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
outdoor
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
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
Free Pumpkin Party at Gallagher Way
Go pumpkin hunting, dance to live music, create arts and crafts and enjoy the season at Gallagher Way's annual Pumpkin Party on October 25, 2025, in the Wrigleyville neighborhood. Bring the kids for a fun-filled day of costumes, trick-or-treating and non-stop activities. The Old Town … [Read more...] about Free Pumpkin Party at Gallagher Way
Free Bird Walks at North Park Village
Enjoy a free guided walk and search for migratory birds every Saturday in September and October at the North Park Village Nature Center. Join Jorge Garcia of Windy City Bird Lab and discover the beauty of birding on September 20, 27 and October 4, 11, and 18, 2025. The walk is less than … [Read more...] about Free Bird Walks at North Park Village
Arts in the Dark Halloween Parade
Head to State Street to celebrate Halloween as the "artist's holiday" with an evening of wonder and creativity at the Arts in the Dark Halloween Parade on October 18, 2025, in the Loop. Recognized as one of the top six Halloween events in the world, the tenth annual Arts in the Dark parade … [Read more...] about Arts in the Dark Halloween Parade
