We just got back from a week-long trip to Chicago and Michigan to visit my parents. We hadn’t spent much time in Chicago before (thanks again for your advice!) so it was awesome to explore all the neighborhoods. Here’s what we did…

We rented an apartment in Lincoln Park, and my mom drove down from Michigan to join us. (The apartment was bright and airy and we all secretly wished we lived there; the photos don’t do it justice!)

Lincoln Park was a great neighborhood for a family vacation, since we could easily walk to the zoo, the beach and two playgrounds; and the streets were lovely for evening walks.

We went to a Cubs game, and, as we walked into Wrigley Field, Alex murmured, “It’s like walking into heaven.” Toby was less enthused, since the cheering scared him, but he warmed up quickly. (The team spirit was contagious.)

I wanted to eat a classic Chicago hot dog, but wasn’t sure what people traditionally put on them. So I piled on everything. Did I get it right? Totally wrong? It was delicious nonetheless.

One (hot!) morning, we took an architectural boat tour, which about 583,294 people had recommended. We learned tons of fun facts, including how they once reversed the direction of the river and that Chicago has so many clock towers because back in the day no one wore watches.

We rented bikes at Heritage Bikes, a gorgeous design-y bike shop that welds their own bikes by hand right there in Chicago. Very cool.

The best part was, as soon as we walked into the bike shop, we ran into our old friend from New York, Max Wastler, who had recently moved to Chicago. What a small world! During our trip, he cut his hair and beard, so, just for fun, here’s his before-and-after. (Doesn’t he kind of look like the actor Hank Azaria?)

Chicago is a great food town. We ate our weight in deep-dish pizza, and had delicious dinners at Au Cheval (an upscale diner), Avec (French small plates) and Big Star (fantastic tacos, which Toby devoured). One evening we also met Max and friends for cocktails at the Violet Hour, which is a dark, moody bar without a sign (which I always secretly get a kick out of:) We went really early, since we heard the line can get crazy.

One evening, my mom and I stayed home to drink wine and catch up (and watch The Bachelorette, if you must know:), while Alex took an evening bike ride. When he got back, he breathlessly told us that he had spontaneously gone up the Sears Tower to the Skydeck (pictured above). Alex’s biggest fear is heights, so he almost turned around many times, but pushed himself to ride the elevator up 103 floors and step out onto the glass floor. “You can’t capture it in words or pictures,” Alex told us, “It’s literally like stepping off a skyscraper. I had to basically tiptoe out there.” Yikes? Have you ever gone up?

The final weekend, we drove up to Traverse City, Michigan, to visit my dad and his lovely girlfriend. Toby fell madly in love with “Opa,” and not just because he gave him a lollipop every afternoon. We swam in the lake by day and chatted around the bonfire by night. And my dad made everyone squeeze onto the same side of the picnic table, so we could all enjoy the view of the lake. (Ahh, dads.)

Finally, happy and exhausted, we headed home. Even though I’m 33, I was sort of homesick as we drove back to the airport. The trip made us look forward to many more vacations visiting family; there’s something so restorative about going home again. Hope you had a happy fourth wherever you were!

(All photos taken by us, except the haircut and storm shots, which were by Max Wastler, and the skyledge photos, which were courtesy of the Sears Tower. (Update: My swimsuit is from J.Crew. Thanks for asking!))