20 Most Exciting Winter Activities in Chicago

There’s a reason why Chicago is consistently rated one of the country’s most exciting cities, and we’re not just referring to the hot dog stands. With so much diversity and energy, there are plenty of winter activities in Chicago to keep you, your friends, and your family entertained. So, it doesn’t matter if you’re looking for a family-friendly activity or something more adventurous, because Chicago got you covered.

Chicago has bold flavors, cutting-edge ideas, and not to mention, exciting experiences. We know exactly what you’re looking for, and we understand why you only have time to read the best recommendations. Based on that reason, we’ve pulled the best winter activities in Chicago for your next visit in the windy and cold season. So, bundle up and get ready to explore the best winter activity in Chicago!

Is it Worth Visiting Chicago in Winter?

Yes, it is worth visiting Chicago in winter. In fact, winter is arguably the best season to enjoy the city. You can join so many indoor and outdoor activities, and you will have a great and memorable holiday with your family. Even better, there are so many winter attractions you can enjoy for free, too!

What Are the Snowiest Months in Chicago?

The snowiest months in Chicago are during January and February. The snow can get up to 21,9 inches. However, the snowfall can vary each year, and you need to look at the weather forecast before deciding to get on outdoor activities, to ensure that there is enough snow for snow activity but also safe for being outside.

BEST Winter Activities in Chicago

1. Explore The Loop

The Loop is an area of downtown Chicago that surrounds Michigan Avenue and Grant Park. The area is full of things to do, see, eat and drink, all within walking distance of each other. With so many excitements, we can totally understand why visiting the area is one of the most recommended winter activities in Chicago.

It has been called “The Center of The City” since its construction in 1871, and it offers something for everyone during Chicago winter. From museums and art galleries to shopping at some of the best stores in town, the are has it all.

2. Observe The City View from Willis Tower Skydeck

If you’re looking for a breathtaking experience that makes you feel like you’re floating above Chicago, we recommend you to visit the Willis Tower Skydeck. It is located on the 103rd floor of the Willis Tower (formerly Sears Tower), and it offers you the most amazing views of the city that are unlike any other.

In our opinion, the Willis Tower Skydeck is one of those places where it’s best to go with someone else to share the experience together. Tickets are $41 per adult for 30 minutes experience.

3. Walk The Sculpture Garden in Lincoln Park

There are many reasons to travel from Chicago’s downtown to The Sculpture Garden in Lincoln Park. Of course, you’ll see The Standing Lincoln sculpture and some other fantastic works including those by Alexander Calder and Henry Moore.

The garden offers a special charm that will stay that way throughout all seasons. It has over 20 miles of walking paths, which we believe will help warm you up in the windy, cold winter. And best of all, it is free, so you can spend time with your family or friends without worrying about traffic or parking, at least for a while.

4. Take a Selfie at The Bean

It’s a rite of passage for both tourists and locals. Without a doubt, the bean is truly one of the most Instagrammed spots in the city. It’s got that perfect combination of kitsch, whimsy, and also artistry that makes taking a selfie at the bean so much more than just another excellent shot.

Located in the Millenium Park, The Bean is simply hard to miss. However, do remember that it can be pretty crowded since almost everyone wants to take a selfie there. One simple advice, we would suggest that you wear a bright and colorful outfit, especially if you’re going to take a selfie that pops.

5. Delight in Holiday Lights

The best holiday-light winter attraction in Chicago is definitely the Magnificent Mile Lights Festival. As one of the most famous annual events in the city, this event gets better every year, and you just can’t miss it.

The festival usually features more than 100 light displays, including a giant Christmas tree, a life-sized gingerbread house, and a snow globe that will make you feel like you’re inside the famous animation movie, Frozen. In addition, there will also be live music from local bands and performers throughout the day. The festival takes place at the Michigan Avenue between Oak Street and Lake Shore Drive, and it’s free to attend!

6. Visit the Christmas Market

If you are looking for fun things to do during winter in Chicago, we recommend you to visit the Christkindlmarket at Daley Plaza in Millennium Park. It is an annual German-style Christmas market, and it opens from November 21st through December 24th.

The market has over 200 vendors selling goods like handmade jewelry, food & drink, crafts, and more. In addition, you and your kids can also meet Santa Claus here from 10:00 A.M. until 01:00 P.M. In our opinion, this is one of the must-visit winter activities in Chicago for everyone in the family.

7. Sip the Best Cocktails

No matter how much snow falls outside, a great bar in Chicago will never stop serving the best cocktails. Hence, we believe that sipping cocktails can be a great Chicago winter activity for adults.

When it comes to cocktails, we can assure you that Arami is the ultimate bar to go to. They have over 50 drinks on their menu, so we’re pretty sure you’ll find something delicious for you and your friends. Furthermore, the cozy, dimly lit atmosphere and friendly staff at Arami will also make you feel like you’ve been transported to a secret spot where you can relax and forget all your worries.

8. Adventure at the Ice Rinks

Ice skating in Chicago is a beloved pastime. There are many places to enjoy the sport in this city, including one of the most famous, which is the Millennium Park. This park boasts an ice skating rink that is open year-round, and in our opinion, it’s a great place to take your family or friends for some fun on the ice.

You can even take one of their skating classes available for beginners, experienced skaters, and even if you are interested in Hockey. So, what are you waiting for? Head to their website now to check the availability of the tickets.

9. Get Entertained at the Jazz Bar

Green Mill is the ultimate place to go for those of you who are looking for a place to enjoy a drink while listening to good live music performances. The place was officially opened in 1907, and it has been playing host to the best jazz artists since then.

It’s a small, intimate venue, yet it has a laid-back atmosphere and a fantastic selection of drinks. In our opinion, this place is one of the must-visit bars in Chicago. The good news is that the jazz bar hosts over 100 shows every month, featuring some of the biggest names in jazz and blues music.

10. Take the Historical Walk

There’s no better way to experience Chicago in winter than by taking a historical walk. By doing so, you’ll learn everything from its earliest settlers to its most influential architects. You will learn about its most famous landmarks to its most notorious crimes.

Moreover, this activity is entirely free, and in our opinion, this is one of the best winter activities in Chicago for those of you who want to enjoy the time walking by yourself. But if you feel like going in groups, you can also join the guided historical tours with different themes. The admission fee varies, starting only from $30 per person.

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11. Historic Water Tower District Tour

There are plenty of things to do in Chicago in December. For example, you can tour the historic water tower district. As one of the most historical spots in the city, it has been around since 1869. Plus, it is one of the oldest neighborhoods in the city.

It was once home to many wealthy families, but now it’s full of unique shops and restaurants that reflect the neighborhood’s history and character. The water tower is also the only survivor of the infamous Chicago fire.

12. Watch an Improv Comedy Show

If you opt for a non-skating activity, we believe without a doubt that improv comedy can be a great getaway to relax and enjoy. Many improv shows are happening all over the city, and we have to say that it’s easy to find one that’s right for you.

If you’re looking for something more traditional and structured, The Second City is your best bet. They have shows on Wednesday through Saturday nights and Sunday afternoons, with performances starting at 08:00 P.M. on Saturday nights. Tickets start at $25 and go up depending on the night.

13. Have Fun at Chicago Park District

Next up we have the Chicago Park District, a place that offers tons of kids’ winter activities in Chicago. So, if you’re planning to visit the city with the kids, this is one of the spots that you just can’t miss.

You can rent cross-country skis at several parks or bring snowshoes and hike through one of their many trails. Moreover, there are also sledding hills throughout the city, which are perfect for younger kids. If you don’t want to go outside, you can always take your child skating at one of their indoor rinks instead.

14. Go on a Winter Culinary Tour

Go On A Winter Culinary Tour

A winter travel activity in Chicago can only be complete with the city culinary tour. For the budget-minded traveler, we think a food truck tour is the perfect way to sample some of Chicago’s best street food. You can try everything from hot dogs and deep-dish pizza to tamales and tacos for just a few dollars.

On the other hand, if you’re looking for a more upscale experience, we recommend you to sample some of the city’s finest cuisine. For that purpose, Alinea is the restaurant to go to. Plus, it has also been named the best restaurant by numerous publications. The pricing is higher, but in our opinion, you will get a fine dining experience you can always remember.

15. Admire the City Architecture

Admire The Architecture

You probably know that Chicago is also home to many iconic buildings, right? In order to enjoy the best view of the buildings, we think the best time to admire the city’s architecture is during Chicago’s winter months. You will be able to see them when the city’s buildings are most visible, as there are no leaves on the trees to block your view.

If you’re interested in learning more about Chicago’s architectural history, we highly recommend you to go to the Chicago Architecture Center. This museum is devoted to the city’s architecture and features several interactive exhibits. The ticket price varies for different tours, but the group tour starts from $37,5 per person.

16. Sledding Hills Spree

Sledding Hills Spree

Do you know that Chicago has numerous dedicated sledding hills during winter? Do you also know that it is so popular that it can be considered Chicago’s favorite winter activity? One of the most popular sledding spots is Cricket Hill, which hosts the annual kids and kite festival.

It is located at the northern end of Lincoln Park, and you’ll be able to enjoy the view of Lake Michigan from the top of the hill. Moreover, it is also kid-friendly and safe even for younger kids, making it a perfect snow activity for kids in Chicago.

17. Join the Botanic Garden Winter Activities

Join The Botanic Garden Winter Activities

Another outdoor activity you can take part in during the Chicago winter month is visiting Chicago Botanic Garden. There are plenty of activities you can take part in, including botanic art class and photography. Even during the winter, you can still explore peaceful nature and breathe fresh air.

In our opinion, some of the best activities that you can join at the park is the guided woods walk, create garden art, and of course, admire the beautiful winter birds. The admission fee starts from only $9,95 for adults, and you can also visit their garden view cafe and garden shop afterward.

18. Observe the Animals at Brookfield Zoo

Observe The Animals At Brookfield Zoo

If you want to witness how animals do their activities in the snow, then we think you should visit Brookfield Zoo. You’ll see animals such as tigers, lions, and bears being cute in the snow. Being the perfect place for family, there are also plenty of activities for the whole family, including penguin-feeding adventures. They are open daily from 10:00 A.M. to 05:00 P.M. and you can get tickets for $24,95 for adults and $17,95 for kids.

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19. Art Exchange in the Art Institute of Chicago

Art Exchange In Art Institute of Chicago

While there are many family-friendly events in Chicago, we have to remind you that you can always go to the Art Institute of Chicago. Besides exhibiting the best arts from different artists and cultures, they also host various events and classes you can participate in.

For your info, one of the most exciting activities is the art exchange, where visitors of all ages are invited to create an art project, explore the multisensory gallery, and go on a custom museum tour. In addition, visitors are also provided with materials and guidance for free.

20. Take a Breather at the Garden of The Phoenix

Take A Breather At the Garden of The Phoenix

Once you step foot in this place, we can guarantee that you won’t regret anything. The view it offers during the winter is simply breathtaking, and we’re pretty sure that you will want take many pictures to keep as many memories as possible.

The Garden of The Phoenix is in Jackson Park, right behind the Science and Industry Museum. Interestingly, the park has a zen vibe that allows you to relax and reflect. In our opinion, this is the perfect place for a winter getaway when you want to take a breather from your busy life.

Final Thoughts

Planning a winter trip needs to be completed with a complete to-do list, plus a list full of places to go. If you are thinking of going to Chicago this year, we think Chicago is definitely one of the best cities to go for your next winter trip. Therefore, we believe a list full of the best recommendations of winter activities in Chicago will come useful for you. So, before you pack your bags and winter boots, make sure you check out out list above and we believe you will have the best moments to remember in Chicago!

Latest Post:

What activities can toddlers do in Chicago in the winter?

There are still many activities toddlers can do in Chicago in the winter. Even though some outdoor activities involving snow adventure may be limited for toddlers, they can still have fun sledding on short hills. They can also observe animals in the zoo and participate in art activities in museums and galleries.

What to do in Chicago when it’s snowing?

You can do many things in Chicago when it’s snowing. Ice skating is one of the most popular snow activities in Chicago. You can also take a walk in the Chicago historic district to stay active. However, if you prefer to keep warm indoors, you can spend your time in museums or get a cocktail at nearby bars.

What winter activities can you do with your boyfriend in Chicago?

If you want a romantic time and memory with your boyfriend in Chicago, you can take a walk at the Garden of Phoenix. It offers peaceful vibes allowing you to have a deep heart-to-heart conversation. You can also enjoy a romantic dinner in one of Chicago’s best restaurants.

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