Travel Magazine

The Ultimate Chicago Winter Bucket List

By Urbanmatter Chicago @UMatterChicago

What to do in Chicago this Winter

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 (soon to be) snowy days and nights with wreath-making workshops, ugly Christmas sweater dance lessons, ice curling competitions, and more.

Any of these spark your interest? Let us know.


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

winter bucket list

Photo Credit: Kaiser Tiger via 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

winter bucket list

Photo Credit: Chicago Trolley & Double Decker Co.

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

winter bucket list

1 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 F’s (fun, family-friendly, and free), then it doesn’t get much better than this. From 4:30pm – 9pm on December 8-23, 26-31, and January 1-7, walk through Lincoln Park Zoo’s amazing light display while enjoying snacks, carousel and train rides, crafts, photos with Santa, and more.

… and don’t forget BrewLights

winter bucket list

Photo Credit: Lincoln Park Zoo

2001 North Clark Street

It’s all the fun of ZooLights, but with beer! Enjoy an illuminated Lincoln Park Zoo as you sample local, seasonal, and international beer. The 21+ event is tomorrow from 5:30pm – 9:30pm, so get tickets ASAP!

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

winter bucket list

Photo Credit: Scratch Goods via 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 yoga 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 final resting place. Trust us, you’ll never want to leave.

Find your signature scent at Aroma Workshop

winter bucket list

Photo Credit: Aroma Workshop via Instagram

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

winter bucket list

Photo Credit: Flowers for Dreams via 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

winter bucket list

Photo Credit: Bang Bang Pie & Biscuits via Instagram

2051 North California Avenue

Enjoy one of the best parts of Bang Bang Pie & Biscuits’ take on “Midwestern cooking traditions” – which is indulging in fresh, hot pies during the winter. Their December Pie Class is sold out, but hurry and grab your ticket for one of two classes the shop is offering in January: Wednesday, January 17, 2018, from 6pm – 9pm and Wednesday, January 31, 2018, from 6pm – 9pm.

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 15, from 9pm – 10:30pm.

Featured Image Courtesy of Brad J.S. (@brad.j.s)

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