How to spend 4 days in Chicago with Kids 

Chicago is one of the best family-friendly cities in the Midwest, and after spending four full days exploring it with my kids, I can confidently say it deserves a spot on every family’s travel bucket list. From world-class museums and hands-on science exhibits to beaches, parks, and iconic city views, Chicago offers the perfect balance of learning, play, and adventure.

If you’re planning a kid-friendly Chicago vacation, this 4-day itinerary covers exactly what to see, where to stay, and how to get around. Whether this is your first visit or a return trip, this guide will help you make the most of your time in the Windy City.

Getting to Chicago

We drove to Chicago, but it’s incredibly accessible no matter where you’re coming from. Chicago is served by two major airports: O’Hare International Airport (ORD) and Midway International Airport (MDW)- both offering nonstop flights from across the country.

If you’re flying, you can easily reach downtown via the CTA Blue Line (from O’Hare) or Orange Line (from Midway), or use rideshare services, like Lyft or Uber. For families who prefer rail travel, Amtrak provides comfortable service to Chicago Union Station, while Metra is a great option for regional travelers.

If you’re driving, major highways like I-90, I-94, and I-55 make getting into the city straightforward, though parking downtown can be expensive.

Where to Stay in Chicago with kids

We stayed at the Hyatt Regency Chicago, and while it does lean more business-style, the central downtown location made it a great base for exploring the city with kids. Many attractions, restaurants, and transit stops were within walking distance, which saved us a lot of time and energy.

👉 You can read more about how we stayed here for $0 in this post.

Parking Tip:
If you’re staying downtown and have a car, download the SpotHero app before your trip. Our hotel charged nearly $90 per night for parking, but we found a spot less than a quarter mile away for about $20 per day using SpotHero.

Getting around Chicago as a Family

Chicago is one of the easiest big cities to navigate without a car. We relied almost entirely on CTA buses and the L train.

Before your trip, download the Ventra app, which makes paying fares and navigating routes simple, even with kids in tow.

Day 1: Lincoln Park & Other Free Family Attractions

Lincoln Park Nature Boardwalk

We started our first day in Chicago at the Lincoln Park Nature Boardwalk, arriving around 9:30 near the Farm Gate. The farm area opens earlier than the rest of the zoo, making it a perfect first stop.

The boardwalk is an accessible, stroller-friendly path that winds through a pond and prairie ecosystem filled with birds, turtles, fish, and insects. It’s a great reminder that Chicago has incredible green spaces, even in the heart of the city.

Lincoln Park Zoo

Right next door is the Lincoln Park Zoo, one of the best free zoos in the country. It’s compact enough to explore with kids without feeling overwhelming, and there are stroller rentals are available if you need one.

We were lucky enough to catch the lion feeding, which was a highlight, and the sea lion show is a must-see. We grabbed lunch at Park Place Café, but it’s also a great spot to pack a picnic.

Peggy Notebaert Nature Museum

After the zoo, we walked to the Peggy Notebaert Nature Museum, where our ASTC reciprocal membership gave us free admission.

The Butterfly Haven alone is worth the visit here! They do a daily butterfly release at 2:00 p.m., where dozens of newly hatched butterflies are released into the exhibit. The rest of the museum is so much fun, and perfect for kids. We spent a couple of hours here, and then wandered around outside to see the trails and butterfly garden.

Lincoln Park Conservatory

Just across the street is the Lincoln Park Conservatory, which is free but requires advance reservations. We spent about 30 minutes inside and another half hour wandering the surrounding gardens.  The conservatory and grounds are lovely, and definitely worth a stop!

To end the day, we headed back to our hotel and enjoyed deep-dish pizza from Giordano’s, which absolutely lived up to the hype.

Day 2: Museum Campus & Lake Michigan

Field Museum 

We started our morning by taking the bus to the Museum Campus. We used our ASTC reciprocal membership to get in free to the Field Museum. This museum is huge. Like, enormous. We wandered around for about 2 hours before my kids got bored here. There aren’t a ton of hands on exhibits here, so it’s probably better suited for kids a bit older. However, if you have an ASTC membership and can get in free, I would definitely recommend a stop, even for just an hour or 2! Seeing Sue, the most complete T-Rex skeleton ever discovered, was pretty awesome.

Shedd Aquarium 

After lunch from food trucks nearby, we headed to the Shedd Aquarium.

Tip: buy tickets ahead of time. Same-day tickets often sell out or push entry times later into the afternoon.

From beluga whales to immersive aquatic exhibits, this was one of our kids’ favorite stops of the entire trip. They have some really great touch tanks, and the dolphin and beluga show cannot be missed.

Grant Park, Lakeshore Drive & Buckingham Fountain

After we finished at the aquarium, we headed towards Lake Shore drive. There were some food trucks parked, and we grabbed a Chicago style hot dog and a famous rainbow cone (both were yum!). Then we walked along Lake Shore drive to take in the views on Lake Michigan and the Chicago Skyline. We stopped at Buckingham Fountain, one of Chicago’s most iconic landmarks, before catching the bus back to our hotel.

Day 3: Skyline Views & Beach Day

Chicago Architectural Boat Tour

We started our morning on an architectural tour taking in the views of the Chicago skyline. This is by far one of the coolest things to do in Chicago, and really immerses you in the history of the city. The loading dock was right across from our hotel, which was very convenient. We did a 1 hour tour, which was the perfect length for our family. The tour guide was great, and we learned so much about this unique city. I highly recommend this activity on any trip to Chicago!

Check out the tour we did here. 

Water Tower Place 

After our boat tour, we took the bus a couple of blocks to the Water Tower Place for some shopping. My daughter was so excited to visit the American Girl store and personalized her very own doll. We also hit up the Lego store and created our own custom Lego minifigures. 

Ohio Street Beach

In the afternoon, we grabbed our swimsuits and took the bus to Ohio Street Beach, one of the best beaches for families visiting Chicago. It offers calm water, skyline views, and lifeguards on duty.

It was a bit crowded when we arrived, but by late afternoon had cleared out. We ate dinner at Caffe Oliva right on the beach, and then rented a quad bike to explore the Lakeshore Trail. So fun, but best for bigger kids who can help pedal.

Day 4: Hands-On Fun & Iconic Chicago Sights

Museum of Ice Cream 

We kicked off our final day at the Museum of Ice Cream, a quirky, colorful experience that our kids loved. You get unlimited ice cream samples, and some of the flavors are so unique (think hot dog flavored ice cream). End your time at the museum by diving into the massive swimming pool of sprinkles.

Check out ticket prices and hours of admission here.

Maggie Daley Park 

This park is an absolute must when visiting Chicago with kids. Maggie Daley Park features climbing structures, playgrounds, and seasonal splash areas that are perfect for burning off energy. Just be aware that it’s a big place- so you definitely want to keep an eye on your kiddos!

Museum of Science and Industry

We needed an indoor activity in the afternoon to cool off, so we jumped on the bus and headed to the Museum of Science and Industry. Admission was free using our ASTC reciprocal membership. 

This was such a fun place to explore! There were so many hands-on exhibits, and it is perfect for kids of all ages. We spent several hours here, and our kids would have stayed even longer if we let them!

Millennium Park and The Bean 

We ended our trip at Millennium Park, home to the iconic Cloud Gate (The Bean). While it’s walking distance from Maggie Daley Park, we chose to visit later in the evening when temperatures cooled down.

With restaurants, shops, a splash pad, and city views, it’s the perfect final stop on a family-friendly Chicago itinerary.

While we definitely didn’t see and do everything that this amazing city has to offer, we felt like we got a great feel for it! We can’t wait to come back and experience even more of the Windy City someday!

Final Thoughts: Is Chicago Worth Visiting With Kids?

Absolutely. Chicago is a city that truly delivers for families- offering free attractions, educational museums, outdoor spaces, and unforgettable experiences. This 4-day itinerary gave us the perfect mix of adventure and downtime, and it’s a trip I’d recommend to any family looking for a memorable Midwest getaway.