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11 Fun Things to Do in Chicago With Kids Right Now

Chi-Town. The 312. Windy City.

Chicago sure has its fair share of nicknames. It also has its fair share of cool museums, interesting attractions, best-in-class theatre and Insta-worthy restaurants. And with the crisp autumn air (and potentially a whack of snow) whistling between the buildings that line its famous waterfront — thinning out the tourist traffic — this is a great time to make your way to Chicagoland. Whether you only have a weekend or a whole week to spare, there are plenty of fun things to do in Chicago; and if you have kids, bring ‘em along!

This city is built for everyone — even your threenager.

Here are 11 fun things to do in Chicago with kids this fall:

Find The Bean. Although it has a much fancier, artsier name, you’re better off finding this iconic structure in Millennium Park by asking for directions to The Bean. Anish Kapoor’s huge bean-shaped installation is made up of 168 perfectly fused stainless-steel plates that create a 360-degree funhouse-style mirror reflection of the city and sky that surround it.

Get on The Ledge. A short walk from The Bean is the Willis Tower’s Skydeck. On the 103rd floor of this former Sears building, the stars of the show are four glass boxes that extend more than four feet beyond the building itself; towering more than 1,350 feet above the ground, you can look around in every direction — including straight down. Have your camera ready to roll because your time on The Ledge is limited. Lines start early, so plan your day accordingly.

Splurge on a mind-blowing freakshake. Looking for the most monstrous milkshakes imaginable? JoJo’s Milk Bar will check that box. Impress your kids by ordering any one of JoJo’s towering shakes that are part culinary masterpiece, part art and all decadence. Pro Tip: see if you can head upstairs to look for the biggest Lite-Brite ever.

Explore Navy Pier. Take in the stunning Crystal Gardens, a one-acre indoor botanical garden with leapfrog fountains and 80 palm trees housed in a six-story glass atrium. Or ride in The Centennial Wheel, another weatherproof activity at the Pier that’ll take your family 200 feet in the air and offer spectacular views of Lake Michigan in an enclosed gondola that’s just for you.

Visit The Field Museum. One of the biggest and most awesome museums in the world, The Field Museum of Natural History has some 40 million artifacts and specimens spanning the dinosaur age to up-close-and-personal bug encounters. Kids can easily spend an entire day here and barely scratch the surface. There are even working scientists in glass-fronted laboratories throughout the museum who you can watch doing research.

Nosh on banana bread pancakes. Because breakfast should be fun, too. At 676 — a restaurant in the Omni Chicago — ask for a window seat so you can eye The Magnificent Mile while you take down a stack of these pancakes that are good enough to be called dessert.

Create a JourneyMaker guidebook at The Art Institute of Chicago. Catering to families isn’t always easy in an art gallery — especially one that’s a million square feet, comprised of several interconnected buildings across three floors with a whopping 300,000 works. So, head to the Ryan Learning Center as soon as you arrive and have your kids play at the digitally interactive, choose-your-own-adventure-style kiosks. Based on their choices, it spits out something that’s a cross between a worksheet and map, encouraging families to visit the gallery through a child’s eyes.

Stop for original Chicago Mix popcorn at Garrett. It’s a love story between caramel and cheese-flavoured popped corn and it’s a beautiful thing that shouldn’t be missed.

See a play or musical. Chicago Shakespeare Theater has kids’ shows throughout the year that are the perfect way to introduce little ones to the theatre. And Chicago is still the easiest place to get Hamilton tickets (at least until it leaves in January 2020).

Bundle up and go on a mural hunt. Chicago is full of public art just begging to be discovered. From scoping out sculptures around one of the many city corners to finding any of the 40,000 square feet of murals and other street art, this is certainly one of the most fun things to do in Chicago during your stay — and it’s free. Don’t forget to look for digital art! The Crown Fountain in Millennium Park rotates LED-lit faces on two towering glass-brick structures with water running down all four sides. Then there’s Art on theMART; with projections beginning 30 minutes after sunset and running for two hours every night (look for the big Merchandise Mart building along the River), it’s also the perfect opportunity to catch the gorgeous Chicago River views by night.

Eat deep-dish pizza. Obvs. You really can’t come to Chicago and not leave room for ‘za. This is the home of deep-dish and though there’s a pizza joint every block or two, hit up Lou Malnati’s Pizzeria for its buttercrust Chicago Classic. Bring an appetite and order a smaller pizza than you would at home, because they’re at least three times as thick (and three times as yummy).

For more fun things to do in Chicago, along with family-friendly accommodations and even more restaurants perfect for wee ones, this Chicago with kids post has you covered. Or if an epic road trip is in the cards, Chicago marks the beginning (or end) of Route 66 — just be sure you get some deep-dish to go.

All in-post photos credit to Andrea Traynor / Mommy Gearest

Andrea Traynor

Andrea is the founder of award-winning lifestyle and travel site, where she helps inform and inspire discerning travellers.