What to Expect This Christmas in Chicago Loop!
Plan your holiday adventure in Chicago Loop with our comprehensive event guide. Whether you're rediscovering Chicago Loop or falling in love with it for the first time, our guide maximizes your festive experience. One highlight of the season is the Christkindlmarket, a charming German-style Christmas market where you can explore festive stalls offering handmade ornaments, delicious treats, and warm drinks. Another must-see event features the dazzling holiday lights along Michigan Avenue as part of the Magnificent Mile Lights Festival, transforming the city into a twinkling winter wonderland. And the Christmas Tree Lighting at Millennium Park is something you definitely don't want to miss, showcasing a stunning tree accompanied by delightful holiday music. See more details on these and other fun events and activities below!
Find the best Christmas events in Chicago Loop this year!
Top Christmas Events In and Around Chicago Loop
- Maggie Daley Park Ice Skating Ribbon (Chicago)
- Christkindlmarket Chicago (Chicago)
- Christkindlmarket Chicago - Wrigleyville (Chicago)
- A Christmas Carol (Chicago)
- Allstate CTA Holiday Train & Bus (Chicago)
- City of Chicago Christmas Tree Lighting Ceremony (IL 60602)
- McCormick Tribune Ice Rink (Chicago)
- Navy Pier Winter Fireworks (Chicago)
- St. Jude River North Pole at Trump Hotel Chicago (Chicago)
- Millennium Park Holiday Sing-Along (Chicago)
🎃 Explore all 10+ featured events below!
Chicago Loop Christmas Events
Chicago Loop Christmas Markets and Shopping (8)
When
Friday, November 21, 2025
Event Details
Event Description
Step into a magical European winter wonderland at the Christkindlmarket Chicago. This beloved holiday tradition transforms Daley Plaza into a bustling marketplace filled with over 100 vendors offering unique gifts, handmade crafts, and festive treats. Savor the flavors of Germany with authentic food and warm Glühwein while enjoying live entertainment. It's the perfect place to find unique holiday treasures and soak in the festive spirit.
More
When
Friday, November 21, 2025
Event Details
Event Description
Immerse yourself in the magic of the Christkindlmarket in Wrigleyville, a cherished holiday tradition. This authentic German-style market offers a delightful outdoor experience for the entire family. Wander through stalls filled with unique gifts, handmade crafts, and sparkling ornaments, all while savoring the aromas of roasted nuts, pretzels, and warm Glühwein. Enjoy festive music and a truly enchanting atmosphere.
More
When
Monday, September 1, 2025
Event Details
Event Description
Experience the magic of the holiday season at the Trump Hotel Chicago's St. Jude River North Pole event. This festive gathering offers a unique opportunity to immerse yourself in holiday cheer within a luxurious setting. Discover special offerings and enjoy the upscale ambiance that Trump Hotels are known for.
More
When
Friday, November 22, 2024
Event Details
Event Description
Discover a vibrant holiday art market nestled in Millennium Park, featuring dozens of local artists. Browse unique handmade items like jewelry, pottery, and paintings, perfect for finding special gifts. Enjoy festive food, warm drinks, and live music in a cheerful atmosphere.
More
Event Details
Event Description
Get ready for a magical holiday experience as Jack Frost returns in November 2025. This festive pop-up event promises to bring the enchantment of the North Pole to life. Join their VIP list for exclusive updates and surprises, ensuring you don't miss out on the holiday cheer.
More
When
Sunday, October 19, 2025
Event Details
Event Description
Discover the best of Chicago's independent artisans at the Fulton Market location. This vibrant market features a curated selection of top creators in food, fashion, home goods, and art. Meet the makers, find unique gifts, and support local small businesses in a lively atmosphere.
More
When
Saturday, December 20, 2025
Event Details
Event Description
Discover unique, handmade treasures at the Renegade Craft Fair's Winter event in Chicago's West Loop. Browse offerings from over 170 curated artists, perfect for finding distinctive holiday gifts. This indoor market provides a vibrant atmosphere to connect with creators and support the independent arts community.
More
When
Thursday, December 4, 2025
Event Details
Event Description
Discover Chicago's premier holiday shopping destination at The One of a Kind Holiday Show. This highly anticipated event brings together over 600 talented artists, designers, and makers, offering a vast array of unique, handmade gifts. Browse thousands of handcrafted items across 20 categories, ensuring you'll find the perfect present for everyone on your list.
MoreChicago Loop Christmas Movies, Theater and Entertainment (4)
When
Saturday, November 16, 2024
Event Details
Event Description
Step into the magic of Charles Dickens' "A Christmas Carol" at the Goodman Theatre. This critically acclaimed production, hailed as a "perfect Chicago holiday tradition," offers a heartwarming and visually stunning adaptation of the classic tale. Follow Ebenezer Scrooge's journey from miserly disdain to holiday cheer, brought to life by a "first-rate cast and marvelous staging." It's an unforgettable theatrical experience that promises to ignite your holiday spirit.
More
When
Tuesday, December 10, 2024
Event Details
Event Description
This holiday season, experience a groundbreaking fusion of Tchaikovsky's classic score and electrifying hip-hop dance. The Hip Hop Nutcracker reimagines the beloved tale with a contemporary New York City vibe, featuring a dozen all-star dancers, a DJ, and a live violinist. It's a heart-stirring, inspirational event perfect for the whole family.
More
When
Friday, December 5, 2025
Event Details
Event Description
Step into a spellbinding holiday adventure with The Joffrey Ballet's "The Nutcracker." Set during the 1893 Chicago World's Fair, this Tony Award-winning production follows Marie on a fantastical journey. Experience Tchaikovsky's beloved score as you're transported through dreamlike fairgrounds, encountering dazzling international attractions and a thrilling battle between toy soldiers and the Rat King.
More
When
Friday, December 13, 2024
Event Details
Event Description
Relive the heartwarming holiday classic 'Elf' this season as it's shown on a giant screen, accompanied by the magical live score performed by the Chicago Symphony Orchestra. Follow Buddy's journey from the North Pole to New York City in this festive cinematic and symphonic experience.
MoreChicago Loop winter_activities (1)
Event Details
Event Description
Experience the magic of winter at Maggie Daley Park's Ice Skating Ribbon. This unique, winding rink offers a picturesque setting for ice skating enthusiasts of all levels. Whether you rent skates or bring your own, prepare for an unforgettable time surrounded by stunning city views. Check back in the fall for the 2025-26 season details.
MoreChicago Loop seasonal_activities (1)
When
Friday, November 15, 2024
Event Details
Event Description
Lace up your skates for a magical winter experience at the McCormick Tribune Ice Rink in Chicago's Millennium Park. This beloved seasonal attraction offers free admission for skaters who bring their own equipment. Enjoy the crisp air and festive surroundings as you glide across the ice. Complimentary skating lessons are available on weekend mornings, making it a perfect outing for all skill levels.
MoreChicago Loop Christmas Light Displays (1)
Event Details
Event Description
Hop aboard a festive trolley for a magical journey through Chicago's most dazzling holiday light displays. This enchanting tour offers a unique perspective on the city's spectacular Christmas decorations, providing a comfortable and memorable way to experience the festive spirit. Perfect for families and friends looking to create lasting holiday memories.
MoreChicago Loop Christmas Food, Drink and Parties (1)
When
Saturday, November 18, 2023
Event Details
Event Description
Experience the magic of the season at Rudolph's Rooftop, a festive winter wonderland atop LondonHouse Chicago. Sip on holiday-inspired cocktails while enjoying breathtaking panoramic views of the city skyline. For an intimate celebration, book a private, heated igloo, perfect for gatherings with friends and family.
MoreChicago Loop Other Christmas Activities (5)
When
Tuesday, November 26, 2024
Event Details
Event Description
Embark on a magical journey with the Allstate CTA Holiday Train and Bus, a cherished Chicago tradition. Ride through festive neighborhoods aboard a train and bus adorned with thousands of twinkling lights, featuring Santa and his reindeer. Capture memorable photos with Santa on select dates and witness the heartwarming tradition of food basket deliveries to local charities.
More
When
Friday, November 21, 2025
Event Details
Event Description
Join the city of Chicago for the 112th Annual Christmas Tree Lighting Ceremony in Millennium Park. This cherished event officially ushers in the holiday season, illuminating the city's official Christmas tree. Gather near Michigan Avenue and Washington Street to witness this spectacular tradition.
More
Event Details
Event Description
Experience the magic of winter with breathtaking fireworks displays over Lake Michigan at Navy Pier. These spectacular shows light up the night sky, offering a dazzling visual treat for all ages. Gather on the pier to witness the vibrant explosions of color and light, creating unforgettable holiday memories.
More
When
Friday, December 5, 2025
Event Details
Event Description
Gather at Millennium Park's Cloud Gate for a heartwarming holiday tradition. This free event invites everyone to sing along to classic carols, celebrating diverse holiday spirit. It's a perfect way to embrace the festive season in a beloved Chicago landmark.
More
Event Details
Event Description
Step into a magical winter wonderland at the Museum of Ice Cream's Pinkmas celebration. This unique holiday event transforms the popular interactive museum into a festive, pink-themed paradise. Guests can enjoy unlimited ice cream, discover exclusive seasonal treats, and explore art installations adorned with holiday cheer. It's an unforgettable experience filled with sweet delights and whimsical photo opportunities.
MoreNear Chicago Loop
Near North Side Christmas Events
Near South Side Christmas Events
West Town Christmas Events
Lincoln Park Christmas Events
North Center Christmas Events
Hyde Park Christmas Events
Oak Park Christmas Events
Berwyn Christmas Events
Rogers Park Christmas Events
Elmwood Park Christmas Events
View Our Interactive Map for More Events Around Chicago Loop
Discover thousands of christmas events across the country
Explore Other Cities
Find events in different locations
Our Process
With 20 years of experience, we use AI technology to build the most comprehensive list of christmas events events.
Our goal is complete coverage—from major festivals to small community celebrations, ensuring you never miss anything happening in your area.
Learn More About Our Process