Traveling to Chicago with kids?!
Today I’m sharing what we did on our lil’ family vacation to the Windy City last summer. I have visited Chicago a few times to visit friends and for Bachelorette trips… but this was our family’s first time going together! It was an easy, quick 6 hour drive for us. We had so much fun together and I already can’t wait to go back. Read on for our recommendations!
Chicago with Kids: What to Do
1.) Take the Chicago Short Architectural Boat Tour.
If you’re visiting Chicago for the first time, this is absolutely A MUST DO. And even if you’ve visited before, this is an essential! Hands down, this was the most memorable experience from our trip! We made a reservation and hopped on a tour boat the last evening we were there. I purposely planned this on our last night because I had heard so many great things about the architectural boat tours.
We went during golden hour (right before the sun started to set) and the skyline was glowing and simply magical! We opted for the shorter tour which was more family-friendly with it only being 45 minutes vs. 90. Our guide was outstanding and we learned so much about Chicago’s famous architecture. The views are absolutely incredible from the Chicago River and I can’t wait to go again! Such an experience!!!
2.) Find a Rooftop Pool in Downtown Chicago.
If you visit Chicago during the summer time, staying at a hotel with a rooftop pool is a luxury – but will absolutely make your trip! We loved spending mid-day at the pool at the Viceroy. There’s no better way for everyone to let their shoulders down!
From the Viceroy’s rooftop pool, you not only have an amazing view of the city but also of Lake Michigan. True transparency: This is definitely more of an adults pool and isn’t that big – but everyone there was very kind and understanding. We also didn’t stay for extended periods of time – we just popped in for an hour or so…. but a few times a day! 🙂 All that to say, I still highly, highly recommend and would stay here again!
3.) Where to Shop in Chicago with Kids: American Girl
This place on Michigan Avenue is a little girl’s dream! Ava got her first American Girl here. Ellie loved riding the escalators! Afterwards, we took the girls and the dolls to the American Girl Cafe, which is a MUST-DO when in Chicago with kids. They serve the dolls and offer the absolute cutest experience there.
4.) Watch the sunset on Oak Street Beach.
We visited Oak Street Beach during the day and also to watch the sunset! I recommend both. The girls were able to put their feet in the sand… and in Lake Michigan! Definitely no swimming when we went – the water is very chilly! Located off of Lake Shore Drive near the Gold Coast, we were able to walk here from The Viceroy. They have concessions, volleyball, bike rentals and restrooms.
5.) Chicago Parks & Playgrounds
We couldn’t visit Chicago with kids and not find a playground or two… or three! This is one of our favorite things to do while on vacation – it’s free, the girls love to explore, and it gives us a minute to not entertain. Our favorites were Oz Park in Lincoln Park and the quaint Goudy Square Park, located within walking distance from our Gold Coast hotel.
Although we didn’t visit Maggie Daley Park, we heard a lot about it and it does look so awesome! Chicago has sooo many great playgrounds and parks though – you really can’t go wrong! Here is a great website rounding up the best.
6.) Lincoln Park Zoo
Founded in 1868, Lincoln Park Zoo is a FREE zoo in the heart of Chicago that is impressively open 365 days a year! During our trip, we spent a morning here before we ventured over to a nearby playground & restaurant for lunch (mentioned, below).
7.) Where to Eat in Chicago with Kids
Our Chicago friends gave us an excellent recommendation for our trip: Nearly every restaurant in Chicago is kid-friendly as long as you go early enough! We took this advice to heart and went to dinner before 7pm every night. Here’s a list of what we loved:
- Carmine’s – this iconic Italian restaurant in the Gold Coast is currently being rebuilt and won’t be open until 2025 but this was a standout for us! They treated the girls so well and I just remember Ellie being so happy – eating a plate full of spaghetti as big as her, haha!
- The Original Pancake House – We ate breakfast here everyday! It is a chain but it didn’t feel like it. The Gold Coast (again, close to our hotel) location was a cozy & quaint lil’ house nestled in the neighborhood. The girls loved the pancakes!
- Summerhouse Santa Monica – Located in Lincoln Park, this restaurant has a California vibe, filled with natural light and green plants. They have a fabulous kids’ menu!
- Blue Door Kitchen & Garden – This southern restaurant is stunning!!! We got here very early & did a lil’ happy hour w drinks & apps. We had the courtyard patio nearly to ourselves. No kids’ menu here but we pieced together some basics for them & it worked!
- JoJo’s Shake Bar – We retreated here during a rainy day for the biggest milkshakes, ever!
- Chicago Riverwalk – We had drinks & apps here before the Architectural Boat Tour. There are so many fun + casual spots – just be sure to go early as this area gets very busy!
- Lou Malnati’s – You can’t go to Chi-town and miss Chicago deep dish pizza!
8.) Visit Chicago’s Navy Pier.
Navy Pier is a stop that can’t be missed while in Chicago with kids! This destination has something for everyone – restaurants, ice cream, and loads of enterainment such as live music, rides, & games. During the summer, you can even catch fireworks!
During our visit, we got ice cream from The Original Rainbow Cone. Be sure to visit the Chicago Children’s Museum there, too! The best view of Chicago can arguably be found atop the historic Centennial Wheel.
9.) The Bean
Located downtown in Millennium Park, The Bean, otherwise known as Cloud Gate, is one of those things you have to do at least once when visiting Chicago! If you visit this public work of art in the winter, there’s also a free ice skating rink beside The Bean.
10.) Shop on Chicago’s Magnificent Mile.
We shopped ’til we dropped on The Magnificent Mile, otherwise known as Michigan Avenue. With more than 450 retailers, there’s something for everyone here. We even popped in Tiffany’s and the staff was so sweet, they gave the girls a lil’ coloring book with colored pencils… in a lil’ blue bag!
Full disclosure: Our girls love to shop, so we knew they’d enjoy Magnificent Mile but if yours don’t, I would skip this!
More Things to Do in Chicago with Kids
Some other places that we’re on our list but we ran out of time to do:
- Shedd Aquarium
- Art Institute of Chicago
- Sloomoo Institute (basically a slime museum)
- Skydeck Chicago in Willis Tower
- TILT at 360 Chicago
- Chicago Children’s Theatre
You can view more of our travel posts here!
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