Top 20 Best Things To Do In Chicago In Winter

Winter in Chicago can be truly magical. When snow blankets the streets and twinkling lights shine everywhere, the city transforms into a winter wonderland. Whether you love ice skating, cozy indoor activities, or festive events, there’s something for everyone during this chilly season. Chicago offers a variety of fun things to do that will warm your heart and create lasting memories.

Today, we’ll share some exciting activities and attractions you can enjoy in Chicago this winter. From holiday markets to winter festivals, there are plenty of ways to embrace the season. Get ready to bundle up and make the most of what Chicago has to offer!

Things To Do In Chicago In Winter

1. Ice Skate at Millennium Park’s Maggie Daley Park Ice Skating Ribbon

Ice skating at the Maggie Daley Park Ice Skating Ribbon is a fun winter activity. This unique ice skating path winds through beautiful park scenery. It’s perfect for both beginners and experienced skaters looking to enjoy the outdoors.

The rink is open to all ages, making it a great family outing. You can rent skates on-site if you don’t have your own. The ribbon has a winding path, offering a delightful skating experience. As you skate, enjoy views of the Chicago skyline.

At night, the rink sparkles with lights, creating a magical atmosphere. Skating here is not just about fun; it’s a perfect romantic date idea too. Grab a warm drink nearby after skating and relax in the cozy park setting.

Check for special events throughout the season, including themed skating nights. Maggie Daley Park also has a climbing wall and playgrounds, so bring the kids along! The park truly transforms into a winter wonderland.

Don’t miss this chance to skate in one of Chicago’s most iconic parks. It’s a winter experience you’ll cherish!

Address: 337 E Randolph St, Chicago, IL 60601.

2. Visit the Christkindlmarket in Daley Plaza for Holiday Shopping and Treats

The Christkindlmarket in Daley Plaza is a charming holiday market that captures the spirit of the season. Enjoy the delightful atmosphere filled with festive lights and holiday music. The market celebrates German-style traditions and is open from mid-November to Christmas Eve.

You will find over 50 vendors selling unique gifts, from handcrafted ornaments to beautiful decorations. It’s a perfect spot for holiday shopping. Don’t forget to treat yourself to scrumptious seasonal goodies like bratwurst, pretzels, and spiced wine.

The market’s quaint wooden stalls add to its magical feel. You can soak in the festive cheer while strolling through the decorated plaza, which also features a giant Christmas tree. There are live performances and entertainment happening throughout the market.

Bring your friends or family along for this delightful outing. Each corner offers surprises that make it fun for everyone, from kids to adults. Try traditional foods for a full festive experience.

Whether shopping for unique gifts or enjoying tasty treats, the Christkindlmarket is a must-visit during the holiday season.

Address: 50 W Washington St, Chicago, IL 60602.

3. Explore the Art Institute of Chicago to See Winter-Themed Exhibits

The Art Institute of Chicago is an iconic destination for art lovers. Visiting during the winter is special because many exhibits embrace seasonal themes. You can explore classic and contemporary art surrounded by stunning architecture.

Make sure to check out the museum’s winter-themed exhibits, featuring works that evoke the beauty of the season. Seasonal art-inspired activities may also be available for families. It’s a perfect way to spark creativity and inspiration.

The museum also houses famous pieces from artists like Grant Wood and Vincent van Gogh. Each visit reveals new insights into artistic expressions. After exploring, take a break in the museum café, which offers delightful refreshments.

In addition, admission offers access to multiple exhibitions, so plan on spending a few hours immersing yourself in art. Guided tours are available for those looking to learn more about specific pieces or exhibits.

A visit to the Art Institute during winter will not only warm your heart but also enrich your mind with creative inspirations.

Address: 111 S Michigan Ave, Chicago, IL 60603.

4. Take a Stroll Along the Chicago Riverwalk and Enjoy the Winter Views

The Chicago Riverwalk is a beautiful outdoor destination, especially in winter. Strolling along the Riverwalk offers stunning views of the city’s skyline and the serene riverside. As the water partially freezes, the scenery transforms into a winter wonderland.

Bring a camera along to capture picturesque moments. The Riverwalk is well-lit, making it safe and inviting for evening walks. Along the way, you’ll find pop-up winter activities, including cozy seating areas where you can enjoy hot cocoa.

The winter months bring a unique quietness to the river. Watch the boats pass and enjoy interactions with local wildlife. Many nearby cafes and restaurants offer warm meals and drinks, perfect for warming up after your stroll.

This is also a great spot to admire seasonal decorations that add cheer to the landscape. Don’t forget to appreciate the iconic bridges that span the river and create perfect photo opportunities.

For a memorable experience, make it a part of your winter itinerary in Chicago. The Riverwalk embodies the city’s beauty in every season.

Address: 25 E Wacker Dr, Chicago, IL 60601.

5. Experience the Lincoln Park Zoo Lights, Featuring a Festive Light Display

Lincoln Park Zoo Lights is a spectacular winter event that illuminates the zoo with captivating light displays. Every December, the zoo transforms into a magical wonderland with thousands of twinkling lights. It’s a beautiful way to embrace the holiday spirit with your family or friends.

As you wander through the zoo, you’ll encounter artistic light installations that transform the pathways and exhibits. Each year brings new displays, ensuring that returning visitors always find fresh surprises. Hot chocolate vendors add to the festive atmosphere.

You might even spot some of the animals, as the zoo stays open for visitors during the event. Bring the kids to see animated light displays that tell festive stories. It’s an interactive experience that excites and delights people of all ages.

Live entertainment may be available, including festive music and performances. Plan to snap some photos to preserve these magical winter memories.

Visiting the Lincoln Park Zoo Lights is a joyous holiday tradition in Chicago. It’s a must-see event for anyone looking to enjoy the seasonal cheer.

Address: 2001 N Clark St, Chicago, IL 60614.

6. Attend the Holiday Shows at the Chicago Theatre or Goodman Theatre

The Chicago Theatre and Goodman Theatre are fantastic venues to enjoy holiday performances. Each year, they host a selection of festive shows, from classic plays to contemporary musicals. Treat yourself and your loved ones to an evening of entertainment this winter.

The Chicago Theatre is known for its stunning marquee and historical significance in the city. It hosts a variety of holiday shows, including concerts and theater productions. The ornate architecture adds a magical touch to every performance.

Goodman Theatre offers original holiday plays that often reflect the spirit of the season. Each performance is a blend of talent and creativity, making it a perfect night out for families, couples, or friends. Check their schedule for special holiday events.

Enjoying a show at one of these theaters is more than just watching a performance; it’s about creating unforgettable memories. Arrive early to appreciate the venue and its vibrant surroundings.

Whether you love musicals, drama, or holiday-themed performances, these theaters promise to provide entertainment that captures the joy of the season.

Address: 175 N State St, Chicago, IL 60601 (Chicago Theatre); 170 N Dearborn St, Chicago, IL 60601 (Goodman Theatre).

7. Visit Navy Pier for Winter Activities and the Winter WonderFest

Navy Pier is a popular destination, especially during the winter months. Visit for fun and excitement at the annual Winter WonderFest. This festive event brings together joy and seasonal celebrations for everyone. You’ll find rides, games, and holiday attractions for all ages.

The indoor wonderland is packed with family-friendly activities, including an ice skating rink. You can glide on ice or enjoy the holiday-themed decor throughout the space. The festive atmosphere is perfect for creating lasting memories.

Explore unique shops and grab seasonal treats, from warm drinks to tasty snacks. During Winter WonderFest, there are scheduled activities, like visits with Santa and live entertainment. Families can enjoy crafts and games designed to keep the fun going.

Don’t forget to check out the beautiful lights and decorations that cover the pier, adding a magical touch to your experience. It’s breathtaking to stroll along the pier while enjoying winter views of the lake.

Navy Pier offers a festive escape that fills the holiday season with laughter and joy. It’s an experience that will warm your heart, even when the temperature drops!

Address: 600 E Grand Ave, Chicago, IL 60611.

8. Take a Guided Architecture Boat Tour to Admire the Skyline in Winter

Taking a guided architecture boat tour in winter is a unique way to enjoy Chicago’s iconic skyline. Although it’s colder, winter offers clear views of the stunning architectural masterpieces that define the city. The boat is heated, so you will stay warm while learning about Chicago’s rich history.

As you glide along the river or lake, knowledgeable guides provide insights into the stories behind the famous buildings. It’s both educational and entertaining, making it perfect for architecture enthusiasts and newcomers alike. Be sure to bring your camera for breathtaking winter photography!

With fewer tourists in winter, the tours feel more personal, providing a cozy atmosphere to enjoy the sights. Chicago’s skyline is particularly beautiful against the backdrop of winter skies. You’ll see everything from historic landmarks to modern skyscrapers.

Don’t overlook the seasonal decorations that adorn the waterfront and buildings. It’s a beautiful sight that can only be experienced during this time of year. Ending with a hot drink as the tour concludes is the icing on the cake.

This unique perspective of the city captivates the magic of winter while showcasing Chicago’s architectural beauty.

Address: 112 E Wacker Dr, Chicago, IL 60601.

9. Go Snowshoeing in Lincoln Park or at One of the City’s Parks

Snowshoeing is a fun winter activity that allows you to explore Chicago’s parks in a unique way. Lincoln Park is an excellent choice for snowshoeing, offering wide paths and beautiful scenery. It’s a great way to get outdoors and enjoy the fresh winter air.

The park provides rental options for snowshoes, making it easy for beginners and visiting families. You can course through picturesque trails that showcase lush trees and serene spots. Snowshoeing is a low-impact workout, ideal for all fitness levels.

Among other city parks, find smaller, quieter spots to snowshoe like Washington Park or Humboldt Park. Each offers trails that wind through winter landscapes, providing a peaceful escape from the holiday hustle and bustle.

Pack some snacks, and make it a fun day out in the snow! Experiencing nature while exercising is both refreshing and invigorating. Winter brings a unique beauty that deserves to be explored.

Overall, this winter activity offers both adventure and fun for all ages. Embrace the winter wonderland of Chicago, and enjoy snowshoeing!

Address: 2001 N Clark St, Chicago, IL 60614 (Lincoln Park); Various locations for other parks.

10. Enjoy a Warm Beverage at a Cozy Café in the Loop

In the bustling Loop, finding a cozy café is a perfect way to escape the winter chill. Many cafes serve delicious warm beverages, such as hot chocolate, lattes, and seasonal teas. This is an enjoyable way to recharge during a day of sightseeing or shopping.

Each café has its own unique ambiance, often featuring comfortable seating and lovely decorations. Some popular choices include Intelligentsia Coffee and Merci Galore. Each serves specialty drinks that will satisfy your taste buds.

Spending time in a café allows you to relax and soak in the local vibe. You can take a break, read a book, or enjoy people-watching through the window. Pair your drink with a freshly baked pastry for a delightful treat.

Many cafes in the Loop also feature artwork or offer live music, enhancing your experience. The warmth of the cozy environment contrasts perfectly with the brisk winter air outside.

Whether you’re a local or a visitor, enjoying a warm beverage at one of these cafes creates heartwarming winter moments. So, make time to unwind and enjoy these cozy spaces!

Address: Various locations in the Loop.

11. Explore the Field Museum’s Winter Exhibits and Programs

The Field Museum is one of Chicago’s top attractions, offering exciting winter exhibits and programs. During winter months, the museum showcases seasonal exhibits that captivate visitors of all ages. From ancient artifacts to natural wonders, there’s always something intriguing to explore.

Be sure to check out special winter programs, such as guided tours and family-friendly activities. These events allow you to engage with knowledgeable staff and learn more about the fascinating displays. The museum often hosts temporary exhibits that provide fresh experiences with each visit.

For a fun twist, bring the kids along for hands-on activities related to winter themes. The museum also features IMAX films that immerse viewers in stunning visuals and storytelling.

After exploring, visit the café for a warm meal or drink to recharge. The museum’s welcoming atmosphere makes it a great place to escape the cold while enriching your mind.

Spending a day at the Field Museum guarantees an unforgettable experience that combines education and adventure. Don’t miss out on this winter gem!

Address: 1400 S Lake Shore Dr, Chicago, IL 60605.

12. Attend a Blackhawks or Bulls Game at the United Center

Experiencing a Chicago Blackhawks or Bulls game at the United Center is an electrifying winter activity. The atmosphere is filled with excitement as passionate fans cheer for their teams. It’s a unique way to engage with Chicago’s vibrant sports culture during the chilly months.

Grab your tickets ahead of time for a chance to watch thrilling basketball or hockey matchups. The venue offers fantastic views from every seat, ensuring an enjoyable experience. Enjoy the energy of the crowd and the enticing aromas from concession stands!

During games, you can expect to see fun halftime shows and interactive fan activities. Whether you’re a sports enthusiast or a newcomer, attending a game is a great way to socialize and have fun.

Wear your team colors proudly to show your support; it’s part of the game-day experience! The atmosphere is electric, making it perfect for family outings or outings with friends.

Catching a Blackhawks or Bulls game promises excitement and unforgettable memories. Get your tickets and cheer on Chicago’s teams this winter!

Address: 1901 W Madison St, Chicago, IL 60612.

13. Visit the Museum of Science and Industry for Interactive Exhibits

The Museum of Science and Industry is an excellent place to explore during winter. It offers a variety of interactive exhibits that engage visitors of all ages. As the largest science museum in the Western Hemisphere, it provides endless fun and learning opportunities.

You can explore hands-on displays about everything from space to trains. The museum features a variety of seasonal programs, which may include special holiday-themed activities. Plan ahead for certain exhibits that may require timed tickets.

Don’t miss the chance to see the stunning Christmas Around the World exhibit, which showcases holiday traditions from various cultures. It’s a visual delight and provides enriching insights into festive customs.

The museum’s welcoming atmosphere makes it perfect for family outings, school trips, or solo explorations. End your visit by enjoying a meal at the museum café, with a view of the beautiful lagoon.

Spending a day at the Museum of Science and Industry offers great fun, education, and inspiration during your winter visit. It’s a destination you won’t want to miss!

Address: 5700 S Lake Shore Dr, Chicago, IL 60637.

14. Take a Walk Through the Festive Decorations in the Magnificent Mile

The Magnificent Mile transforms into a winter wonderland during the holiday season. Taking a walk along Michigan Avenue offers a vibrant experience filled with holiday decorations. You’ll find twinkling lights, stunning window displays, and festive decorations adorning shops.

Strolling the Magnificent Mile allows you to soak in the festive atmosphere while enjoying seasonal music and cheer. Famous stores create eye-catching window displays to capture attention and tell holiday stories. It’s a photographer’s dream with plenty of beautiful backdrops.

From shopping to dining, you can explore various options while walking through this bustling area. Treat yourself to a warm beverage from a nearby café as you take in the sights.

Don’t forget to visit the iconic landmarks that line the street, such as the historic Chicago Water Tower and the Tribune Tower. The Magnificent Mile boasts a holiday ambiance that enhances the overall experience of visiting Chicago.

So take your time, and enjoy the beauty of the holiday decorations. It’s an unforgettable way to celebrate the season in the heart of the city!

Address: 800 N Michigan Ave, Chicago, IL 60611.

15. Go to the Chicago Botanic Garden for the Holiday Train Display

The Chicago Botanic Garden is a lovely destination, especially during the winter months. Visit the Holiday Train Display for a delightful spectacle that showcases miniature trains winding through elaborate garden landscapes. This enchanting display will warm your heart as it captures the holiday spirit.

The garden features a beautiful setting adorned with seasonal decorations. The train display is located inside a greenhouse, making it enjoyable even on chilly days. Families will love watching the trains while surrounded by stunning plant life.

In addition to the train display, explore the various gardens that showcase winter beauty. Each garden transforms into a peaceful winter escape, perfect for leisurely walks. Interactive family activities may be available depending on the season.

Don’t forget to stop by the garden shop for holiday gifts and decorations. Enjoy a warm drink at the café nearby while soaking in the beautiful views.

Overall, visiting the Chicago Botanic Garden for the Holiday Train Display is a joyous experience. It’s an excellent way to celebrate the holiday season with family and friends.

Address: 1000 Lake Cook Rd, Glencoe, IL 60022.

16. Experience the Chicago Polar Plunge for a Unique Winter Challenge

For the adventurous, the Chicago Polar Plunge offers a one-of-a-kind winter experience. Participants jump into the icy waters of Lake Michigan to raise funds for Special Olympics Chicago. It’s a thrilling event filled with excitement, camaraderie, and good-natured fun.

Each year, plungers dress in creative costumes, adding to the festive spirit. The event typically takes place in March, providing the perfect cool-down challenge as winter gradually fades. Whether you’re plunging or cheering from the sidelines, the atmosphere is exhilarating.

Registration opens in advance, and participants can collect donations to support their plunge. It’s a wonderful way to engage with the community and make a difference in the lives of others. Each plunge creates unforgettable memories for everyone involved.

After the plunge, join the post-event party, complete with food, drinks, and music. Catch up with fellow participants and relive the excitement of the day. It’s all about fun, fitness, and supporting a great cause.

Taking part in the Polar Plunge is a thrilling way to embrace the winter season. Will you dare to take the plunge?

Address: 9999 S Lake Shore Dr, Chicago, IL 60617.

17. Try the Chicago Winter Brewfest for Local Craft Beers

For beer enthusiasts, the Chicago Winter Brewfest is a fantastic way to warm up this season. Held annually, this event showcases local breweries offering samples of their finest winter brews. It’s a great opportunity to taste unique seasonal flavors crafted by Chicago’s best breweries.

You’ll find a variety of beers, ranging from rich stouts to crisp lagers. The event atmosphere is lively, with plenty of booths and tastings available to explore. Food trucks and vendors often provide delicious food options to pair with your brew.

Attending the Brewfest is also an excellent way to meet fellow beer lovers. Enjoy live music and entertainment, enhancing your experience. Whether you’re a craft beer aficionado or just looking to have fun, this festival caters to all.

Don’t forget to bring your friends along for an enjoyable day of tasting and celebrating local flavors. It’s a fun winter outing everyone will enjoy.

Joining the Winter Brewfest is a perfect excuse to explore Chicago’s craft beer scene. Cheers to good friends and good brews!

Address: 2020 S Racine Ave, Chicago, IL 60608.

18. Discover Unique Gifts at the Gem and Mineral Show at the Field Museum

If you’re searching for unique gifts, don’t miss the Gem and Mineral Show at the Field Museum. This annual event is a treasure trove for collectors and enthusiasts alike. You’ll find stunning gemstones, fossils, and minerals – perfect for gifts or personal collections!

Vendors display a variety of beautiful and rare pieces, showcasing their unique craftsmanship. The event often includes expert talks and demonstrations that provide insights into the fascinating world of gems. It’s educational, fun, and perfect for all ages.

While you’re there, take advantage of the chance to explore the museum’s many permanent exhibits, showcasing science and natural history. This makes a perfect outing combining shopping and education in one fascinating day.

The Gem and Mineral Show usually occurs in late winter, giving you time to find special gifts for upcoming occasions. Whether it’s a birthday, anniversary, or just because, you’ll find something unique.

Plan for a family outing to enjoy holiday shopping while learning something new. It’s an unforgettable experience for everyone involved!

Address: 1400 S Lake Shore Dr, Chicago, IL 60605.

19. Attend the New Year’s Eve Celebration at Navy Pier

New Year’s Eve at Navy Pier is a spectacular way to ring in the new year. The celebration features an amazing fireworks display over Lake Michigan as the clock strikes midnight. It’s a magical moment that you don’t want to miss, with a stunning backdrop of the city skyline.

Arrive early to enjoy live music, entertainment, and various activities throughout the day. The festive atmosphere attracts visitors of all ages, making it a fantastic family-friendly event. Gather with friends and loved ones to reflect on the past year and make new memories.

Local vendors will be on-site to offer delicious foods and warm beverages to keep you cozy throughout the evening. Explore the pier, stroll along the waterfront, and take in the stunning views. There are plenty of photo opportunities to cherish the moment.

Consider making dinner reservations at one of the restaurants at the pier for a memorable experience. Having a meal with a view adds to the excitement of the night.

Celebrating the New Year at Navy Pier is a vibrant way to begin the year ahead. Embrace the joy and festivities in this beautiful setting!

Address: 600 E Grand Ave, Chicago, IL 60611.

20. Take a Cozy Walk Through the Chicago History Museum’s Winter Exhibits

The Chicago History Museum is a great place to explore during the winter months. The cozy atmosphere indoors invites you to learn about Chicago’s rich history. During winter, special exhibits capture the essence of the season and its impact on the city.

Wander through the museum and discover exhibits that tackle various historical topics. Engaging displays tell unique stories about the city, making it an educational outing for everyone. The museum’s knowledgeable staff often provide tours to enrich your experience.

Take your time and dive into the interactive exhibits, which are perfect for curious minds. The warmth of the museum offers a pleasant escape from the cold outside. Special winter activities might be available for families, adding to the fun.

After your visit, stop by the museum café for a warm drink or snack to complete your outing. The museum provides a lovely atmosphere to relax and reflect on the enlightening experiences you had.

Exploring the Chicago History Museum during winter will leave you inspired by the stories that shaped the city. It’s a charming way to enjoy the season!

Address: 1601 N Clark St, Chicago, IL 60614.

Final Thoughts

Chicago in winter is a magical place filled with exciting activities and beautiful sights. From skating in Millennium Park to exploring the wonders of museums, the city offers a rich array of experiences. Each event and location captures the unique spirit of the season, making it easy to create memories with family and friends.

Whether you’re enjoying holiday lights at the zoo or indulging in warm drinks at cozy cafes, Chicago transforms into a winter wonderland. The festive atmosphere fosters joy and togetherness, strengthening community bonds as people come together to celebrate.

The activities highlighted here showcase just some of the wonderful winter festivities available. Each experience offers a chance to enjoy the cold months while embracing the warmth of the city’s culture.

As you plan your winter outings, embrace everything that makes Chicago special during this time of year. And if you’re interested in exploring more delightful winter activities, check out some amazing things to do in Edinburgh at Christmas or discover more adventures in Utica, IL!