Chicago with the kids: 5 ways to make it a perfect trip to the Windy City

Be flexible, eat the pizza, do all the touristy things

Anish Kapoor's "Cloud Gate", with buildings from the Michigan Avenue skyline in view in Chicago. (Raymond Boyd, Getty Images)

Whether you’re just a road trip away from Chicago, you go there on business every so often, or you’d love to visit someday, it’s truly a fantastic city, with so much to offer.

There’s culture, food, history and more. It’s a Midwest staple, and as someone who grew up visiting the Windy City, it only recently occurred to me (especially based on my family’s proximity!), that my husband and I should help make our kids fall in love with Chicago, too. From a young age, I want them to soak in the hustle and bustle of such a rich city.

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So we took a weekend! My kids are 6 and 4, and I’ll include what worked for us -- along with some context as someone who has frequented Chicago a LOT over the years. I say ...

1. Do the touristy things.

We took our kids up to 360 Chicago, which is an observation deck (formerly the John Hancock Center, which looks like it switched names in 2018). I thought the littles might be freaked out by the fast elevator ride up, or the view itself, but they were pretty awestruck by it all! It was cool to witness. Plus, no matter how many times you’ve been up, the views are incredible. My husband and I had a cocktail while the kids ran around, and it was a good hour spent -- plus, the bottom of the building is packed with Chicago history and exhibits. I don’t remember that part from when I was younger, so we actually took some time to enjoy it.

My son at the observation deck (this picture doesn't do justice to the view). (Michelle Ganley/GMG photo)

Some other touristy things you can do include ... eating Chicago-style pizza (what’s not to love if you’re a kid?). Shopping. Staying in a centrally located hotel or Airbnb so your children can take in the sights and sounds of the big city. We would have definitely done a Cubs game if it were that time of year, but maybe next time!

2. Make it a trip your kids will enjoy.

This one might sound obvious, but don’t drag them to too many stiff places that will make them groan.

We DID persuade our kids into walking just more than a mile to an adult-leaning brunch one morning (just meaning, it was more geared toward grown-ups than children), but we still made sure there was plenty on the menu that they could eat, and then we rewarded them afterward with an Uber back to the hotel, and then a trip to the Shedd Aquarium.

There’s so much to do in the city for kids. Here are some recommendations:

  • The Chicago Children’s Museum at Navy Pier -- We wanted to do this, but it was actually closed the day we intended to visit (but it looks great!)
  • Any of the major attractions of the Museum Campus: As mentioned, the Shedd Aquarium; or the Field Museum; or Adler Planetarium, which are all tied together by green space and right on Lake Michigan. They’re all kid-friendly, especially the Shedd, our personal favorite.
  • Shopping -- I’m still putting off our first American Girl Store trip, only because my daughter doesn’t seem to care much, and I’m postponing the wallet-emptying experience as much as possible, but there are obviously a million places you can shop in Chicago. We let our kids pick out a few things at the Water Tower because there was gloomy weather that day, and I didn’t want to get drizzled on, but they were wildly overjoyed by the experience. And yes, the Water Tower is just like a mall, but it’s right on the Magnificent Mile, and it does pack some cool stores that you most certainly don’t have at home.
  • Parks -- As someone who grew up visiting Chicago fairly regularly, I can tell you from experience that especially in the warm months, there’s just something always going on, especially at the parks. Taste of Chicago, art exhibits set up, cool fountains and music, gardens ... just look at everything Grant Park entails, and then go from there.
  • Go see the Bean! We actually spaced on this one, but I think our kids would have loved it. Again, a little cliche, but it’s a fun photo-taking opportunity, and we’ll most definitely keep it on our “next time” list.

3. Eat some fun meals, but make it easy on yourselves, too.

As you likely know if you’ve traveled with children, it’s best not to think of your trip as a typical vacation. I read somewhere once, something along the lines of, “It’s not a vacation. It’s a memory-making trip.”

Between the logistics, tired little feet and feeling a bit restricted in what you can and can’t do, you might be TIRED by end of your days.

Here’s what I recommend: One night, just DoorDash yourselves some dinner from a local restaurant: Remember, you’re in Chicago, which is restaurant heaven. No one said you had to make it boring or fast-food!

This frees you up from at least one night of reservations, wait times and navigating a menu while your server’s waiting on you along with five other tables.

It might feel good to relax in the hotel and check out the pool (if you have one!), and your kids will probably love the change of pace.

We ordered in Small Cheval, and the burgers absolutely lived up to the hype!

Other places to check out IRL include: Ann Sathers (multiple locations; you and your kids will adore the homemade cinnamon rolls for breakfast) and Giordano’s (this is the classic pizza; order right when you sit down, considering pies can take up to 45 minutes in the oven), and if you have a sitter or someone in the area to help with the kids, I’d send you to Trivoli Tavern, RPM Steak and/or Siena Tavern. Or if you have something else in mind ... give it a Google. Guaranteed, Chicago’s got it.

4. As mentioned, stay on the Mile, if you can!

We did the OMNI, and it was great. We valeted our car right away, and didn’t snag it back till the end of our long weekend.

The walking was fine, even with the little ones, and everything seemed relatively close to our hotel, even with some not-so-ideal weather.

It was nice to be able to run across the street to Walgreens, too, when we realized we forgotten our hairbrush.

Otherwise, if you stay at a hotel or Airbnb farther from the attractions, it might save you some money -- but you’ll also have to think about travel logistics, just within the city. The ‘L’ train (a now-official name originally short for “elevated”) is fairly easy to navigate, although I haven’t done it in years, and I believe we used city buses as a kid, too. Plus, Ubers and taxis are always an option.

These are all just things to think about! You likely DON’T want to deal with finding street parking, or paying for lots, too much over the course of your stay.

Analisa, 6, at left, and Robby 4, at the Shedd Aquarium. (Michelle Ganley/GMG photo)

5. Be flexible.

Chicago is a huge place, and if you need to adapt, adapt. There are so many places you could be exploring at any given moment -- and pop-ups, new restaurants and weekend events.

If your kids aren’t up for whatever you had planned, hop on your phone or tablet, ask around, and depending on the time of year, you’ll likely find another option. Don’t fret!

Final note: You’ll want to check on this if and when you actually plan your trip -- but when we visited, in late January 2022, there was a mask mandate inside most, if not ALL city buildings, and we had to show our vaccine cards to enter most indoor establishments, as well. I don’t think this applied to our hotel, but it did include all the restaurants, and this went for all children ages 5 and older (meaning, of vaccination age). Just thought you should know! Happy travels.

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