Snowy Days, Windy City Ways: Chicago’s Must-Do Winter Activities
When it comes to Chicago in the winter, The Windy City doesn’t just blow a gale; it throws a party, covering itself in a sparkling layer of snow and transforming into a winter wonderland that could rival the North Pole. Forget what you’ve heard about the chill—this city’s vibrant spirit and bustling atmosphere keep the cold at bay.
From the glittering ice rinks to the cozy jazz clubs, Chicago in winter is an experience not to be missed. Whether you’re a thrill-seeker looking to embrace the frost or someone who prefers the warmth of indoor activities, there’s something here for everyone. Buckle up as we dive into a guide that’ll have you seeing your breath in the air as a badge of honor, exploring everything that makes Chicago the place to be when the temperatures drop.
1. Ice Skating at Millennium Park
Starting with a classic, ice skating at Millennium Park is as Chicago as deep-dish pizza. There’s nothing quite like gliding across the ice with the city’s towering skyscrapers serving as your backdrop. The McCormick Tribune Ice Rink is where you’ll want to lace up your skates. It’s a popular spot, so hitting the ice during weekdays or in the mornings can help you avoid the crowds.
And don’t worry if you didn’t bring your skates; rentals are available for a nominal fee. Whether you’re performing pirouettes or clinging to the edge for dear life, it’s a must-try winter activity.
Location & Costing: Millennium Park, free admission with skate rental fees around $13-15.
2. Christkindlmarket
If you’ve ever dreamed of strolling through a European Christmas market, then dream no more. The Christkindlmarket in Daley Plaza brings the Old World charm right to Chicago’s doorstep. Wander among the wooden stalls adorned with twinkling lights, sipping on hot spiced wine or indulging in some hearty German fare.
The market is a treasure trove of unique gifts, from hand-blown ornaments to traditional crafts. It’s the perfect place to find something special for the holidays or simply to treat yourself.
Location & Costing: Daley Plaza, free entry, prices vary for goods.
3. Winter WonderFest at Navy Pier
Imagine a playground so vast and so filled with holiday cheer that it could only belong in Chicago. Winter WonderFest at Navy Pier is exactly that—a fantastical indoor wonderland complete with ice skating, rides, giant slides, and more holiday decorations than you can count.
It’s the perfect escape from the cold, offering fun for the entire family. Tickets can be purchased in advance, which is a good move during the busier days of the season. Don’t miss the indoor Ferris wheel, which offers a cozy ride with spectacular views of the winter festivities below.
Location & Costing: Navy Pier, ticket prices vary based on activities and age, starting from around $20 for general admission.
4. Chicago Cultural Center Events
The Chicago Cultural Center is a beacon of arts and culture year-round, but it shines even brighter in the winter months. Offering a wide range of free events, from music concerts to dance performances and art exhibitions, this historic landmark is a testament to the city’s rich cultural fabric.
The building itself is a masterpiece, with its stunning stained glass domes and intricate mosaics. Check the center’s schedule before your visit to catch the best of what’s on. Whether you’re looking to expand your artistic horizons or simply escape the cold for a few hours, the Cultural Center welcomes you with open arms—and for free.
Location & Costing: Chicago Cultural Center, free for all events.
5. Hot Chocolate Tour
Who knew that a cup of hot chocolate could be an adventure? In Chicago, it’s a decadent expedition through the city’s best chocolatiers and cafes, each offering their unique twist on this classic winter warmer. From thick, European-style concoctions to spicy, innovative creations, the Hot Chocolate Tour is a must for anyone with a sweet tooth.
Make your first stop at Mindy’s HotChocolate in Bucktown, where the James Beard Award-winning chef serves up a variety of flavors. Don’t forget to check out Katherine Anne Confections in Logan Square for some handcrafted marshmallows to top off your drink.
Locations: Vary across the city, with prices for a cup ranging from $3 to $7.
6. The Art Institute of Chicago
An oasis of culture and calm, the Art Institute of Chicago becomes even more magical in the winter. Wander through the halls adorned with holiday decorations and discover seasonal exhibitions alongside the museum’s extensive collection of artworks spanning thousands of years.
The Thorne Miniature Rooms, decorated for the holidays, are a particular delight. Don’t miss the chance to see the iconic “American Gothic” and spend some time in the modern wing, a masterpiece of architectural design in its own right.
Location & Costing: Downtown Chicago, general admission is around $25 for adults, with discounts available for students and seniors.
7. Lincoln Park Zoo Lights
The Lincoln Park Zoo transforms into a luminous fairyland with its annual ZooLights celebration.
With over 2.5 million lights illuminating the grounds, it’s a spectacular sight that enchants both the young and the young at heart. This free event includes not just impressive light displays but also live ice carving, hot chocolate stands, and the chance to see some of the animals at night. It’s a festive way to enjoy the zoo in a whole new light—literally.
Location & Costing: Lincoln Park Zoo, free entry, though some activities inside may have fees.
8. Snowshoeing at Northerly Island
For those looking to add a dash of adventure to their winter, snowshoeing at Northerly Island offers a unique urban outdoor experience. This peninsula jutting into Lake Michigan provides serene views and a surprisingly remote feeling, considering its proximity to the downtown area.
Snowshoeing here is dependent on snow conditions, so it’s a bit of a spontaneous adventure. When the snow is right, rental equipment is available, making it easy for beginners to give it a try. It’s a peaceful way to explore the natural beauty of Chicago’s winter landscape.
Location & Costing: Northerly Island, snowshoe rental fees are around $5-10, contingent on snow conditions.
9. Chicago Architecture Foundation River Cruise
Believe it or not, winter might just be the secret best time to embark on a Chicago Architecture Foundation River Cruise. While most associate this activity with warmer months, the winter cruises offer a unique perspective on the city’s stunning architecture, free from the crowds and with the buildings framed against crisp winter skies.
Bundle up and listen as knowledgeable guides share stories of the city’s architectural marvels. It’s a peaceful, awe-inspiring way to see Chicago from a different angle.
Location & Costing: Prices and availability vary, with adult tickets typically around $40-$50. Winter schedules may be limited, so check in advance.
10. Brewery Tours
Chicago’s craft beer scene doesn’t cool down with the weather; in fact, it might just be the perfect antidote to a chilly day. Many of the city’s breweries offer tours, giving you a behind-the-scenes look at the brewing process, complete with tastings of unique winter brews.
Revolution Brewing and Lagunitas Brewing Company are among the fan favorites, offering insights into the art of beer making. These tours are not just about sampling the goods; they’re educational experiences that highlight the passion and creativity behind Chicago’s craft beer culture.
Locations & Costing: Various breweries, with tours generally ranging from free to $15, often including tastings.
11. The Magnificent Mile
No winter visit to Chicago is complete without a stroll down The Magnificent Mile, especially when it’s decked out in its holiday best. This famous stretch of Michigan Avenue is a paradise for shoppers, with everything from luxury boutiques to iconic department stores.
But it’s more than just shopping; the festive lights, window displays, and street decorations add to the joyous atmosphere. Even if you’re just window shopping, the energy of The Magnificent Mile in winter is contagious.
Location: Michigan Avenue, free to explore, shopping costs vary.
12. Winter Theater Season
Winter in Chicago is a fantastic time for theater enthusiasts. The city’s vibrant theater scene comes alive with an array of performances, from Broadway hits in the Theatre District to innovative productions in smaller venues across the city.
The Goodman Theatre’s annual production of “A Christmas Carol” is a beloved tradition, while companies like Steppenwolf and the Chicago Shakespeare Theater offer compelling dramas, comedies, and everything in between. It’s a chance to see top-tier talent in some of the most intimate settings.
Locations & Costing: Various theaters, ticket prices vary widely depending on the show and seating options.
13. Sledding at Soldier Field
Sledding is a winter classic, and in Chicago, you can enjoy this beloved pastime with a view of Soldier Field as your backdrop. The park district sets up a sledding hill whenever there’s enough snow, making it a popular spot for families and those young at heart.
It’s an exhilarating way to enjoy the outdoors and get a unique perspective on one of the city’s iconic sports stadiums. Best of all, it’s completely free—just bring your own sled and a sense of adventure.
Location & Costing: Just outside Soldier Field, free of charge.
14. Museum of Science and Industry
The Museum of Science and Industry becomes a wonderland of its own during the winter months, offering a warm escape with fascinating exhibits that are perfect for curious minds of all ages. From the mesmerizing mirror maze to the U-505 submarine and the interactive science storms exhibit, there’s no shortage of awe-inspiring discoveries.
The museum also hosts seasonal exhibits and events that are sure to add an extra layer of excitement to your visit.
Location & Costing: Located in Hyde Park, ticket prices start at around $21.95 for adults and $12.95 for children, with additional charges for some exhibits.
15. Ice Climbing at Maggie Daley Park
For those looking for a bit more adrenaline, Maggie Daley Park offers a unique urban adventure with its ice climbing wall. Whether you’re a seasoned climber or a novice eager to try something new, this activity provides a thrilling and utterly unique perspective of the Chicago skyline from your icy ascent.
The park offers equipment rental and instruction, making it accessible for climbers of all levels. It’s a fantastic way to challenge yourself and experience the joy of ice climbing right in the heart of the city.
Location & Costing: Maggie Daley Park, prices vary for climbing sessions and equipment rental.
16. Chicago Restaurant Week
Chicago’s culinary scene shines even brighter during Restaurant Week, a celebration of the city’s diverse and delicious dining options. This event allows foodies to explore a wide range of restaurants through prix-fixe menus at a fraction of the normal cost.
From Michelin-starred fine dining establishments to hidden local gems, it’s the perfect opportunity to taste your way through the city’s best dishes. Make sure to book reservations in advance, as spots fill up quickly for this popular event.
Locations & Costing: Participating restaurants throughout the city, prix-fixe menu prices typically range from $24 for lunch to $48 for dinner.
17. Polar Adventure Days
Embrace the chill and head over to Northerly Island for Polar Adventure Days. This series of events is designed to connect you with nature and wildlife, offering a unique winter experience right in the city. You’ll have the opportunity to meet Siberian huskies, watch birds of prey in action, and even explore the island on snowshoes, conditions permitting.
It’s a day of adventure and education, perfect for families or anyone looking to add a bit of wilderness to their urban exploration.
Location & Costing: Northerly Island, free entry, some activities may have nominal fees.
18. Jazz Clubs
Chicago’s jazz scene doesn’t cool down in the winter; it sizzles. The city is renowned for its contributions to the genre, and what better way to spend a chilly evening than in one of its legendary jazz clubs? Green Mill in Uptown offers a trip back in time with its vintage decor and lineup of top-notch performers.
For a more contemporary setting, check out the Jazz Showcase in the South Loop. Sipping on a warm drink while the smooth sounds of jazz envelop you is the perfect way to unwind after a day of exploring.
Location & Costing: Various clubs across the city, cover charges and drink prices vary.
19. Chicago Botanic Garden’s Wonderland Express
Just because it’s winter doesn’t mean you can’t enjoy the beauty of nature. The Chicago Botanic Garden’s Wonderland Express transforms the gardens into a stunning winter landscape, complete with a miniature train weaving through replicas of Chicago landmarks.
It’s a magical experience for visitors of all ages, offering a peaceful break from the hustle and bustle of the city. The indoor gardens also provide a lush, warm environment where you can enjoy exotic plants and flowers.
Location & Costing: Chicago Botanic Garden, ticket prices for Wonderland Express may vary, check in advance.
20. Ice Fishing on Lake Michigan
For a truly unique winter activity, why not try ice fishing on Lake Michigan? It’s a peaceful yet exhilarating way to enjoy the great outdoors and maybe even catch your dinner. Several local companies offer guided trips, providing all the necessary equipment and expertise you need to safely enjoy this winter pastime. Whether you’re a seasoned angler or new to the sport, ice fishing offers a serene escape from the city’s pace and a chance to connect with the natural world in a different way.
Location & Costing: Various locations along Lake Michigan, prices for guided tours vary.
Chicago’s winter landscape is as varied and vibrant as its summer counterpart, offering an array of activities that appeal to every interest and age group. From the thrill of ice sports to the warmth of indoor cultural experiences, the Windy City proves that winter can be a time of discovery and delight. So, bundle up and embrace the chill, because Chicago in winter is a playground waiting to be explored. Whether you’re gliding across an ice rink, warming up in a cozy jazz club, or marveling at the twinkling lights of the city, each moment spent here adds up to an unforgettable winter experience.
Remember, Chicago’s winter charm is all about diving into the experiences it offers, each one a testament to the city’s enduring spirit and warmth. So, lace up those boots, pull on your gloves, and get ready to make some chilly memories in this spectacular city.