Family-friendly chicago

In Chicago, my kids walked for miles and miles each day. Aside from the trip to and from the airport, there was not one Uber and not one complaint.

The secret? No hills. Welcome to the Midwest.

According to Alaska Airlines, Chicago is one of Seattle’s top five summer travel destinations. And no wonder: Chicago has everything. An amazing aquarium, museums, Navy Pier, and the Art Institute. Inexpensive direct flights from Seattle make the Windy City an easy getaway.

Waterfront walking path along Lake Michigan. Photo by JiaYing Grygiel

Look, Ma, no hills!

Chicago has a flat and walkable downtown core known as the Loop. Nearly all the kid-friendly attractions are on the same stretch. (Notable exceptions are Lincoln Park Zoo, where admission is free, Wrigley Field, and the Museum of Science.) There’s a beautiful walking path along the shores of Lake Michigan, where you can easily stroll from Navy Pier to Adler Planetarium.

Chicago is magical to explore with kids. Go walk around, find some pizza, and have fun.

Where to stay

Staying near Grant Park gives you the easiest access. Our hotel room was on the 40th Floor of the Chicago Stock Exchange building, where the kids loved watching the L (the city’s elevated rapid transit line) rattle by. River North, the neighborhood just north of the Chicago River, is touristy but nicer, with lots of hotels and restaurants. Here’s what to do while you’re there”

Field Museum is home to Sue the T Rex. Photo by JiaYing Grygiel

Don’t skip the museums

Chicago has incredible museums, full stop.

The Shedd Aquarium, Field Museum, and Adler Planetarium are all located on one museum campus. It is a 15-minute walk at most from one to the other. You could easily spend an entire day here.

The Shedd is at least three times the size of the Seattle Aquarium. Check out the beluga whales from the underwater viewing window and catch a dolphin show.
The Field is a massive natural history museum. It’s home to Sue the T. Rex, the largest and most complete Tyrannosaurus Rex specimen discovered.
The Adler Planetarium is the first planetarium in the Western Hemisphere. It has wonderful interactive exhibits inside and offers a terrific view of the Chicago skyline outside.

The Museum of Science and Industry is Chicago’s version of MOHAI, and it’s 6 miles south of the museum campus. A bit of a schlep, but it’s very hands-on and great for kids who need to be active. Step into a tornado, go down a coal mine, and watch model trains pass through a huge landscape from Chicago to Seattle.

Pro tip: Seattle’s Pacific Science Center members get free admission to the Field Museum, Adler Planetarium, and MSI.

The Bean sculpture, officially titled ‘Cloud Gate’ by artist Anish Kapoor . Photo by JiaYing Grygiel

Head to Millennium Park

The name of Chicago’s iconic Bean sculpture is actually Cloud Gate, and artist Anish Kapoor hates that people call it the Bean. But what do you expect when you create a chrome jelly bean?

Next to the Bean, there’s an amazing fountain to play in and giant video towers projecting faces. Heading west toward Lake Michigan, you’ll walk past a bandshell and across the BP pedestrian bridge with wavy stainless-steel shapes that feel familiar. (Architect Frank Gehry also designed Seattle’s Museum of Pop Culture). Cross the pedestrian bridge to Maggie Daley Park, an unbelievable 3-acre playground with very fast slides.

Wonderful playground at Maggie Daley Park. Photo by JiaYing Grygiel

Millennium Park is considered the world’s largest rooftop garden because it was built over a rail yard and parking garages. This park, in the middle of downtown, is safe and spotless, with not a leaf out of place.

Millennium Park connects to the Art Institute of Chicago. I know art museums are typically challenging for young children (mine included), but hear me out. You can’t be near “American Gothic” and not go in for a peek. As an extra enticement, children under 14 are free. The famous bronze lions stand guard at the Michigan Avenue entrance.

The view from Chicago River architecture boat tour. Photo by JiaYing Grygiel

Take an architecture boat tour

Like Seattle, Chicago had a great fire that completely gutted and reshaped the city. The architecture boat tour is a great way to see and learn about the city. On a nice day, there’s nothing better than relaxing on the upper deck while your guide tells stories about the quirky buildings you pass. There’s a trio of towers that look like blue french fries, a pair of giant corn cobs, and by the lake, a building shaped like a fidget spinner.

Now there are many boat tours, but Wendella is the original one. They offer 45-minute family-friendly cruises, but we opted for the standard 90-minute version, and it was perfect. There are restrooms (and a full bar) on board, and it’s fine to get up and walk around.

Chicago skyline, seen from Adler Planetarium, tall black building is Willis Tower. Phot by JiaYing Grygiel

Stroll the river

Or skip the boat ride and go for a stroll along the Chicago River all the way out to Lake Michigan. The Riverwalk is a string of cafes, taco stands, public art, and even a small playground.

The Wendella dock is under the historic Wrigley building. Kitty corner across the street is the old Chicago Tribune Tower, now luxury condominiums. The building has famous rocks embedded on the surface. See if you can find a chunk of the Great Wall of China, the Taj Mahal, and the Parthenon. There’s even a piece of Mount Rainier.

From the Tribune Tower, it’s less than a 10-minute walk to Eataly, a two-story wonderland of fresh pasta, formaggio, and gelato.

Salute the fun at Navy Pier

Navy Pier is an amusement park adventure in the city. It has a wonderful Children’s Museum, carnival rides, speedboat rides, and the 200-foot-tall Centennial Wheel. You can knock out your entire Chicago must-eat list here, too:

Giordano’s for the deep-dish pizza
the cheese and caramel Chicago mix at Garrett Popcorn Shops
and a Chicago-style hot dog, on a poppy seed bun with bright green relish, mustard, and sport peppers but no ketchup from any street vendor.

Ride up the Sears Tower

For nearly 25 years, the 110-story Sears Tower was the tallest building in the world. Its name is now Willis Tower, but no one in Chicago calls it that.

Start your Sears Tower visit with an interactive walkthrough, which offers a bit of history and a ton of cute photo ops. Then, up to the Skydeck, where you can view the city and four states from 1,353 feet above the ground. For an extra thrill, step into an all-glass balcony.

The building was built to sway. On a windy day, the water in the toilets at the top will slosh around.