Enjoy holiday festivities with the dramatic backdrop of the Chicago skyline at Rudolph's Rooftop at the LondonHouse Chicago. Take in twinkling lights, nostalgic decor,heated igloos, holiday cocktails and spectacular views of the Chicago River through January 25, 2026. Head to the … [Read more...] about Rudolph’s Rooftop
holiday events
Free Tuba Christmas at the Palmer House
Enjoy the sounds of the holiday on the biggest scale ever at the 52nd annual Tuba Christmas at the historic Palmer House Hotel on December 20, 2025. Tuba players from around the world will descend upon the Grand and State Ballroom in the Plamer House to perform a spirited concert of holiday … [Read more...] about Free Tuba Christmas at the Palmer House
Pre-Kwanzaa Celebration and Marketplace
Chicago celebrates the seven-day, African American holiday of Kwanzaa with performances, plays, story-times and festivals throughout the city. Head to the Washington Park refectory for a free day of music, cultural experiences and a marketplace with the Pre-Kwanzaa Holiday Celebration and … [Read more...] about Pre-Kwanzaa Celebration and Marketplace
Music Box Annual Christmas Sing A long
Celebrate the holiday season in the old school style with classic Christmas movies and a fun-filled sing-along. One of Chicago's most unique holiday traditions is enjoying classic Hollywood holiday movies, singing along to the beloved tunes and accompanying a live organist to sing Christmas carols … [Read more...] about Music Box Annual Christmas Sing A long
Free Sauced Night Market
Welcome the holiday season with shopping, food, music and vibes at Sauced Night Market, on December 12-13, 2025, at the Chicago Athletic Association downtown. This free roving market supplies over three dozen vendors selling hand-crafted artisan goods and food. The holiday festivities … [Read more...] about Free Sauced Night Market
Chicago Artisan Market
Kick off your holiday shopping experience and discover the best in Chicago's handcrafted goods at the Chicago Artisan Market on December 14, 2025, in the West Loop. Shop for one-of-a-kind fashion, food, jewelry, art and home goods at this curated specialty marketplace. This flagship holiday market … [Read more...] about Chicago Artisan Market
Ride the CTA Holiday Train
One of the things that makes the holidays in Chicago extra special is the CTA Holiday Train. For 34 years, a festive train carrying Santa and his reindeer runs through all of the CTA lines, carrying joy and food baskets to Chicago community organizations. The train runs through … [Read more...] about Ride the CTA Holiday Train
Holidaze at Lincoln Park Zoo
Stroll around Lincoln Park Zoo under the glow of millions of lights while enjoying a live DJ during the annual Adults Night Out event, Holidaze, on December 11, 2025. Feel jolly as you dive into the spirit of the season with live ice carvings, pop-up bars and food carts, free rides on the … [Read more...] about Holidaze at Lincoln Park Zoo
Winter WonderFest at Navy Pier
Enjoy all that's jolly and bright during the festive season at the beloved Winter Wonderfest at Navy Pier. Slide, skate, ride and soak up holiday fun at this indoor fest from December 5, 2025, to January 4, 2026. Head to Navy Pier's Festival Hall and take in the 420-foot holiday … [Read more...] about Winter WonderFest at Navy Pier
Garfield Park Conservatory Winter Flower Show
The Chicago holiday season is never complete without the natural beauty of the Garfield Park Winter Flower Show. This year's theme is Merry & Bright, celebrating the festive colors and foliage of the season through January 6, 2025. Stroll through the displays of boldly colored … [Read more...] about Garfield Park Conservatory Winter Flower Show
St. Lucia Festival of Lights
Celebrate the beautiful Swedish tradition of St. Lucia Day at the Swedish American Museum in the Andersonville neighborhood. The annual candlelit procession down Clark Street will take place on December 13, 2025. Starting at sunset around 4:45 pm, specially selected St. Lucia girls" wearing … [Read more...] about St. Lucia Festival of Lights
Andersonville Holiday Trolley
Get ready for the holidays with Swedish goods and hand-crafted gifts while riding the annual Andersonville Holiday Trolley on December 13-14, 2025. Roam through the Andersonville business district with a free holiday trolley that runs all weekend. Sip on steaming cups of … [Read more...] about Andersonville Holiday Trolley
