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 again.
Luckily, it’s not all doom and gloom. The many holiday traditions and 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, Christmas cheer, and then an array of activities to .
From sipping Glühwein in Daley Plaza to gliding around the quarter-mile ice rink in Maggie Daley Park, here are our Chicago Winter bucket list must-do activities, in no particular order.
1. Go ice skating at Maggie Daley Park
There’s no better way to glide into winter than with 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 the Chicago winter bucket list activities is, of course, ice skating. The Maggie Daley ice rink 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!
Read more about Chicago ice rinks.
2. Drink in a personal snow globe
As winter gripped hold of Chicago and the global pandemic forced restrictions on indoor dining in recent years, some of the places we turned to were Chicago’s renowned rooftop bars and rooftop restaurants.
Thriving utopias in the summer months, we saw these reinvent themselves during the winter months offering winterized rooftop escapes across Chicago kitted out with igloos, fire pits, and more.
Boasting Chicago’s largest indoor-outdoor rooftop with a retractable roof, the Godfrey Hotel in River North is one of the most amazing of these boasting a winter wonderland of signature heated igloos that offers guests the chance to 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.
Read more about The Godfrey Hotel rooftop.
3. Enjoy a rooftop curling and cocktails experience
Another unique winter experience can be had 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 and cocktails experiences. The hotel kits out its rooftop with no igloos, no 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.
Read more about The Gwen Hotel’s luxury rooftop curling experience.
4. Go snow tubing
When you’re enjoying the exhilarating extreme activities that the snow provides, all sense of the weather’s frigidness disappears as adrenaline and joy take over. Getting out and exercising is good for the mind and body; we all need that kind of lift in winter.
While skiing and snowboarding are more challenging winter activities to learn, snow tubing has quickly become one of the fastest-growing recreational winter activities, and it is easy to see why. All you have to do is grab a tube, have a seat, and let gravity be your friend.
Luckily there are plenty of opportunities across the Chicago area.
View our full list of the best places for snow tubing near Chicago.
5. Browse a world-class museum for free
Chicago has one of the best collections of museums and attractions on the planet. Visiting all of them can get a little costly, especially if you’re taking the family. So it’s understandable why free admission days generate quite a lot of hype!
It’s during winter when Chicago’s tourism experiences its bleaker months when free days come thick and fast. Illinois Resident Free Days can be enjoyed throughout January, February, and March at some of Chicago’s top attractions like Shedd Aquarium, Field Museum, Museum of Science & Industry and Art Institute of Chicago.
Read our guide on free museum days in Chicago.
6. 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 consider your well-being during these hostile months.
Spas are more rewarding than ever at the start of the year offering a mental and physical refuge from the cold and the chaos of Chicago.
Whether you’re looking to soak away stress and restore your mental balance, alleviate aches and pains in bones and muscles, or escape the numbing chill courtesy of a warm bath, spas are medicine for the mind, body, and soul.
Read more about Chicago spas where you can warm up this winter.
7. Chicago Electric Boat Company is now offering rentable Hot Tub Boats
If you’re prepared to brave it, this season a new unforgettable winter activity has been added to the mix courtesy of The Chicago Electric Boat Company.
Since opening in early 2012 the company has offered a unique, environmentally friendly way to see the city of Chicago all the while expanding and improving the variety of boats it has to offer.
Today the fleet includes such options as 22ft long luxury Duffy boats for 12 passengers and unique donut boats with circular seating designs and round tables that were introduced in 2020.
Now an incredible new addition has joined the Chicago Electric Boat Company fleet, this time in the form of Hot Tub Boat Cruises.
Yes, you read that correctly. Launching out of the docks at Marina City, the new zero-emissions vessels takes up to six people at a time floating along the main branch of the Chicago River in a boat equipped with a fully functioning hot tub.
Read more about the new hot tub boats.
8. Head out of the city and see Illinois’ natural spectacles
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 from December through March.
From monolithic marvels covered in snow to cascading waterfalls frozen in time, there are natural wonders in all corners of Illinois that should be on your Chicago winter bucket list.
View our full list of natural sites near Chicago.
A range of annual early winter activities that have passed but should not be missed:
Marvel at Chicago’s official Christmas tree
The Millennium Park Christmas tree is no doubt Chicago’s “official” Christmas tree. The lights are switched on every year during a jubilant annual ceremony that marks the start of the festive season later in November.
From then on, the great tree illuminates the intersection of Michigan Avenue and Washington Street, filling onlookers with joy and festive cheer.
All other Christmas trees pale compared to Millenium Park’s, and it is worth wrapping up, taking some hot chocolate, and seeing the tree up close and personal, bathing in the sea of lights that blanket it.
We don’t know what will if that doesn’t fill you with festive cheer!
Sip Glühwein at Christkindlmarket
Chicago’s German-inspired Christkindlmarket is another extremely popular wintertime event. The annual Christmas markets in Daley Plaza, Wrigleyville, and Aurora welcome guests into villages to peruse handmade gifts while enjoying German food and beverages beneath the snowflakes and glistening lights.
Every year visitors are welcomed with the smell of roasted nuts, fresh pretzels, bratwurst, hot spiced wine, and the magic of festive music, all in the coziest of atmospheres!
Read more about Christkindlmarkets.
Catch the holiday train
Santa’s holiday train trip around Chicago is always one of Chicago’s most eagerly anticipated winter bucket list activities, providing affordable fun for families all over the city.
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 as Santa and his reindeer whizz around all eight lines, the Holiday Fleet also delivers donated food baskets to local community organizations and charities.
Read more about the CTA Holiday Train.
Check out a light show
Chicago’s many light shows are some of our most treasured winter traditions. Gorgeous natural backdrops, cutting-edge light art installations, and festive cheer all combine, providing us with magical multi-sensory holiday experiences.
Lightscape at Chicago Botanic Garden, Illumination: Tree Lights at The Morton Arboretum and ZooLights at Lincoln Park Zoo are a few of our favorites but every year light shows illuminate parks and zoos all across the Chicago area from November through January.
Read our full list of magical must-see light shows in and around Chicago.
Indulge in the exorbitance of Chicago’s Christmas pop-ups
Another thing you’ll find from November through to January every year is an abundance of holiday pop-ups. Various bars and restaurants across Chicago transform their spaces and decorate themselves head to toe with an exorbitant amount of holiday decor.
While the boozy milkshakes and Christmas-themed cocktails can sometimes border on the obscene, if there is one time of the year to indulge yourself, we all know it is Christmas.
Read more about Chicago Christmas Pop-Ups.
[Featured image from Unsplash]