The beloved Chicago holiday tradition of lighting the Christmas tree that towers over Millennium Park will kick off on November 21, 2025. This live event will fill Millennium Park with music, fireworks and thousands of twinkling lights. A 53-foot-tall Colorado blue spruce was selected for … [Read more...] about Millennium Park Holiday Tree Lighting
family friendly
New Flyover Chicago Attraction
Chicago's iconic skyline and skyscrapers got a little closer since the opening of the Flyover 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 through … [Read more...] about New Flyover 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
Chicago Artisan Market
Start shopping for the holidays and discover the best in Chicago's handcrafted goods at the Chicago Artisan Market on October 19, 2025, in the West Loop. Shop for one-of-a-kind fashion, food, jewelry, art and home goods at this curated specialty marketplace. The Chicago Artisan Market showcases … [Read more...] about Chicago Artisan Market
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 Movies at Gallagher Way
Enjoy the fun of viewing movies al fresco during the Gallagher Way Outdoor Movie Series. The screenings will feature the spooky season theme on October 15 and 22, 2025. The line-up of family-friendly films includes "Hocus Pocus," the classic wacky witches film with Bette … [Read more...] about Free Movies at Gallagher Way
Free National Museum of Mexican Art Dia de los Muertos Chicago
Celebrate the Mexican tradition of Dia de los Muertos or Day of the Dead with the free "Dia de Los Muertos Xicago" event organized by the National Museum of Mexican Art on October 25, 2025, in the Pilsen community. Honoring loved ones who have passed away with ofrendas or altars filled with … [Read more...] about Free National Museum of Mexican Art Dia de los Muertos Chicago
First Lady Fall Cruises
One of Chicago's most iconic experiences is sailing on the scenic Chicago Architecture Center (CAC) River Cruise aboard First Lady and absorbing the city's stunning skyline while learning about its design history. The fun continues through the fall, with cruises floating along the shore … [Read more...] about First Lady Fall Cruises
Free Slightly Spooky Saturday at Navy Pier
Spend Halloween trick or treating at Navy Pier and enjoy interactive art and performances during Slightly Spooky Saturday at Navy Pier on October 25, 2025. Put on your costume and stop by 30 indoor candy stations during this all-day, free event. Besides sweet treats, look out for aerial … [Read more...] about Free Slightly Spooky Saturday at Navy Pier
Destinos Chicago Latino Theater Festival
Celebrate Latino theater and dramatic creativity at the eighth annual Destinos: Chicago International Latino Theater Festival for an entire month, from October 1 to November 2, 2025. , at theaters across the city. The Chicago Latino Theater Alliance presents this anticipated annual … [Read more...] about Destinos Chicago Latino Theater Festival
Free Lincoln Park Spooky Zoo
Celebrate the scary season with a visit to Lincoln Park Zoo for trick or treating among the animals at the annual Spooky Zoo event on October 18, 2025. Stroll around the zoo and collect treats while supplies last. Kids can also enjoy interactive storytelling and live music on the Main Mall … [Read more...] about Free Lincoln Park Spooky Zoo
