Our 2025 Winter Events Calendar highlights unique and exciting activities around Chicagoland. Check out the full list below to add a little more magic to your holiday memories!
Experience the magic of skating at McCormick Tribune Rink in Millennium Park, surrounded by Chicago’s dazzling skyline, the twinkling city Christmas tree, and the iconic Bean. Admission is free (reservations required); skate rentals are available. (November–March 2026)
Skate in Hyde Park at the site of Chicago’s 1893 World’s Fair, surrounded by the gothic architecture of the University of Chicago. Free admission, with rentals and skate aids available. Perfect for hockey games or skating lessons on select days! (November – February 2026)
Skate high above Michigan Avenue on this picturesque rink featuring festive music, snowflake lighting, and seasonal treats. Admission includes skate rentals and benefits children’s charities. Private events and group rentals available. (November – February 2026)
State Street comes indoors for a magical shopping experience with local artisans and Sundays on State small businesses.
The German-style outdoor market has grown so popular that it now spans several locations. With festive shopping, cheerful entertainment, and traditional treats like imported Glühwein, Christkindlmarket remains a beloved holiday destination highlighted by major media outlets.
Chicagoland’s favorite holiday tradition returns with more than 3 million lights, nostalgic displays, and festive experiences throughout Lincoln Park Zoo. Wander through the glowing light tunnel, ride the Ferris wheel for skyline views, and enjoy seasonal treats like hot chocolate, churros, and s’mores.
Slide down a 200-foot sledding hill near historic Soldier Field, with sweeping views of Lake Michigan. A perfect winter outing in the heart of Chicago!
Explore global holiday traditions at the Museum of Science and Industry, where exhibits highlight festive customs and create opportunities for cherished memories.
Cruise down the Chicago River in a heated hot tub! Chicago Electric Boat Company launches from Marina City docks at 300 N. State Street. Reservations are required for guests 13 and older.
Located in Wrigleyville, this multi-level, over-the-top holiday bar is filled with festive decor, themed drinks, and plenty of holiday spirit.
Visit the Woodstock Opera House for the annual Christmas Tree Walk, a local favorite that fills the space with festive charm. This year’s theme, The Golden Age of Christmas, features beautifully decorated trees that capture nostalgic holiday traditions and community spirit.
Board the CTA Holiday Train and Bus for a festive city tour, starting in late November. Enjoy decorations, lights, and treats as you travel through Chicago in holiday style.
Ride the Illinois Railway Museum’s Happy Holiday Railway in Union, Illinois. This event runs select dates through December 23 and features festive train rides with Santa. Trips depart at scheduled times; arrive early to check in.
Craft your own spirit-free cocktails while you decorate your own gingerbread house doormat!
Stroll through twinkling lights, sip seasonal refreshments, and meet special guests at this family-friendly event. Cameras, strollers, and wagons are welcome. Rain, snow, or shine—dress for the weather and soak in the holiday magic.
Celebrate the season with a Santa parade, horse-drawn carriage rides, hot chocolate and cookies, and performances from local school groups. A warm and festive tradition for all ages!
Select Frankfort homes will be decorated for the holidays, certain to put visitors in the mood for Christmas. As an added highlight, the Frankfort Arts Association will host an open house featuring upcoming exhibits and activities.
Join us for a magical winter weekend filled with festive cheer, seasonal treats, and perfect gifts for every occasion. From handmade crafts to holiday-inspired treasures, this is an event you won’t want to miss.
Kick off the season with the Bolingbrook Area Chamber of Commerce at its Annual Holiday Party and Charity Challenge at Ashbury’s at Boughton Ridge. This festive evening features the popular Charity Challenge, where bartenders from local favorites compete by crafting signature cocktails.
The One of a Kind Holiday Show brings together hand-crafted goods, specialty items, unique artwork, gourmet food, live music, and hands-on activities for a truly memorable shopping experience.
Gather at The Bean for holiday sing-alongs led by local Chicago choral groups. Celebrate diverse holiday traditions as you join in the fun with friends and family. Singing begins at 6 PM each Friday.
Shop one-of-a-kind handmade works by over 160 artists at Evanston Art Center. Find jewelry, ceramics, photography, and more while supporting local artists and the center’s programs.
This holiday season, enter a spellbinding world where history and dreams intertwine. Join Marie and her Nutcracker prince on a fantastical adventure in Tony Award-winning Christopher Wheeldon’s reimagining of The Nutcracker, set amid the spectacle of the 1893 Chicago World’s Fair.
Join the City of West Chicago in its historic downtown for the annual Frosty Fest. Held on the first Saturday of December, the event commemorates the start of the holiday season in the community.
Beat the winter blues by catching a live comedy show. From improv to stand-up, these local venues offer plenty of laughs and an easy night out whether you’re meeting friends or planning a date night.
The Paramount Theatre in Aurora offers $1 Movie Mondays in December. Catch family favorites like The Grinch Stole Christmas (December 15) and The Polar Express (December 22). Perfect for a family outing!
Created to celebrate creativity, passion, and innovation, the museum lets guests learn about ice cream history while enjoying immersive ice cream-themed installations.
Explore three unforgettable experiences at the Skydeck in the Willis Tower. Visit The Chicago Museum, step out onto The Ledge, and take in breathtaking views from America’s highest observation deck.
Step into an enchanting 1.3-mile trail of twinkling lights and showstopping displays expertly curated each year. Bundle up, grab a hot chocolate, and see the Chicago Botanic Garden glow beyond the expected.
Jingles the Reindeer invites you to join local organizations across Lombard for an evening of holiday sights and sounds. A complimentary trolley will run from 4:30 to 8:30 p.m.
Jazz trio Mr. Chair performs the timeless Vince Guaraldi album along with other holiday favorites.
Bundle up and enjoy the season with a scenic winter hike. These nearby destinations offer peaceful trails, beautiful views, and a refreshing break from the indoors.
Local designers and greenscape experts team up to decorate homes around Geneva, offering ideas for holiday décor. Each designer incorporates items available at local shops.
Cozy up at Hawthorn Row for a festive evening the whole family will love. Sip, stroll, and soak in the holiday magic.
Join Elsa, Olaf, Elf, and Santa for a day of holiday cheer at Wheaton’s Town Square! Enjoy strolling carolers, complimentary cocoa, and festive giveaways.
Celebrate the shortest day of the year with a lantern-lit walk through snowy trails. We’ll begin at Heller Nature Center by making nature lanterns, then parade through the park while sharing poems, songs, and stories from winter traditions. After the walk, we’ll return to the Nature Center for a warm beverage.
Wander through downtown Downers Grove and enjoy festive holiday window displays. Last year featured over 40 gingerbread-themed designs—cast your vote for the best one!
Brookfield Zoo hosts a magical holiday buffet featuring festive treats and a special visit from Santa. Explore the zoo’s illuminated grounds for an enchanting seasonal experience.
Create your own artwork, explore the Multisensory Gallery, and build a custom museum tour with JourneyMaker at the Art Institute’s Ryan Learning Center. A perfect creative outlet for visitors of all ages.
Enjoy some friendly competition this winter by booking an indoor golf bay or pickleball court. Whether you’re looking for a fun night out or an active weekend plan, these indoor options let you stay warm while staying active.
Sharpen your culinary skills by signing up for a hands-on cooking class. From beginner basics to themed seasonal dishes, these experiences offer expert instruction and a fun way to try something new.
Take a guided horseback trail ride through the rolling hills and vast fields of a 140-acre eco-friendly farm. Experienced trail guides help you feel safe and relaxed throughout the one-hour ride, which includes mounting and dismounting time. No experience is required.
Treat yourself to a relaxing winter escape with a restorative spa experience. Enjoy massages, hydrotherapy, or thermal baths as a way to unwind, recharge, and warm up during the colder months.
Get creative this winter with a hands-on arts and crafts class. Whether you’re painting, working with pottery, or designing jewelry, these workshops offer a fun way to explore your artistic side.
Over 1 million synchronized LED lights!
A magical holiday lights event at Willow Hill Golf Course.
Choose between two shows: a drive-thru orchard light display or a dazzling light show from your parked car.
For over 20 years, The Gift Theatre is an intimate space that showcases new works and reimagined classics.
As the University of Chicago’s professional theatre, Court Theatre is known for taking classic American works, and then adapting and expanding them.
This new venue in Arlington Heights seats up to 350 in comfort, with state-of-the-art sound and lighting.
Start the new year with a fitness goal of walking or running 25, 50, or 100 miles. Log your miles virtually or at The Morton Arboretum to support a greener, healthier world. Pre-registration required.