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The first time I ever stepped foot in Chicago was January 4th, 2004. I was about to start grad school mid-year, and I was terrified . . . not of school, but of those infamous Chicago winters. Turns out, I was about to fall in love with Chicago—and its winters. What would the Windy City be without its cozy restaurants, its snow-covered Bean and its super fun winter activities? (Not to mention its rock bottom winter hotel rates.) Nowadays, I look forward to December, when I can grab my winter coat and go play in Chicago. Here are 10 reasons why you should as well.

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Melt away at a fancy Korean bathhouse

One of the best things about being ridiculously cold is getting ridiculously hot. Naked hot. Take a rideshare to suburban Niles (30 minutes from Chicago), the home of King Spa & Sauna, where you’ll be instructed in just a few words (unless you speak Korean) to strip down and hop into the gender divided areas. There, you’ll get to soak for up to 24 hours (seriously, some people use it as a hotel) in the hot tubs and steam rooms. Body scrubs cost extra, but you should totally indulge, as they’ll scrape away all your dead skin cells and you’ll feel as soft as a baby’s bottom when you’re done. Next, don some provided PJ’s and head to the coed area, where you can try a bunch of saunas, each suggesting a different health cure. Don’t forget to check out the Korean cafe, where you can eat in your pajamas before heading back to the sauna.

Lace up like Adam Rippon

Chicago has the best ever ice-skating rinks. Our two favorites are right in the center of the city, surrounded by the Chicago skyline (hello, Instagram!). They’re new, they’re free (just pay to rent skates) and they’re open to the public. Choose between the Millennium Park McCormick Tribune Ice Rink, which is literally on Michigan Avenue and sports that gigantic Christmas tree in the background. Or, head a few blocks east, and you’ll hit the Maggie Daley Park Skating Ribbon, where you can go round and round and round and feel like you’re a champion skater gliding your way through the city. Of course, there’s hot chocolate available at both.

Rock out with your scarf out

Green Mill

Green Mill | Flickr CC: BriYYZ

Here’s a little known secret: The best music happens during the winter months. Sure, if you visit here when it’s warm, you can experience the city’s many street fests (not to mention Pitchfork and Lollapalooza) but come in winter, and you’ll be treated to the Chicago Symphony when they play downtown; and the elaborate productions of the city’s Lyric Opera. Plus, there’s the city’s storied rock venues like the Metro, Schubas Tavern, Double Door and Aragon Ballroom, plus famed jazz hall the Green Mill.

Go Dome or go home

This deserves its own blurb because it’s that amazing. At the newish Riverwalk (one of the best views in Chicago), the City Winery has erected heated domes that look like see-through igloos. You can reserve one, and you can sit inside, sipping your wine and eating your cured meat flight with a side of artisanal cheese, while watching Chicagoans stumble by, all bundled up for the snowpocalypse.

Go cuckoo for hot cocoa

holding hot chocolate

In Chicago, we treat hot chocolate like it’s an art form. We even have a James Beard-award winning restaurant—Mindy’s Hot Chocolate—that’s essentially dedicated to it (though you can also order a yummy meal there, too). One of our favorite winter traditions is popping into BomboBar in the West Loop for a s’mores hot chocolate (even better than it sounds) paired with a Nutella bomboloni (Italian hole-less donut). You won’t feel the freeze if you have those warm sugar-filled treats in your hands.

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Raise the roof

Hanging out on a rooftop is fab during the summer, but it’s even better when it’s freezing outside. That’s when spots like the Peninsula Chicago’s new Z Bar pulls out its blankets, hot cocktails and outdoor fireplace. Cuddling under a blanket in front of a fireplace while it’s snowing and you’re on a fancy hotel rooftop? You’ll feel like you own Chicago.

Give a standing ovation

Chicago’s theater scene gives New York’s a run for its money, and there’s no better time to experience it than fall or winter. You can catch a five-star show at critical darling Victory Gardens Biograph Theater, see where legends are born at the Steppenwolf or go for all the glitz and glam of big Broadway production like Hamilton at the historic CIBC Theatre. Since most of the tourists flood Chicago during the spring and summer months, you’ll have a better pick of shows.

Soldier on, with sled in hand


Sure, Aspen has skiing. But we have sledding, and anyone can do it (plus it’s free). The best spot in the city is at Soldier Field, where you’ll get to experience the 33-foot drop (who said sledding wasn’t challenging?). While snow covers the ground nearly the entire winter, the Chicago Park District provides faux snow if the real stuff is ever lacking.

Light your fire, fill your belly

Chicagoans are totally used to the cold months, so we really know how to do comfort food with a side of a fireplace. The Green Door Tavern is a Chicago staple, having been here since 1921. It screams “comfort food.” Our favorite on the menu is the chili with a side of Chicago-style poutine (topped with Italian beef gravy, cheese curds and giardiniera). Don’t knock it till you try it.

You go, curl!

Just because Chicago is a major metropolis doesn’t mean we don’t have curling, where players use brooms to slide stones across ice—we just happen to play it on the terrace of a fancy hotel. Every winter, The Gwen transforms its 5th floor outdoor terrace into a wood-paneled curling cabin, complete with a swing seat for two, Adirondack chairs, an electric fireplace and faux furs. Oh, and there’s even an iceless curling rink, too ($25 per person, which includes a cocktail and 30 minutes of curling).

Tagged: Chicago

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Danielle Braff

Danielle Braff

Danielle lives in Chicago with her family, two cats and a dog, but she's constantly researching her next vacation. Check out her other articles at

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