A Chicago Winter Bucket List: 10 Essential Winter Experiences In Chicago

Elliot McGowan Elliot McGowan

A Chicago Winter Bucket List: 10 Essential Winter Experiences In Chicago

Your winter to-do list.

Chicago’s notoriously harsh winter needs no introduction. If you’re a Chicagoan you know full well what winter means and if you’re not, well there’s very little chance you’ve not been warned already if you’re visiting this time of the year. Fall’s ephemeral beauty comes and goes in the blink of an eye, snowfall quickly goes from exciting to exasperating, and before you know it that teeth-chattering chill has settled in Chicago and we bed down to see it out once more.

Luckily it’s not all doom and gloom. The many holiday traditions and many exciting events that emerge this time of the year are our shining lights in times of darkness. As winter sweeps through the city it is countered with festive fun and Christmas cheer. From sipping Glühwein in Daley Plaza to gliding around the quarter-mile ice rink in Maggie Daley Park, here are our must-do winter activities in Chicago in no particular order.

1. Marvel at Chicago’s official Christmas tree

The Millennium Park Christmas tree is no doubt Chicago’s “official” Christmas tree. Every year the lights are switched on during a jubilant annual ceremony that marks the start of the festive season. From then on the great tree illuminates the intersection of Michigan Avenue and Washington Street filling onlookers with joy and festive cheer.

The annual Christmas Tree Lighting Ceremony in Millennium Park went virtual last year in order to prevent crowds from gathering during the pandemic. This year, the 108th Annual City of Chicago Christmas Tree lighting ceremony will be in-person on Friday, November 19 starting at 6 pm (with the actual lighting at approximately 6:30 pm).” More information can be found at Chicago.gov.

If you miss the tree lighting ceremony, standing next to the great tree and embracing the festive cheer is still worthwhile!

More information can be found here.

2. Sip Glühwein at Christkindlmarket

Chicago’s German-inspired annual Christmas market is another extremely popular Christmas event. After taking to the internet last year, the 25th edition of the beloved Christmas market returned on Friday, November 19th, and will run through to Christmas.

This year both The Christkindlmarket Daley Plaza and The Christkindlmarket Wrigleyville are welcoming guests into villages to peruse handmade gifts whilst enjoying German food and beverages beneath the snowflakes and glistening lights. Enjoy the smell of roasted nuts, fresh pretzels, bratwurst, hot spiced wine, and the magic of festive music all in the coziest of atmospheres!

More information can be found here.

3. Go ice skating at Maggie Daley Park

Photo from Instagram / @borntoseephoto

There’s no better way to glide into winter than with some winter skating. Though ice rinks in Millennium Park and Rosemont offer wonderful skating experiences there are none quite like the Maggie Daley Park ice rink.

One of Chicago’s best winter-time activities, the Maggie Daley ice rinks offers an “alpine in the city” experience skating down a quarter-mile rink in the heart of Chicago. The winding ribbon of ice curves up and down around a 40-foot climbing wall with the city’s stunning skyline in the backdrop. It’s a must for your winter bucket list. It’s also free Monday-Thursday if you bring your own skates!

More information can be found here.

4. Catch the holiday train

Santa’s holiday train trip around Chicago is always one of the most eagerly anticipated providing affordable fun for all Chicago families. The Chicago Transit Authority’s train and bus are decorated inside and out with festive decorations and thousands of lights to make them glow as they glide and glimmer around Chicago. The mere sight of the CTA Holiday Train or Holiday Bus is enough to brighten anyone’s day but jumping on board to be serenaded by jolly elves is the real experience.

In addition to spreading joy and the holiday spirit to thousands of Chicagoans the Holiday Train and Holiday Bus also deliver donate food baskets to local community organizations and charities along the way. Families can look out for the holiday train which will travel all 8 lines starting from Friday, November 26.

This year guests will once again be able to jump on board after inevitable changes last year though face masks will be required this year no matter age or vaccination status. The CTA Holiday Train will travel all 8 lines from Friday, November 26 through Wednesday, December 22ndwhile the CTA Holiday Bus will travel 14 different routes serving all areas of the city from Tuesday, November 30th through Thursday, December 23rd.

You can find the full schedule here.

5. Check out a light show or three

Photography by Alex Hewitt

Chicago’s many light shows are some of our most treasured winter traditions and they’re coming back thick and fast to the Windy City this year! In 2020 all light show experiences turned to drive-thru events or were heavily adapted hindering the real light show experience. This year they’ve returned to their true formats and in some cases expanded and evolved.

Gorgeous natural backdrops, cutting-edge light art installations, and festive cheer all combine providing some of Chicago’s most magical multi-sensory events and we’ve rounded up the best of them all.

Head to our list of 10 magical must-see light shows in and around Chicago for more.

6. Drink in a personal snow globe

Last year, as winter gripped hold of Chicago and the global pandemic forced restrictions on indoor dining some of the places we turned to were Chicago’s renowned rooftop bars and rooftop restaurants. Thriving utopias in the summer months, we saw rooftops reinvent themselves during the winter months with igloos, fire pits, and more offering memorable moments up among the Chicago skyline.

Boasting Chicago’s largest indoor-outdoor rooftop with a retractable roof, the Godfrey Hotel in River North puts on a whimsical winter wonderland with signature heated igloos where guests can shelter from the winter elements in style. The clear-domed igloos cover the rooftop’s portico and offer the perfect place to cozy up with a cocktail, s’mores, and sweeping skyline views.

More information can be found here.

7. Enjoy curling and cocktails at Gwen Hotel

Another unique winter experience can be had up on The Gwen Hotel’s luxury rooftop. While you won’t find lavish igloos here you’ll instead be able to enjoy the hotel’s annual Curling & Cocktails experiences. The hotel kits out its rooftop out with not igloos, not ice skating, but an outdoor curling rink high in the sky.

Curling sessions come with small bites and a complimentary round of cocktails meaning you can sip away on your favorite tipple while battling your buddies on the state-of-the-art curling rink.

More information can be found here.

8. Embrace the winter at Chicago’s largest patio

Back down at ground level, you can bet that Recess, Chicago’s largest patio, has turned its 14,500 square feet of space into a reliable winter hideout. Nestled within 30 shipping containers on a West Loop corner Recess is home to a cozy amalgamation of bars, food stands, and cabana houses that are transformed with the seasons change.

Last year’s Fire & Ice pop-up involved ice sculptures and winter photo ops providing a feast for the eyes and the perfect Instagram material whilst fire pit tables, S’mores kits, and boozy hot chocolates provide the perfect recipe to enjoy a toasty trip outside. There’s no doubting that Recess will offer another snug sanctuary worth checking out this winter.

9. Warm-up and revitalize at Chicago’s unique spas

Christmas is full of magic but it can also be stressful. Add to that Chicago’s unforgiving frostiness and you’ve got to take your wellbeing into consideration during these hostile months. Luckily Chicago is full of answers to combat both the Christmas chaos and the numbing chill that settles into your bones.

There is simply no better place in Chicago for some rest and relaxation than AIRE’s Ancient Baths located inside a restored historic River West factory. Inspired by the traditional Roman, Greek, and Ottoman ancient experience of bathing, this preserved structure has been restored to its original splendor and you can now find optimum relaxation within the exposed brick, wooden beams, and industrial columns of the building.

Another option comes in the form of PIVA Beer Spa where guests can sink back into a huge larch wooden tub filled with near 100-degree beer, herbs, and hops. Whilst swearing that soaking in beer can have numerous benefits, PIVA Beer Spa provides a variety of services both beer-related and non-beer related from rejuvenating salt room experiences to luxury massages.

10. Head out of the city and see Illinois’ natural spectacles

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Ok, this last one isn’t strictly in Chicago we know. But with so much going on in the city it can be nice to escape to the quiet of Illinois’ natural beauty. Though our state may not boast wonders with the universal magnitude of the Grand Canyon nor the grandiose reputation of Niagra Falls, Illinois is teeming with diverse ecological landscapes that transform into incredible winter wonderlands this time of the year. From monolithic marvels covered in snow to cascading waterfalls frozen in time, here are 7 natural wonders of Illinois that you can visit while they’re a different beast in winter:

  • Garden Of The Gods: Saline County
  • Wildcat Canyon In Starved Rock State Park: La Salle County
  • Cache River State Natural Area: Johnson County
  • Cave-In-Rock: Hardin County
  • The Pomona Natural Bridge: Jackson County
  • Cascade Falls In Matthiessen State Park: La Salle County
  • Bork Falls In Ferne Clyffe State Park: Johnson County

More information can be found here.

See more: 25 Must-See Street Art Murals That Prove Chicago’s Art Scene Is Legendary

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