Yes, downtown Chicago is safe for tourists. Chicago frequently makes headlines for its crime rate, but these crimes generally occur on the city's south and west side. Downtown Chicago is well-populated, well-lit and patrolled regularly by local police. What's more, Chicago's violent and property crime rates were lower than the national average in 2020.
Now is the time to hit the slopes, enjoy winter activities, and stay warm this season in the Windy City.
By Elanor Bock, and Jay Gentile
Updated on 8/17/2022 at 5:05 PM
The Gwen, A Luxury Collection Hotel
It’s coming. We all know it’s coming. It might not be this week, it might not even be next week, but very soon our city will be blanketed with a soft layer of snow as the temperatures drop into the single digits. But just because Chicago is going to become a blustery winterscape soon doesn’t mean there aren’t still fun things to do. Brave the cold, and experience the best our city has to offer, even despite subzero temps.
Hit the slopes
Chicago may not have any mountains, but you don’t have to drive far to find someplace that does. Wisconsin’s Alpine Valley is only a two-hour drive from the city, and features a variety of runs for skiers and snowboarders of all levels, complete with a bougie lodge with restaurants, bars, and lounges aplenty. There’s also Wilmot, only 90 minutes away, that features a gigantic tubing hill, and for those willing to trek a little further afield, Devil’s Head is one of the biggest resorts in the midwest, featuring a 500-foot vertical rise. Just make sure to pick up some New Glarus on your way back from Wisconsin.
Recapture some snow day magic by sledding down the only hill in Chicago
A hill? In Chicago? No, that’s not a typo. Right by Soldier Field, there is a 200-foot hill that, in warm seasons, just kind of looks out of place—but in the winter months after some snowfall becomes the city’s premier (and only!) sledding destination. Hop over to Goodwill or Play It Again Sports to grab a secondhand sled, then brave the snowy trip downtown to recapture some of the snow day magic of your youth. Sure, plodding back up the hill after you sled down is a bit of a bummer, but the view of the snowy skyline from the top will be more than worth it.
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Try out curling
Pay tribute to our neighbors to the north by taking part in bocce’s cooler cousin. Kaiser Tiger’s outdoor beer garden curling is legendary, and for those looking for a luxe experience, you can battle ends over cocktails at The Gwen’s rooftop. For those of you who really want to test your skills though, we recommend Stone’s Throw Curling at The Emily Hotel, where you can reserve up to four Olympic-sized curling rinks for a night of heated competition between their heated yurts.
Strap on some skates in the heart of the city
Make the trek downtown to Maggie Daley Park to enjoy some of Chicago’s best winter activities. Tickets are on sale right now for The Ribbon, a beautiful, winding ice skating loop that offers up wonderful, romantic views of the city. Reserve your time slot now, but be sure to linger around the park after your skating sesh and check out the park’s other attractions—particularly their cafe and full mini-golf course.
Experience Chicago’s newest live music venue: The Salt Shed
The highly anticipated venue, The Salt Shed, opened in early August and has already had quite an impressive lineup for its debut season. The now-open outdoor venue is built on Chicago's historic Morton Salt Factory complex, while the indoor venue is set to open in 2023. Kicking off its outdoor season were iconic bands like Fleet Foxes, Sharon Van Etten, and Andrew Bird, with veteran indie rock band Death Cab for Cutie closing out the year. Coming up this winter are legends like Iggy Pop, The Roots, and Third Eye Blind. With a great selection of local food and drink vendors, superb acoustics, a sophisticated lineup, and an unparalleled view of Chicago's skyline, the venue checks all the boxes. Check the website for the rest of the season’s lineup and get your tickets.
Take in some outdoor art at Millenium Park
The summer concert series may be over, but that doesn’t mean there’s not fun to be had in Millenium Park this winter. The park will be featuring art installations from local artists all winter, alongside a humongous Christmas tree. Don’t miss Christine Tarkowski’s installation, a thought-provoking amalgamation of blown glass and rock that provides a beautiful commentary on the intersection of nature and design.
Find tranquility at a nearby nature conservatory or botanic garden
Sometimes spending a peaceful hour or two inside a nature-filled haven tucked inside the city is just what the doctor ordered. Nature conservatories and botanic gardens are accessible ways to enjoy the natural beauty of the season without having to drive very far. Chicago Botanic Garden, Garfield Park Conservatory, Lincoln Park Conservatory, and Oak Park Conservatory are great destinations to press pause and recharge. The Chicago Botanic Garden in particular is featuring a newly redesigned holiday lightscape through January 8.
Shove off to sea—or, rather, lake
The city sure looks beautiful shoreside, but the best way to capture Chicago’s impressive architecture is from a few knots off the coast. You won’t need any excuse to round up some buddies and check the upcoming events calendar for any of the ships docked at Navy Pier. There are regular architecture tours, culinary cruises, and party jaunts—something for every Chicagoan scouting for a sail. Check schedules and book on Viator or City Cruises.
Scream your face off at a football or hockey game
The Bears, Blackhawks, and Wolves are all well into their seasons, and if you haven’t been to a single game, you’re missing out. Whether you’re a hockey fan or a football fan, make sure to grab your tickets early and often (or just post up in an outstanding local sports bar for the ultimate game day festivities). Blackhawks and Bears tickets are available through all the normal methods, though we recommend trying to snag them at official team sites when you can. That said, if you’ve never been to a Chicago Wolves game, let this winter be the one where you finally do. The Wolves are the top minor league affiliate of the Carolina Hurricanes, so the competition is still fierce—but ticket prices are much more affordable.
Slather yourself in Chicago’s BBQ scene
It ain’t quite KC or Memphis, but Chicago’s barbecue landscape has certainly come a long way, and winter is the perfect time to warm yourself up with some smoky-spicy goodness. 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. Don’t be shy and pick up a full spread from one of Chicago’s top smoker specialists.
Lose yourself in a dive bar… or double your luck at a slashie
Fancy new rooftop bars are cool and all, but once the chill of winter makes Chicago rooftops inhospitable to most forms of sentient life, it’s time for Chicago’s rich civic treasure—aka dive bars—to really shine (metaphorically, of course). Polar vortexes mean it’s time to hole up in your favorite old man bar and drink until spring 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?
Visit a world-class cultural institution
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. There’s even a museum dedicated to leather and bondage.
Gear up for a thrilling road trip
While air travel has mostly returned to its pre-pandemic form, 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 destinations near Chicago, from snowbound forest trails to indulging in some warm wintertime R&R at a luxurious cabin or resort, preferably with a fancy outdoor hot tub. Looking for a staycation? No problem. Need an Airbnb? We’ve got you covered.
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Elanor Bock is a contributor for Thrillist.
Jay Gentile is an award-winning freelance journalist specializing in travel, food & drink, culture, events and entertainment stories. In addition to Thrillist, you can find his work in The Washington Post, The Guardian, CNN Travel, Chicago Tribune, Lonely Planet, VICE, Outside Magazine and more. Follow @thejaygentile