How to Spend a Few Days in Chicago With Kids

Chicago (aka Chi-Town) is a great weekend getaway whether you’re traveling solo, with your boo, or like us, with kids in tow! While the weather can put a damper on some plans, there is so much to do in the city that Conde Nast readers have declared the number one “best big city” for tourists, making it a year-round destination.

We spent a quick weekend in Chi-town so it was relatively packed and brief, but I thought I’d share our favorites, and of course, if you’re headed there for longer – consider grabbing Caroline’s comprehensive travel guide. Here’s how we suggest you spend a few days in Chicago with kids:

Pizza & other food!

We decided to keep our first night pretty low key. I had a hard time choosing between Pizzeria Bebu and Spacca Napoli. We drove in from Minneapolis, so it made sense for us to stop on the outskirts of the city. We chose Spacca Napoli and it was dee-lish! I was super happy with our decision. It was a traditional spot for Neopolitan style pizza, but a long line meant we knew we’d picked a special spot. Their burrata is shipped in from Italy once a week. YUM. You most likely can’t go wrong with either spot. We did stop at The Warbler for a pre-dinner beverage and appetizer. Super cute.

We made a brunch reservation at popular, Etta. We heard it’s a great spot for dinner too. It was also delicious.

Eating your way through the city is how we like to spend a few days in Chicago with kids!

Chicago With Kids

See a show!

We surprised our kids with Hamilton tickets – they/we are obsessed. It was the first time they had seen it and it was such a highlight of our Chicago weekend. Apparently it ends in January 2020. So, go now if you can!

Check out Broadway in Chicago to see what else is playing during your travel dates.

See a Show in Chicago

Be a tourist!

There is so much to see and do. We definitely hit all of the tourist spots. We decided to do 360Chicago¬†instead of Willis Tower/Skydeck. It added up with five of us and we didn’t spend a ton of time up there, but it was nice to see the city and Lake Michigan from above.

The Bean/Millenial Park – also known as Cloud Gate. Definitely a must.

Walk to Navy Pier and if you’re up for it – see the city from the Ferris Wheel.

Walk the lakeshore.


We planned to make it to the Science Museum but didn’t end up going. The kids wanted to swim at the pool instead.

My husband took our boys to the Chicago Bears game while my daughter and I had a couples massage at Allyu Spa. We would have all loved the game, but Ella and I decided to do our own thing instead.

Being a Tourist in Chicago

Where to Stay

There are so many options, neighborhoods, Airbnbs. Always reach out to to chat all things travel. We stayed at The Peninsula Hotel (we had Flexperks points and used for our accommodations) – it was PERFECT. I would stay there again in a heartbeat. We had one room for the five of us and it was more than enough space.

Of course, we would have loved to spend more time in Chicago, exploring and hitting all of the sites, walking through neighborhoods like Lincoln Park and discovering the hidden gems, but we just didn’t have the time. Whether you have a quick 48 hours or more, Chicago is a great choice for a getaway with kids.

Happy #wildbumming!

Mollie Krengel

Mollie Krengel