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 even 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 (throwing it back to 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.

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. ResortPass also offers day pass to a few Chicago area hotels if you’re looking to lay by the pool.

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).

Photo Credit: Kim Scarborough

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.

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 Wilmot 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. Watertower 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 standup 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.

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.

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If you're looking for things to do in Chicago in winter, we have plenty of cold weather fun in the Windy City from what to do in Chicago during the holidays to beautiful places to ice skate, shop at Water Tower, and photography for Lake Michigan. Put it on your bucket lists -- the cold never bothered me anyway! #chicago #winter #travel #trips #holidays

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