Fun Things To Do in Chicago in December [2021 Christmas and Winter Guide]

If you’re wondering, is December a good time to visit Chicago? The answer is a resounding yes! Visiting Chicago in the winter during Christmastime (or beyond) can be a magical yet freezing experience. As a local, I assure you that you won’t regret your wintry trip to the city.

The streets are wonderfully decorated for the holidays with twinkling lights and numerous Christmas trees throughout town. There are so many fun and unique things to do in Chicago in December that this list got a lot longer than I expected.

Just make sure to pack lots of layers, boots, and the warmest outerwear you own. Regardless of the temps, you’ll see why the city has been topping travel lists for several years now.

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Weather in Chicago in December

The weather in Chicago in December can still be pretty mild. I can’t remember the last time we had a white Christmas though it’s very possible. The (Fahrenheit) temperature ranges from the high 30s to the low 20s.

Visiting in winter certainly has its perks. It’s not as cold as January and February tend to be, and as I mentioned, not nearly as snowy (if at all). So if you’re planning to come then, dress warm and aim for a hotel with a fireplace.

Note: For any tours mentioned below, I’m linking from GetYourGuide and Viator because they offer different things and are reputable companies with great cancellation policies. I’ve personally used them both. I may receive a small commission for purchases made through these links at no extra cost to you.

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Things to do in Chicago in December/Winter

With the weather outside being frightful, most visitors prefer to find indoor activities in Chicago. I’m listing some of those here, but don’t be afraid to venture outside. Sometimes the best way to experience a place is to bundle up and do a bit of outdoor walking. You can also check out this post for some of the best places to take pictures in Chicago. I’m linking all the coolest tours below; click through to learn more.

Cool Museums

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A big city like Chicago has no shortage of excellent museums to choose from. I haven’t visited them all, but one of my favorites is the Museum of Science and Industry.

During Christmastime, they have the most stunning exhibit called “Christmas Around the World,” where they fill the museum with over 50 trees and displays representing holiday traditions from all over the world. It’s inspiring, educational, kid-friendly, and one of my favorite things to do during the holidays in Chicago. The exhibit runs from mid-November to early January.

Another excellent museum to check out is the Chicago History Museum. They have exciting exhibits, including one about the Great Chicago Fire of 1871. Other well-rated and famous museums include the Art Institute of Chicago and the Field Museum.

Chicago Food + Drink Tours


Underground Donut Tour Not much explanation is needed here. Do you love doughnuts? So do we. Visit four top Chicago shops, and enjoy various doughnuts at each place. Plus, learn about the city’s food scene in the process. Two of the stops include Sawada and Do-Rite, which are some of my top shops in Chicago. Another Underground Donut Tour with great reviews makes stops at different places, I’ll link that one right here, and you can decide which you prefer (or do both, you’re on vacation).

Chicago Craft Brewery Barrel Bus TourIf you’re a beer lover, this one is for you. Visit local breweries for craft beer samples, plus an additional brewing production facility for an in-depth tour.

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Chicago Pizza TourEnjoy a delicious pizza tour with bus transport included. Eat like a local and savor the best pizza as you travel into Chicago neighborhoods with an expert guide.

If you prefer to explore the food scene on your own, check out this popular post where I list my top 40 places to eat in Chicago or this one where I share the best Chicago coffee

Chicago Winter Walking Tours

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Holiday Hike If you’re visiting during the holidays, don’t miss this gourmet food tour. You’ll experience the festive lights downtown, visit the popular Christkindlmarket, sample Chicago’s pizza, and so much more.

Dazzling Interiors of the Loop This unique Chicago architecture walking tour is focused on the building’s beautiful interiors. It’s a 2-hour tour where you’ll follow a specially-designed route with an experienced guide.

Indoor Activities in Chicago

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360 Observation DeckThe deck is located on the 94th floor of the John Hancock building (above) and shows off Chicago from all angles. If you only have time or money to see Chicago from 360 Observation or the Skydeck in the Willis tower, I vote for 360. I feel like it offers different views of the lake that the Skydeck doesn’t.

Willis Tower Skydeck and The Ledge TicketKnown as the Sears Tower to almost anyone who grew up in Chicago, the Skydeck also offers incredible city views. I took the photo above from the Skydeck. Take in the architecture from floor 103! Sunset is the perfect time to be there. You can also step on “The Ledge” and see the city below you through a glass floor.

Chicago Architecture Tours

Architecture Cruise Wendella offers a Chicago architecture boat tour all year long (weather permitting). They have an indoor space to take in the city sights while staying warm. I’ve personally done the Wendella tour and enjoyed it.

Navy Pier Centennial Wheel See the sparkling city lights from above on the new and improved Navy Pier Centennial Ferris Wheel.

Hop-on Hop-off BusIf you’re not renting a car, this is one of the easiest ways to see a lot of the city. There are 13 stops where you can hop off to visit attractions and explore places of interest. They offer live guides, plus you’ll get a free bag of the famous Garrett’s Popcorn.

Chicago in a Day TourIf the cold doesn’t scare you and you have limited time in the city, you can do a one-day tour of Chicago’s food, history, and architecture. It’s an excellent choice for first-time visitors.

Christmastime in Chicago 

Chicago is filled to the brim with things to do during the Christmas season; you’ll find Christmas markets, light displays, and pop-up bars aplenty! I’m sharing my favorite yearly events along with other notable things to do.


I never miss this Christmas market! You’ll feel like you’re wandering the streets of Europe with mulled wine in hand as you shop for crafts and treats from local and European vendors. It’s a free-entry event and not to be skipped if you’re in Chicago. It usually runs from mid-November to Christmas Eve.


Christmas Around the World

I already covered info on this above, but it’s worth another mention. If you purchase the Go Chicago Card, the entrance to The Museum of Science and Industry is included (along with many more). You may want to consider the card if you plan to visit multiple locations in the city.

Light Displays

Chicago lights up even more in December. You’ll find beautiful light displays everywhere you turn. Start with the official Chicago Christmas tree at Millenium Park and work your way up the Mag Mile. You can also walk down State Street to enjoy all the twinkling for free or visit one of the many events held throughout the city. I’m listing some of the more popular ones below. Prices vary for the events; click the links to learn more.

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Ice Skating in the City

Ice skate with the city as a backdrop at the picturesque Millenium Park rink with the perfect view of the official Chicago Christmas tree. Admission is free, but you will need to reserve tickets online.

You can also skate nearby at Maggie Daley Park. This fantastic ice skating ribbon rink weaves through the park, surrounded by the city skyline. You’ll also need to reserve tickets online.

Another unique option is The Peninsula Sky Rink, located on the terrace of the Peninsula Hotel right above Michigan Avenue. I love this one because the proceeds from the skate rentals are donated to two Chicago children’s charities: Ann & Robert H. Lurie Children’s Hospital of Chicago and Hephzibah Children’s Association.

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Christmas Shows

Christmas shows are a classic thing to do during the holiday season. Catch a live show like The Nutcracker ballet, ‘Twas The Night Before Christmas by Cirque du Soleil, or A Christmas Carol at the Goodman Theater.

Christmassy Restaurants + Pop-up Bars

Chicago has countless great restaurants and bars that get into the Christmas spirit. I’m sharing a few here to get you started on that holiday ride.

Walnut Room is located inside Macy’s on State Street. During Christmas, you’ll find beautiful holiday decor and a massive Christmas tree right at the center. A photo-worthy place for a meal.

The Lobby at the Peninsula Hotel offers several options to celebrate the season. You can book a Holiday Afternoon Tea while you enjoy their huge tree and lavish decor. And if you’re in the city during Christmas Eve or day, you can reserve a gourmet dinner or brunch around the Christmas tree with a string quartet to top it off!


Reinder Room at Tack Room is a bar that’s dressed up for the holidays with its very own piano man who takes requests.

Jingle Bell Square at Lost Lake will offer up festive decor with a mix of tropical vibes. I love this bar, and you will love the drinks!

Rudolph’s Holiday Rooftop at LondonHouse Chicago hotel will greet you with rooftop igloos and Christmas decor. This rooftop has some of my favorite views in the city.


Happy’s at Chicago Athletic Association hotel is an annual Christmas pop-up bar. It’s right across from Millenium Park. So when you’re done with the skating, you can warm up at Happy’s. Don’t leave without checking out the view from Cindy’s rooftop in the same building.

Santa Baby is a multi-level pop-up bar filled with Christmas decor. This is the type of place where I’d go for the photos but not expect much from the drinks.


Frosty’s Christmas Bar is the original Christmas pop-up bar in Chicago. You’ll find over-the-top decor with specialty cocktails and photo opportunities galore.

Jack Frost’s Pop-Up has managed to combine lots of Christmas activities into one impressive place. You can visit for photo ops, seasonal drinks, ice skating, bumper cars, or even buy your Christmas tree from their tree farm!

Spot the holiday train or bus

Whether you rented a car or not, make sure to catch the CTA holiday train. I’ve yet to ride it (can you believe this?), but it’s a tradition loved by locals. The CTA holiday train will be dashing through downtown Chicago after Thanksgiving- December.

You’ll find train cars decorated with cheer, tons of lights, and Santa’s sleigh leading the way! If you miss the train, you can try to catch the holiday bus on the city streets.

By chance, Jorge rode the bus years ago and was so excited to run into Santa and his elves, proof on the left photo below. It’s a fun experience for adults and kids alike.

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As you can see, there is so much magic in Chicago during winter and Christmastime. The summer crowds are gone, the streets are sparkling, and the restaurants are dressed to the nines. I’d dare to say that it’s one of the best times to visit!


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