10 Essential Winter Activities That Should Be On Every Chicago Winter Bucket List (2023)

Your winter to-do list featuring a range of holiday events in Chicago.

Elliot McGowan

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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

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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.

All other Christmas trees pale in comparison to Millenium Park’s and it really 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. If that doesn’t fill you with festive cheer, we don’t know what will!

The Millenium Park Tree will begin shining from an official lighting ceremony at 6 pm on Friday, November 18 through January 9, 2023.

More information can be found here.

2. Sip Glühwein at Christkindlmarket

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Chicago’s German-inspired annual Christmas market is another extremely popular Christmas event. After taking to the internet last year, the 26th edition of the beloved Christmas market will return on Friday, November 18th, and will run through to Christmas Eve.

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

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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

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Santa’s holiday train trip around Chicago is always one of the most eagerly anticipated winter bucket list activities in Chicago 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 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 usually begins traveling all 8 lines towards the end of November through late December. It’s likely it will again be the last Friday of the month (November 25th) but an official statement has yet to be released by CTA.

The full schedule will be posted here in due course.

5. Check out a light show or three

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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. Last year many returned to their true formats and this year they’re back to their former glory and in some cases, they’ve 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.

  • Lightscape at Chicago Botanic Garden
  • Illumination: Tree Lights at The Morton Arboretum
  • ZooLights at Lincoln Park Zoo
  • Holiday Magic at Brookfield Zoo
  • Let it Shine Light Show at Northbrook Court in Northbrook and Wintrust Field in Schaumburg

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

6. Drink in a personal snow globe

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As winter gripped hold of Chicago and the global pandemic forced restrictions on indoor dining over the last couple of 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 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

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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 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. Indulge in the exorbitance of Chicago’s Christmas pop-ups

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Each year various bars and restaurants across Chicago transform their spaces and decorate themselves head to toe in an exorbitant amount of holiday decor. You’ll find all manner of bedecked patios, festive rooftops, and magical outdoor winter wonderlands in and around Chicago this time of the year.

While the boozy milkshakes and Christmas-themed cocktails can at times border on the obscene, if there is one time of the year to indulge yourself, we all know it is Christmas. One of our top picks from the array of Christmas pop-ups in Chicagoland has to be the immersive Santa Baby Pop-Up that takes over Deuce’s Major League Bar in Wrigleyville every year.

Here you’ll find a wide selection of decadently garnished boozy milkshakes and Christmas cocktails as well as a food menu from ‘Santa’s Snack Shack’ providing more than 20 different Christmas-themed bites.

More information can be found here.

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

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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 well-being 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.

Whether you’re looking to soak away stress and restore your mental balance, alleviate aches and pains in bones and muscles, or simply find refuge from the cold in a warm bath, spas are medicine for the mind, body, and soul.

From therapeutic massages to rejuvenating facials, there are so many Chicago spas and bathhouses that cater to all. So if you’re seeking somewhere to obtain that ethereal feeling you have returning to the real world after a restorative spa day head to our article on 10 serene Chicago spas where you can warm up this winter.

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


10 Essential Winter Activities That Should Be On Every Chicago Winter Bucket List? ›

Chicago winters are a magical time of the year. The city unfurls all its finery, with decorated storefronts, streets draped with thousands and millions of lights, ice skating and festivals and a real, live holiday evergreen tree culled from a local's land and towering over Michigan Avenue.

What is Chicago known for in winter? ›

Chicago winters are a magical time of the year. The city unfurls all its finery, with decorated storefronts, streets draped with thousands and millions of lights, ice skating and festivals and a real, live holiday evergreen tree culled from a local's land and towering over Michigan Avenue.

How do I prepare for winter in Chicago? ›

How to Survive a Chicago Winter
  1. Stock up on Chicago Winter Essentials & Invest in Great Winter Gear. ...
  2. Dress in layers. ...
  3. Tighten the grip on hand warmers. ...
  4. Salt the streets, sidewalks and driveways. ...
  5. Seek reprieve in the Pedway System. ...
  6. Get regular movement. ...
  7. Download the Snow Plow Tracking App.

Is Chicago fun in winter? ›

Winter in Chicago is the best time traipse through shimmering holiday lights with a mug of hot mulled wine, glide around one of the city's many outdoor ice rinks, or cozy up in a museum cafe. Besides, everyone knows hot chocolate tastes better while walking down snow-covered streets!

What year was the worst winter in Chicago? ›

1978-1979: Many Chicagoans who were here in the late 1970s would argue that those years were the harshest ever. That season can be best defined by an extremely brutal month of January.

Is Chicago one of the coldest cities? ›

Chicago's all-time record low was -27 degrees set on Jan. 20, 1985. On average, subzero cold occurs 8-9 days each year, while subfreezing temperatures occur 127 days a year there.

How can I make winter more enjoyable? ›

Tips For How To Enjoy Winter More
  1. Make a list of things I love about winter. ...
  2. Make a list of things I want to do or hobbies I want to try that I never NORMALLY have time for. ...
  3. Have a more appropriate wardrobe. ...
  4. Embrace hygge. ...
  5. Throw it back to childhood. ...
  6. Make an ultimate cozy winter reading list. ...
  7. Force yourself outside.

What is the best winter month to visit Chicago? ›

If you want short lines and cheaper hotel and flight rates, and don't mind cold weather, coming in January, February, or November might be the best choice for you. These are considered the low season months when deals such as Chicago Restaurant Week take place.

How do people dress in Chicago in cold weather? ›

In Chicago, everyone should pack a winter coat, hoodie, gloves, scarves, and hat for December. When the weather is under 5 degrees and especially when there are winds, snow, or rain, you must wear outer layers or jackets.

What pants to wear in Chicago winter? ›

Warm Bottoms

Anything from stretchy jeans, to joggers or loose-fitting trouser pants, will not only look great but also be warm because of the base layer underneath. I personally love and use Lululemon's jogger pants because of their soft materials, sweat-wicking material, and variety of colors and styles they come in.

What should I pack for Chicago weather? ›

Layers. Layering in Chicago is a must, and the best way to dress for changes in the weather forecast. For example, layer a couple of shirts and wear a jacket or vest on top. Just a few warm layers can make a big difference.

How should I pack for Chicago? ›

If you plan to tour the city, here are some packing tips and what to bring to Chicago:
  1. Comfortable Shoes.
  2. Weather Appropriate, Layered Attire.
  3. Light Jacket.
  4. Purse/Backpack.
  5. Camera.
  6. Extra Batteries/Charger.
  7. Refillable Water Bottle.
  8. Extra Cash.

What is the coldest winter month in Chicago? ›

January tends to be the coldest month, but also the snowiest month of the year. The temperatures reach between 26 °F and 36°F (-3 - 2 °C), with an average high of 31 °F (-1 °C). On the other end, the average low this month is 17 °F (-9°C).

Is Chicago colder than New York in the winter? ›

It's a common misconception that New York City is as cold as Chicago. Actually, one of the benefits of living in NYC is its winters are actually pretty mild and usually 10 degrees warmer than Chicago! Year-round, New York City has more mild weather than Chicago, especially in the summer and winter.

Is Chicago or NYC colder in winter? ›

New York has an Average high of 39 F and Average low of 26 F. Chicago's Average high is 32 F and Average low of 18 F. Snow total wise, on average, New York gets about 30 inches and Chicago gets 37 inches. By both standards, Chicago has harsher winter as it colder and snowier.

What kind of winter does Chicago have? ›

The climate of Chicago is classified as hot-summer humid continental (Köppen: Dfa) with hot humid summers and cold, occasionally snowy winters.

What is Chicago famous for? ›

Chicago is known for its jaw-dropping architecture, vibrant music scene, amazing food, — including deep-dish pizza — and iconic neighborhoods. Let's explore some of the best things that make Chicago special and unique.

Is Chicago known for snow? ›

With records going back to 1900, the National Weather Service has tracked how much snow falls in Chicago. Seasonally in the years from 1900-present, the average inches of snow in Chicago have annually ranged from 9.8 inches in 1920 – 1921 to 89.7 inches in 1978 – 1979. That's quite a range of inches of snow in Chicago!

Why is Chicago's winter colder than New York? ›

Chicago's climate is "continental," far from the warmth and humidity of ocean air. Interior North America loses heat in the winter, aided by extensive snow cover. New York is "modified maritime," warmed and moisturized by the Atlantic Ocean but only somewhat chilled by continental air.

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