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
Kids' Activities
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
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
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
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
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
ZooLights at Lincoln Park Zoo $7 plus free nights
Lincoln Park Zoo's annual Zoo Lights is the highlight of Chicago's holiday season, with hundreds of lights twinkling across the grounds. Tickets are on sale now for the event, which opens on November 21, 2025. Stroll through the zoo and enjoy an illuminated holiday wonderland of animal … [Read more...] about ZooLights at Lincoln Park Zoo $7 plus free nights
Winterland at Gallagher Way
Dive into a quintessential Chicago holiday experience by skating around the iconic Wrigley Field as well as enjoying live music, holiday decor, classic holiday movies and more at Winterland at Gallagher Way, November 23-December 31, 2025. Head to the Wrigleyville neighborhood to … [Read more...] about Winterland at Gallagher Way
New Flyover in Chicago Attraction
Chicago's iconic skyline and skyscrapers got a little closer since the opening of the Flyover in Chicago immersive flying experience at Navy Pier. This exciting attraction that soars over downtown Chicago just added another experience: Call of the Canadian Rockies. Leave the city and fly … [Read more...] about New Flyover in Chicago Attraction
Maggie Daley Park Skating Ribbon
Whirl around the twirling ice skating ribbon at Maggie Daley Park for the ultimate winter season experience. The Maggie Daley Park Ice Skating Ribbon is open every day from November 14, 2025, through March 8, 2026. Roll around the whimsical ice skating ribbon for a more exciting ride than … [Read more...] about Maggie Daley Park Skating Ribbon
Free Polar Adventure Days
Explore the natural beauty of the winter season during the annual Polar Adventure Days on February 22, 2025. Bundle up and enjoy chilly fun on the 300 acres of Big Marsh Park in the South Deering neighborhood. Connect with nature during a day of winter adventures … [Read more...] about Free Polar Adventure Days
