We have to hand it to COVID. If there’s a positive to be found, it’s that Chicagoans have built up even more resistance to the bitter cold. We’re eating outside. In winter. Whoever would’ve thought? Strength of spirit is being tested and Chicago is shining. Extend this newfound sense of imperviousness to the elements to your family fun time. Ski, tube, skate, take a hike. . . bundle up because we’re throwing out ideas to keep you outside all winter long.


photo: Maria Chambers

Shred at Four Lakes in Lisle

Snow skiing lovers in the flat terrain of Chicago are hard-pressed to find even a bunny hill to practice their craft. But journey 45 minutes west of the city to Lisle and you'll find Four Lakes and much-needed winter fun. 

From ski and snowboard lessons for beginners to a challenging terrain park for the most adventurous, Four Lakes is the close-by cure for your winter blues.

photo: Wilmot Mountain

Road trip to Wisconsin's Wilmot Mountain

In just a bit over an hour, you can hit mountainous slopes at one of the area's best ski destinations, Wilmot Mountain in Wisconsin. Dust off the ski gear and have a laugh-filled romp in the snow. 

photo: Morton Arboretum

Cross-Country Ski or Snowshoe at Morton Arboretum

When more than 4 inches of snow is on the ground, head to Morton Arboretum for snowshoeing or cross-country skiing. Stop by the Visitor Center for directions to the onsite ski trails. Guests are welcome to bring their own skis or snowshoes or rent from Morton Arboretum. 


photo: Morton Arboretum

Track gnomes at Morton Arboretum

Garden gnomes have invaded Morton Arboretum for a game of hide-and-seek in the Children's Garden. Can you spot them all?

Let Chicago Children's Theatre guide your walk

Chicago Children's Theatre got creative during COVID shutdowns! They commissioned fun, totally original audio experiences that facilitate families exploring Chicago neighborhoods called Walkie Talkies. Take a self-guided tour through South Shore, Little Village and around the North Pond Nature Sanctuary in Lincoln Park. Even during the winter months, you can be outside learning about the beautiful city we live in. 

photo: Morton Arboretum

Hunt for Trolls at Morton Arboretum

COVID gifted us with an extended stay for the Trolls at Morton Arboretum, but they'll be leaving town soon! Measuring 15- to 20-feet tall, the mammoth mystical creatures of Troll Hunt are a special sight to see. These guardians of the forest are trying to make sense of the human world and make us think about our impacts on the planet. Take a gorgeous walk as a family and enjoy their presence. 

Have a scavenger-hunting adventure

Show your kids the coolness of their hometown with this scavenger hunt idea. It’ll take you to peek at the Navy Pier Ferris Wheel and stroll 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. 


photo: istock

Find a favorite trail & tackle it

Chicago has plenty of urban exploration to go around, but it also offers oodles when it comes to nature-y adventure. A giant 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. Lace-up your hiking boots, strap an infant to your back and find a Chicago-area hiking trail (or two) to conquer.

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!


Have inflated fun at Wilmot Mountain

Wilmot Mountain is known for great skiing, but for those that prefer their thrills sitting down, their tubing hill is pretty stellar. The lighted 22-lane tubing area is perfect for a nighttime adventure. The best part: you won’t have to drag the tube—or yourself—back up the hill. A conveyor belt will do that for you. 


Lace-up at Maggie Daley

Newbie skaters will appreciate the railing that lines the ice skating loop at Maggie Daley Park that helps steady the wobble. Parents will swoon over the lake and city views that are picture-perfection. 

Make the day special at The Forge

Teleport yourself to childhood memories and create new moments to cherish with your family at The Forge's Skating Shelf. 

Double the fun at Watts Center

Glencoe's Watts Center has not one, but two lighted outdoor rinks. You can even sign up for hockey, figure skating and recreational skating lessons. 


Plenty of soup for You!

The absolute best and most-cozy food to eat on a bitterly cold Chicago day is soup. And boy does Chicago deliver the goods. From a Jewish deli with great Matzah balls to an Argyle Street pho haven, read our story and get your steaming-hot fix. 

Share a meal in a winter wonderland at Jo Jo's Shake Bar

Jo Jo's Shake Bar in River North created a 5,000-square-foot outdoor Winter Wonderland. Their festive experience features over-the-top treats including hot chocolate and shakes and a wide range of food the whole family will love. 


Warm your hands with hot cocoa

Winter is a whole lot easier to swallow with a steaming cup of hot chocolate nestled in your mittens. When Jack Frost comes looking to nip, it's time to sip. If your kids love cocoa—or need a good intro to it—check out local hot spots that make their own from scratch. 

— Maria Chambers

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