The Ultimate Chicago Winter Bucket List

As soon as that first snowfall hits the ground, Chicagoans everywhere will be making plans to check their favorite seasonal activities off their list. Well, as we always hope to do, we’ve made it easier for you by compiling the city’s best. Get ready to occupy your snowy days and nights with wreath-making workshops, ugly Christmas sweater dance lessons, ice curling competitions, and more.

After all, ’tis the season.


Enjoy drinks inside an igloo

winter bucket list
Photo Credit: IO Godfrey via Instagram

127 West Huron Street

This seasonal, VIP experience will make you the envy of your Instagram followers. Take in stunning skyline views as you enjoy dinner and drinks inside a heated, transparent “igloo” atop The Godfrey Hotel. Fancy, huh?


Compete in curling at Kaiser Tiger

Kaiser Tiger Chicago
Photo Credit: Kaiser Tiger Chicago Instagram

1415 West Randolph Street

As winter rolls in, the bocce courts and corn hole boards at the West Loop’s Kaiser Tiger are switched out for a curling rink. Grab your friends, put your game face on, and give this winter sport a try.


Hop aboard a Holiday Lights Trolley Tour

Chicago Trolley & Double Decker Co.
Chicago Trolley & Double Decker Co. Instagram

875 North Michigan Avenue

Board a holiday trolley at the John Hancock Center that will take you on a two-and-a-half hour excursion through brightly lit shopping districts in the Loop, stopping at the famous Christkindlmarket at Daley Plaza, then heading to illuminated holiday fun at ZooLights, before circling back to the Hancock.


Go ice skating with your sweetheart in Millennium Park

Millennium Park
Photo Credit: Millennium Park Instagram

Michigan Avenue

Even though it might be the most traditional winter activity there is, it never gets old. Now through March 4, grab your loved one and step on the rink that overlooks one of the city’s best views. Admission to the rink is free, but skate rentals are $12 Monday through Thursday and $14 Friday through Sunday and on holidays.


Take a stroll through ZooLights

winter bucket list
Photo Credit: Lincoln Park Zoo

2001 North Clark Street

If you’re looking for your next winter excursion to meet the three Fs (fun, family-friendly, and free), then it doesn’t get much better than this. From 4:30 pm – 9 pm on December 1 – 31, and January 1 – 6, walk through Lincoln Park Zoo’s amazing light display while enjoying snacks, carousel and train rides, crafts, photos with Santa, and more.


Sip mulled wine at the Christkindlmarket

winter bucket list
Photo Credit: Christkindlmärket

50 West Washington Street

Out of all the activities you’ll find this winter, this one is a true must. The lights, the cute little trinkets, the pretzels, and (our personal favorite) the mulled wine – an atmosphere like this just can’t be beat during the holidays.


Treat that dry, winter skin at Scratch Goods’ Mask Bar

Photo Credit: Scratchgoods Instagram

1046 West Fulton Market

It’s no news to anyone that Chicago’s blistery cold and wind takes a toll on our skin; but no fear, we’ve got just the trick! Snag a seat at Scratch Goods’ Mask Bar and pamper your skin to its best self. Scratch Goods is a gem in Fulton Market and a brand known for their quality skincare and beauty products.


Warm up your body with yoga at Greatly Gracious

winter bucket list
Photo Credit: Greatly Gracious via Instagram

1619 West North Avenue

Offering both vinyasa and holy yoga style classes, this studio tucked away in the cutest storefront on North Avenue in Wicker Park is the place to be this winter. Breathe in the signature blend of oils diffusing through the room and stare up at the beautiful and eclectic tin ceiling during that final resting pose. Trust us, you’ll never want to leave.


Find your signature scent at Aroma Workshop

Aroma Workshop
Photo credit: Aroma Workshop Facebook

2050 North Halsted Street

Being outdoors in the winter is great and all, but at a certain point in this city especially, you have to head indoors. This space is perfect for doing just that, so grab your girls, a bottle of wine, and enjoy creating your own, affordable fragrance tailored exactly to your taste. Not to mention, this makes for an awesome gift.


Make a DIY wreath for your home at Flowers for Dreams

Photo Credit: Flowersfordream Instagram

1812 West Hubbard Street

Not only does Flowers for Dreams offer gorgeous, seasonal arrangements, they are also leading philanthropists and, in our opinion, role models for other local business owners. This winter, join them for a wreath-making workshop and head to their Insta account for an overload of floral beauty (and adorable dogs).


Enroll in a pie baking class at Bang Bang Pie & Biscuits

Bang Bang Pie & Biscuits
Photo Credit: Bang Bang Pie & Biscuits Instagram

2051 North California Avenue

Get a group together and enjoy a Bang Bang Pie & Biscuits private class, where you’ll learn to bake fun goodies while indulging on provided snacks. Classes are held on various days during the week, from 6 – 9 pm, and for groups up to 12. BYOB. For information and pricing are available here.


Dance your winter blues away at Duet Dance Studio

winter bucket list
Photo Credit: Duet Dance Studio via Instagram

2412 West North Avenue, #201

This studio, located in Wicker Park, offers a weekly variety of private and group dance classes, with no previous dance experience needed! One of particular interest is their Ugly Sweater Swing Class on Friday, December 14, from 9 pm – 10 pm.

Any other events happening this winter that you feel should be on our list? Let us know below!


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