Chicago
What Are the Best Things to Do in Chicago in Winter?
Writen By: Ramsha Rehan
Chicago
What Are the Best Things to Do in Chicago In Winter?
Chicago is one of those cities that never slows down, not in summer, not in fall, and definitely not during Chicago in winter. Whether you’re visiting for the first time or exploring as a local, this guide covers the best things to do in Chicago, from popular attractions to hidden gems, food spots, parks, outdoor adventures, and the best winter activities in Chicago.
SIGHTSEEING & ICONIC CHICAGO LANDMARKS
1. Millennium Park & Cloud Gate (The Bean)
One of the top Chicago tourist attractions, Millennium Park, is iconic. Cloud Gate, known as The Bean, reflects the skyline and has become one of the most photographed spots in the city.
In Chicago in winter, the area looks especially stunning with snow on the ground and seasonal lights. This spot should be on every traveler’s list of things to do in Chicago.
2. Chicago Riverwalk
The Chicago Riverwalk is a scenic waterfront walkway filled with restaurants, photo spots, and viewpoints. It’s beautiful year-round, but winter in Chicago, IL, gives it a cozy, dramatic look with reflections and cold breezes off the river.
You can walk, relax, or grab a warm drink along the way. It’s also the starting point for most Chicago boat tours.
From
$19
Unveiling Chicago's Riverwalk: A Historical Walking Tour
Chicago's Riverwalk & History Tour explores the city's iconic skyline from a unique riverfront perspective. Discover architectural marvels and the rich history of the Chicago River. This walk offers an intimate, Instagrammable experience led by a local guide, revealing hidden stories of the Windy City. Perfect for architecture and history enthusiasts.
Book Now3. Chicago Architecture Center & Chicago Architecture Boat Tour
If you’re searching for a classic experience, the Chicago architecture boat tour is the city’s signature attraction.
You float through the skyline, pass famous buildings, and learn how Chicago’s architecture shaped the world.
Even in colder months, some cruises operate enclosed boats, great for things to do in Chicago.
From
$44.43
Chicago Architecture River Cruise: See the Skyline!
Chicago Architecture River Cruise lets people see Chicago in a fun way. This boat tour goes down the Chicago River. People can see over 40 famous buildings, like the John Hancock Center and the Wrigley Building. An expert guide tells people about the buildings and their history. It's a great way for everyone to see Chicago, even if they live there! People can sit and relax while seeing the city's amazing buildings. The boat goes to places like the Chicago River, Chicago Skyline, Navy Pier, and the Willis Tower. People will learn a lot about the city's buildings as they float by. This boat tour includes live talking from an expert, and a tour of the Chicago River. Drinks cost extra to purchase, and there is no WIFI on the boat.
Book NowFOOD, CAFÉS & WINTER COMFORT EATS
4. Deep Dish Pizza — A Must Experience
Deep dish is an essential part of the Chicago experience. Gooey cheese, buttery crust, rich sauce, the perfect winter comfort meal. Great for warming up after a long sightseeing day.
Popular spots: Giordano’s, Lou Malnati’s, Pequod’s.
5. Chicago Hot Dogs & Local Eats
A true Chicago-style hot dog (no ketchup!) is a must. In the colder months, comfort foods like Italian beef sandwiches, soups, and winter specials dominate menus across the city.
6. Cozy Cafés & Local Bakeries
Chicago has endless cozy cafés, especially perfect for Chicago in the winter when you need something warm:
- Cocoa + pastries at small bakeries
- Lakeside café views
- Warm, quiet reading corners
7. Chicago Food Halls
Food halls like TimeOut Market Chicago and Revival Food Hall offer global cuisines, local favorites, and warm indoor seating ideal for things to do in Chicago this weekend when the weather is unpredictable.
HIDDEN GEMS & OFF-THE-BEATEN-PATH EXPERIENCES
8. Neighborhood Walks: Pilsen, Andersonville & Wicker Park
Chicago’s neighborhoods are full of stories. Wander through mural-filled streets in Pilsen, cozy Swedish cafés in Andersonville, or vintage shops in Wicker Park.
Neighborhood exploring is one of the most enjoyable fun things to do in Chicago outside the usual tourist route.
From
$65
Pilsen Chicago Walking Tour: Art, Murals & Mexican Culture
Walking Tour: Pilsen Chicago - Creativity & Community invites everyone to explore one of Chicago's most vibrant neighborhoods. This walking tour dives into the heart of Pilsen, a place that Forbes magazine calls one of the "15 Coolest Neighborhoods in the World". It's a journey through art, culture, and community, perfect for those wanting to see Chicago beyond the usual tourist spots. The adventure starts at the famous Four Seasons Mosaic by Marc Chagall. From there, the tour takes a ride on the 'L' train from the historic Quincy station to Pilsen. Once in Pilsen, get ready for a taste of real Mexican food and a walk past colorful murals and unique buildings. The tour also includes a visit to the National Museum of Mexican Art, where you can see amazing art exhibits. The tour wraps up with a trip back to the Loop to see the iconic Picasso sculpture in Daley Plaza. With an expert local guide leading the way, this small-group tour ensures a personal experience. It includes transit tickets and a museum donation. Keep in mind that food, drinks, and gratuities are not included. This tour shows you the real Pilsen, a neighborhood full of creativity and community spirit.
Book Now9. Garfield Park Conservatory
This warm indoor garden makes a perfect winter escape. You walk into a tropical jungle while it’s snowing outside, unmatched vibes for Chicago in winter.
10. Underground Speakeasies & Jazz Bars
Chicago’s jazz and speakeasy culture goes deep. Hidden bars, candle-lit music rooms, and intimate performance venues make for perfect winter nights.
PARKS, NATURE & LOCAL OUTDOOR ACTIVITIES
Even though winters can be cold, there are surprisingly many winter activities in Chicago that get people outside.
11. Lakefront Trail
A stunning 18-mile path along Lake Michigan. In winter, it’s peaceful, quiet, and beautifully atmospheric. Bundle up, but the views are worth it.
12. Lincoln Park & Lincoln Park Zoo
A huge park with ponds, skyline views, wildlife, and more. During winter, the zoo hosts seasonal light displays (more on that below).
One of the best things to do in Chicago in winter for families.
13. Maggie Daley Park Ice Skating Ribbon
One of the most unique skating experiences in the U.S. is a winding ribbon-shaped ice path surrounded by city views. This is easily one of the top winter activities in Chicago.
MUSEUMS, CULTURE & INDOOR EXPERIENCES
For days when Chicago’s weather goes full winter mode:
14. Art Institute of Chicago
One of the world's top museums. Warm, quiet, and full of breathtaking art, perfect for an indoor day.
From
$90.01
Chicago Art Institute: Skip-the-Line Private Tour
Private Art Institute of Chicago Skip-the-Line Guided Tour. This is a special walking tour for people who love art and want to see the best pieces at the Art Institute of Chicago without waiting in long lines. The tour is just for the group and a guide, so it feels personal. What to Expect: The tour visits famous artworks like 'Paris Street, Rainy Day' and 'Sunday on La Grande Jatte'. People will also see 'Nighthawks' and 'The Old Guitarist'. The guide shares stories about the art and artists. The Art Institute of Chicago is a very big museum with lots of famous art. It has art from all over the world and different times in history.This private tour lasts for 2.5 hours and includes a professional tour guide just for the group. It also includes all entrance fees. The tour is wheelchair friendly. This tour does not include hotel pickup or drop-off, but the guide suggests using UBER or a taxi. Gratuities (tips) are not included in the price.
Book Now15. Museum of Science & Industry
Great for families and curious minds, full of hands-on exhibits, simulations, and seasonal displays.
From
$52
Explore Chicago's Museum of Science & Industry (Audio)
Explore Chicago's Museum of Science and Industry (MSI) at a comfortable pace with this audio tour. It's a self-guided adventure that lets visitors discover the wonders of science and technology at one of the world's largest science museums. This audio tour is perfect for anyone who wants to learn about cool stuff like how bodies work, the future of tech, and even see baby chicks hatch. The tour includes entrance tickets, a downloadable audio guide in English, and easy-to-follow directions through the museum. Visitors will get to wander through exhibits like the Pioneer Zephyr Train, Colleen Moore's Fairy Castle, and the Genetics Gallery. Please note that this experience does not include a personal guide or headphones. The Museum of Science and Industry has interactive exhibits and immersive experiences, ensuring a fun and educational visit. It allows for planning flexibility and exploration, and guarantees admission with pre-purchased tickets.
Book Now16. Chicago Cultural Center
A free cultural hub with exhibitions, shows, and the largest Tiffany dome in the world.
UPCOMING WINTER EVENTS IN CHICAGO
These help your blog feel fresh and updated. Here are major events in Chicago your readers will love:
17. Christkindlmarket Chicago
Chicago’s iconic European-style Christmas market with gifts, ornaments, pretzels, mulled wine, music, and more.
A classic winter attraction.
18. Magnificent Mile Lights Festival
A beautiful parade with music, lights, fireworks, and festive décor. One of the most magical things to do this winter in Chicago.
19. ZooLights at Lincoln Park Zoo
A stunning holiday light festival is extremely family-friendly and fun.
20. Ice Skating at Millennium Park
A seasonal must-do, locals and tourists gather here to skate under city lights.
21. New Year’s Eve Fireworks at Navy Pier
One of the biggest winter celebrations in Chicago.
22. Winter Solstice Concerts & Indoor Seasonal Shows
Great for cozy winter evenings when you want to stay indoors but still experience culture.
SHOPPING & MARKETS
23. State Street & The Magnificent Mile
Endless shopping, holiday decorations in winter, and fun weekend activities.
24. Local Boutiques & Winter Pop-ups
Chicago often hosts small indoor holiday markets, perfect for local gifts and handcrafted goods.
Conclusion
Chicago is a city that never stops offering something new, from architecture and food to parks, neighborhoods, and seasonal Chicago events. Whether you’re exploring Chicago in the winter, planning weekend activities, or looking for hidden gems, the city gives you plenty of ways to experience it your own way.
Use this guide to plan what matters most to you: sightseeing, food, local culture, or the best winter activities in Chicago. And if you want more city guides, travel ideas, or easy ways to discover things to do anywhere you go, explore more on Dyvarcity, your simple and reliable place to find and plan great experiences.
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