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…
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.
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.
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.
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.
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.
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.
The Poetry Foundation
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.
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.
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.
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.)