29 Actually Cool Things to Do in Chicago This Winter
Because just like death and taxes, the winter blues come for us all.
There’s a lot more to do this winter than lounging on your living room couch and catching up on reruns of Law and Order SVU. And before you embark on a full-on bread-baking breakdown, we have some other suggestions. Apart from the freezing temps, Chicago is truly magical in the winter months, offering many outdoor activities from ice skating, sledding, and Christmas markets to indoor options like bowling, speakeasies, and hockey games, all here to help you stifle that urge to book a flight to the Florida Keys. Mask up, vax up, and grab your buddies, because unlike last year, it's time to conquer the cold together. Here’s everything fun you can do in Chicago this winter.
Back this year in full swing, the 25th annual Christkindlemarket is slinging steins, hawking sausages, and selling handmade items from all around the world at Daley Plaza in the Loop and Gallagher Way in Wrigleyville. Along with some yummy authentic German food and bev, the 82 local, national, and international vendors will have you loading up on one-of-a-kind gifts like delicately carved chocolates, colorful glass figurines, hand woven outerwear, gorgeous painted ornaments, and other surprising goodies.
Hit the ice and test out your skate skills
Whether it's your first time strapping on some winter blades or not, you’re in luck—the skating rinks in Chicago cater to both pros and first-timers alike. Downtown, Maggie Daley Park sports a quarter-mile ice ribbon that winds skaters down a circuitous path, while nearby, McCormick Tribune Skating Rink provides beautiful skyline views near Chicago’s famous Christmas tree—not to mention an onsite Momentum Coffee serving apres-skate snacks and hot drinks. Meanwhile, Light Up The Lake in Navy Pier hosts skating under twinkling lights inside their indoor Alpine rink, alongside other holiday festivities like an indoor light garden, craft beer and cocktails from Alpine Pub, and a holiday market where guests can purchase festive momentos. Out by O'Hare International inside Rosemonts Parkway Bank Park, Chicago Wolves Ice Rink is an NHL regulation-sized facility open to the public, while over in Hyde Park, Midway Plaisance Park offers an expansive rink complete with bargain-priced rentals.
Grab a sled, innertube, or toboggan and set off to the races
Us real Midwesterners know that once the snow starts to stick, the old-fashioned (and totally cost-free) winter fun truly begins. Literally any incline is a potential sledding hill, and from bunny hills to propper slopes, there are plenty of spots for a nice intentional tumble in the snow. A few favorites? The approachable, four-sided Cricket Hill near Montrose Beach, the well-kept slope in Soldiers Field’s south parking lot, Evanston’s 65-foot slow-covered former trash mountain (dubbed Mount Trashmore, of course) inside James Park, and, last but not least, the quaint bunny hill in Humboldt Park near the lagoon with its an army of snowmen obstacles. If you’re looking for something finely groomed and well-lit, Cook County Forest Preserve hires staff seven days a week (weather permitting) to upkeep hills in the Dan Ryan Woods, Caldwell Woods, Swallow Cliff Wood North, and Westchester Woods.
Embrace all things frosty with Winterland Gahalger Way
This year at Gallagher Way in Wrigleyville, a plethora of holiday themed events are bound to delight the grinch in all of us. Through February 20th, Winterland will host a number of holiday programs including ice skating, wreath making, curling lessons, holiday movie screenings, ice bumper cars, and some other events hosted at Hotel Zachary. And, as a bonus, Gallagher Way also will be hosting a Christkindlemakert where German delicatessies are among the many alurs.
Because drinking is always better with a view. Luxury outpost Gwen Hotel not only boasts a heated roof deck complete with fire pits where guests can enjoy delicious signature cocktails, but also offers a more peculiar attraction: a real-deal curling rink (make sure to book your reservation ahead of time). This year, the Godfrey is inviting guests to reimagine what a wintery rooftop might look like, providing heated igloos for guests to reserve as part of their annual Winter Wonderland. Grab a cocktail and step out of your igloo to keep warm beside a decked-out fire pit—marshmallows for s'mores are just inches away. Cindy’s Rooftop atop the Chicago Athletic Association is always a great place to enjoy the sips and sights, with tasty food and drinks plus spectacular panoramas of Millennium Park’s wintery snow globe below.
Every year since the 1870s, Macy’s has created elaborate window displays on State Street, bringing Christmas to life through interactive storytelling. This year’s theme is the story of a blue reindeer named Tiptoe who, with the help from her friends, overcomes her fear of flying by believing in herself. Afterwards, head inside to see the famed Macy’s decorated Christmas tree and perhaps even pick up a present or two for someone topping your “Nice” list.
Venture out amid the twinkling lights
If your block hasn’t stepped up its holiday decor game this year, fret not. Through January 2, the celebrated Lincoln Park Zoo Lights will drench its lush landscape in a multicolored light bath, Morton Arboretum’s Illuminate features 50 acres of illuminated trees inside their serene, snow-dusted paradise, the Botanic Garden’s Lightscape guides guests through glittering trails, Amaze Light Festival Festival in Rosemont boasts a lively light show, and don’t forget the majestic Magnificent Mile, where you can marvel at decorated glowing downtown Chicago.
Both the Bulls and the Blackhawks are welcoming guests back to the United Center to enjoy some puck- and/or rock-passing thrills. The hockey faithful can pick up a game day experience package including a behind-the-scenes locker room tour, pregame buffet, and the chance to skate on the rink like the pros, while Bulls die-hards can book a private meet-and-greet with Benny the Bull, gorge on top-tier food and drink vendors, or simply celebrate the fact that hey, we’re finally—finally—good this year.
Strike out with some buddies at a bowling alley
It’s been awhile since the crew has been able to roll up to the bowling alley, lace up some bowling shoes, and try their luck at the lanes—pizza and beer in-hand, of course. Take advantage of some indoor fun at Waveland Bowl on Western Avenue, serving Alley Dogs with billiards as a bonus, or Diversey Bowl in River North, with lanes strewn in LED and laser lighting (if that's your sort of thing). 10 Pin Bowling Lounge, also in River North, provides a full bar paired with elevated pub grub, while Kings Dining & Entertainment in New City stocks cocktails and speciality menus to please more sophisticated bowlers.
Northerly Island’s 119-acre natural expanse sits just south of downtown and makes for an ideal outdoorsy getaway when you’re itching to escape the dirty city snow. For some pre-planned entertainment, hit up Polar Adventure Days on January 22 and February 26 for wintery events like snowshoeing and wildlife experiences with Siberian Huskies.
Yeah, we know—every city claims to have a “great beer scene, bro.” Chicago may be the Windy City, but such claims around these parts are far from hot air. While we may not be on par with, say, Denver or Portland in terms of breweries per capita, Chicago’s massive craft scene continues to expand its ever-growing beer belly with no signs of drying up. From up and coming breweries and brewpubs reinventing themselves to classic beer bars and local scene staples, you won’t have to wander too far to cop a warming stout on a blustery winter day.
Event season certainly isn’t as predictable as it once was, but there are still a few winter classics Chicagoans can count on. From the annual Millenium Park Holiday Sing Along in front of Cloud Gate (6 pm every Friday until December 17th), the cosplay-drenched C2E2, and the drunk-before-noon TBOX Christmas Bar Crawl Christmas bar crawl, there’s something for every kind of yuletide reveler.
It ain’t quite KC or Memphis, but Chicago’s barbecue landscape has certainly come a long way, baby. From iconic haunts like Lem’s and Earl’s to more modern outposts like Lillie’s Q and Smoque, BBQ is enjoying something of a Renaissance, as newer spots like Babygold continue to push the envelope. Ease those winter blues while working on your hibernation-ready extra layer by picking up a full spread from one of Chicago’s top smoker specialists.
Fancy new rooftop bars are cool and all, but once summer winds down, it’s time for Chicago’s rich civic treasure—AKA dive bars—to really shine (metaphorically, of course.) With cooler air bringing out the shut-ins, it’s time to mask up and hole up in your favorite old man bar and drink until summer rolls around (or 4 am, whichever comes first). Quality options run rampant in this city, but no one’s ever regretted a late-night foray into Old Town Ale House. And if a “slashie” (half bar/half liquor store) is more your style, may we humbly suggest Rite Liquors?
With museums back in operation, you can once again go full Ferris Bueller ogling the Monets at the Art Institute or spend some time hanging out with Sue at the Field Museum, where over 300 artifacts including costumes, comics, and interactive displays should tide you over until C2E2 returns. For more offbeat options, including the perennially creepy International Museum of Surgical Sciences, check out our full museum guide. Did someone say there’s an entire museum dedicated to leather and bondage? Sure did.
There’s a reason why the speakeasy never goes out of style. Sometimes you just need to hide out in a dark hole and drink cocktails like it’s illegal. Whether or not our own ‘20s turn out to mirror the Roaring ones of yore, Chicago still offers plenty of options to unleash your inner Capone. Here’s our full roundup of local speakeasies and secret bars, since you asked. Shh.
While air travel has clearly returned to its pre-pandemic form (with just a touch more rage), it’s clear that the Great American Road Trip isn’t going out of style anytime soon. Luckily, you don’t have to venture too far to get in on some amazing winter destinations near Chicago, from exploring ice caves and cruising the slopes on a souped-up snowmobile to indulging in some wintertime R & R at a luxurious cabin or resort. Looking for a staycation? No problem. Need an Airbnb? We’ve got you covered.
Park it at a local drive-in (or, gasp, see a movie in an actual theater)
One positive byproduct of this annoyingly resilient pandemic has been the re-emergence of the drive-in theater, with al fresco flicks screening on a regular basis at ChiTown Movies in Pilsen. And if you’re masked and vaxxed, local movie emporiums like the historic Music Box Theatre should never be overlooked. Ever.
The stateside premier of this international project continues to wow crowds at Chicago’s Germania Club Building with an immersive experience featuring moving images illustrating the works of Vincent Van Gogh. The 600,000-cubic-foot experience includes bright flashing lights set to soundtracks in a historic Gold Coast building. And, ahem, date night packages are available to anyone looking to woo a special art-lover in their lives.
The Chicago Lakefront Trail is always a popular choice, but it’s not the only place to ingest some crisp winter air. Did you know the entire Chicago metro area is surrounded by a 210-mile nature trail complete with campsites and lakes? How about a 2.7-mile urban hiking trail along a former railway corridor? How about one of America’s newest national parks, perched just across the border in Indiana? And be sure to stop by Morton Arboretum to peep its jaw-dropping holiday light display. Want more? Right this way.
Whatever else you do this winter, be sure to continue to do your part in making the community we live in a better place for all its residents. Aid in the fight for racial justice and social equity taking place across the city by supporting Chicago’s Black community via everything from BIPOC-focused nonprofits and community organizations to Black-owned restaurants and bookstores. Here's how to get started.
Music venues around town have reopened for live events, with heavy hitters City Winery, Carol’s, Martyrs’, Rosa’s, Reggie’s, Green Mill, Montrose Saloon, Uncommon Ground, FitzGerald’s, Kingston Mines, and Empty Bottle leading the charge. So what the hell are you waiting for? If you’re looking for something with a more romantic vibe, check out the Fever’s candlelight concert series to catch classical music in unique outposts like Stan Mansion and Salvage One. Pretty hard to screw up that date night.
If Netflix reruns of The Office aren’t quite as funny as you remember, turn to the experts for your giggle fix. Comedy clubs across the city are doing their best to keep you laughing through America’s somehow-still-not-over pandemic, including live stand-up shows at Zanies and, of course, the world-famous improv-sters at Second City. In the meantime, head over to Lincoln Lodge to bask in the oddball glory of the nation’s longest running independent comedy showcase, recently back from hiatus. For even more options, check out this handy rundown.
From ice skating, ice sculpting, and fat tire racing to laser tag and escape rooms, The Forge: Lemont Quarries certainly isn’t lacking when it comes to winter-centric entertainment. If that’s not enough, you can also fill up on cheffy post-adrenaline rush cuisine at Forgefire Adventure Dining. Suddenly, a trip to the ’burbs doesn’t sound like such a terrible idea.
Cruise Chicago’s Emerald Necklace
A scenic drive around the city is never a bad idea, especially now that winter in all its glittery snow glory is just around the corner. Yes, you could certainly parade down Lake Shore Drive—and by all means, you should. But for a lesser-known option that allows you to see the actual beating heart of the city instead of a few stretches of concrete, head to Chicago’s Emerald Necklace, a 26-mile network of interior city streets and wide boulevards. Linking together some of the city's most grandiose green spaces like Humboldt, Garfield, Washington, and Jackson Parks, this is the way Chicago was meant to be seen—with the added bonus of being excellent quarantine-era therapy.
Who knew that just a few months after Illinois became the 11th state to legalize recreational marijuana, a full-blown public health emergency would bring our society to its knees? And, furthermore, can you imagine dealing with the past year-and-a-half without a little green? We don’t even want to think about it, and you don’t have to either. Deemed essential businesses with more than $1 billion in sales in 2020, legal weed is clearly here to stay in Illinois. Check out our full dispensary guide for all the hairy details.
Tune into a local podcast
If the sheer number of choices between new streaming services has left you overwhelmed, it might be time to catch up on that podcast you’ve been meaning to listen to. Luckily, Chicago is rife with an array of interesting city-centric options. Get your politics fill with David Alexrod’s The Axe Files, nerd out on music with Greg Kot and Jim DeRogatis on Sound Opinions, learn about unique aspects of local life with WBEZ’s Curious City, drink a virtual beer while exploring the brewing industry with Good Beer Hunting, or give Hollywood a lesson or two via Chicago-based Please Make This. And that’s barely scratching the surface.
Chicago’s world-renown pizza bonafides grew even stronger during the pandemic, with a wave of new pie-centric eateries opening up throughout this comfort food-crazed city. Recent-ish headliners include Pizza Friendly Pizza next to Empty Bottle, Pizza Lobo in Logan Square, PB&J in the West Loop, Pizzeria Portofino from Lettuce Entertain You, Pazza Pizza for pizza by-the-slice in Old Town, Detroit-style pies from Five Squared, and new deep dish entry Ruth’s Panmade Pizza from the folks behind Roots Handmade Pizza, among others. Throw in offerings from Honey Butter and Hot Doug’s at Piece and there’s never been a better time to carbo-load in Chicago.
Don’t make a rookie mistake and behave like some bewildered out-of-towner by thinking all of Chicago can be experienced downtown. Sure, the Loop is great and all but, as any self-respecting Chicagoan knows, the real heart of the city lies within its spectacularly diverse 77 neighborhoods. From the laid-back residential enclave of Norwood Park to the historic sights of Bronzeville, there’s always something to discover. Bundle up, snag a mask, and get out there and pound the pavement.