Embrace the winter season with icy escapades at Gallagher Way. Glide around the ice skating rink, skid across the rink in ice bumper cars or learn how to play ice bocce through February 15, 2026. Whirl around in the frosty air with historic Wrigley Field in the backdrop. Admission to the rink … [Read more...] about Ice skating at Gallagher Way
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Free Things To Do During the Chicago Winter
Chicago's winters boast a well-deserved reputation for being brutal. It's true that the wind chill can make a snowman cry but that doesn't mean you can't still enjoy the frozen beauty of the city. When the Chicago weather hits above 35, consider heading out into the icy magic and … [Read more...] about Free Things To Do During the Chicago Winter
Free Polar Adventure Days
Explore the natural beauty of the winter season during the annual Polar Adventure Days on January 24, 2026. Bundle up and enjoy the chilly fun on the 119 acres of Northerly Island Park, located along the shoreline of Lake Michigan. Connect with nature during a day of … [Read more...] about Free Polar Adventure Days
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
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
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
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
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
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 Chicago Hauntings Night Tour Walk
Listen to creepy stories, walk around spooky downtown landmarks and discover Chicago's eerie past with the free Hauntings Chicago Night Tour with Chicago Walking Tours on October 31, 2025. Follow the trail of the most haunted spots in Chicago with this guided two-hour tour. Learn … [Read more...] about Free Chicago Hauntings Night Tour Walk
Free Meet Me on Milwaukee
Roaming through car-free streets is one of the joys of Chicago street fests and just because the summer is over doesn't mean you can't still experience this favorite pastime. Head to the Wicker Park neighborhood for the Meet Me on Milwaukee event, where the busy intersection of Milwaukee at … [Read more...] about Free Meet Me on Milwaukee
