Discover underwater wonders at the Shedd Aquarium. Photo courtesy of Shedd Aquarium
Discover underwater wonders at the Shedd Aquarium. Photo courtesy of Shedd Aquarium

25 Things To Do with Chicago Preschoolers Before They Turn 5

While there are thousands of tourist attractions and cultural experiences in Chicago (and about 100 of them that you should do with kids before they grow up!) not all of them are great for babies, toddlers, and preschoolers. So, after creating a list of things you should do with Chicagoland babies before they turn one, we set about making the ultimate list of 25 things to do in Chicago before your little one turns five. From zoos to gardens to museums, much of this list is especially great for preschoolers and kids about to enter kindergarten. 

A few of our selections are well-known favorites with specific attractions for preschoolers, while other ideas are more off the beaten path, but all are things we've enjoyed doing with tots before they turn 5!

25 Things To Do with Chicago Preschoolers Before They Turn 5: Ride a water taxi

Teach tots to explore the Chicago River from a young age. Photo courtesy of Chicago Water Taxi

Outdoor Activities with Preschoolers in Chicago

1. Ride Down the Chicago River

The Chicago River is one of the coolest parts of Chicago. Take little ones to walk the Riverwalk, get a bite to eat, and watch the boats go by. The bridges lift for taller ships and tour boats which is a really fun spectacle for tots and small kids. After the walk, catch a tour boat or water taxi to another neighborhood. Kids love the adventure of boarding a boat and heading somewhere new to explore. 

2. Bike the Lakefront Trail

The lakefront trail on Lake Michigan stretches from Edgewater Beach down to South Shore/Jackson Park—the trail is 18.5 miles total. Choose a spot to hop on and bike along the lake through the loop, the Mag Mile, Lincoln Park, or the beautiful South Shore. Tots can bike a short while on their own trikes or training wheels, or hop on a parent's bicycle for a longer ride.

3. Swim in Lake Michigan

Chicago is home to 24 beaches along the lakefront. The best part is that each beach is free and open to the public. Build sandcastles, picnic on the beach, and go swimming on a hot summer day. Check out our favorite family-friendly beaches.  

4. Take a Dip in Your Neighborhood Pool

Chicago has 50 (you read that right, 50) free outdoor pools open during the summer months. From the baby pools and splash pads to the diving wells, there are pools in Chicago for every age and swim level. Check out our favorite family-friendly pools

25 Things To Do with Chicago Preschoolers Before They Turn 5: Maggie Daley Park

Maggie Daley Park is one of the great city parks in the country, and it's all ours. Photo courtesy of Maggie Daley Park

5. Play in Maggie Daley Park

Maggie Daley Park is a great outing for a day downtown. This 20-acre park overlooks Lake Michigan and is centrally located in the heart of the Loop. The sprawling park features a play garden, mini golf course, climbing walls, and acres of playground. There are different areas separated by age recommendation making it easier to stay in a safe play zone. 

6. Go To a Baseball Game

In Chicago, you have two hometown teams to choose from: the Chicago White Sox and the Chicago Cubs. Get some nachos in a helmet, bring a glove to catch a foul ball, and take them out to the ball game to root, root, root for the (right) home team. 

7. Visit a Zoo

A zoo is a magical place for anyone from 0 to 99. With aquatic shows, petting zoos, and even life-sized dinosaurs, the zoos in Chicagoland are some of the best. Check out our go-to zoo guide for everything you need to know about the best zoos in Chicago for littles. 

8. Scooter Down the 606

The 606 is an elevated former train line that stretches 2.7 miles from Bucktown/Wicker Park to Humboldt Park. You can hop on and off the trail at various points on a scooter, bike, or by foot. There are some great green spaces and playgrounds just below the access points; try exploring a new one on each visit.

Museums and Cultural Experiences for Chicago Preschoolers

9. Visit the Shedd Aquarium

The Shedd Aquarium is one of the largest indoor aquariums in the world. With whales, dolphins, penguins, and jellyfish, there are over 32,000 species of marine animals to see. Travel to the oceans, rivers, lakes, and reefs across the globe—right here in Chicago. 

10. Visit the Adler Planetarium

For any little space-lover, the Adler Planetarium is a great place to explore and learn. There are interactive exhibits that let little ones touch and feel space along with interactive sky shows. Check out a sneak peek of a sky show online, where kids can take a tour of the solar system, fly through the skyline, and more. 

11. Check out the Chicago Botanic Garden

The Chicago Botanic Garden is where toddlers and preschoolers can explore 27 different gardens across 385 acres. There are even nature preschool classes and camps throughout the year specifically designed for tiny nature lovers. 

12. Visit a Children’s Museum

Chicago has several great children’s museums across the city and suburbs. Many of these hands-on museums are designed just for toddlers and young children to explore. We love the Chicago Children's Museum, the Bronzeville Children’s Museum, the Kohl Children's Museum, and of course, the DuPage Children's Museum.

25 Things To Do with Chicago Preschoolers Before They Turn 5: The Peggy Notebaert Nature Museum

What's the difference between a tadpole and a pollywog? Photo courtesy of the Peggy Notebaert Museum

13. Check out the Peggy Notebaert Nature Museum

The Peggy Notebaert Nature Museum is located in the heart of Lincoln Park. Play at the water tables, see favorite animals, and explore the wildlife of the world. The museum is most famous for its butterfly haven where kids can walk through and have live butterflies surrounding them. Don't forget your camera for this!

14. See an Exhibit at the Field Museum

The Field Museum is a great place for toddlers and young children to explore. If there's a dino lover in your family, this is sure to be a hit. See Sue the T-Rex in addition to several other real dinosaur fossils.

15. Explore the Museum of Science and Industry

The Museum of Science and Industry is located in Hyde Park. This science and technology-based museum is great for kids to learn and explore through hands-on experiences from a tornado to a submarine. And the special exhibits, like Marvel: Universe of Superheroes, are amazing!

Sightseeing with Chicago Preschoolers

16. Take a Train To Union Station

For your little train lover, a trip to or from Union Station is an awesome experience. You can go into the city from your neighborhood or suburb before a day at the museum, a baseball game, or just take a ride for a quick bite and head back. Explore Union Station, located right on the Chicago River, and admire the nearby skyscrapers. 

17. Visit the Signature Room

The Signature Room is an upscale restaurant located high above the skyline in Chicago’s Hancock Building. This restaurant and skydeck on the 95th floor make a great experience for a young kid for lunch or a weekend brunch in the clouds. The entire restaurant features panoramic views of the skyline, lake, and city. 

25 Things To Do with Chicago Preschoolers Before They Turn 5: The Skydeck

Pushups over Chicago! Photo courtesy of Skydeck Chicago

18. See the View from the Skydeck

The Skydeck is an awesome outing for little thrill-seekers. Located on the 103rd floor of the Willis Tower is a 30-60-minute interactive experience featuring the best of Chicago’s rich history. Next, step out onto The Ledge of the third tallest building in the Western Hemisphere. 

19. Ride the Ferris Wheel at Navy Pier

The Centennial Wheel at Navy Pier stands a staggering 200-feet above the ground. This is not an old-school carnival wheel—visitors are fully enclosed in a glass box, making it cozy and safe for a group of four to take a ride with children as young as infants. Soar in the air to look at the Chicago skyline and lakefront from high up in the clouds. 

20. Shop on State Street

While the thought of taking a small toddler shopping doesn’t always sound like a party, your soon-to-be five-year-old will love the adventure of taking a shopping trip downtown along the famous State Street. Set a small budget and grab a few things they need or even some fun stuff. Check out Macy’s or beat the heat in Block 37 mall. Don't forget to grab a selfie in front of the iconic Chicago Theatre sign.

21. Visit Water Tower Place

Water Tower Place is located at the start of Chicago’s Magnificent Mile, also known as Michigan Avenue. Kid-favorite stores like American Girl and the Lego Store, just to name a few, are so fun to play in that kids won't even mind if you don't buy anything. Whoosh tots out of the store onto an open-air bus ride down Michigan Avenue.

25 Things To Do with Chicago Preschoolers Before They Turn 5: Eat a Chicago hot dog

Every Chicagoan has a dog preference. Even (especially) the young ones. Photo courtesy of Gene & Jude’s

Iconic Eats for Preschoolers in Chicago

22. Eat a Chicago Dog

While many Chicago natives have different opinions on who has the best Chicago dog, little locals should sample a few to form their own opinion. Grown-ups can get one with all the fixings and let preschoolers choose their own toppings. Gene & Jude’s is a great place to start. This is one of the most iconic dog spots in the city; they’ve been in business since 1946. 

23. Visit Aster Hall Food Court

Aster Hall is a culinary delight for kids and adults. Not only can kids dine out on the Mag Mile with award-winning burgers, pasta, and tacos but parents can chow down on some of the best food in the city. For a sweet treat, finish with ice cream or cookies from the Chocolate Bar. The elevated food court is located in the 900 North Michigan Shops across from Water Tower Place. 

24. Get a Slice of Chicago Pizza

Chicago is (justly) famous for pizza. What kid (or adult) doesn’t love a hot slice? Chicago-style pizza is known for its unique deep-dish crust. Even if your little one has had pizza a million times before, treat them to a special trip downtown for a delicious slice of the good stuff: Famous Chicago pizza restaurants include Lou Malnati’s, Gino’s East, Pizzeria Uno, Rosati’s, and Giordano’s

25. Get Ice Cream at Margie’s Candies

Logan Square is home to one of Chicago’s most iconic ice cream shops. With famous banana splits as big as a kid’s head, there’s enough to go around for the whole family. There’s family-friendly indoor seating along with chairs outside to people watch as you wait.

Library of Congress National Book Festival
Library of Congress and Virtual - 9:00 AM Pick
Children's Movies at Gallagher Way
Gallagher Way - 11:00 AM Pick
WPB Art Quest
Wicker Park and Bucktown Neighborhoods - 9:00 AM
Free Tuesdays at the Museum of Contemporary Art
Museum of Contemporary Art - 10:00 AM
Manga Fun for Kids Virtual Class
Creatively Wild Art Studio - 3:30 PM
Neighborhood Guides
Activity Guides