Savvy Mom’s Guide to Walking Downtown Chicago with Kids


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Whether you’re visiting or living in downtown Chicago, there are tons of fun things to do with kids. Sometimes, transporation can be a hassle, getting on and off a train, catching a Lyft or cab, or figuring out the bus schedule. This list of activities are all within walking distance while in the heart of Chicago. Skip the car, grab the stroller, and explore!

Maggie Daley Park

Maggie Daley Park is all the rage for Chicago visitors with little kids. The playground is huge and widespread. In addition to the playground there is mini golf, open fields, the rock wall, and the skating rink. In cold months, you can hit the ice and take a twirl. In the warm months, strap on your roller blades and go for a warm skate. Your kids will be ready to nap hard when you leave here.

Millennium Park

This is another tourist and resident hot-spot. Kids will have fun staring at their own reflection in the giant bean and taking fun silly photos. If the heat is getting to you, head over to the Crown Fountains. Can’t find them? Look for the giant digital faces spewing water on giggling children. Kids can splash and run in the giant waterfall streaming from the faces. There are plenty of snack and meal choices in the park and even good slushies!

Lakeshore East Park

This is a hidden gem, nestled in between a wall of high-rise buildings. A beautiful green and flower-filled park, with a large open field, fountains, shady pathways, a playground, and a dog park. The playground is friendlier for smaller children and it has a spray park in warm months. Transport yourself to a green oasis among the skyscrapers. Swing on the swings, play catch in the field, or just enjoy the peaceful serene fountains along the pathways.

The Drunken Bean

After you play at Lakeshore East Park and pet all the friendly dogs, stop in at the Drunken Bean. Adults can enjoy a hot or iced coffee, some wine or beer, or tea. Kids can choose from their gelato bar or their collection of baked goods, like giant cookies, donuts, and other pastries. Then sit down and relax in the calming yet trendy environment. Try to spot all the unique images painted on the wall murals.

Lakefront Trail

Take a scenic stroll or bike ride down the Lakefront trail. Watch the boats come in and out of the harbor. Run in the grass, enjoy a picnic, or just take in the crystal sparkling blue waters of Lake Michigan. You can stop for a bite to eat or cool down with some gelato at Café Michelle at DuSable Harbor.

Museum Campus

After your pit stop for gelato, you can keep heading south on the Lakefront Trail, and you’ll end up on Museum Campus. Here you and your family can visit the Shedd Aquarium, The Field Museum, or the Adler Planetarium. You will not be bored or lack for adventure on this campus. Enjoy the beautiful view of the lake, shady spots, sno-cones, and hot dog stands. Plus all the fun the museums have to offer.

FTW Chicago

Located in the same building as AMC River East and a part of Lucky Strike, FTW is a family-friendly arcade. It caters to kids and adults. It’s a great birthday party space, or just a place to hang out after you catch the latest Pixar film at AMC. Power up your game card, hit the arcade, collect your tickets, and before you head home, stop by the redemption store to load up on fun prizes.

Festival Season

If you like art, food, and music, summer in Chicago is your time to shine. Wells Street Art Festival to the Taste of Chicago to Grant Park Music Festival, there is a fest going on every weekend somewhere in Chicago. Check out Wells Street Art Fest at the beginning of June. Enjoy different artists from around the city and country, drink a smoothie from a pineapple, and stop at Jeni’s Splendid Ice Creams for a fun frozen Treat. In July tempt your taste buds at the Taste of Chicago. Enjoy every food imaginable and check out the live music. All summer long, check out the music at Grant Park Music Festival. The performers vary and it is always a nice idea for just dropping by with a picnic dinner and enjoying some lovely time outside in the fresh air, listening to good music. There are many more festivals throughout the entire city all summer long. You’re bound to find the perfect fit for you and your family.

This is a time-sensitive event, but is a fun time with family. Enjoy seeing different artists from around the city and country. Drink a smoothie from a pineapple. Stop in at Jeni’s Splendid Ice Creams for fun frozen treats. Use inspiration from all the art you viewed to draw on their chalkboard wall, then head back out to find some unique treasures. Miss out on the Wells St. Art Festival? Don’t worry, Chicago summers are filled with art festivals.

Watertower Place

From American Girl Store to the sprawling food court to Build a Bear to The Painted Penguin to Gamer’s World to The Lego Store and more, you will find something for everyone in the family. There are tons of shops for parents too!

Navy Pier

No list would be complete without Navy Pier. Families can spend an entire day here enjoying all there is to offer. From the famous Ferris Wheel to the Chicago Children’s Museum, there is nonstop fun. Take a walk through the Crystal Gardens and watch the water perform tricks. We love to pack a lunch and eat at a table in the Gardens. Explore the booths and stores throughout the Pier. Head to the Children’s Museum to dig for dinos in Dinosaur Expedition and get in some fishing and rock climbing at Treehouse Trails. The front of Navy Pier regularly has interactive art installations, so be sure to spend some time there before you or after you explore the pier. Check their site for fun events in their event halls, like Winter Wonderland.

Nicole is boy mom to two small dudes that never stop moving or eating. She is a Pilates instructor and all around fitness junkie. She's a Chicagoan through and through. She loves reading, writing, philanthropy, and using a good dose of aromatherapy in a hot bath to unwind.

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