Traveling to Chicago with four kids ages 7, 5, 3, and 1 might sound a little ambitious—but Chicago ended up being such a fun city break for our family of six.

I often hear that city breaks aren't ideal with young kids, but I actually think they can work really well when you choose the right mix of attractions, build in breaks, and balance everyone's interests. You don't have to see everything to have a great trip!

Over Labor Day weekend, we explored some of Chicago's biggest attractions, ate plenty of good food, and found a balance between sightseeing and activities that kept even our youngest kids happy.

We also loved how much we could fit into a long weekend without constantly feeling like we were rushing around. Staying near Michigan Avenue gave us a convenient home base for exploring the Riverwalk, Navy Pier, museums, restaurants, and many of Chicago's iconic sights.

Here's exactly how we spent our Chicago weekend with four kids—and why we'd happily do a city break like this again.

For our trip, we stayed near Michigan Avenue, and I think it’s a great area for families visiting Chicago—especially if it’s your first time.

We loved being able to walk to restaurants, coffee shops, the Riverwalk, and several of the attractions on our list. With four kids, not having to load everyone into a car every time we wanted to go somewhere was a huge plus. It was also nice having such a central location for stroller walks.

The downside? You’re definitely paying for the location, and the area can feel pretty touristy. And while a lot is walkable, Chicago is still a big city, so we did use rideshares when we wanted to save everyone's little legs.

When choosing a hotel, I’d look beyond the nightly rate and consider things like room size, sleeping arrangements, parking, breakfast, and whether there’s a pool—especially when traveling with kids.

→ [Check Chicago hotels on Booking.com]

Our Chicago itinerary was a mix of museums, sightseeing, and hands-on activities that worked surprisingly well for our four kids, ages 7, 5, almost 3, and 1. We tried to balance things our older kids would enjoy with plenty of opportunities for the little ones to move and explore.

We started our first day with a walk along the Chicago Riverwalk. It's a great way to take in the skyline, watch the boats, and let the kids get some energy out before heading into the museums. We loved that it was an easy, scenic walk from our hotel.

Tickets: The Riverwalk is free and doesn't require tickets.

Our kids are obsessed with aquariums, so we visited Shedd Aquarium, which was a highlight for all four kids. The beluga whales, dolphins, and colorful fish kept everyone entertained, and because it's indoors, it's also a great option if the weather isn't cooperating.

Tickets: We recommend purchasing tickets in advance, as there are designated time slots for admission. [PURCHASE SHEDD AQUARIUM TICKETS]

From Shedd Aquarium, we walked over to the Field Museum, making it easy to do both in the same day. With four kids, we didn't try to see everything—instead, we focused on the kids section (an interactive space for the kids to play and learn) and the ‘biomechanics’ section of animals. Our kids loved it. We were also surprised at how the cafe had decently tasting food items that even the adults enjoyed.

Parent tip: Don't feel like you need to "complete" the museum. Pick a few things your kids will love and call it a win!

Tickets: We recommend purchasing tickets ahead of time, especially on busy weekends. [PURCHASE FIELD MUSEUM TICKETS]

The Chicago Architecture Boat Tour was one of my favorite experiences of the trip, as well as the kids!

Cruising down the Chicago River while learning about Chicago's famous buildings gave us a completely different view of the city. Being on a boat also made sightseeing feel more exciting for the kids. It went slow and steady so motion sickness and nerves about being on the water with kids wasn’t too much of an issue. They sell snacks on board, so our kids enjoyed a few packs of chips.

Tickets: Boat tours can sell out, so I recommend booking in advance. Personally, the 1 hour was long enough for our family. [BOOK CHICAGO ARCHITECTURE BOAT TOUR]

We also visited the Chicago Children's Museum at Navy Pier, which was the perfect change of pace after a morning of sightseeing.

This was especially great for our younger kids because they could run, build, touch, and play rather than having to quietly look at exhibits. There was a designated room for babies and toddlers, which was perfect. Our older kids enjoyed the hands-on science, building, and tinkering activities too.

Tickets: Admission tickets can be purchased online. [PURCHASE CHILDREN'S MUSEUM TICKETS]

With four kids, we kept our meals pretty casual and chose places that were convenient to our itinerary. Here are the spots we tried during our Chicago trip:

We started one morning at Joe & The Juice for an easy breakfast before a full day of sightseeing. With coffee, juices, smoothies, and sandwiches, it was perfect for grabbing something quick and getting everyone fed before heading out.

One of my all time favorite cuisines is Afghani food. So we tried Afghan House. We enjoyed the bolani (fried bread with potato) and the chicken. The chapli kabob, usually our favorite, was just okay. The spicy green chutney made it worth it!

Couldn't visit Chicago without trying deep-dish pizza - and at one of the most popular spots! We stopped at Giordano's for lunch after our architecture boat tour and before the Childrens Museum. The pizza is easy to share, making it a good option for families, although keep in mind that deep dish takes a little longer to cook.

After the Children's Museum, we made a stop at Ghirardelli for dessert. It's right near Michigan Avenue, so it was an easy place to grab ice cream and chocolate after a busy day. It was a fun treat for all the kids to indulge.

On our final morning, we stopped at the Hello Kitty Café Chicago for coffee and pastries. This was especially fun for our daughter, and myself, as I love nostalgic things.

The café is right on Michigan Avenue and has two floors of Hello Kitty-themed décor, food, drinks, and merchandise. It's an especially fun stop if you're traveling with little ones who love Hello Kitty.

Reservations: Regular café visits don't require a reservation, but the Bow Room Afternoon Tea does.

Chicago turned out to be such a fun city break with littles—there’s so much to see, do, and eat, and with a little planning, we found it surprisingly easy to enjoy as a family of six. We definitely didn’t get to everything, so for our next trip, Nutella Café, the Adler Planetarium, the butterfly garden, and Lincoln Park Zoo are all on our list. Sounds like we’ll just have to go back!