu), which is unlike anything I have ever tasted — tart, sweet, funky — and one of the absolute best things to eat in Chicago.

City Guide: Chicago

Mi Tocaya Antojería

For exceptionally good Mexican food, dinner at Mi Tocaya Antojería (Logan Square) can’t be beat. Diana Dávila’s spot gets lots of attention from the press (Bon Appetit named it one of the best restaurants in the country in 2017), but it is, at its heart, a neighborhood place serving favorites like Peanut Butter y Lengua (beef tongue with spicy peanut-based salsa) and the frequently photographed Tres Leches. In warm weather, snag a table outside on one of the city’s prettiest boulevards and watch the neighborhood go by.

Lula Cafe (Logan Square) might be my all-time most favorite restaurant anywhere. It opened in 1999 and I’ve been eating there ever since. A truly all-day cafe that is appropriate for everything from a solo breakfast (get the burrito) to a working lunch (I could eat a bucket of their spicy spaghetti) to a celebratory dinner (try whatever is on special). It is the quintessential Chicago neighborhood spot that also happens to be a destination, and proves that a 20-year-old restaurant can be cooler than the new kids on the block.

City Guide: Chicago

Field & Florist

WHERE TO SHOP

My friends Heidi Joynt and Molly Kobelt own Field & Florist, which is both a sustainable flower farm in southwest Michigan and a perfect little shop in Chicago’s Wicker Park neighborhood. They sell their blooms, as well as a stellar range of accessories, home goods and beauty products. They even let me curate a collection of cookbooks (both vintage and recent releases) that are for sale in the shop. Stop by for a copy of Vibration Cooking and an armful of peonies.

City Guide: Chicago

Peach Fuzz

I am a pretty devoted uncle and am often annoyed by the cultural messages and gender stereotypes embedded in so much kids’ stuff. Which is why I’m never happier shopping for the little ones than I am at Peach Fuzz (Humboldt Park). It is a genuinely inclusive space that avoids gender-norming and sells products that reflect a more sustainable and loving world. I’m an especially big fan of the coveralls they’ve recently started carrying because is there anything cuter than a toddler in a one-piece? They also have a fantastic selection of children’s books.

Andersonville’s Martha Mae: Art Supplies & Beautiful Things — their name kind of says it all — stocks the finest art and office supplies from all over the world. On a recent visit, owner Jean Cate had me giddy over the handblown glass pens from Japan that are such a pleasure to write with. It is physically impossible for me to leave the shop without buying something. An added bonus is meeting Martha herself, Jean’s dog who hangs out in the shop and gladly accepts attention.

City Guide: Chicago

Biking on Lake Michigan

WHERE TO HANG

Chicago’s crowning glory is its incredible lakefront. Ride your bike the length of the city on the easily accessible 18.5 mile lakefront path, relax on a beach (my favorites are Loyola Beach and 31st Street Beach), or take a boat out onto the water (you can rent or charter a boat from Belmont Harbor.) Lake Michigan is our inland sea and the place Chicagoans flock to when the weather is good. And if you’re up early, there is no better place to watch the sun rise.

Garfield Park Conservatory. If it’s cold when you’re in town, join locals for some warmth at this botanical oasis located on Chicago’s West Side. The greenhouses contain an incredible collection of plants, from a lush fern room to an arid desert, and its outdoor space is in the middle of one of Chicago’s prettiest public parks. The conservatory is especially charming in a snowstorm and is a great place for kids (and adults!) to burn off some energy when it is -20°F outside.

City Guide: Chicago

The Poetry Foundation

noname chicago

Noname

Chicago’s rich poetry tradition extends back from people like Gwendolyn Brooks and Carl Sandburg to contemporary writers like Eve Ewing and Nate Marshall. A visit to The Poetry Foundation on the Near North Side is a great way to explore this legacy. You can read in the light-filled library or attend one of their regular events, most of which are free. For a preview of what the next generation is up to, attend Word Play, the Tuesday open mic night at Young Chicago Authors. One of Chicago’s most important cultural institutions, Young Chicago Authors was a launching pad for artists like Chance the Rapper, Jamila Woods and Noname.

Spend a Saturday exploring Hyde Park, one of the most beautiful neighborhoods. The 61st Street Farmers Market is my favorite and a lovely place to start your day with a fruit galette from Pleasant House Bakery. After the market you might engage with contemporary art at The Renaissance Society or Hyde Park Art Center or check out Middle-Eastern antiquities at the time capsule that is the University of Chicago’s Oriental Institute. Stop by 57th Street Books for a browse or Cornell Florist to admire Cecile Deladier’s ceramics. Hungry? Grab a tray at Valois for some old-school cafeteria-style food (I love their omelettes) or Plein Air Café for a coffee, a pastry, and a view of Frank Lloyd Wright’s Robie House. Finish up the day with a walk along the lake north to Promontory Point where you will find great views of Chicago’s skyline.

City Guide: Chicago

An apartment rental in Logan Square

WHERE TO STAY

If you’d prefer to rent a place, consider getting out of the city center into neighborhoods like Pilsen (Mexican cultural hub with a thriving art scene), Logan Square (beautiful boulevards and popular restaurants), or Andersonville (charming, LGBTQ-friendly shops and cafés). Chicago has 77 official neighborhoods, so with a little research you’ll find one that seems like a good fit for you. Staying in a rental outside of the center, you’ll find a different perspective and get an experience most tourists never do.

The Robey in the heart of Wicker Park is well designed and in a great location for exploring neighborhoods like Wicker Park, Humboldt Park and Logan Square. The views from the top-floor rooms are incredible, and the rooftop bar is a great place to see the city’s grid stretched out around you. The ‘L’ train is a block away, connecting you to the rest of Chicago and giving you easy access to O’Hare.

City Guide: Chicago

The Langham hotel

If you’d like to stay in an architectural masterpiece, try The Langham, arguably Chicago’s finest hotel. Housed in a stunning Mies Van der Rohe tower built in 1972, The Langham opened in 2013 and takes full advantage of its riverside location with sweeping views of the river, buildings and lake. The central location just north of the Loop means you can easily walk to most downtown shops and attractions.

City Guide: Chicago

Noon-O-Kabab

FINAL TIPS

Like any major city, Chicago is impossible to summarize and any list of suggestions will fail to reflect the diversity of this sprawling place. Every part of Chicago is worth exploring, and I encourage visitors (and my fellow Chicagoans) to try everything from the incredible donuts at Old Fashioned Donuts on the far south side to the delicious Persian food at Noon-O-Kabab in Albany Park.

People often ask me where to get the best versions the most iconic Chicago foods. And like many Chicagoans, I will defend my choices to the end. For deep dish pizza (a food that Chicagoans don’t often eat but is worth a try) go to Pequods for its deeply caramelized crust. The best Italian beef sandwich is at Johnnie’s Beef in Elmwood Park — order it with sweet and hot peppers. And the best Chicago dog (though not strictly traditional) is at Gene and Jude’s, where ketchup is not even allowed on the premises.

Chicago summers get all of the attention, but for me October will always be my favorite month here. The air has cooled, the farmers markets are overflowing with produce, and the cultural season has begun. October’s energy is palpable and will make it even easier for you to fall in love with my beautiful city.

Thank you so much, Tim! What else would you add to the list?

P.S. More city guides, and a weird thing we do on vacations.

(Opening photo by B.Harvey for Stocksy. Cannelles by Loba Pastry. Mi Tocaya by Taylor Glascock for Bon Appetit. Conservatory by San Diego Reader. Field & Florist by Jaclyn Simpson for Chicago Reader. Poetry Foundation by On The Grid. Chance the Rapper/Word Play. Plein Air Cafe by citylikeyou.)

  1. Tyan Wheeler says...

    Chicago DEF eat deep dish pizza and Lou Malnatis cannot be beat! That is a myth that we don’t!

  2. Such a helpful guide! I’m holidaying in Chicago this Christmas and when it comes to neighbourhoods I had no idea where’d be good to stay ! I’ve also noted the cafe which sounds igh up my street !

    • Nicole Gelinas says...

      You should check out the Christkindlmarkt! It’s in the loop so it’s easily accessible. You can get keepsake mugs of mulled wine, walk around, and look at the beautiful ornaments for sale. Then walk over the the bean and watch the ice skaters (or join in!). I may be biased because it was my first date with my fiance but it is such a magical feeling to have something like that in the middle of the city.

  3. Martha Patterson says...

    I had the good fortune of being in Chicago on St. Patricks Day last year for work. The conference kept us inside (and away from the rowdy drunks) but I was right on the river when it was dyed green. The next day the sun came out, the temp warmed up to 55 degrees or so, and I went on an architecture boat tour…absolutely fascinating!

  4. Born a South sider:Englewood but, spent my entire adulthood as a North sider: Andersonville. Husband is White. I am Black. Our kids are the People of Tomorrow.
    I gave this post a quick peek expecting to see the usual problematic bullet points…namely pizza, Sox vs Cubs and don’t travel beyond Chicago’s downtown.
    Hence, I must say how pleased I was at this post’s honesty in even including the word *segregation*. Most Americans consider segregation a dead-word like dirigible or crinoline. Obama was president, isnt racism dead? Nope. Racism is alive and enjoying a cold beer even our urban hubs. And in Chicago it’s an especially fascinating phenomenon since most of the segregation is de facto. There is (generally) absolutely nothing stopping someone from buying and renting in a desired sector. And yet, the racial lines are so sharp that “Black” neighborhoods and “White” neighborhoods are generally demarcated by less than a single city block. And it doesn’t stop there. While most of the North side is LGBTQIA friendly-we have a “Boystown” AND a “Girlstown”. We have a campus of museums. And several of America’s best colleges and Unis (De Paul,Loyola, SAIC) rub shoulders with each other.
    We are an exceptionally hardworking and resilient city whose people expect and encourage a drop or two of corruption in our politicians because-that’s just the way it is. *Shrug*
    So for visitors who find themselves interested in the social and political nuances of our gorgeous city, keep this in mind. If New York is defined by !energy! Chicago likewise runs on !pragmatism!
    Learn this phrase-
    “It is, what it is.”

  5. Simone says...

    Chicago was our sort-of baby moon ( 5 months pregnant with a 16 month old in tow) and it was a magical city. The Art Institute will stay with me forever.

  6. Lily says...

    Tim helped lead my freshman year orientation class at DePaul!!!! I have had the same Lottie + Doof mac and cheese recipe saved on my computer FOREVER because of that.
    Loved this so much.
    omg
    <3

  7. Jaime says...

    UGH, my heart. I went to school in Chicago and always get nostalgic to move back.

    Hidden gems: Columbia College Chicago’s Museum of Contemporary Photography. The Harold Washington Library’s atrium. Summer Dance in Grant Park. The Art Institute followed by tea at the Russian Tea Room. It’s an amazing city.

  8. Alexandra says...

    PEQUODS. I moved away over 10 years ago and I still dream about that pizza.

    Seattle’s Windy City Pie is doing a respectable job replicating it, but nothing beats the original.

    • After moving to the burbs we still talk nonstop about peqouds. Hands down the best pizza.

  9. Rebecca says...

    Spot on with pequod’s and 31st Street Beach. As a former Bridgeporter, you can’t beat that beach, so much less crowded than any of the more we’ll known or north side ones. And Pequod’s, is the. best.

  10. Kaylie says...

    For the booklovers visiting Chicago:

    Women & Children First in Andersonville is one of 10 feminist bookstores left in the United States & had loads of events (with both big and small names)! Uncharted Books also opened on Clark street in Andersonville and is a great new/used store with comfy couches (& a store dog!).

    Unabridged Books in Lakeview has the BEST sale section of any bookstore I’ve been visited and has a lovely staff.

    The Dial bookstore in the Fine Arts Building downtown is a new/used bookstore (also currently owned by the people who run Pilsen Community Books, probably one of the most Instagram’d stores in the city, though they’re looking to sell) and is BEAUTIFUL, with amazing views of Grant Park.

    Quimby’s in Wicker Park is an institution and down the street from Myopic Books, too.

    The city has a pretty thriving literary scene, from an indie bookstore and live lit perspective!!

    • Lily says...

      LOVE LOVE LOVE Unabridged

    • Kate says...

      YES the Unabridged sale section! And just the book store in general :)

  11. Kelly says...

    fellow Chicagoan here! great guide and love that Tim highlights so many neighborhoods (and there are many more!).

    the comments are gold as usual but i haven’t seen mention of Rosa’s Lounge, which is in Logan Square and near many of the sites Tim mentions. It’s an awesome spot to see authentic Chicago blues…the later you are there, the more blues musicians might show up to jam…even if you aren’t familiar with the blues it’s a mind-blowing experience! (and eardrum-blowing, consider earplugs!)

    • Quinn Keller says...

      Thank you! New to Logan and my dad lives the blues. Can’t wait to take him when he visits.

  12. Littany says...

    Literally gasped as I scrolled through this post, seeing Field & Florist – I grew up with Heidi (and her family, her husband’s family, etc.) and it has been incredible to watch her passion and business grow through hard work and joy for what she is doing. So happy to see their small business spotlighted here!

  13. Kelsey says...

    I’m so happy this series is back! It’s always the first thing I search for when visiting a new city and I feel like I’ve really scored when I find you’ve done one. We are visiting Seattle + Vancouver in the fall and I’ve referenced the Seattle guide many times while planning (crossing my fingers for a Vancouver one!!) my go-to for finding the cool parts of a new town if there’s no city guide: search for the anthropologies and lululemons. I don’t necessarily do a ton of shopping at these stores but they seem to have their real estate selections down :)

  14. 1. chicago is one of my favorite cities, and i love seeing some of my staples on here as well as lots of places that are new to me. can’t wait to return soon!

    2. let me know if you ever want a city guide for memphis :)

  15. Lily says...

    I was chuffed to bits to see Tim on CoJ! I love it when my favorite corners of the internet collide. (And yes to Eve Ewing–her latest book about the inequities of Chicago’s public schools is a must-read!)

  16. chicago is such a charming city! i was there last month and if it wasnt so far from ny/family i’d move there in a heartbeat. no one has mentioned the chicago athletic association – it’s really fun and right by the art institute.
    excited to check out these recommendations in the future – hoping to make a trip out there a yearly ritual while we can :)

  17. Avi says...

    Lived most my life in Chicago since immigrating from the USSR and we made the path through Rogers Park before heading to the northern suburbs, as all the ruskis did at the time. Chicago is so amazing, I’m longing to see more of it even while currently living here. We have night life, amazing food, museums, downtown, beaches, sky line, cute neighborhoods, quiet suburbs. Chicago is like the cleaner and more charming cousin of New York!! I lived temporarily in many cities throughout the world, and while many cities are nice to visit, Chicago is the only one to call home ❤️

    • Shanna says...

      I live in Rogers Park currently and have for the last 8 years! (Went to Loyola University Chicago). Love seeing comments from people like yourself who have lived there. It is, in my opinion, the best neighborhood in Chicago. <3

    • Judy says...

      Totally agree… as a Canadian, Chicago is the perfect embodiment of the glorious, brash yet charming American city.

    • Kiri says...

      We lived in Rogers Park for 13 years! It’s a special neighborhood, and so incredibly diverse. We left the city a few years ago and now live in Michigan, but we go back often to Chicago for work. It’s always fun making that familiar drive north on Lake Shore Drive and turning into Sheridan. :)

  18. Laura says...

    I’d love to see a city guide on Denver!

    • Amanda says...

      I’m not a blogger or anything, but I’ve lived in Denver for most of my life and would happily write that city guide haha. I love my city!!

  19. Caroline says...

    I moved to LA three years ago from Chicago. I miss Chitown every day! The people, the trains, the food, the lake, the beautiful architecture, the grime, the cost of living, everything.

    • Therese says...

      Caroline – I’m the same! Its fun to explore the west coast but my heart and soul are content when I hear the L train rumbling above, the harsh Chicago accent and feel the energy of the city. I miss the first nice day of Spring when the city explodes outside, the smell of Autumn, and the stillness of snow. Plus, you can’t beat the deep kindness of Midwesterners, sprinkled with sarcasm and a great work ethic. I’ll be back one day :)

  20. Cat says...

    Nearly 10 Chicago resident here! (Raises arm)
    Loved this Chicago city guide, and can vouch for many of these spots! (Lula Cafe is my favorite)
    I still always feel like there’s so much to explore, and I’m excited to try some of these spots in Hyde Park!

  21. Mimi says...

    Wonderful guide!

    I live close to downtown and second somebody’s comment about Bavette’s (order the Champagne Smash), and the Library speakeasy in the basement of Gilt Bar is awesome for that “downtown” feel.
    Eduardo’s Enoteca is an amazing Italian bistro, wonderul thin crust pizzas and whole menu really, on the edge of Gold Coast (Dearborn and Division) without all the stuffiness.
    Further on the north side, Irazu in Bucktown is a great Costa Rican restaurant…close to Cafe Robey which we LOVE!!! Amazing 13th floor lounge.
    I’ve only lived here 7 years (transplant of Portland, OR via NYC), and I need to explore much more of this city. Thank you for writing, Tim! And for referencing some of Chicago’s challenge while still encouraging visitors to come!

  22. Rachel says...

    As a Chicagoan this post makes my heart swell. I was considering moving for a job but have recently decided to stay, and things like this reaffirm that decision so much❤️

  23. Logan says...

    I live in Logan Square. This is wonderful. But Tim. Tim. If you live in Oak Park, you do not live “on the west side.” You live in Oak Park! It’s not Chicago! Be about it!!!!

  24. Morgan says...

    If you’re on the north side at Martha Mae (highly recommend!) you’re right nearby:
    – Smack Dab – amazing breakfast sandwiches with every gluten free/vegan/food allergy combo as well
    – Women & Children First bookstore
    – Annapurna – Indian food
    – Rosehill Cemetery (yep) for a tour: https://www.atlasobscura.com/places/rosehill-cemetery

    Oh, and if you want a spa trip, Cowshed in the Soho house is wonderful, stop at Sawada across the street while you’re at it!

  25. Trish says...

    Tim – three cheers for the Young Chicago Authors shoutout!

    I, too, have a deep and unwavering love for my hometown. This list is thoughtful and interesting, and I love many of the recommendations in the comments, as well (Brown Elephant in Andersonville, Hopleaf, Green Mill, Estereo, Merz Apothecary, Pritzker Pavilion). If you’re an omnivore, skip the pizza and go straight to meaty sandwiches because Chicago corners the market – the aforementioned Italian beef (Johnnie’s!) and Chicago-style hot dog, plus jibaritos (Puerto Rican sandwich with plantains in place of bread) in Humboldt Park and a gringa (el pastor-quesadilla mashup) from L’Patron in Logan Square.

    • Heidi says...

      Please do San Francisco- traveling there for work in September- need recommendations!

  26. Kaye says...

    Oh man, Chicago will have my heart forever. Other must dos:
    Avec- best dinner ever
    Intelligentsia- best coffee ever, go to the Lakeview location
    Spacca Napoli- best wood fired pizza ever (and where I got engaged)
    The Bagel- best brunch and pickles for days
    Longman and Eagle- get the frizzled sage sloppy joe

  27. Ashleigh says...

    Hi- I’m visiting Chicago from New Zealand in November this year. So happy to have found this article! One question I do have; is there anywhere to get a decent flat white?! Or latte at a stretch (please don’t say Starbucks. Yuck. ) Thanks!

    • Poppy says...

      i don’t think we drink flat whites really, not by that name. what is it, like an au lait? half milk half coffee? there are both tons of chains and tons of small coffee shops, the former will be easy to find and you will probably say yuck to and the latter not so easy but yum ¯\_(ツ)_/¯ probably ask at where you’re staying, you’re not going to go halfway across the city for a coffee

    • ClareV says...

      Heritage in Lakeview is where all us Chicago based Aussies go!

    • Rachel says...

      Hi Ashleigh! Not sure where you’re staying, but my favorite coffee shop is Dark Matter. They have a few locations around the city and love everything they make! Hope you have a wonderful trip!!

    • M says...

      You’re in luck! Chicago is home to Intelligentsia coffee – a company that has been at the forefront of the third wave of coffee since the mid-2000’s. The drinks are delicious, the coffee is some of the most thoughtfully-sourced you’ll find in the world. There are 7 in Chicago so you’ll easily find one near you!

    • SN says...

      There is actually a New Zealand based cafe that has a few locations in Chicago called Mojo. Their coffee is EXCELLENT, and their avocado toast is literally the best I’ve ever had.

    • Sasha says...

      Try Cafe Integral

    • Angela says...

      Agree with M! Mojo is a New Zealander-owned coffee shop, and when I have coworkers from Australia visit, they always order the flat white, and they melt with happiness. :) And double agree on the avocado toast — a huge pile of avocado on a lovely nut bread with a bit of chili oil to give it a kick. Definitely a treat.

    • Joanna says...

      Ashleigh, check out Mojo Coffee – run by Kiwis! Colectivo, La Colombe, Intelligentsia and Goddess and the Baker also do great coffee.

    • Ashleigh says...

      Thanks everyone for your suggestions!

  28. CMS says...

    It made my day to see Tim writing this post! As a fellow Chicagoan, I so appreciate how he views this wonderful city, for all its charm and faults. His recs are always top notch, and his own recipes are pretty damn good too. His tomato soup is the best. Hooray for the Midwest and Tim!

  29. Liz says...

    Chicago has been the love of my life for as long as I can remember. My father worked there growing up so we were spoiled with frequent visits. My obsession grew as a teen and my dream of living there in my 20’s was everything I imagined it would be. I moved away 3 years ago and my heart actually aches for it, like a heart break for my one true love. I’m trying my hardest to talk about the city and visit with my girls as often as I can so we can trick my husband into moving back :)
    Thanks for sharing such a lovely post on Chicago.

    • Christine says...

      My heart also aches for Chicago, I love it so! My husband and I lived there for 2.5 years and I miss it tremendously, 7 years later.

    • Julie says...

      I absolutely understand how you feel, Liz. I lived in Chicago for twelve years and moved away a few years ago. My heart still aches for it. Such a beautiful place.
      Thanks for the lovely post, Tim. It brought back so many memories.

  30. Marlena says...

    Tim and Lottie + Doof is one of the best persons/writing on the Internet! He offers such a thoughtful, kind, and nuanced voice. Follow his gift guides! Make his recipes! Thanks, Tim, you’ve reminded me I’m overdue for a Chicago trip.

    Maybe Tim could do a standing Midwest is Best column for COJ?

    • Liz says...

      Yes!

  31. Emmy says...

    Wow, this is radiant! His love for Chicago is irresistible. I can’t wait to visit again. (And will start reading Tim’s site.) Thank you, Tim and Cup of Jo!

  32. Katy says...

    I’ve lived in Chicago my whole life, but learned about many new places from this lovely guide. If you are going to be in Chicago in the next few weeks I highly recommend MARY SHELLEY’S FRANKENSTEIN at the Lookingglass Theatre.

  33. Wynn says...

    I’ve been visiting Chicago every year for the past four, but have only ever gone in December. I think maybe my first visit was in September, but it was a long time ago and not the most enjoyable trip. I forget sometimes that Chicago exits outside of December/winter. Ha!

  34. Sasha L says...

    Any interesting recs for Winnetka?

    In a seach for his father, my husband recently found out his paternal grandmother’s family (Ancestry.com) lived there, she graduated from high school there and the kind archivist at the school has shared some info with us. Sadly she is already passed away and we’re still searching for his father, and lately, partly to ease the horrible anxiety of just not knowing and feeling powerless, we’ve been talking about visiting some of his *family tree* places *.

    • Morgan says...

      Winnetka’s a pretty cozy little town but is near Chicago (obvi!) and Evanston, which is a great little town in and of itself. In Winnetka I recommend Centennial Park or any lakefront beach, Reprise coffee, and a visit to the Bahai’i temple down the road in Wilmette. (Random: If you’re a fan of the movie Home Alone you can check out the house on Lincoln Ave in Winnetka.)

      Sounds like a lovely trip, hope you enjoy it!

    • Sasha L says...

      Thank you so much Morgan.

    • Avi says...

      I think the scene from Ferris buelers day off where the car flies off the house on a cliff (to the best of my memory!) was also filmed in winnetka. Winnetka has beautiful homes along Sheridan drive on the lake. Just drive through and look around!

    • Julie says...

      Once Upon a Bagel is great for breakfast! You can grab some and eat it in the park or take a walk on the Green Bay path which spans for miles along the railroad tracks.

  35. bethany says...

    Wow, way to make me so homesick I’m crying at my desk. This is a beautiful tribute to my home city. I’ve lived in Nashville for the past five years and it’s cute, but my love for Chicago runs deep and I miss it every day.

    By the way, if you can’t visit Chicago any time soon and are looking for a book that makes you feel like you’re there, “The Time Traveler’s Wife” captured the essence of it beautifully. (The movie adaption sucked but the book is wonderful, don’t @ me, haha.)

    • Liz says...

      In Nashville 10 years, but my love for Chicago also runs deep, and I miss the place every day. And also loved the book.

    • Katy says...

      Agree 100!! The “Time Traveler’s Wife” nails the Chicago scene and vibe and beauty perfectly. Read that book while living in Chicago, and fell in love. The audio book is great, too. Listen to chunks of it every so often. We saw the author at a book fair in Chicago, and she was great, as well.

  36. Maggie says...

    Love Chicago! Growing up in Michigan it was always the destination city to visit (and now many friends, including my brother in law, call the city home!).

    I’d love to see a Philadelphia city guide. I moved to Philly in the fall & am always looking to hear about new great places from those who have called the city home for years!

    Xx

    • Joanna Goddard says...

      philly is a great idea!

    • YES! I feel about Philly the way Tim feels about Chicago and would love to share any recommendations with anyone coming to this incredible city. 💕

  37. Helen says...

    Love these city guides!!!! Going to Hawaii in a month or so, would love one for any of the cities/towns there!

  38. Erin says...

    So excited that city guides are back!

  39. angela says...

    Can someone do Seattle?? Thank you!

  40. Dana says...

    Another Chicagoan here! (Although soon to be relocating to Minneapolis…upcoming city guide?!?)

    I had a really relaxed and pleasant Chicago afternoon recently. Here’s how to do it:

    * bike your way over to Holstein Park Pool (all the public pools in Chicago are free!) using this easygoing map as your guide: https://m.chicagoreader.com/chicago/mellow-bike-map/Content?oid=50772951
    * after swimming and sunning, stroll just a few blocks over to Quesadilla La Reina del Sur, for delicious vegetarian style Mexican food
    *that’s it! enjoy!

    • Sasha L says...

      Mexican vegetarian!?!? Woohoo!

    • Liz says...

      Minneapolis is wonderful! You’ll love it here – truly a vibrant, diverse city with great food, art, music, lakes, and there is always so much going on. I loved this city guide to Chicago and can’t wait to pop down for a visit after reading it. I can’t help but think mpls has very similar things to love about it, but on a scale befitting our smaller city.

    • Dana says...

      Thanks for pointing that out Amanda! Excited to read it.

      And thanks, Liz. Can’t wait to move up there & you make it sound A+.

  41. Emily says...

    I love Tim’s blog and writing so much. His enthusiasm for the Midwest is contagious, I need to visit Chicago soon! I visited Detroit following his guide last year and it was a lovely experience.

  42. alison says...

    I love Tim so much! He has no idea who I am, but we used to work on the same college campus and I’d get all weird and fan girly when I saw him just walking around.

    I just left Chicago after 10 years and I 100% whole heartedly agree with his suggestions. But also – everyone should get one of everything at Fat Rice bakery in Logan Square.

  43. Maire says...

    Not a resident, but a long time Chicago visitor and enthusiast. I’d recommend the Architecture Boat Cruise, a visit to the Chicago Cultural Center which is free and has rotating exhibits + a gorgeous Tiffany glass dome, the International Museum of Surgical Science (creepy and cluttered and kind of disorganized in all the best ways), and both Loyola and DePaul’s small art museums. (The Art Institute just goes without saying.) My favorite restaurants there currently are Dos Urban Cantina (Mexican), Fat Rice (Macanese), and The Chicago Diner (vegan/vegetarian) in Logan Square, The Gundis Kurdish Kitchen (go for Kurdish brunch for two) in Lincoln Park, Cafe Iberico for tapas in River North, Duck Duck Goat in the West Loop.

    • Sasha L says...

      Sigh. These restaurant recommendations alone make me want to visit!! I love where I live, but we are sadly lacking in interesting and inventive cuisines. Wow, Kurdish?!? Macanese?!? I don’t even know what that is, but I’m down for it.

    • Morgan says...

      +++++ for Dos Urban Cantina. The owners are good people. Actually, great list in general!

    • Katy says...

      Yes to the Architecture Boat Cruise. When I lived in Chicago (Lincoln Square then Wicker Park), that was always on the list to-dos for visitors.

  44. Kristyn says...

    Hello random Thursday wave of bittersweet nostalgia! There’s just nothing like the down-home reliable comfort that is Chicago, especially compared to charming but oh-so-aloof Boston where I currently live.
    Always a special place in my heart for HopLeaf, Common Ground, Bang Bang pies, Big Star, and definitely Noon-o-Kabob, too.

    Lastly… after several minutes of, “Do I know him???” I realized Tim was a student advisor (I think?) during part of my time at the DePaul School of Music!

  45. Savannah says...

    When I graduated from high school my mom took me on a trip anywhere I wanted to go… and I chose Chicago. I’m not sure why I had this obsession with the city but it was as wonderful as I had built it up to be! Even with the summer heat (I’m a Seattle girl and anything over 70 is toooo much) I have nothing but the best memories from that trip! We were there over 4th of July and it is so smart how they do fireworks on the 3rd so you can sleep in on the holiday! Loved it.

  46. Alice says...

    I have never been to Chicago (or anywhere in the States…yet!) and this makes me want to go.
    Thank you Tim for a warm, heartfelt, and interesting guide. I love cities, endlessly fascinating in so many ways.

  47. Roxana says...

    CHICAGO!

    I’ve lived here my entire life (40 years!), and even though so many things here are jacked-up (Tim said it), I still love it!

    Thank you for featuring our great city!

  48. Julia says...

    Ditto!

  49. Michelle says...

    OH! And do not miss grabbing a pizza at Spacca Napoli. Don’t bother with any deep dish. This is legit best pizza ever.

    • L says...

      yessss I saw someone mentioned it above as well. I lived for 5 years just a block from spacca napoli and never realized just how lucky I was til we left….

  50. Michelle says...

    A solid guide! Lula Cafe forever!
    I recommend a visit to Lincoln Square – Merz Apothecary, open since 1875 in the old German neighborhood is stocked with all sorts of old school and new school beauty/wellness goodies. Their herbalist and pharmacist are legit. Also, Augusta wine shop around the corner is a gem. Down the street is The Old Town School of Folk music – so many amazing musicians.
    Longmen and Eagle may not have their Michelin Star anymore but their menu is delicious. Pro tip: order their simple green salad, its no longer on the menu but the’ve got the goods to whip it up for you.

  51. Beth says...

    Thank you COJ & Tim for such a lovely round-up. Having lived here for years now, I am so pleasantly surprised to see such a diverse list of neighborhoods, places and a few new-to-me things to add to my “I’m bored today” list. I just love this city!

  52. Anna says...

    How fun! One of the best things about Chicagoland is the distinct seasons- true extremes of heat, humidity, cold, snow, wind. I lived in Evanston for a year and I loved taking the el and seeing different neighborhoods. A friend of my husband lived in Marina City (a downtown high rise) and took us to the top of the building one night- you could see so far in every direction- suburbs north, west, and south, and the total darkness of the lake to the east. A beautiful city in an unusual setting.

    • Sarah says...

      Definitely check out Local Foods in Bucktown. It is a cafe, grocery store and butcher shop that only sells delicious local products from the bounty of the Midwest. http://Www.localfoods.com

  53. Rebecca says...

    I love this so much- having lived in Chicago for six years I was so glad to see a guide that doesn’t just list the pizza and the architectural tour. What a beautiful guide! I can’t wait to go back for a visit and check out all these spots. And noon-o-kabob! What a treasure. So glad they got a shoutout. Also Lula cafe- OMG it had just opened when I lived there, and I’m so happy to hear that it has stood the test of time. I once had an art exhibit there. :-)

    • There are still art exhibits at Lula Cafe, Rebecca! The restaurant’s commitment to supporting artists is as strong as ever.

  54. AMR says...

    Here are a few additional recommendations from a long-time south side resident. If you make the trip to Hyde Park, try to find time visit the Du Sable Museum of African American History and the Museum of Science and Industry. (The U-Boat exhibit at MSI is incredible.). The lobby bar at the Sophy Hotel on 53rd street has a nice vibe and good drinks.

    I second the recommendations for Monte Verde for Italian Food (reservations can be hard to come by, but seating at the bar is first come first serve) and Wiener Circle for hot dogs.

    My next two recommendations probably reflect my status as a transplanted dyed-in-the-wool easterner: Piece in Wicker Park/Bucktown for pizza and Conte di Savoia on Taylor Street (in the old Little Italy) for sandwiches.

    Homestead on the Roof in West Town is an excellent place for a nice meal outdoors.

    • Emily says...

      Monteverde is my favorite restaurant and I book reservations there for every birthday or special celebration! Everything I’ve eaten there is my favorite thing :)

    • katy says...

      Piece in Wicker Park!!!

    • L says...

      Also when going to Piece get the clam and bacon white pizza. I know I know it sounds terrible but JUST DO IT. you will not be disappointed.

  55. AC says...

    Tim nailed it!!
    Other faves to add to the growing list:
    – All Together Now (Ukrainian Village) is a hip wine bar with a super friendly & knowledgeable staff, an amazing food menu, great decor/vibe
    – High Five Ramen (West Loop) is easily the best ramen in Chicago. The space only seats 15 so wait is always long but worth it. I go upstairs to Green Street Meats and get a pitcher of “Black Gold” until my table is ready below.
    – Best Intentions (Logan Square) is still a neighborhood dive even though its been made famous by the Netflix show ‘Easy”. Killer drinks & killer patio

    I could go on forever, as any Chicagoan can, just come visit!! And ask locals where to go, we are all Midwest friendly :)

  56. Stefanie M says...

    * they work

  57. Kara says...

    We LOVE Chicago as well, and have found it to be a pretty kid-friendly travel destination. Our son loves trains, so on a recent Chicago vacation we made it our mission to ride as many of the different train lines as possible. We also had a ton of fun at the (free!) Lincoln Park Zoo, exploring the beautiful U Chicago campus, and splashing in the amazing public fountains and spray parks.

  58. Stefanie M says...

    Austrian reader here. Thank you so much for sharing this City Guide. I’m both fascinated and often irritated about Us American cities and how to work/ not work. Do you happen to have any further reading material on some of the challenging factors Chicago is facing like segregation and violence nowadays? thank you so much again for your honesty and for introducing the blog and work of Tim Mazurek!

    • J. says...

      This may be more than you want, but it’s a good bibliography exploring racial segregation and related challenges in Chicago: https://www.cct.org/2018/07/segregation-in-chicago-an-annotated-bibliography/

      The Chicago Community Trust’s features on their “Insights” and “Features” pages also have some good, short articles on other important contemporary issues in Chicago, like environmental justice: https://www.cct.org/insights/

      So does the MacArthur Foundation (headquartered in Chicago): https://www.macfound.org/programs/chicago-stories/

    • Hi Stefanie! There is so much incredible writing about Chicago. But in terms of a good one-stop text, I think Natalie Moore’s “The South Side: A Portrait of Chicago and American Segregation” does a good job of addressing many of the issues. And anything by Eve Ewing.

    • I second Natalie Moore’s “The South Side: A Portrait of Chicago and American Segregation”. Just read it this year and wanted to give a copy to everyone I knew.

    • Hi Stefanie,
      Both gun violence and segregation/economic inequity are systemic problems in Chicago, and we as a city need to address them on the systems-level, rather than trying to cure the symptoms. I think our new mayor is on the right track on this. That being said, The Trace (https://www.thetrace.org/) has some really good pieces about Chicago and gun violence. Also this: https://www.nbcnews.com/news/us-news/they-re-soldiers-chicago-s-children-are-learning-save-lives-n1018196.

    • Kelly says...

      the warmth of other suns is not chicago-specific (though part of the book focusing on a person’s experiences in chicago) but is a fascinating analysis of the great migration of blacks from the South to Northern cities and helped me understand the foundations of many of the issues Chicago still deals with today.

    • Stefanie M says...

      Thank you so much for all the reading material!!
      All the best from Vienna!

  59. Raspberry coffee cake says...

    Well, as usual Tim has brought a new level of heart, warmth, and humanity to something as seemingly standard as a city guide. Chicago is a wonderful city with great food, kind people, and lots to do, but I so appreciate that he recognized where the city fails. For those who are into the ‘food blog’ (eyeroll) scene, the writing and recipes (yup, in that order) on his blog are #1 and this COJ crossover is giving me joy, along with some new places to seek out around Chicago. Thanks xoxo

    • I swear I didn’t write this comment! (thank you to this kind person)

  60. Hit up Agitator Gallery in Wicker Park for a local co-op artist run gallery!

    Agitator cooperative gallery is a worker cooperative that makes decisions by consensus, valuing each member’s input equally, relying on non-hierarchical collective decision making. Agitator seeks to promote and engage significant art, including art made by conventionally overlooked artists.

    Members of Agitator are diverse artist-curators with various racial, socioeconomic, gender, and sexual identities. Members share a common goal to curate art work that agitates or campaigns to provoke dialog and generate diversity, while respecting each artist’s vision and self-definition.

    • Wow I’m an artist and I’ve lived in WP for 3 years and so disappointed in myself for not knowing about this group- can’t wait to check it out, thanks for the rec!

  61. Rachel says...

    I live in Chicago and still found this guide incredibly helpful! I agree, while the summers in Chicago are prime, the falls in Chicago are unmatched. The sunsets and sunrises here are INSANE. More beautiful then either U.S. coast.

    • Joaquina says...

      Genuine question here from a Californian, are the summers in Chi not hot and humid? I am curious why summers there are prime. I have never been and am dying to explore your city. I have avoided going in the summertime but that is when I have the most time off. Perhaps I should reconsider, based on a few comments about summers there!

    • Rebecca Ringquist says...

      I agree completely- Lake Michigan sunsets are the best!

    • Roxana says...

      Life-long Chicagoan here and I have to say that hands-down summer in this city is THE BEST, but it’s not because of the weather, it’s because the city just comes ALIVE. So many events (many of which are free), like concerts in the park (e.g. Yo-Yo Ma recently gave an incredible free concert in Millennium Park), street/neighborhood fairs, ethnic fairs, restaurants have a ton of out door seating so it’s just fun to be out, and generally there are tons of other things going on. Plus, it’s prime-time to hang by the lake. It really is a blast in the summer.

      The summers can be hot and humid, but I’d characterize the weather as generally unpredictable. It might be crazy hot one day and then drop twenty degrees the next. You just never know. So far this summer (with the exception of today and the next few days) has been cooler (i.e. 70s).

      I hope you visit, and I hope you love it!

    • J. says...

      Joaquina–Chicagoans experience so much bad weather in the winter that our expectations for “good” weather are pretty low. Mid-July through mid-late August is generally hot and humid. Mid-May through June and September through early October are probably the best, weather-wise (to a non-Chicagoan who didn’t spend multiple days surviving a polar vortex earlier in the year, and is just grateful to leave the house without a coat).

    • Long time Chicagoan says...

      Agree with all the comments here. The city comes alive in the summer and it is a jewel. Our reward for all the harsh winters. Fall is pretty spectacular as well but there is nothing like the lakefront in summer.

  62. Emily says...

    What a fantastic and personal guide. I look forward to checking some of these places out this fall on my next trip out. Also adding a big shout out to Floriole Bakery in Lincoln Park!

    • Laura says...

      I used to work near Floriole, and I miss their sandwiches and desserts. So delicious!

  63. Lindsey says...

    Growing up in Milwaukee, Chicago was like the cooler older sister everyone would visit on long weekends. It’s such a fantastic city! I wonder, would it be possible for city guide posts to contain a google map with the mentioned locations starred? It would be nice to see where everything is in relation to each other, especially when you don’t know where Logan Square is in relation to Wicker Park or downtown, etc. Just a thought!

  64. Sandra says...

    My town! I lived in Chicago for 21 years (most of my adult life) and now we are 30 miles north and even though we go downtown a lot I still miss being in the city every day.

    The things I miss:

    Dinkel’s Donuts (Lakeview) – They’ve been around since 1922 and offer solid, old school donuts

    Club Lucky (Budktown – Neighborhood Italian spot with a retro vibe great for martinis in the front bar or Italian dining in the back dining room.

    Cafe Tola (Southport Corridor)- Walk-up empanada joint (no indoor dining at the one I used to go to, but they have opened a few new locations). Empanadas are SOOO good

    Best spot for Chicago photos/view of the city – out by the Adler planetarium. You’ll have the whole city skyline in the background.

    The 606 trail – Not really like the high line in NYC since it was mostly designed for bike transit, but if you stay to the right and keep an eye out for bike traffic it a great way to take a walk and hop on and off and check out the neighborhoods. Or get a divvy bike and go for a ride!

    Super touristy, but if you want a few of the city from above go the the Hancock building (or whatever they are calling it these days) but instead of paying to go to the observatory get a drink in the cocktail lounge that has the same view

    Wiener’s Circle (Lincoln Park) – Iconic hotdog /hamburger stand

    So many more places I’m forgetting about…it truly is such a great city.

    • JODIE L RESENDIZ says...

      Club Lucky is so good. They used to have insane decorations around the holidays! Not sure if they still do but it was fun.

    • Yes Club Lucky still goes all out for holidays! Such a special neighborhood spot.

  65. What a wonderful guide! I love that Tim did a great job of covering neighborhoods all over the city. I can vouch for his suggestions, as I just got married at Garfield Park Conservatory last month and my dear friends at Field & Florist did the flowers! If anyone wants tips on unique and unusual places in Chicago, check out my book ‘Secret Chicago!’ https://www.secretchicagobook.com

  66. Sophia Casas says...

    Hi! Just a heads up that the link to “More city guides” doesn’t work :(

    • Joanna Goddard says...

      fixing now, thank you!

  67. Katrina says...

    King Spa! (Korean spa) Check their website or Groupon for deals + splurge on a treatment!

    • Rebecca Ringquist says...

      OMG -yes! I would kill for one of their scrubs right about now.

    • ClareV says...

      All the thumbs up for this. Nothing like a scrub and then dinner in pjs.

  68. Carly says...

    Hi! Chicago native here! I love reading city guides for my own city as a lot of these recs I have never heard of. One place I would add for amazing Korean food is Jin Ju in Andersonville. That’s my favorite restaurant, hands down. Also, could not agree more that October is the best month here. Tim said is best: the vibe is palpable.

    • Sandra says...

      Jin Ju!!! I am glad to hear they are still around since I haven’t been in a few years. I love that place.

  69. Jodie says...

    OK, need to check out his site because this guide was excellent. I was nervous that it would be centered in certain neighborhoods but nope…he covered a lot and all over the city I love. I can’t believe he even mentioned Noon a Kabob in my old hood Albany Park! One restaurant to add: Monteverde in the West Loop. You can watch them make the pasta. So good.

  70. Dori says...

    So timely! I will be in Skokie for a girls’ getaway this weekend. Any recs for that area?

    • Chelsea says...

      Not sure what vibe your girls’ getaway is, but you can kayak in the Skokie Lagoons which would be a fun way to break up patio drinking in the sweltering heat this weekend!

    • Roxana says...

      The Botanic Gardens! It’s really beautiful up there. We have a membership and go all the time. Although, as Chelsea already said, it’s going to be sweltering : /.

      Also, Evanston won’t be far from you (just east) and there are some fun little shopping districts in E-town (Central street and Dempster street both have some great little shops) and great restaurants (including Lou Malnati’s and Giordano’s – I prefer the latter ;). Northwestern’s campus is also pretty and has a nice lakefront trail.

      Hope you enjoy your time!

    • Julie says...

      Kauffman’s! It’s a fantastic deli great for breakfast and lunch.

  71. rachel f says...

    Throwing out some love for Cafe Orchid. Amazing Turkish food. Don’t forget – it’s BYOB! http://www.cafeorchid.com/

  72. Yes Tim so good! So excited to check out the 61st Farmer’s Market. Another Lou Malnati’s fan here, no offense to Pequod’s lovers but their tomato sauce just doesn’t hold up. And for this native New Yorkers’ slice craving, Dante’s and Jimmy’s are pretty damn close to NYC pizza. Also gotta add Greenmill and Le Piano for jazz. And every single corner bar (shoutout to The Charleston and Cody’s) because Chicago does ’em best. Thanks for sharing Tim!

    • Elise says...

      I went to Greenmill Lounge my last visit to Chicago and it was absolutely amazing. Love the interior, love the jazz, loved the drinks.

  73. Yael says...

    Fantastic guide. Chicago also has the third largest Chinatown in the US — worth visiting.

  74. Em says...

    I love Chicago and I love this guide! What a fantastic city, I miss it dearly.

  75. Edith says...

    I really liked this guide because it felt personal. He didn’t just give us a list of “everything we need to do and see and experience”.

    I love Quartino’s and Heritage Bicycles + Coffee.

  76. Amanda says...

    Yay! My boyfriend just moved to Chicago (the Logan Square neighborhood mentioned throughout the post) for a year long internship and I’ll be visiting frequently so the timing is perfect. Thanks for sharing!

    • MCF says...

      Hot tip from a longtime Logan Square-er—check out the Whistler for cocktails and late night DJs. They’re the OG cocktail bar in the neighborhood but easily overlooked. Amazing patio out back where the bartenders juice apples at night and mix them fresh with whiskey or tequila. Have fun when you come visit!

    • ClareV says...

      Billy Sunday for cocktails and Giant for dinner are also excellent local spots.

  77. N says...

    Tim, can we hang out? I move to Chicago in one week (!), and you seem so fun! Thanks for this great guide.

  78. Pooja Rao-Pennington says...

    We’ve been living in Chicago for six years now (Indian/British transplant, moved from Battery Park (NYC) to the West Town/Ukrainian Village neighborhood. I must add, all the neighbourhoods in Chicago have their very own “best of”. For food I would recommend Takito Kitchen, Craft Pizza, Alliance Bakery (for the best Almond croissants) and Smoke Daddy BBQ. For the kiddos, there is the famous Shedd Aquarium, Chicago Children’s Museum (a hands-on experience) and Crystal Gardens in Navy Pier (a cultural landmark and a must for any first time visitor to Chicago. And if you’ve got time, pop over to Millenium Park to view the Bean. It’s quite neat! Happy explorations – Pooja

  79. Clare Agra says...

    Best way to see the city is the Chicago Architecture Center River Cruise. It’s a 90 minute cruise through the middle of the city – and through the best architecture – on the Chicago River. Super fun! I’ve been here 15 years & still love taking out of town guests on the cruise. It’s relaxing, gives the absolute best views & they have a full bar on board ;)

    • M. says...

      I second this! I’ve taken students on this tour throughout the years and had some awesome tour guides (and some rather dry ones). The city is an architectural time capsule for modern through contemporary styles and a boat tour can be a nice break if you’re doing a lot of walking with your group.

    • Maire says...

      Also fully support the plug for the Architecture cruise- I have also been on it so many times and it is always wonderful!

    • Mimi says...

      Yes! I take all my guests on this! Make sure to do the (Wendella might be the only?) one that offers the lake and the river combined tour.

    • Jessica says...

      Ten-year Chicago resident here. Totally concur. When visitors come to town, they always want to go to Navy Pier and I’m always pushing the architecture tour instead. They ALWAYS thank me later! :)

  80. Brenna Finnegan says...

    I’m approaching my 10 year mark here in Chicago and I am so impressed with this city guide. Great thought and care went into this tribute to the city:) What I appreciate most is that smack dab at the start of the guide Tim called out the struggles, injustice and conflicting sentiments that shape our relationship with the city.
    Bravo and thank you for an exciting lineup of new spots to explore!

  81. Shannon says...

    No one has mentioned the Green Mill yet! Stop by for a cocktail and late-night jazz, or check out the free “live magazine” show called Paper Machete on Saturday afternoons. Get there early to snag a seat, it’s always a full house!

  82. Sarah Rose says...

    Some Other Recommendations:
    Family Favorite for Mexican: Taqueria El Mezquite – visit Pilsen! They have amazing street art and the Mexican Museum of art (if I’m not mistaken) is free and filled with Latinx artists. Unfortunately, like many of the neighborhoods, gentrification is rapid BUT Pilsen holds a place in my heart. If you’re lucky there are street craft fairs and the Festival of the Sun is coming up soon!

    Family Favorite for Italien Ice: Annette’s in Lincoln Park – Cash only, but seriously it’s fantastic and Annette is the sweetest lady!

    Foster Street beach is the – Like said before, Foster Street beach is the *best* beach on the north side! I mean it’s really great, especially for kids. If you get there at 9 left by 12, you’ll have an amazing time before the crowds set in!

    Bike Tour: I’m sure this has been mentioned elsewhere but take an independent (as in not through a company) bike tour of the city! We live here, but we took the kids on a 20-mile bike ride down Lakeshore trail and they LOVED IT. Stop at the beach, went to Navy Pier, and headed over to Maggie Daley as well. Plus lots of ice cream stops and even though it was hot pulling over and hopping in the lake is perfect! Check out Four Star Family Cyclerly (Bucktown + owned by the coolest lady Elsbeth) – you can rent electric cargo bikes (!!!) if you’re visiting w/ kids and save some $$ for the tours. If kids can bike pretty well, lots of rental bike options! Just research!

    Andersonville: I know it got shouted out, but if you want a really unique experience try out Wooly Mammoth. It’s the weirdest and slightly creepy store/ museum ever. Google before going – squeamish people be warned – my kids love going in when we walk over to Andersonville for ice cream. It’s bizarre but a fun experience! Also the Puppet Bike – currently in Andersonville seen it the last couple of weekends there. Kids will love it and tip the performers! They’re great.

    For Jazz Lovers – Green Mill in Uptown. Depending can be pricey but- AMAZING!

    Also, ShopColumbia is a really cool little gift store with handmade items by the kids at Columbia College! It’s in the south loop and it goes right back to the artists if I’m not mistaken!

    Chicago is the best city and this doesn’t even include my Southside recommendations – but there’s something for everyone!

    • Sarah Rose says...

      One more! – Everyone I’ve suggested to go also like Busey Beaver Buttons Store & Museum! Kids love to make buttons there and they add every button you make to the Museum – kids get a kick out it.

    • Katie says...

      Sarah Rose, I love your recommendations! I’ve lived in Chicago for going on 20 years. I live in the Rogers Park neighborhood, so I’m partial to the little beaches you find up there at the end of North Shore Ave (Hartigan Beach), Albion, and Columbia. They are less crowded & beautiful. Also, if you’re up there, explore Loyola’s Lakefront campus – just gorgeous!

    • Emily says...

      Hi neighbors who also read COJ,
      Another Rogers Park resident here seconding Katie’s recommendation of our neighborhood beaches. Low-key and not super crowded! I love living within a quick walk of the beach, all stress seems to melt away when you’re wading through the cold water after a long day at work.

  83. Kelly Kennedy says...

    Ah he didn’t even comment on the thriving comedy scene in Chitown. I would recommend the classic Second City (many SNL cast picked directly from these groups) but for a truer improve experience IO is where it’s at.

    Also you could spend a week in Wicker Park I swear, there’s Big Star (tacos), Small Cheval (burgers), Violet Hour (speakeasy), Stans Donuts (self explanatory, also originally LA based) and amazing shopping!

    • Megan says...

      I also came to comment about the comedy! I went to Second City a few years ago on a trip to Chicago and absolutely loved it.

  84. jackie says...

    hey cup of jo! is motherhood around the world not coming back this summer?

  85. Shannon Downe says...

    Going on 10 years in Chicago and LOVE this guide. Tim covered so much and made me yearn for October in Chicago, couldn’t agree more. That line about the farmer’s market abundance…sigh. Also, thanks for the call out of Chicago’s struggles & challenges <3

    Lula is also my #1 resto rec. I highly suggest Cellar Door Provisions & 4lw Turkish coffee (across the street) too if you're in Logan. Lost Larsen & Passerotto in Andersonville are also certainly worth a visit!

    • MCF says...

      Cellar Door is great and I just had a sandwich that CHANGED MY LIFE at Lost Larsen last week!

  86. h says...

    If you’re in Logan Square in summer or early fall you have to go to Miko’s, too! Basically required.

    • Dana says...

      ❤! Passionfruit!

  87. Diana says...

    YES finally a city guide on my city! I live in the quaint Lincoln Park neighborhood. I always recommend strolling through the lily pool and nature boardwalk by the lake, brunch at Cafe Ba-Ba-Reeba, checking out cute stores on Armitage. Other fun activities include spending a whole day at the Art Institute (my favorite place in the world), taking an architecture boat tour, and watching a Cubs Game at Wrigley Field.

    Other restaurants/food: Girl and the Goat and Au Cheval in West Loop, Chicago French Market, Lou Malnati’s or Pequod’s for deep dish, Bavette’s, Portillo’s

  88. Katie says...

    I’ve been reading Lottie+Doof for years, Tim is a delight!! Thanks for inviting one of the greatest Chicago residents to write this article.

  89. Natalie says...

    I just glanced at Bryan’s blog and I’m so happy to see someone from Oak Park featured on here! When he mentioned Johnnie’s Beef and Gene and Jude’s, it was a dead giveaway to me because they’re such staples for people who live in the OPRF area.

  90. Paula says...

    Great. Thanks a lot. Now I’m on page 100000 of his blog because it is so good and I can’t stop and I have a project that I’m suppose to finish and I just took a lunch break, and now….

  91. Yes, this guide is so good!

    Other things to add:
    – seeing a midnight show at the Music Box Theatre
    – picnic-ing at the Pritzker Pavilion in the summer and watching an outdoor movie or concert with the rest of the city
    – the Mexican Museum of Art in Pilsen
    – Devon St. for Indian food
    – free impov at iO on Wednesday nights
    – sitting at Lincoln Park beach at night with a (concealed) bottle of wine and reveling in the best view of the city at night

    • Naomi says...

      Friends of mine drive from Iowa to attend the Christmas Double-Feature at Music Box. They go on and on about it.

    • Such good suggestions!

    • Liz says...

      Yes!! Music Box is my favorite place in the city.

  92. Amanda says...

    I moved to Chicago 11 years ago and am so proud to call this city my home. Some other VERY Chicago places I love are:
    -Merz Apothecary in Lincoln Square for all the niche and European beauty finds (love shopping in here before a movie at the beautifully rehabbed Davis Theater!)
    -Spacca Napoli in Ravenswood–BEST non deep dish pizza and GET THE BURRATA!!!!
    -Ann Sather—you must eat an Ann Sather cinnamon roll at least once in your life.
    -Peckish Pig (technically on the Evanston side of town) –has amazing cocktails, a GORGEOUS patio and is so so so cozy in the winter time.
    I loved reading this guide as I haven’t been to 90% of these places and I can’t wait to explore this city further!

    • Shannon says...

      YES Mertz and Spacca! Two things I miss so much since moving away. Also, my husband and I yearn for Del Seoul weekly. Go there for amazing Korean tacos! Dear God, I miss Chicago.

    • Amanda says...

      Hi Shannon! I’ve never been to Del Seoul but now I need to check it out :)

      So many Chicagaoans commenting on here Joanna, I think you need to have a MidWest meet up ;)

    • Caroline says...

      Merz!!!!!!!! Fave place. I always make a stop in Lincoln Square when I visit from CA.

    • L says...

      ohh my gosh I am so happy to see Spacca napoli mentioned a few times in these comments!! I miss it so. Second the recommendation to get the burrata!! My husband and I just ordered burrata at a nice hip trying to be like spacca napoli restaurant in our new city and we were CRUSHED when it didn’t come close.

  93. celeste says...

    Wisconsinite here. Lou Maneti’s for Chicago deep-dish pizza. Yummmm.

  94. Lauren says...

    As a Chicago resident, this is the best Chicago city guide I’ve ever read. Everyone should check out downtown (The Art Institute of Chicago!!) but then, leave!! Get out of there!! There is so much more to Chicago—north, south, and west! Also, Noon-O-Kabab is an A+ call out.

  95. Jessie says...

    As a Chicago resident myself, this guide is truly delightful and a great representation of our city! I live in Andersonville (one of the suggested north neighborhoods to visit) and can recommend my perfect day: start the day with brunch at M Henry (my favorite brunch in the city hands down), wander the used furniture and finds at Brown Elephant (proceeds benefit Howard Brown Health, which specializes in LGBT healthcare in Chicago), get a coffee at Collectivo or La Colombe, get a pastry at Lost Larson (incredible local bakery and they serve dinner), pick up a book at Women and Children First, and then get dinner at Big Jones (seasonal southern food with a home-y flair). From Andersonville, you can walk to Foster Beach or Winnemac Park for a touch of nature. I love this neighborhood and I love this city!

    Bonus Tip: The best dancing can be found at Beauty Bar and Danny’s!!

    • Beth says...

      Beauty Bar is the best!!!

    • Addie says...

      I live in Andersonville, too, and I’m digging all the love it’s getting!

      I echo every single one of your recommendations. I’ll also add: Hopleaf for Belgian beer and fare. :)

  96. Chelsea says...

    Thanks for the reminders on why I love my adopted city! I whole-heartedly agree with the Lula, Loba, Plein Air, Mi Tocaya (okay all the food) recos and can’t wait to try some new things – like The Poetry Foundation events. Also want to add Estereo (try the Beer cocktail) and The Bungalow by Middle Brow for the best toast in the morning or pizza and beers at night.

    • Such a strong agree on Middle Brow. Quickly becoming one of my favorite places in the city.

  97. a.n. says...

    love this! his food recs made me drool. (as a side note – would love to see a city guide for savannah, ga! or…cleveland!)

    • Hannah says...

      Seconding Cleveland!

    • megan says...

      third-ing CLE!

  98. Louise says...

    Garrett’s popcorn, late November. That is all.

    • Lindsay says...

      Arcona facial at Ruby Room in Wicker Park.
      My Pi Chicago deep dish spinach pizza in Bucktown.

  99. rose says...

    As a lifelong Chicagoan this makes my heart sing.

    I can attest that Johnnie’s is the best Italian Beef in the city – if not the country. Order it “juicy sweet” – dipped in ausjus with sweet peppers. Just down the block on North Ave., Alpine Italian Deli has an EXCELLENT italian sub that I still frequently make the trek for (better than Bari’s – don’t @ me).

    Going to have to STRONGLY disagree on Gene and Jude’s, though. They may not allow ketchup on the premises, but their dogs lack celery salt, sport peppers, tomatoes, and cucumbers — all the standard fixings of a traditional Chicago dog. They also have soggy fries.

    • Rose, we may disagree on hot dogs but I am 100% on board with Alpine. It is our go-to for subs. : )

    • Morgan says...

      Long-time Lottie & Doof reader here – yay Tim! I left Chicago 20 years ago and Alpine subs are still number one. Tim has shared on his bog and I agree that true Chicago style pizza is 1. Thin crust and 2. Cut into squares. Add an Italian ice at Johnnie’s and oh Tim, does the Oak Park farmers market still have the best cinnamon sugar doughnuts?

  100. Sarah says...

    Yay Chicago! Far northsider here, and a big lover of the Andersonville scene for tourists and guests. We adore taking visitors to Jerry’s Sandwich and hitting up George’s Ice Cream after. And visiting locally-owned feminist bookstore Women and Children First is a must! If you’re venturing out for breakfast or brunch, I highly recommend Nookie’s (order off the seasonal menu on the weekends, though I’ve never had anything disappoint) and Ann Sather (get the cinnamon rolls)! Also, as a Chicagoan, I rarely eat deep-dish–only when guests are in town–but I *swear* by Pisano’s thin-crust if we happen to be downtown and have a hankering for pizza!

  101. kathy says...

    His love for his city is palpable. I’m going to start reading his blog!

  102. Holly says...

    Couldn’t agree more on fall in Chicago. September/October is a great time to visit. I swear the skies are a sapphire blue all September long.

    And because I’m from Chicago, I have to enter the pizza fray. Lou Malnati’s is my recommendation! Their “Lou” is the best deep dish because it’s not too greasy (quite a feat for deep dish). And they are a great company. Opened a location in the Lawndale neighborhood where they give all the profits back to community programs. Love supporting that.

    Great roundup! Thanks for featuring our wonderful city!

    • Jenny says...

      I agree with the Lou from Lou Malnatis! My favorite Chicago-style pizza! (But I guess I should try Peqouds sometime since I’ve never had it…)

  103. As a fellow Chicagoan transplanted to Phoenix, this was such a pleasure to read! It brought back some cherished childhood memories (we moved west when I was 13) and made me eager to take a visit back home soon <3 Thank you for sharing!

  104. katie says...

    Two years ago, I moved from Lakeview to West Town. My favorite Sunday morning ritual was grocery shopping at Whole Foods then hitting up Loba on the walk home for a coffee and a pastry despite being a few blocks out of my way. I deeply miss my weekly treat to myself and have yet to find something equally as great in my new neighborhood. Loba is a hidden gem that I rarely hear people talk about, I love that’s the first mentioned.

    My vote goes for September.

    • Shannon says...

      If you’re looking for a new weekly treat option near West Town, check out Spinning J (in Humboldt, technically).

  105. I’m in Chicago right now and just last week checked Cup of Jo to see if you’d done a city guide! With two days left in the city, this timing couldn’t be more perfect. Thank you!

    • Joanna Goddard says...

      have fun!!

  106. Ashley Butler says...

    Tim is the best there is! Thank you to my dear friend for such a lovely guide!

    • Joanna Goddard says...

      i can spend hours on his site. he’s so wonderful!