One Day in Chicago with Kids: Our Pit Stop on the Road to Washington

One day, countless memories—our perfect Chicago pit stop!

When you’re moving cross-country with four kids in tow, the idea of making a fun pit stop might seem like wishful thinking. But as we made our way from New York to Washington, we decided to do just that—stop in Chicago for one day of adventure. We needed a break from the long drive, and what better way to stretch our legs than in the Windy City?

If you’ve ever moved cross-country, you know those car days can feel never-ending, so we were all more than ready to enjoy some time outside the vehicle. Our Chicago stop wasn’t long, but we made it count. Here’s how we packed as much fun as possible into one day in Chicago with the kids—complete with deep-dish pizza, Navy Pier, and of course, The Bean!

1. First Stop: Deep Dish Pizza

You can’t go to Chicago without getting your hands on some authentic deep-dish pizza. We knew this had to be our first stop since the kids were ready to eat. It was their first time trying Chicago-style pizza, and let me tell you—they were hooked from the first bite. The pizza was everything you’d expect: gooey cheese, buttery crust, and toppings so thick you need a fork. Watching them dig into their slices, with sauce all over their faces, was pure joy. If you’re doing a quick stop in Chicago with kids, this is an absolute must.
Pro Tip:

Where to go for pizza? We tried one of the city’s local favorites, and it was worth the hype. Check out Lou Malnati’s or Giordano’s—both are perfect for a classic Chicago pizza experience.

2. Navy Pier: Fun for Everyone

After filling up on pizza, we headed to Navy Pier for some fresh air and family fun. Navy Pier has it all: stunning lake views, carnival rides, and plenty of space to let the kids run wild after being cooped up in the car. They loved the Ferris wheel—getting to see the city from up high was a highlight for everyone (even me, though I’ll admit heights aren’t my thing!). There’s something for every age here, so whether you’ve got little ones or older kids, Navy Pier is a great stop to let loose and make some memories.
Pro Tip:

Pack snacks and water! Navy Pier has plenty of food options, but we found it helpful to have a few snacks on hand to keep the energy up (and the grumpiness down) between activities.

3. The Bean: A Quick Photo Op You Won’t Want to Miss

You can’t go to Chicago without snapping a family photo in front of The Bean! It’s one of those iconic spots that’s fun for the whole family, and the kids got such a kick out of seeing their reflections warp and twist in the shiny surface. It’s located in Millennium Park, which is perfect for a little stroll and some downtime before you hit the road again. Even though it was just a quick stop, it’s a fun, free way to wrap up your day in Chicago and get that “we were here” picture for the memory books.
Pro Tip:

Go early or late if you can, especially if you’re visiting on a weekend. The Bean can get pretty crowded, but if you time it right, you can snag that perfect family photo with fewer people around.
A Perfect One-Day Stop with Kids

Our Chicago stop was just one day, but it was packed with fun, food, and sights that gave us a much-needed break from the road. The kids loved every second, from their first bite of deep-dish pizza to running around Navy Pier and seeing The Bean up close. It was a great reminder that even when you’re in the middle of something as stressful as a cross-country move, you can still make time for little adventures along the way.

If you’re traveling through Chicago with kids, even if you only have a day, I can’t recommend this stop enough. You’ll leave with full bellies, great memories, and some fantastic family photos!