Every Single Fun Thing to Do in Chicago This Winter

As it turns out, that whole “winter wonderland” thing is not a joke. From December on, Chicago bursts with some of our favorite activities to do—hello, ice-skating, restaurant week and cozy fireplaces. Yep, we’re definitely seeing the silver lining in all that gray. 

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Anthony Tahlier

1. Pretend It’s Summer at Somerset
From the nautical decor to the refreshing coconut LaCroix-infused piña colada, Somerset is our new place to pretend it’s summer. When June finally rolls around, you can be sure to find us on the Gold Coast restaurant’s patio (piña colada in hand).

2. Stop by Rosé Fest
For an extra shot of summertime, hit Rosé Fest at I|O Godfrey (January 13, 2 to 5 p.m.). You’ll get unlimited tastings of 12 different rosé varieties, aka unlimited fuel for your “it’s still August” fantasy.

3. Hop on the Holiday Trolley Ride
The Chicago Trolley Holiday Lights Tour starts at John Hancock Center, tools down the Magnificent Mile and ends at Lincoln Park Zoo for its ZooLights display. Oh, and did we mention your ticket includes a Sprinkles cupcake?

4. Book a Treatment at Skin Laundry
Hallelujah, Skin Laundry has arrived in Chicago. Already popular in L.A. and Hong Kong, the 15-minute laser therapy skin clinic revives dull, uneven skin (in other words, the scourge of winter). Find it in the Michigan Avenue Ulta.

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5. Have a Fireside Chat at the Violet Hour
Winter means more excuses to cozy up by a fire with your bestie. We love the Violet Hour’s hearth because it brings easy access to punch and bacon-wrapped dates, but these six other restaurant fireplaces do not disappoint, either.

6. Catch a Concert at Constellation
Chicago’s independent arts scene has launched a number of famous names, but that’s not the only reason to visit small music venues like this one in Roscoe Village. Catch an intimate performance by the graduates of the Blackbird Creative Lab (taught by Grammy Award-winning ensemble Eighth Blackbird) on January 20.

7. Give Curling a Try
Whether at Kaiser Tiger, The Gwen or Windy City Curling Club, curling (picture shuffleboard, but on ice) is having a moment. Give it a try (your Netflix can wait).

8. Savor Citrus Season
Winter’s biggest bright spot is that it also happens to be peak season for oranges, tangerines and grapefruits. The aroma, color and natural sweetness perk us right up, and we can always use more vitamin C when cold season hits. (Plus, those easy-to-peel clementines are the perfect snack to throw in your bag.)

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9. Plan a Getaway at Lake Geneva
The Wisconsin resort town isn't just for summer anymore. The historic Baker House Hotel’s cozy and romantic atmosphere feels just right for winter. If a day of skiing or snowboarding is more your speed, there's plenty of that up north, too.

10. Make Restaurant Week Reservations
If the word “caviar” brings to mind the food delivery app, not the delicacy, you may be overdue for a night out on Chicago’s world-class restaurant scene. This year’s restaurant week is slated from January 26 through February 8—fingers crossed brand new hotspot Bellemore participates.

 11. Volunteer at 826CHI
Set a resolution to make a difference, and start with Chicago’s youngsters. 826CHI offers free after-school tutoring to CPS students from its Wicker Park center. It’s way more fun than your usual post-work beeline-home, throw-on-sweatpants routine.

12. Celebrate the Lunar New Year
The Year of the Dog commences February 16. The two-week celebration kicks off with a parade in Chinatown. Keep an eye on the schedule for even more events from dumpling-making to dance performances.

Chicago Botanic Garden

13. Browse the Blooms at the Orchid Show at Chicago Botanic Garden
The need for greenery reaches its peak in February, so it’s perfect timing for Chicago Botanic Garden’s annual Orchid Show (February 10 to March 25). You don’t have to become a real-life orchid thief to take one home: just stick around for the post-show sale on March 29.

14. Slurp Pho at Tank Noodle
When it’s below freezing, nothing hits the spot like a big bowl of pho from Tank Noodle...or clam chowder from GT Fish & Oyster...or ramen from Ramen Takeya. Guess we’ll be revisiting every one of our favorite soups this winter.

15. Ski at Alpine Valley Ski Resort
Just two hours outside Chicago, Alpine Valley boasts three terrain parks, 21 trails spanning 90 acres and a 388-foot drop. If you need more proof that it’s possible to ski in the Midwest, check our list of Chicagoland’s best options.

16. Give a Gift with Purpose
Packed with Purpose’s boxes are stocked with handmade foodstuffs, candles and other goodies that all benefit a cause, from sustainable farming to childhood obesity. Annnnd you’ve finally figured out what to gift your coworkers/neighbors/in-laws/basically everyone.

17. Snap the Perfect Winter Instagram
Hello, gorgeous. For the perfect winter wonderland photo, head to the historic Water Tower building at magic hour. While you’re at it, we have nine more spots that are completely photogenic all year long.

18. Try HIIT at Exhale
Exhale’s combination of spa treatments with yoga and barre classes makes working out so much more pleasant. Now the spa-studio offers a 30-minute HIIT workout that will snap you into shape...before you melt into a massage table.

19. Skate Maggie Daley Skating Ribbon
Skating in circles around a regular ice rink can get a little tedious. This winding strip covers twice the distance of one rink lap and unfurls through a rolling landscape dotted by trees and views of the Chicago skyline.

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20. Have a Fancy-Pants Evening at Dinner and the Opera
Shake off the winter doldrums with an über-romantic date. First stop: Pearl Brasserie for its nightly prix fixe dinner ($35). Second stop: Lyric Opera for a performance of Turandot, Puccini’s final masterpiece.

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