Our Best Family Activities for Winter in Chicago

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Oh sure, hunkering down at home in your PJs and baking cookies sounds tempting, but there are loads of winter activities in Chicago. So much so, you’ll want to slip into those winder duds and get outside STAT. From light shows to skating and exploring new neighborhoods, there’s a winter adventure awaiting. Read on for events, exhibits and activities to add to your winter playlist.

photo: Amaze Light Festival, Impact Field

Be Inspired by a Lights Display

If there’s just one thing that makes the bitter cold of a Chicago winter just a smidgen better, it’s just how gorgeous she is all decked out for the holidays. We’ve scoured the city to find the best holiday light displays in Chicago to lift your holiday spirits, and fill the Insta feeds with gorgeous Christmas and Hannukah photos. Leave your grinch-y feelings at home and get out there and explore these memory-making gems with the littles. To find our favorites, read our story Lights, Camera Phone, Selfie! Best Holiday Light Displays

photo: Museum of Illusions

Share Your Biggest Wishes with Santa

The man in red is back in town! Checking his list, once, twice, three times! The season of wonder calls for a visit with Mr. Claus, if only to ensure that you’re off the naughty list for 2021. Whether you want a few pics or a quick check-in with the North Pole’s toy manufacturer-in-chief, read our story Magical Places to Meet Up with Santa (& Mrs. Claus, Too!)

photo: Joffrey Ballet

See an IRL Performance

Holidays in Chicago are brimming with magic and stellar live performances fill your heart with festive spirit. Catching a play, ballet or musical performance is an unforgettable experience for kids—and this season’s shows in Chicago are real memory creators. Start a new family tradition and check out our picks for the top kid-friendly holiday shows and plays in and around Chicago.

photo: iStock

Spruce up Your House with a Fresh-Cut Christmas Tree

Lumberjack your way into the season by visiting a local cut-your-own Christmas tree. Or, skip the chilly stroll through the countryside by opting for a tree delivery service. Let us help you decide by reading our story Timber Time: Christmas Tree Farms to Spruce Up Your Holiday

photo: Brookfield Zoo

Bundle Up & Figure 8

Sock skating on a wooden floor might be fun, but there’s nothing like feeling the cool breeze on your face as you glide across a real ice rink. It’s time to lace up your skates for an essential winter activity. Some are free, some are new — and many offer loads of other activities in the same location. See for yourself by reading Ice, Ice Baby: Chill Places to Ice Skate in Chicago.

photo: Jo Jo's Shake Bar

Have Festive Fun at Jo Jo's Shake Bar

Jo Jo's Shake Bar in River North is back at it again! Jo Jo's heated Winter Wonderland tent boasts a massive Christmas tree, oversized presents, private igloos and a red vintage Ford pick-up truck, making it the perfect backdrop for festive family photos. Kids will get a kick out of the biggest milkshakes and hot chocolates they've ever seen, while mom and dad can sip Santa's Sangria and Jingle Juice. Open through Jan. 17.

Book a Holiday Tea Time

We live in one of the best cities in the world for working your way through the holiday wish lists. But all that shopping can be exhausting. Take a much-needed timeout for afternoon tea to rest and recharge. Our fair city offers the time-old tradition that will turn a day of shopping with the kids into a cherished memory. Here are our picks for getting in touch with your inner Brit with a spot o’ tea.

Have a Scavenger-Hunting Adventure

Show your kids the coolness of their hometown with this scavenger hunt idea. It’ll take you to the tippy-top of the Navy Pier Ferris Wheel and strolling the Chicago River to see the moveable bridges. Best part? You can do all this in a totally safe, socially distanced way that’ll keep Covid-19 far, far away. Mask up, hop in the car (or two-wheel-it on your bikes) to seek out these Insta-worthy Chicago landmarks. You can download this scavenger hunt for kids here.

Try WhirlyBall

Combat cabin fever by taking the family for a game of WhirlyBall, the most fun you can have at 4 mph. This laugh-out-loud experience combines lacrosse, hockey, basketball and bumper cars in a game of skill, coupled with a bit of chance. They have locations in Bucktown, Naperville and Vernon Hills. Some locations also feature laser tag and bowling, making it a great spot to host a birthday party, mitzvahs or family reunions.

photo: Art Institute of Chicago (ARTIC)

See the Barbara Kruger Exhibit at ARTIC

Don't miss your chance to see Barbara Kruger's exhibition at the Art Institute of Chicago, through Jan. 24. For over 40 years she has been a consistent, critical observer of the ways in which images circulate our culture. Combining images with provocative text, Kruger uses direct address—along with humor, vigilance and empathy—to expose and undermine the power dynamics of identity, desire and consumerism. Her immersive installations and widely circulated pictures and words invite us to reconsider how we relate to one another.

See Eagles at Starved Rock State Park

Winter, spring, summer or fall, all you have to do is haul your crew to Starved Rock State Park for hiking with a stellar view. Starting in mid-January, thousands of eagles migrate to Starved Rock State Park and stay through March. They’re easy to spot as they soar through the sky or perch on the treetops. Bring binoculars!

Hunt for Chicago’s Best Cup of Hot Cocoa

Make Chicago's winter a little easier to swallow with a steaming cup of hot chocolate. When Jack Frost comes nipping at your nose, it’s time to go sipping. If your kids love cocoa—or need a good introduction to it—check out local restaurants or cafes that make their own from scratch. 

Bundle up for a Wintry Hike

We’ll admit, a Chicago winter can be tough. But, a dose of fresh air, unforgettable scenery and a chance to spy on animals in their natural habitat is a guaranteed day of wintry family fun. There are beautiful trails all around the city that'll have you lacing up your boots, strapping an infant to your back and exploring. 

photo: Art on TheMART

See CPS Student Artwork at Art on TheMART

Art on theMART is collaborating with the Chicago Department of Cultural Affairs and Special Events to celebrate visual art, dance and music created by current and past students in Chicago's After School Matters program. The projection, entitled Shaping the Future, will run nightly at 7:30 p.m. & 8 p.m., Nov. 26-Dec. 30.

Find a New Favorite Neighborhood Toy Store

We all know COVID hasn't been easy on small businesses. This Christmas, consider granting your kids' wishes at small, locally owned toy stores. Or, find a new game or puzzle and host a family game night by the fire in your PJs at home. You can also use our holiday gift guide for more ideas that support local businesses. 

photo: Gallagher Way

Guten Tag, Santa! Christkindlmarkt Chicago Is a Must-Do!

Christkindlmarket — Chicago’s take on a traditional German Christmas market — is back with locations in the Loop and Wrigleyville. Should you take the kids? Ja!  Shop, eat, enjoy free entertainment, shop some more, and even say “guten tag” to Santa Claus. Read our story On the Top of Your Holiday Must-Dos: Christkindlmarket for all the details. 

Fill Your Bellies with a Hearty Bowl of Soup

Slurp it. Stir it. Make waves. Blow on it. Nibble the good stuff and use a straw for the rest. No wonder kids love soup; it’s so fun to eat. And it keeps us warm and cozy, which right now is a very good thing. From a Jewish deli with great Matzah balls to an Argyle Street pho haven, we'll help you get your fix by sharing our favorite Chicago restaurants for soup. 

Intro Your Kids to a Chicago Hot Dog

Love ’em or leave ’em, hot dogs are big in Chicago, and if your kids haven’t begged for one yet, they will soon. We love the on-the-go ease (no silverware!) and colorful condiments (kids get a pass where the sacrilege of using ketchup is concerned). Grab one at a legendary local hot dog spot and turn eating into an adventure. 

Plan a Staycation

Chilly snow-globe temps are here and there’s plenty to do in the city to celebrate. Whether you’re interested in checking out one of Chicago’s world-class museums, seeing the ice form on Lake Michigan, or eating your weight in hot deep-dish pizza, you’ll need a cozy base camp to rest your head. Whether you're a family of two or twelve, dress warm, pack your sense of adventure and we'll help you find a unique and fun Chicago Airbnb

photo: Gallagher Way

Some Chicagoans live by the rule that there are only two seasons: winter and baseball. Baseball season has dawned on the city (there's always next year, Cubbies!), but spending time at Wrigley Field this winter is still a fabulous way to score a home run with your kids. Once the famous chill hits, Gallagher Way at Wrigley Field becomes a wonderland, a virtual north pole right here in Chicago!  In fact, it's actually called Winterland. Taking place, Nov. 19-Feb. 22, you can find all the details in our story Gallagher Way is Knocking Cold Weather Fun Outta the Ballpark

— Maria Chambers & Amy Bizzarri

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