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The Drawing Room at Chicago Athletic Association
Photograph: Clayton Hauck

The absolute coziest things to do in Chicago

When the temperature begins to fall, warm your bones (and soul) at some of Chicago's coziest spots

By Zach Long

We can all agree that while the freezing temperatures that typically accompany winter in Chicago can be rough, being chilly is entirely optional. Beyond buying a decent parka, there are a lot of ways to warm up and have a good time while the icicles form outdoors. Stave off the frigid weather by sipping a piping-hot beverage at Christkindlmarket, curling up by the fireplace in a popular Loop hotel or attending a sweaty dance party at one of Chicago's best music venues. Here are some of our favorite ways to stay cozy in Chicago when the mercury begins to drop.

The coziest things to do in Chicago

Mindy's Hot Chocolate
Photograph: Anthony Tahlier

1. Mindy's Hot Chocolate

Restaurants Contemporary American Wicker Park

As a kid, you may have gulped down cocoa to warm up after an afternoon outside in the snow, so there’s no reason not to treat yourself to a mug of hot chocolate after commuting home on a chilly day. Mindy Segal’s Wicker Park fave offers no less than six types of the rich beverage—old-fashioned, medium, dark, dark oat milk, Mexican and lemon—which can be spiked with rum, whiskey, cognac or brandy.

AIRE Ancient Baths
Photograph: Juan Serrano Corbella

2. AIRE Ancient Baths

Health and beauty River West/West Town

At this luxurious spa housed in a refurbished River West factory, you can choose between six different baths. But if you want to get a bit toasty, you should stick to the 102ºF caldarium bath or the 97ºF tepidarium pool. If you need even more heat, head to the relaxation area and sit down in the steam room or atop the hot marble stones.

The Drawing Room at Chicago Athletic Association
Photograph: Clayton Hauck

3. The Drawing Room

Bars Cocktail bars Loop

Not content to provide just one fireplace, the Drawing Room at the Chicago Athletic Association is home to three separate hearths, each dating back to 1893. Order a soul-thawing old-fashioned, find a spot on one of the leather couches and bask in the glow of the crackling flames in this Gilded Age den.

Centered Studio Bunny Yoga
Photograph: Courtesy Red Door

4. Bunny Yoga at Centered Studios

Sports and fitness Yoga & Pilates Rogers Park

You may have spread out a mat and struck the warrior pose before, but have you ever done it while fluffy bunnies hop around your feet? Centered Studios’ monthly class lets you find your flow and hug some adorable rabbits—all of which can be adopted from Red Door Animal Shelter. Just make sure to sign up well in advance, because this class is obviously very popular.

Blind Barber
Photograph: Courtesy Blind Barber

5. Hot Shave at Blind Barber

Things to do Loop

Before you head to the Blind Barber’s backroom speakeasy to sip a cocktail, dine on a gourmet grilled cheese sandwich and bust a move on the dance floor, why not plop down on one of the barber’s chairs for a soothing hot shave? A warm towel prepares your face for the 14-stroke straight-razor process, leaving you stubble-free and refreshed.

Photograph: Courtesy Yarnify!

6. Yarnify!

Shopping Classes and workshops Printers Row

Even if you’re picking up a pair of needles for the very first time, this Printer’s Row shop has everything you need to make something cozy: The shelves are stocked with yarn and tools, and private knitting or crocheting lessons can be scheduled ($30 per hour). Find a pattern for a fuzzy pair of gloves or a colorful scarf—step by step, they’ll show you what to do next.

Geja's Cafe
Photograph: Courtesy Adam Alexander Photography

7. Geja’s Café

Restaurants Eclectic Lincoln Park

We can all agree that cheese is delicious, but melted Gruyère blended with wine, brandy and spices is even more enticing. Find someone you want to cuddle up next to and book a table at this romantic restaurant, where you can order a pot of fondue and a bottle of wine.

Soul Summit
Photograph: Mo Manley

8. Soul Summit at the Empty Bottle

Music Rock and indie Ukrainian Village

No matter how blustery the weather, this party’s dance floor is always packed, with vintage soul records serving up the good vibes. If a room full of bodies doesn’t heat you up, boogying down with some fancy footwork should do the trick. Soul Summit's organizers recently announced that they will hold three monthly parties at the Empty Bottle before regrouping to determine the future of the event.

Gluhwein-filled boot at Christkindlmarket
Photograph: Jaclyn Rivas

9. Glühwein at Christkindlmarket

Things to do Literary events Loop

It doesn’t really begin to feel like the holidays in Chicago until you’ve had your first sip of glühwein from a commemorative mug while standing in the middle of Daley Plaza. The hot red wine flavored with nutmeg and cinnamon will keep your hands warm, and the booze will do the same for your insides. Alternatively, you can also stop by the Christkindlmarket at Gallagher Way in Wrigleyville—they're serving the exact same beverages.


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