Chicago in December: Your Guide to the City’s Best Winter Experiences

With sparkling light shows and festive trains to holiday performances and cozy seasonal experiences, December brings some of the most magical moments of the year to Chicago. Here are some of the best places to visit in Chicago in December to ensure you experience the most festive ways to enjoy the city.

1. Experience ZooLights at Lincoln Park Zoo

A Chicago December isn’t complete without a stroll through ZooLights at Lincoln Park Zoo. This annual tradition transforms the zoo into a glowing wonderland filled with colorful displays, festive music, and seasonal treats. Kids can enjoy light tunnels and interactive installations, while adults can warm up with spiced drinks and holiday snacks. It’s one of the city’s most charming cold-weather activities, and is a perfect way to kick off the month.

2. Walk Through Lightscape at the Chicago Botanic Garden

The Chicago Botanic Garden’s Lightscape is one of the most stunning winter experiences in the city. This immersive nighttime trail winds through illuminated gardens, artistic light sculptures, and seasonal installations set to music. It’s a breathtaking outing for families and couples alike, and its creative designs make it one of the best things to do in Chicago in December.

Tip: Tickets sell out early each year, so planning ahead is recommended.

3. Hop Aboard the CTA Holiday Train or Bus

The CTA Holiday Train and Bus are iconic Chicago traditions that delight both locals and visitors. Decorated with thousands of lights, Christmas characters, garlands, and festive displays, these special routes bring cheer to everyday commutes. Santa himself usually rides along, greeting passengers and handing out candy canes! If you’re visiting Chicago in December, catching the train or spotting the bus rolling through the streets is a seasonal highlight.

4. Take a December Architecture Boat Tour

Chicago’s riverfront is stunning in every season, and December is no exception. One of our 90-minute architecture cruises lets you admire the skyline, iconic buildings, and riverfront lights in comfort. For travelers who want beautiful views from a unique and insightful perspective, one of our tour boats is easily among the best places to visit in Chicago in December.

5. Enjoy Pinkmas at the Museum of Ice Cream

For something playful and colorful, the Museum of Ice Cream brings back Pinkmas, a festive transformation of its immersive exhibits. Expect pink holiday décor, themed installations, and seasonal treats served throughout the experience. Families and couples can enjoy sprinkle-filled photo ops and interactive rooms dressed up for the holidays, making it one of the top things to do in Chicago in December for anyone seeking a warm, whimsical indoor escape from the cold.

6. See Art on theMART’s Holiday Projection

Bundle up and head to the Riverwalk to watch Art on theMART, the world’s largest permanent digital art projection. Throughout December, the installation features a special collaboration with the Joffrey Ballet, adding holiday flair and beautifully choreographed visuals to the iconic Merchandise Mart façade. Shows run Thursdays through Sundays, making it a cozy nighttime stop after dinner or a stroll along the river.

7. Explore Chicago’s Holiday Pop-Up Bars

If you’re looking for festive nightlife, December delivers. Throughout the city, bars and lounges transform into themed holiday pop-ups filled with twinkling lights, seasonal cocktails, and over-the-top decorations. These festive venues are some of the best places to visit in Chicago in December, especially if you love cozy winter cabin vibes, kitschy decorations, or neon-lit holiday themes.

8. Attend a Holiday Show

December is one of the best months to experience Chicago’s performing arts scene. The Joffrey Ballet’s Nutcracker is the star of the season, a beautifully staged production that blends classic choreography with Chicago’s own historic influences. Families can also enjoy kid-friendly holiday plays, musical revues, and festive concerts throughout the month. For something more nostalgic, classic holiday films and sing-along screenings at theaters like the Music Box add to the cozy charm of the season.

9. Go Ice Skating in Millennium Park

Ice skating under the skyline is a must-do Chicago December activity, and the McCormick Tribune Ice Rink in Millennium Park is one of the city’s most iconic winter spots. Suitable for both first-timers or skilled skaters, it’s an unforgettable way to enjoy Chicago’s festive atmosphere. Nearby, the giant Christmas tree adds even more holiday sparkle, making this area particularly scenic at night.

10. Visit Chicago’s Holiday Markets

December is full of markets selling handmade crafts, ornaments, seasonal treats, and gifts. From European-style stalls to neighborhood pop-ups, these lively markets stand out among the top things to do in the city around this time, offering a unique way to support local artists while celebrating the season.

11. Warm Up with Indoor Cultural Experiences

When the temperatures drop, stepping indoors is part of the December strategy. Museums throughout the city offer special exhibitions during the winter season, including the Art Institute, the Field Museum, and the Museum of Science and Industry. Many attractions are quieter this time of year, giving visitors a chance to enjoy exhibits without the high-season crowds.

12. Explore Winterland’s Walk-Through Holiday Village

Winter WonderFest at Navy Pier is a must-see for those visiting Chicago with families or young kids. It features a walk-through holiday village, immersive light displays, themed rooms, and colorful photo ops, making this a cozy indoor attraction for those hoping to find something warm and magical during the festive season.

13. Join the TBOX 12 Bars of Xmas Crawl in Wrigleyville

If you’re looking for one of Chicago’s wildest and most iconic December events, the TBOX (12 Bars of Xmas) Crawl is a must-experience. Now celebrating its 29th year, this massive all-day celebration brings thousands of people to Wrigleyville in over-the-top holiday outfits for a festive bar-hopping party across 20+ local bars.

Participants enjoy free breakfast buffets, drink specials, gift cards to use throughout the crawl, live music, DJs, giveaways, themed pop-ups, and plenty of holiday chaos in the best possible way. It’s easily one of the most energetic things to do in Chicago in December, and perfect for adults looking for a lively seasonal event.

Tip: Tickets often offer perks for early buyers, and wristband pickup is recommended ahead of the event for the quickest start to your crawl.

14. Sip Bottomless Mimosas at Old Crow’s Holiday Music Day Party

For a more relaxed but still festive December experience, Old Crow’s “Mimosas & Holiday Music Day Party” in Wrigleyville is a fun mid-day celebration that mixes holiday cheer with three full hours of unlimited mimosas. Hosted inside the bar’s seasonal pop-up, Santa’s Workshop, this event turns a Saturday or Sunday afternoon into a bright, music-filled holiday brunch party.

Expect four different mimosa varieties, $5 holiday-inspired shots, and a playlist of Christmas classics and sing-along favorites. It’s an easygoing way to enjoy Chicago’s holiday season with friends before evening plans or dinner reservations.

Tip: Tickets often sell out on peak December dates, and table seating is mostly first-come, first-served, so arriving early is recommended.

15. Taste Seasonal Cocktails at the Godfrey Holiday Cocktail Fest

If you’re looking for a more elevated holiday outing, the Godfrey Holiday Cocktail Fest offers a stylish afternoon of seasonal tastings atop one of River North’s most iconic rooftops. Held at the I|O Godfrey Rooftop Lounge, this four-hour event features a rotating selection of festive cocktails, giveaways, and panoramic skyline views, complete with fire pits and shimmering water features that make the atmosphere feel especially warm and wintry.

Whether you’re the type to lean into holiday cheer or you prefer a more low-key seasonal vibe, the variety of cocktails ensures there’s something for every palate. It’s a relaxed, social way to enjoy Chicago in December, especially if you’re looking for an indoor–outdoor holiday experience that doesn’t involve bundling up too much.

Tip: Doors close at 4:45 PM sharp, so plan to arrive early to enjoy the full tasting window.

Wrapping Up Your December Visit

Chicago in December is full of festive energy, from glowing gardens and holiday trains to world-class performances and cozy winter experiences. Whether you’re planning a family getaway, a seasonal date night, or a solo adventure through the city’s cultural highlights, December offers something for everyone. Add a river cruise, wander a market, catch a show, or simply enjoy the illuminated streets. However you decide to explore it, December in Chicago is one of the most memorable times of the year.

Preparing for New Year’s Eve in Chicago

If you’re wrapping up your December visit, it’s the perfect time to start planning your New Year’s Eve. Chicago’s biggest events and parties sell out early, especially the all-inclusive hotel parties and high-demand venues with skyline views. Book your tickets now while early bird deals are still available, secure your hotel room close to the action, and decide how you’ll be spending your final evening of 2025.

Planning ahead means you can step into 2026 without stress, just a great outfit, a glass of champagne, and a spot booked at one of the city’s top countdown events.

Now’s the time to lock in early bird pricing across Chicago’s biggest NYE events. Here are the featured venues: