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
Holidays
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
Skate in the Clouds at Peninsula Sky Rink
Ice skating is a beloved Chicago winter tradition with rinks all over the city but one of the most scenic skating experiences is at The Peninsula Chicago's Sky Rink, perched above the Magnificent Mile with sparkling lights and pine trees. The rink is open through February 16, 2026. Ride up to … [Read more...] about Skate in the Clouds at Peninsula Sky Rink
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
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
Chicago Holidays at Macy’s
For generations of Chicagoans, the essence of Christmas in Chicago is a stroll down State Street to view the holiday windows at Macey's (Marshall Field's) landmark department store, lunch at the Walnut Room surrounded by the ceiling-scraping tree, topped off with a visit with Santa. Macy's … [Read more...] about Chicago Holidays at Macy’s
Lincoln Park Conservatory Holiday Flower Show
Lincoln Park Conservatory's beloved Winter Flower Show will explore the enchanting beauty of fireplaces and poinsettias with this year's show, "Fireside," which runs from November 26, 2025, to January 4, 2026. Cozy up at the enormous brick fireplace centerpiece and check out the thrilling … [Read more...] about Lincoln Park Conservatory Holiday Flower Show
Christmas Around the World and Holidays of Light
One of Chicago's most iconic holiday traditions is viewing the holiday trees from around the world at the Christmas Around The World exhibit at the Griffin Museum of Science & Industry. This year's display includes Holidays of Light, a celebration of global holidays that honor light … [Read more...] about Christmas Around the World and Holidays of Light
Millennium Park Holiday Sing-Alongs
Celebrate the season with festive live concerts every Friday with the Millennium Park Holiday Sing-Along starting on December 5, 12 and 19, 2025. Join a diverse group of choirs and ensembles as they light up the park with music. The holiday Sing-Along kicks off on Fridays from 6-7 pm, right … [Read more...] about Millennium Park Holiday Sing-Alongs
Jack Frost Fulton Market
Stroll under 100,000 holiday lights and dive into seasonal fun, including holiday pop-up shops, ice skating and bumper cars at the Jack Frost Holiday Pop-Up at Fulton Market, opening on November 15, 2025. Journey into the ultimate holiday adventure with a … [Read more...] about Jack Frost Fulton Market
