It’s the Windy City… It’s Chi-Town… And it’s the Heart of America… And now it’s My Kind of Town, too. Are you thinking about a quickie Chicago family vacation? There are lots of activities for children in Chicago, and it’s a great city for a long weekend trip.
Here’s a few things to do with kids in Chicago on a quickie family vacation:
Something unusual happened on our quickie Chicago family vacation. It felt like we weren’t visiting at all.
There have always been comparisons between Chicago and Toronto, but that wasn’t it.
It was the grit of the Blues Brothers meeting the angsty comfort of every John Hughes movie ever. It’s urban suburbia and it’s wise guys and gangsters. It’s easy to feel at home in a city that has served as every kind of home on big and small screens. Chicago is everyone’s home away from home. No wonder Neal Page was so desperate to make it back for Thanksgiving in Planes, Trains & Automobiles.
Our family is a bunch of movie buffs. We loved the constant reminders of our favourite movies.
Things to Do with Kids in Chicago:
Formerly known as the Sears Tower, the Willis Tower held the title of world’s tallest building for almost 25 years. In The Dark Knight, Batman stood atop the 110-storey skyscraper to listen to police scanners after Joker crashed his party. Ferris Bueller paid a visit to the observation deck on his day off. And now you can one-up Ferris (but not Batman, obvs) with a visit to Skydeck Chicago. The glass balconies on the 103rd floor of the Willis Tower are definitely worth the effort to visit.
If your Chicago visit is decidedly Ferris Bueller-themed, a visit to the Art Institute of Chicago should be on the agenda. The museum has been remodelled since the movie, but key pieces like Edward Hopper’s oil-on-canvas painting, Nighthawks, are still on display. This is the real one, not the re-imagining with James Dean, Humphrey Bogart, Marilyn Monroe, and Elvis Presley that graced many an ’80s wall (likely accented with neon).
Legend has it that Chicago’s Field Museum is Indiana Jones’ home base, and the Egyptian collection at the Field is definitely stuff that archeology movies are made of. And don’t miss Sue, the most complete Tyrannosaurus rex fossil ever discovered. Sue’s story and research most definitely inspired a few Jurassic blockbusters.
What used to be a military station for pilot training is now a destination with food, rides, and attractions for every member of your family. Avoid the queue for the Centennial Wheel by arriving right when Navy Pier opens, and be rewarded with glorious views of the city skyline and Lake Michigan.
Where to Eat on Your Quickie Chicago Family Vacation:
Chicago is known for deep-dish pizza, and few topics are more contentious than which is the “best” one. And since 1971, one of the top contenders for the title has been Lou Malnati’s Pizzeria. It’s has grown to 60 locations — 57 in “Chicagoland” and three in Arizona. Here, the buttery crust manages to stay crisp and flaky despite the lake of ooey, gooey cheese.
If your kids enjoy escape rooms and you enjoy an excuse to not nag them to sit and finish their dinner, Safehouse Chicago is the perfect restaurant for you! Test your brain cells by solving a mystery in between bites of the burger voted best in Chicago.
*SAFEHOUSE CHICAGO IS CURRENTLY TEMPORARILY CLOSED DUE TO COVID-19*
The baseball version of Hockey Night in Canada’s Bob Cole is arguably the late Harry Caray. The beloved baseball announcer was the voice of the Chicago Cubs from 1982 until his death in 1998, and his legend lives on in seven Harry Caray’s 7th Inning Stretch sports pubs and steakhouses around Chicago. Guests at the Water Tower location, on the Magnificent Mile, receive free admission to the Find the best deal, compare prices, and read what other travelers have to say about Harry Caray’s 7th Inning Stretch at Tripadvisor
If Chicago’s been making you nostalgic for those glory days of homely, homemade prom dresses, and families who forget your birthday, drown those sorrows in Thousand Island dressing and croutons at R.J. Grunts. Largely unchanged since it opened in 1971, the salad bar is pure Ponderosa perfection and a perfect companion to its modern craft beer menu.
Where to Stay in Chicago with Kids:
Centrally located in the area known as Streeterville, Loews Chicago welcomes families with host of family-friendly features including complimentary cribs and baby bath amenity kits – plus, kids under 18 stay free. If you’ve forgotten something, they have amenities like children’s coloring books and crayons, board games and card games, electronic gaming consoles available to loan, plus iPads to borrow that are pre-loaded with games and select movies, and pool toys are available on request.
- Travel Stories: The Resort on Cocoa Beach
- Kid-Friendly Things to Do in Panama City Beach, Florida
- What is the Best Time to Go To Disney World?
- Havana Tours & Day Trips with Kids
- Halloween-Themed Vacations for When the Kids Have Outgrown Trick-or-Treating
- From Have Baby Will Travel: Ontario Resorts
Have Kids Will Travel is a participant in the Amazon Services LLC Associates/Influencer Program. If you make a purchase through this site, we may receive a small commission. Click here to check out our Amazon Store.