Our Best Family Activities for Winter in Chicago

Editor’s note: We’re working through our way through an oddly wet summer, heading toward another Chicago winter. Check back this fall for more ideas on how to spend a fun-filled winter in Chicago as a family!

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: Morton Arboretum

Brighten your winter with a drive-thru Tree Lights at Morton Arboretum

Illumination: Tree Lights at Morton Arboretum dazzles us with lights, sights and sounds to transform a Chicago-area wintertime drive in the woods into a colorful, inspiring experience like no other. 

photo: Lincoln Park Zoo

Razzle and dazzle at Lincoln Park Zoo’s annual ZooLights

One of the nation’s only free-admission zoos flips the holiday switch with ZooLights, Nov.-Jan. With the light displays throughout the grounds, your fam can stroll through the twinkling winter wonderland created by over 2 million lights, take distanced photos with Santa, enjoy food and drinks and get lost and found in a light maze.

photo: City of Chicago

See Chicago's Christmas Tree at Millennium Park

Millennium Park's Christmas Tree stands tall and twinkles brightly to help get families in the holiday cheer. Be sure to plan a visit to enjoy the holiday programming and ice skating.

photo: Naper Lights

Stroll Naperville's riverwalk during their annual Naper Lights

Located on Naperville's beautiful riverwalk, you'll find the 8th Annual Naper Lights display. This free event is meant to bring holiday cheer and festivities to the community in a way that's conducive to social distancing. 

photo: Brookfield Zoo

Meander the brightly lit paths at Brookfield Zoo

Zoogoers can safely enjoy Brookfield Zoo's Holiday Magic by strolling along the many pathways, lit with more than one million twinkling LED lights, including through a brilliantly lit 600-foot-long tunnel featuring thousands of colored lights all synchronized to music.


Pay a visit in person (or virtually) to Santa

Is that the real Santa? How can he be in so many places at once? How does he fit in a chimney? Why does he like to hang out at the mall? Yep, the season of wonder is back (get your answers ready!) and it isn’t complete without a visit with Mr. Claus. Whether you want a few quick Instagram-worthy photos and hear a token ho-ho-ho or are more comfortable with a virtual gab session, we’ll tell you where Santa’s sleigh is parked for the season.

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 farm


Take the family for a spin at Maggie Daley

The Maggie Daley Park ice skating ribbon is one of the best spots in the city to skate a figure eight. The railing that lines the loop is the perfect pick-me-up for wobbly skaters. 

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!

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. 

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.


photo: Goodman Theatre

Listen to A Christmas Carol from your sofa

There are always a few versions of Marley’s thought-provoking caper across town during the holidays. The one that’s everlasting (and truly tear-jerking) is at The Goodman Theatre. There is something about this timeless story, combined with the world-class actors of The Goodman, that keeps the “bah-humbugs” away. Due to COVID, A Christmas Carol will be available via free audio streaming. Hear the voices you adore and the signature soundscape surrounded by the love of family at home. 

photo: Merchandise Mart

See The Nutcracker on Art on TheMART

With the cancellation of The Joffrey Ballet’s The Nutcrackera newly animated digital display will be shown as part of Chicago's Art on theMART, the largest digital art projection in the world. The Nutcracker presentation projected on theMART's 2.5-acre river-facade can be viewed nightly.

photo: PlayMakers Laboratory

Get your giggles out with That's Weird, Grandma

From Christmas and Kwanzaa to Hanukkah and New Year’s, PlayMakers Laboratory rings in the holidays with all-new performances of its popular online revue That’s Weird, Grandma. This creative series of stories written by elementary school students, adapted and performed by PML’s professional actors will bring a whole lot of laughter to the season.

photo: Replay Lincoln Park

Put it in park for a holiday drive-in movie experience

Chicagoans are invited to share in the spirit of the holidays at Chicago's biggest and most festive movie experiences: Miracle on West Madison and Holly Jolly Drive-In with Replay Lincoln Park. In an effort to create magical experiences for families during a non-traditional holiday season, guests will experience a holiday-style movie experience, enhanced with twinkling decor and appearances by The Grinch, Santa, Mrs. Claus, reindeer and other favorite characters.

Experience a bit of holiday theatre

Start loading up the calendar with shows that fill your home with holiday spirit. Many have moved to an online format this year, which just means you get to stay in your cozy PJs and sip hot cocoa as you watch. Catching a play, ballet or musical performance is an unforgettable experience for kids—and this season’s Christmas shows in Chicago are real memory creators. 


Find a new favorite neighborhood toy store

We all know 2020 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.

photo: Wicker Park Bucktown Chamber of Commerce

Do a bit of window peeping at Wicker Park Bucktown's Window Wonderland

The Wicker Park Bucktown Chamber of Commerce is back with its holiday window program, Window Wonderland. Dozens of businesses across Wicker Park and Bucktown are decorating their windows in holiday themes, and shoppers can vote on the best windows for a chance to win raffle prizes using the hashtag #WPBWindowWonderland2020.

photo: iStock

Knock out some holiday shopping at Miracle on Washington Street

Drinking glühwein out of mugs at Christkindlmarket was an annual holiday tradition for Chicagoans, but has moved to a strictly virtual market for 2020. The Press Room is looking to (safely) save the experience and spread a little holiday cheer with their first annual Christmas market, Miracle on Washington St., Nov. 28-Dec. 23. You'll find an immersive holiday market experience with local vendors and unique gifts and a seasonal menu will feature iconic items traditionally available at Christkindlmarket.

Guten tag, Santa! Christkindlmarkt Chicago is a must-do!

Christkindlmarkt brings the cherished German and European tradition of Germany's famed market to Chicago and adds heaps of local charm. 

photo: iStock

Have a vintage-inspired holiday in Long Grove

Historic downtown Long Grove invites holiday revelers to take a break from online shopping and rediscover the magic of the holiday season. The annual Long Grove Vintage Holidays campaign is what the classic holiday experience is all about. . . quaint shops, old-world charms, and family memories. Vintage Holidays 2020 features merchant open houses, holiday music, horse-drawn sleigh rides, holiday selfie station and more! 


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. 

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. 


photo: American Club Resort

Hit the highway for a little escape

Kids dig hotel stays for the chance to sprint down long hallways and jump like monkeys on the bed. Parents love vacay for the squad-bonding opportunity, replacing the same ole for a new scene and having someone else make the bed for a change. Take a winter road-trip escape to destinations that allow for time in the great outdoors and lots of space to socially distance as a family.

photo: Swissotel

Stay in a Santa-inspired suite

Chicago's Swissotel's Annual Santa Suite will include a new private overnight experience. This year, the hotel is unveiling the Holiday Penthouse Hideaway accommodation package available to book in the iconic Santa Suite or Duplex Suite. The experience includes over-the-top holiday decor and guests can cozy up in the comfort of their own space and enjoy activities and amenities for the whole family. The Elf Decorated Room package is also available to book for a more low-key festive stay. 

— Maria Chambers & Amy Bizzarri


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