72 Hours in Chicago with Kids

You don’t have to be a city kid to enjoy a getaway focused on city living, especially when the destination is Chicago. No matter the season, there’s always something going on. From ice skating to climbing walls, to interactive art and tilting skyscrapers, having to make choices may be your only disappointment. Chicago is big and 72 hours is too short to see it all. But that’s OK, because it gives your family a great excuse to visit again.

Best Things to Do in Chicago with Kids

Day 1

Navy Pier

With more than two dozen beaches and 26 miles of lakefront space to choose from, Chicago has a splashy personality. But beach time isn’t the only way to take in breezy Lake Michigan; strolling Navy Pier can be a great introduction to the city, especially if you’ve been belted into a plane seat for awhile.

Make a pit stop at the Chicago Children’s Museum or go on a scavenger hunt of sorts to look for the sculpture art scattered along the pier. (It’s hard for parents to hold back a smile at the Bob Newhart statue; sit down and take a picture.) For a bird’s-eye view of the Windy City, go for a twirl on the Centennial Wheel. Thanks to enclosed gondolas, families can be comfortable regardless of the weather. Fireworks go hand in hand with summer at Navy Pier — biweekly shows light up the sky every Wednesday and Saturday from Memorial Day through Labor Day.

360 CHICAGO

After stepping aboard the elevator at the John Hancock Center, kids might feel like they are shooting into the air. It’s the second-fastest elevator in the United States (behind One World Trade Center in New York, and passengers travel to 360 CHICAGO on the 94th floor at a speed of 20 mph. On a cloudless day, the view from this perch includes four states (Illinois, Indiana, Michigan and Wisconsin) and stretch as far as 55 miles. On a clear night, the city lights are equally impressive.

The view changes ever so slightly with every step, but if you’re looking for that should-be-impossible angle, TILT awaits those who dare. At first glance, it looks like a series of windows lined up in a row. But each of those windows is just the right size for a person to get up close, grab on and, thanks to a moving platform, tilt outward just enough to take in downward-facing views of Chicago, about a thousand feet above the Magnificent Mile. Reactions range from laughter and smiles to outright screams. To ride TILT, guests must be 42 inches or taller and able to stand on their own throughout the 2-minute experience.

TIP: 360 CHICAGO is one of a good handful of signature attractions covered by the CityPASS, along with Shedd Aquarium and the Art Institute of Chicago. Besides saving families money, it can sometimes yield quicker entry.

Day 2

Chicago Cultural Center

Take a few minutes to pop into the Chicago Cultural Center, built more than 100 years ago as the Chicago Public Library and a Civil War memorial. Admission is free, and the stop shouldn’t take more than 10 minutes. The mosaics covering the ceiling are hard to miss when you walk in the door, but the best is yet to come: Head up the staircase to gaze at the world’s largest Tiffany stained-glass dome, then walk to the north side of the building to see the Grand Army of the Republic dome. Although it’s even larger, it tends to live in the shadow of its well-known Tiffany neighbor.

Art Institute of Chicago

If the domes are a hit, keep the momentum going and head straight to the Art Institute of Chicago to show off Marc Chagall’s America Windows. To spend more time in the museum, visit the Family Room, where parents and kids can create a custom art journey — but don’t overdo it. You’ll want all smiles for a family photo at “The Bean” afterward.

Millennium Park

The outdoor Nichols Bridgeway connects the Art Institute of Chicago to Millennium Park. With 25 acres of green space, the park is home to what is arguably the Windy City’s best-known landmark, “The Bean” (the official name is Cloud Gate, so don’t let the dual references confuse you). Along with its reflective qualities, it’s as though this mirrored, stainless steel sculpture has magnetic qualities. Expect a crowd, snapping selfies and taking in the view. After walking underneath and posing for the must-do family vacation photo, you can take a vote on where to visit next.

Mid-November through mid-March, the neighboring outdoor McCormick Tribune Ice Rink offers free public skating. Don’t worry about packing skates; rentals are available for a fee. Or if you’d rather slide than glide, take the BP Bridge to Maggie Daley Park, home to the Play Garden — the playground your kids will be talking about for countless family dinners to come. Climb to the top of a lighthouse, come face to face with a whale and explore an enchanted forest. Slides are plentiful and big enough for parents to join in the fun.

This isn’t a spot to stop when you’re in a rush; come ready to stay and play awhile. If hunger hits, there is a snack bar nearby that just happens to sit next to a skating ribbon by winter and climbing wall by summer.

Day 3

Recharge and Refuel

If your kids are little, you might need a bit of downtime by day three, and if you’re traveling with teens, sleeping in is probably at the top of the request list. Either way, there’s no rush to hit the city streets. If your stay lands on a weekend, River Roast serves up the family-friendly Blues & Brunch. Choose from dishes like Mascarpone French Toast, Biscuits & Gravy Savory Quiche or a twist on a classic, Rabbit & Waffles, and don’t be surprised if the chef makes an appearance in the dining room to sing a tune with the band.

Lincoln Park Zoo and Shedd Aquarium

Animal-lovers have plenty of options in Chicago. Open 365 days a year, the Lincoln Park Zoo is home to more than 1,100 mammals, birds, reptiles and amphibians. Along with being one of the oldest zoos in the United States — it was founded in 1868 — it’s also one of the few major free zoos in the country.

It’s also worth setting aside time for the Shedd Aquarium, boasting one of the largest and most diverse collections of aquatic animals in the world. The Abbott Oceanarium is home to eight mesmerizing beluga whales, along with Pacific white-sided dolphins, Alaska and California sea otters and California sea lions. They’re just a handful of the aquarium’s more than 32,000 animals, so be sure you have plenty of time to wander.

Chicago Architecture Foundation

Adult architecture buffs will enjoy the daily docent-led tours and river cruises organized by the Chicago Architecture Foundation, but traveling families should stop in just to see CAF’s permanent exhibition, Chicago Model. Covering 400 blocks and more than 1,000 buildings, the 320-square foot, 3D-printed scale model is a perfect tool to help kids understand the layout of the city. (It’s updated every year.) Just be prepared: If they’re good at reading maps, they just might realize how close the Maggie Daley Park playground really is.

Where to Stay in Chicago with Kids

Chicago offers a nice selection of family-friendly hotel properties, but The Alise Chicago has a knack for sweetening the deal. Happy hour comes with cupcakes and coffee, and Dash, the hotel’s stuffed dog mascot, can be found on every bed. Give him a squeeze and the kids will be barking to take him home. Room options for families include two queen or two double beds, but Executive King Suites provide a little more room to spread out. As an added plus to the Executive King Suites, French doors separate the bedroom from a living area with a pullout sofa, giving both parents and kids a space to call their own.

Relevant Links:

Browse all family-friendly accommodations and activities in Chicago with kids on Ciao Bambino

7 Hidden Gems for Families in Chicago

Best family-friendly activities in Chicago from a local mom

Editor’s Note: Dana’s trip was sponsored by The Alise Chicago. As always, our thoughts and opinions are our own on Ciao Bambino. Photos by Dana Rebmann except where noted.