Beyond lights and markets, Chicago offers unique winter activities and seasonal attractions. Skate for free at the McCormick Tribune Ice Rink in Millennium Park with stunning skyline views, or visit Navy Pier's Winter WonderFest for indoor holiday fun. From ice skating ribbons to festive attractions, Chicago provides memorable holiday experiences.
City of Chicago Christmas Tree Lighting Ceremony
Location: Chicago
Dates: Friday, November 21, 2025
Cost: FREE
The City of Chicago Christmas Tree Lighting Ceremony, held annually in Millennium Park, marks the official start of the holiday season with the illumination of the city's official Christmas tree. This event features the display of a towering tree that is a beloved tradition among locals and visitors alike.
Highlights:
- The 112th Annual City of Chicago Christmas Tree Lighting Ceremony marks the official start of the holiday season.
- The iconic Christmas tree will be prominently displayed in Millennium Park.
- Witness the illumination of Chicago's official Christmas tree, a beloved annual tradition.
Millennium Park Holiday Sing-Along
Location: Chicago
Dates: Fridays, December 5, 12 & 19, 2025
Cost: FREE
Join the Millennium Park Holiday Sing-Along for a joyful celebration of the season at the iconic Cloud Gate sculpture, where Chicagoans and visitors unite in song to classic holiday carols. Led by local choral groups each week, this free event creates a warm, inclusive atmosphere perfect for making memories with friends and family. Experience the magic of live music, twinkling lights, and the vibrant spirit of Chicago’s diverse holiday traditions in the heart of the city.
Highlights:
- A free, community-focused holiday event perfect for all ages.
- Sing along to beloved holiday carols in the heart of Chicago.
- Join fellow Chicagoans and visitors for a festive community sing-along.
Gingerbread House Decorating Class
Location: Bannockburn
Dates: Seasonal Availability
Cost: $$
Join a hands-on Gingerbread House Decorating Class at Taste Buds Kitchen in Bannockburn, where participants can decorate their own houses using various candies and frosting. The class provides a fun and interactive culinary experience, suitable for families and children, with the option of at-home kits available.
Venue: Taste Buds Kitchen - Chicago - Bannockburn
Address: 2521 Waukegan Road, Bannockburn, IL 60015
Phone: (847) 230-0330
Website: Visit Website
Highlights:
- Signature gingerbread house decorating class for families and children.
- Option for at-home kits to continue the festive fun at home.
- Private party options available for a personalized celebration.
Des Plaines Tree Lighting in Wilder Park
Location: Elmhurst
Dates: Thursday, December 4, 5:30pm - 7:30pm
Cost: FREE
The Des Plaines Tree Lighting in Wilder Park invites the community to participate in the ceremonial lighting of community trees, marking the official start of the holiday season. Attendees can sponsor and decorate a tree, with opportunities to enjoy festive food and warm beverages from on-site food trucks.
Venue: Wilder Park
Address: 175 S Prospect Avenue, Elmhurst, IL 60126
Phone: (630) 993-8900
Website: Visit Website
Highlights:
- Participate in the community tree lighting ceremony to officially start the holiday season.
- Sponsor and decorate a community tree for a chance to win a free tree next year.
- Sponsor and decorate a community tree to be part of the annual tradition.
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Polar Express Train Ride
Location: Mount Prospect
Dates: December 17-19, 2025
Cost: $24
Experience a heartwarming holiday adventure aboard the Polar Express Train Ride departing from Mount Prospect. This enchanting journey transports families to a festive North Pole celebration filled with joyful caroling, storytelling, and a special visit from Santa Claus. Each child receives a memorable gift, making this immersive holiday event a treasured seasonal tradition.
Venue: Mount Prospect Train Station
Address: 13 E Northwest Hwy, Mount Prospect, IL 60056
Phone: 847-255-1200
Website: Visit Website
Highlights:
- A themed train excursion to the North Pole.
- On-site activities at the North Pole station including Santa visits and music.
- A special gift for each child to remember their journey.
Santa Hustle Chicago 5K & 10K
Location: Chicago
Dates: December 6, 2025
Cost: $$
Celebrate the holiday season at Santa Hustle Chicago, a festive running event held at the iconic Soldier Field featuring officially timed 5K and 10K races alongside a Kids' Dash for younger participants. Every runner crosses the finish line with exclusive Santa Hustle gear including a long-sleeve shirt, cozy beanie, and jingling finisher medal, while supporting Cal's Angels pediatric cancer foundation through this spirited community gathering.
Highlights:
- Run a timed 5K or 10K race with awards for top finishers.
- Receive a long-sleeve shirt, beanie, and a commemorative finisher medal.
- Support Cal's Angels, the official charity partner, through donations or volunteering.
Holly Days Winter Festival
Location: Westmont
Dates: November 16 - December 21 (various events)
Cost: $$
Immerse yourself in the magic of the season at the Holly Days Winter Festival, a cherished month-long celebration in Westmont, Illinois, where the community comes together to embrace the spirit of winter and the holidays. From lively parades and craft bazaars to enchanting Santa visits and festive train rides, this festival offers a diverse lineup of events designed to delight visitors of all ages. Experience the warmth of community traditions, the sparkle of holiday lights, and the joy of seasonal activities that make this event a standout winter destination.
Venue: Westmont Park District
Address: 75 E. Richmond Street, Westmont, IL 60559
Phone: (630) 963-5252
Website: Visit Website
Highlights:
- Experience a month-long celebration of winter and holiday cheer in Westmont, Illinois.
- Enjoy a variety of family-friendly events, from parades and craft bazaars to Santa visits and train rides.
- Participate in the Frosty & Friends Parade and Opening Ceremonies to officially ring in the holiday season.
President's Holiday Open House and Festival of Lessons & Carols
Location: Elmhurst
Dates: Friday, December 5, 2025
Cost: FREE
Join Elmhurst University for a cherished holiday tradition blending warmth, music, and community. The President's Holiday Open House welcomes guests to the elegant Frick Center for festive refreshments and seasonal cheer, followed by the beloved Festival of Lessons & Carols in Hammerschmidt Memorial Chapel. This special evening features inspiring readings, timeless carols performed by university choirs, and an atmosphere of unity and reflection, all hosted by the university president for a memorable Chicago-area Christmas experience.
Venue: Frick Center, Founders Lounge
Address: 190 Prospect Avenue, Elmhurst, IL 60126
Phone: (630) 617-3400
Website: Visit Website
Highlights:
- A combined holiday open house and musical festival hosted by the university president.
- Festive refreshments and a traditional carols service.
- Enjoy drinks and heavy appetizers at the President's Holiday Open House.
Winter Holiday Celebration in the Park
Location: Darien
Dates: December 5
Cost: FREE
Join the Darien Park District for an enchanting evening of holiday cheer at Community Park. This festive gathering brings neighbors together to celebrate the season with twinkling light displays, live seasonal music, and warm refreshments. Bundle up and experience the magic of the holidays in a welcoming outdoor setting designed to create lasting memories for the entire community.
Venue: Darien Park District Community Park
Address: 7100 Clarendon Hills Road, Darien, IL 60561
Phone: 630-968-6400
Website: Visit Website
Highlights:
- Celebrate the holiday season with a community gathering in the park.
- Experience a festive atmosphere with music, lights, and treats.
- Enjoy festive holiday entertainment provided by the park district.
Tinley Park Parade of Lights
Location: Tinley Park
Dates: Sunday, December 7th, 2025
Cost: FREE
Experience the magic of the holidays at the 27th Annual Tinley Park Parade of Lights, a dazzling community celebration that transforms downtown into a glowing wonderland. Watch as illuminated floats, spirited marching bands, and festive community groups parade through the heart of Tinley Park, all leading up to a joyful visit with Santa Claus. This beloved tradition brings neighbors together for an evening filled with music, lights, and seasonal cheer, making it the perfect kickoff to the Christmas season in Chicagoland.
Venue: Tinley Park
Address: 177th Street, Tinley Park, IL 60477
Phone: (708) 532-5700
Website: Visit Website
Highlights:
- The 27th Annual Tinley Park Parade of Lights, a cherished tradition kicking off the holiday season.
- A spectacular parade route featuring illuminated floats, marching bands, and community participants.
- An opportunity to connect with Santa Claus and experience the warmth of the holiday season.
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Santa Express Train Ride
Location: Wheaton
Dates: December 12 - December 14
Cost: $24
The Santa Express Train Ride departs from Wheaton Train Station, offering families a festive train journey where Santa visits each passenger to listen to their Christmas wishes. Attendees can enjoy holiday stories, music, and receive goodie bags and snacks upon check-in. This enchanting experience is perfect for creating lasting holiday memories with Santa.
Venue: Wheaton Train Station
Address: 402 W. Front St., Wheaton, IL 60187
Phone: 630-510-4941
Website: Visit Website
Highlights:
- A special train ride experience departing from Wheaton Train Station.
- An opportunity to meet and take photos with Santa Claus.
- Festive entertainment including music and storytelling.
Holiday Trees Downtown & Tree Lighting Ceremony
Location: Schererville
Dates: November 28, 2025
Cost: FREE
The Holiday Trees Downtown & Tree Lighting Ceremony at Schererville Town Hall marks the official start of the holiday season with the illumination of festive trees throughout downtown. Community members are invited to witness the ceremonial lighting and enjoy a vibrant atmosphere filled with holiday spirit. This event serves as a cherished tradition for locals to come together in celebration.
Venue: Schererville Town Hall
Address: 10 East Joliet Street, Schererville, IN 46375
Phone: 219-322-5412
Website: Visit Website
Highlights:
- Join the community for the official start of the holiday season with the Town of Schererville.
- Enjoy a festive atmosphere as the holiday lights are switched on.
- Witness the magical illumination of festive holiday trees adorning downtown Schererville.
Santa's March & Tree Lighting Ceremony
Location: Highland
Dates: November 29, 2025
Cost: FREE
Santa's March & Tree Lighting Ceremony at Main Square Park features a festive parade led by Santa Claus followed by the ceremonial lighting of the holiday tree. Attendees can enjoy complimentary hot chocolate as they gather for the celebration and receive special treat bags from Santa after the ceremony. This event is a wonderful way to bring the community together for the start of the holiday season.
Venue: Main Square Park
Address: 3001 Ridge Rd, Highland, IN 46322
Phone: 838-0114
Website: Visit Website
Highlights:
- Santa's March parade kicks off the holiday festivities.
- The ceremonial lighting of the holiday tree marks the start of the season.
- Enjoy complimentary hot chocolate during the tree lighting ceremony.
Light Up Wheaton Decorating Contest
Location: Wheaton
Dates: The event is an annual decorating contest, typically held during the holiday season.
Cost: FREE
The Light Up Wheaton Decorating Contest invites residents to showcase their holiday spirit through festive home decorations across Wheaton. This community-wide competition transforms the neighborhood with a diverse array of light displays, from classic to elaborate designs. Participants and viewers alike can admire the creativity and effort put into making Wheaton a festive sight.
Venue: Wheaton Park District
Address: 102 E. Wesley St., Wheaton, IL 60187
Phone: 630-690-4880
Website: Visit Website
Highlights:
- Participate in a community-wide decorating contest that brings holiday cheer to every street.
- View a diverse array of home decorations, from classic to elaborate, showcasing residents' holiday spirit.
- Admire the festive and creative holiday decorations adorning homes throughout Wheaton.
Forest Park Holiday Walk
Location: Forest Park
Dates: December 5, 6:00 PM - 9:00 PM
Cost: FREE
The Forest Park Holiday Walk along Madison Street features a charming holiday stroll with open houses from local merchants, horse-drawn sleigh rides, and the opportunity to meet Santa and Mrs. Claus. Attendees can enjoy family-friendly entertainment, including balloon artists and face painters, making this event a delightful outing for all ages. Live window displays and a ceremonial lighting of the Christmas tree enhance the festive experience.
Highlights:
- Experience a charming holiday stroll along Madison Street with merchant open houses.
- Meet Santa and Mrs. Claus for a magical holiday encounter.
- Enjoy family-friendly entertainment including balloon artists and face painters.
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Tinley Toyland Parade
Location: Tinley Park
Cost: FREE
The Tinley Toyland Parade is a festive community event that celebrates the holiday season with a playful 'Toyland' theme. Residents can join in the procession, enjoying whimsical floats and cheerful participants. This parade brings holiday cheer to the streets of Tinley Park, making it a delightful experience for family and friends.
Venue: Tinley Park
Address: 16250 S. Oak Park Ave., Tinley Park, IL 60477
Phone: (708) 444-5000
Website: Visit Website
Highlights:
- Experience a community parade celebrating the holiday season with a playful 'Toyland' theme.
- Join residents in a festive procession that brings holiday cheer to Tinley Park.
- Witness a festive parade featuring whimsical floats and participants decorated in a 'Toyland' theme.
Christmas Classic Chicago South
Location: Schaumburg
Dates: December 13-14, 2025
Cost: $$
The Christmas Classic Chicago South at Schaumburg Convention Center is a spirited national championship event featuring Christmas-themed competitions, including the World's Largest Indoor Snowball Fights. Participants have the chance to win Grand Champion Rings and National Champion Bracelets while enjoying festive entertainment throughout the two-day event. This unique competition combines holiday spirit with friendly rivalry.
Venue: Schaumburg Convention Center
Address: 1551 Thoreau Dr N, Schaumburg, IL 60173
Phone: 1.847.445.5956
Website: Visit Website
Highlights:
- A spirited, Christmas-themed national championship event.
- Opportunities to win Grand Champion Rings and National Champion Bracelets.
- Chance to earn bids for prestigious Allstar World Championship and Alliance events.
City of Des Plaines Annual Holiday Tree Lighting Ceremony
Location: Des Plaines
Dates: Annual Event
Cost: FREE
The City of Des Plaines Annual Holiday Tree Lighting Ceremony is a beloved community event featuring the ceremonial lighting of the city's holiday tree at the Des Plaines Park District. This gathering marks the beginning of the holiday festivities, inviting residents to come together and celebrate as the tree is illuminated with festive decorations. The event embodies the spirit of the season and fosters community connection.
Venue: Des Plaines Park District
Address: 2222 Birch Street, Des Plaines, IL 60018
Phone: (847) 391-5700
Website: Visit Website
Highlights:
- The ceremonial lighting of the city's holiday tree.
- A community gathering to kick off the holiday festivities.
- Gather with the community to celebrate the start of the holiday season.
Naperville Rotary Holiday Parade of Lights
Location: Naperville
Dates: Friday, November 28th, 2025
Cost: $$
The Naperville Rotary Holiday Parade of Lights is a vibrant community event that features local music performers and festive floats, with proceeds supporting local youth non-profits. Attendees can enjoy pre-parade entertainment and participate in the Santa Experience raffle for a chance to ride with Santa. This family-focused evening is designed to delight children and bring the community together in a celebration of holiday cheer.
Venue: Downtown Naperville
Address: 131 W Jefferson Ave, #223, Naperville, IL 60540
Website: Visit Website
Highlights:
- Witness a vibrant parade featuring local music performers and hometown entrants.
- Support local non-profits as net proceeds benefit community youth programs.
- Experience a family-focused evening designed to delight children with holiday cheer.
Rotary Club of Naperville Parade of Lights
Location: Naperville
Dates: November 28, 2025
Cost: FREE
The Rotary Club of Naperville Parade of Lights is a dazzling holiday parade that delights families with its brightly lit floats and a special appearance by Santa Claus. Attendees can enjoy the festive evening as local music performers contribute to the holiday atmosphere. This event showcases community spirit and brings the joy of the season to the streets of downtown Naperville.
Highlights:
- A dazzling holiday parade designed to delight children and families.
- The appearance of Santa Claus, bringing joy to all attendees.
- Enjoy a festive evening parade featuring brightly lit floats.
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Winter WonderFest at Navy Pier
Location: Chicago
Dates: December 5, 2025 - January 4, 2026
Cost: $$
Winter WonderFest at Navy Pier transforms Chicago’s Festival Hall into a vibrant indoor holiday playground from December 5, 2025, to January 4, 2026. Visitors can enjoy a dazzling 42-foot holiday tree, an expansive ice skating rink, and a variety of thrilling rides, all set against festive décor and live entertainment. Each admission includes a ride on the iconic Centennial Ferris Wheel, offering spectacular city views in cozy enclosed gondolas.
Venue: Navy Pier Festival Hall
Address: 600 E Grand Avenue, Chicago, IL 60611
Phone: 312-595-7437
Website: Visit Website
Highlights:
- Indoor ice skating rink
- Ferris wheel included
- 42-foot holiday tree
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McCormick Tribune Ice Rink at Millennium Park
Location: Chicago
Dates: November 14, 2025 - March 2026
Cost: FREE
The McCormick Tribune Ice Rink at Millennium Park transforms into a winter wonderland each holiday season, offering a quintessential Chicago experience beneath the glow of the city’s official Christmas tree. Skaters glide across a spacious outdoor rink surrounded by iconic architecture and festive lights, creating a vibrant atmosphere that blends urban energy with seasonal cheer. Whether you bring your own skates or rent on-site, this beloved tradition invites visitors to celebrate the holidays with friends and family in the heart of downtown Chicago.
Highlights:
- Free with own skates
- Millennium Park location
- Near Christmas tree
Maggie Daley Park Skating Ribbon
Location: Chicago
Dates: Late November 2025 - March 2026
Cost: FREE
Experience the enchanting Maggie Daley Park Skating Ribbon, a quarter-mile outdoor ice trail weaving through lush evergreens and illuminated by the sparkling Chicago skyline. This distinctive skating path offers a dynamic, flowing route that feels like gliding along a frozen river, perfect for all skill levels. Open from mid-November 2025 through early March 2026, it combines natural beauty with urban charm for a memorable winter outing.
Venue: Maggie Daley Park
Address: 337 E Randolph Street, Chicago, IL 60601
Phone: 312-742-3918
Website: Visit Website
Highlights:
- Winding ribbon ice trail
- Scenic park setting
- Free with own skates
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Winterland at Gallagher Way
Location: Chicago
Dates: November 23 - December 2025
Cost: FREE
Winterland at Gallagher Way transforms the Wrigleyville neighborhood into a vibrant winter wonderland each holiday season, offering a unique blend of classic Chicago charm and festive excitement. Visitors can glide across the outdoor ice rink with Wrigley Field as a backdrop, explore a bustling holiday market, and enjoy live entertainment, seasonal workshops, and family-friendly attractions. The celebration stands out with its apres-ski-inspired Lodge, fire pits, and special events like the tree lighting ceremony and holiday movie nights, making it a must-visit destination for locals and visitors alike.
Highlights:
- Near Wrigley Field
- Holiday markets and skating
- Family activities
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360 CHICAGO Observation Deck Holiday Views
Location: Chicago
Dates: Throughout December 2025
Cost: $$
Soar above the city at 360 CHICAGO Observation Deck for a dazzling holiday experience like no other. Perched on the 94th floor of the John Hancock Center, guests enjoy breathtaking panoramic views of Chicago’s twinkling skyline adorned with festive lights and seasonal decorations. This winter wonderland features the thrilling TILT platform, a special holiday market, and cozy spots to sip hot cocoa or cocktails while soaking in the magic of Christmas from 1,000 feet up.
Venue: 360 CHICAGO
Address: 875 N Michigan Avenue, Chicago, IL 60611
Phone: 888-875-8439
Website: Visit Website
Highlights:
- 94th floor observation deck
- TILT platform experience
- Holiday city views
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Chicago Architecture Foundation Holiday River Cruise
Location: Chicago
Dates: Select December dates 2025
Cost: $$
Celebrate the holiday season aboard the Chicago Architecture Foundation's festive river cruise, where the city’s iconic buildings are adorned with dazzling seasonal lights and decorations. This unique boat tour offers an enchanting perspective of Chicago’s architectural marvels illuminated against the winter night sky, enriched by expert narration that weaves together the city’s rich history and holiday spirit. Experience the magic of Chicago’s skyline like never before, from the warmth of a cozy, climate-controlled vessel.
Highlights:
- Architectural river cruise
- Decorated buildings views
- Expert tour guides
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Field Museum Holiday Exhibits
Location: Chicago
Dates: Throughout December 2025
Cost: $$
Celebrate the holidays at Chicago's Field Museum with a festive blend of natural history and seasonal cheer. Guests can explore special holiday-themed exhibits, participate in hands-on crafts, and enjoy exclusive member lounges designed for relaxation and family fun. Unique experiences like holiday photo ops with dinosaur displays and cozy storytimes make this a memorable winter destination for all ages.
Venue: Field Museum
Address: 1400 S DuSable Lake Shore Drive, Chicago, IL 60605
Phone: 312-922-9410
Website: Visit Website
Highlights:
- Natural history museum
- Holiday exhibits
- Educational programming
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Shedd Aquarium Holiday Celebrations
Location: Chicago
Dates: Throughout December 2025
Cost: $$
Shedd Aquarium transforms into a vibrant holiday wonderland this Christmas season, blending festive cheer with unforgettable aquatic encounters. Guests can dance to live house music, mingle with marine animals up close, and explore dazzling seasonal decorations throughout the lakefront venue. Unique experiences like holiday-themed animal feedings and interactive aquatic shows make this celebration a standout winter event in Chicago.
Venue: Shedd Aquarium
Address: 1200 S DuSable Lake Shore Drive, Chicago, IL 60605
Phone: 312-939-2438
Website: Visit Website
Highlights:
- Lakefront aquarium
- Holiday programming
- Marine animal encounters
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Museum of Science and Industry Holiday Exhibits
Location: Chicago
Dates: Throughout December 2025
Cost: $$
Celebrate the holiday season at Chicago's Museum of Science and Industry with the 83rd annual Christmas Around the World and Holidays of Light exhibit. This immersive event showcases over 50 intricately decorated trees, each representing diverse cultural traditions from communities worldwide. Visitors experience a vibrant tapestry of global holiday customs beneath a stunning four-story Grand Tree, creating a unique blend of education and festive wonder.
Venue: Museum of Science and Industry
Address: 5700 S DuSable Lake Shore Drive, Chicago, IL 60637
Phone: 773-684-1414
Website: Visit Website
Highlights:
- Christmas Around the World
- Cultural holiday traditions
- Decorated international trees
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Resources
Helpful information and links for planning your holiday season in Chicago.