17 Awesome Things to do in Chicago That’ll Help You Resist the Urge to Hideout and Hibernate this Winter

Forever known as hibernation season, there are days in winter affectionately known as the Polar Vortex when Chicago is colder than Siberia and the North Pole. Growing up in the suburbs, school was more frequently closed for extreme cold than snow days when leaving the house would result in your hands turning purple and going outside was discouraged. And while the Windy City wasn’t exactly named for the weather, it’s still fitting.

It’s super easy to want to crank up the heat, bury yourself in a blanket, and Netflix and chill from November through April. But fight the urge because Chicago actually has plenty of year-round attractions, many of which are even better in the winter. If you’re tired of hiding out, put the old episodes of Gossip Girl on pause, throw on the long underwear, and get to exploring. If nothing else, it’ll earn you street cred.

Channel Your Inner Nancy Kerrigan

Is there anything more iconic than twirling under the dazzling city skyline practicing your triple lutz, double axel? Ice skating is free at both Millennium McCormick Tribune Park and Maggie Daley Park, you just have to pay to rent skates.   

Tip One Back

Let’s face it, drinking is Chicago’s official winter sport and while you could go to any old watering hole or brewery to warm you up, a number of truly awesome popup bars and restaurants have appeared lately from the Dude’s Abode (a Big Lebowski tribute) to Cosmo Carrie’s (long live SATC). Keep your pulse on the scene to know what’s up because they’re constantly changing (hence the name popup) as witnessed by the wildly popular Saved by the Max (Saved by the Bell) already moving on to another city. Or, go retro and throw it back with a prohibition tour.

Get Some R&R

If a spa day is just what the doctor ordered to heal those cracked lips and dry skin, Chicago has no shortage of luxury hotels to pamper yourself. If you don’t have a ton of cash to blow, the basic rule is if you purchase any treatment, you’re allowed to take advantage of the rest of the facilities. Find the cheapest manicure or facial you can to lounge in the sauna and steam rooms.

Catch Sports Fever

Get ready to rumble at the United Center. It’s the place to root for the home team at a Blackhawks (one of the winningest teams in Chicago history) or a Bulls game (as a tribute to the 90s era powerhouses).

Make it a Museum Day

Chicago has plenty of indoor attractions so pass the time getting cultured at the museum campus.  With exhibits from the future to the past, must-sees include the Art Institute, the Museum of Nature and History, and the Museum of Science and Industry. Pro Tip: Consider getting a CityPASS to save a bunch of money if you plan on visiting more than one.

Hit the Slopes

I know what you’re thinking, skiing in the Midwest? Yup, Wisconsin has some baby hills just over an hour away that is perfect for learning on. Head to either Alpine Valley or Wilmont which used to be a hole, but recently received a multi-million-dollar facelift when it was bought out by Vail Resorts.

Shop ‘til you Drop

Water Tower Place is a great indoor mall on the Magnificent Mile and you know those shops always have great post-holiday deals and steals.

Monkey Around

The Lincoln Park Zoo is one of the only free zoos in the country open 365 days a year. Many of the animals are moved inside in winter, but you can see polar bears and snow monkeys loving the cold. 

Explore a Tropical Oasis

Both the Garfield Park and Lincoln Park Conservatories are open year-round. Gorgeous greenhouses full of exotic plants and blossoming flora and fauna, it’s the quickest way to transport you to the tropics without you know, buying a plane ticket.

Game it Up

Yup, Denver’s iconic Punchbowl Social finally opened an outpost in the Midwest. Part bowling alley, part arcade, part karaoke bar, there’s bocce, ping pong, shuffleboard, and so much more to get your competitive juices flowing. But you know what they say: if you’re not willing to lose friends over board games, you’re not trying hard enough.

Sweat it Out

Keen on sticking to your New Year’s resolutions? Try a new fitness routine. There are a number of cult classes in Chicago from Soul Cycle to Barry’s Bootcamp and more unique workouts like twerkshops and indoor trapeze at TSNY.

See a Show

Broadway in Chicago is one of Broadway’s most successful touring companies. The world-renowned theater district has a rotating lineup of performances from sidesplitting musicals to dramatic renditions. Just try not to sing along with the show tunes.

Jam Out

Chicago’s music scene also packs a punch and you could rock out late into the evening virtually any night of the week. Buddy Guy’s Legends is known for its soulful blues crooners while the Green Mill has been home to iconic jazz performers for over a century.

Laugh it Up

If sarcasm is Chicago’s love language it’s only because the stand-up and improv scene is second to none. Catch a show at Second City, where a surprising number of your favorite comedians got their start.

Snowshoe the City (or Cross-Country Ski)

Chicago is blessed with miles upon miles of running and bike paths that don’t have to go unused just because it’s winter. Gear rental is just $5 for two hours from Northerly Island, which is a great way to get some cheap exercise and explore the snowy cityscape.

Try a New Restaurant

With over 6,000 restaurants in the Chicagoland area, there’s no shortage of good meals in one of America’s foodiest cities (just don’t ask me my favorite). From fine dining to hole in the walls, tasty dishes aren’t hard to come by. But as an extra incentive for leaving the house in winter, Restaurant Week is always at the end of January/beginning of February. It’s a great opportunity to score deals on meals. Or, go on a food tour if you want to try a bunch of bites at once.

Check the Events Calendar

Christkindl is a German-themed Christmas market that appears around the holidays, while Winter Wonderfest at Navy Pier is another month-long tradition full of rides and festivities. Zoo Lights at Lincoln Park Zoo is another epic free attraction to see the animal enclosures bathed in lights. And while New York is technically the city that never sleeps, Chicago might as well be because there’s always something going on.

Chicago in Winter Hits Different

When the temps drop, the city turns up—because the best things to do in Chicago in winter aren’t about hiding indoors, they’re about embracing the season like a true Midwesterner and badge of honor (with layers, snacks, and maybe a flask). From festive lights to fireside eats, ice skating under skyline views to museum marathons, winter here is more than bearable—it’s kind of beautiful. So lean in, bundle up, and let the Windy City surprise you and earn your street cred.

Plan Your Trip: Book a Hotel in Chicago

More Winter Ideas:

• 10+ Epic Colorado Winter Activities Beyond the Slopes
• 5 Unique Things to do in Phoenix this Winter
• 11 Fun Things to do in Dallas in Winter
• 7 Bucket List Trips to Inspire Serious Wanderlust this Winter
• The Most Magical Christmas Cities in America

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