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
outdoor
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
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
West Town Art Walk
Enjoy visual art, music, and fashion while browsing restaurants and shops along Chicago Avenue in the bustling West Town neighborhood during the 15th annual West Town Art Walk on October 3-5, 2005. The West Town neighborhood bubbles with color, food and art in all forms during this popular … [Read more...] about West Town Art Walk
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
Riverwalk Fall Fest
Experience the beauty of the fall season with the Chicago River as the backdrop at the Island Party Hut Fall Fest on the Chicago Riverwalk on Saturdays, September 20-October 25, 2025. Enjoy autumn festivities like hay rides on the river, pumpkin patches and eating apple cider donuts along the … [Read more...] about Riverwalk Fall Fest
St. Benedict’s Oktoberfest
Get ready for the welcoming traditional German toasts of "Prost!" to echo throughout the courtyard during the 59th annual St. Benedict Oktoberfest on October 3-5, 2025. St. Benedict parish celebrates its German roots with a family-friendly fest that includes German food and … [Read more...] about St. Benedict’s Oktoberfest
Randolph Street Market
In honor of the fall season, Chicago's signature open-air market, the Randolph Street Market, is hosting its fall market with vintage treasures, live bands, food and fun on September 27-28, 2025, in the West Loop. Celebrating 22 years, the Randolph Street Market Festival features an … [Read more...] about Randolph Street Market
Jack’s Pumpkin Pop Up
Wander through pumpkin patches and corn mazes while you enjoy the season at Chicago's largest fall festival, Jack's Pumpkin Pop Up, located near Goose Island, from September 18 to November 2, 2025. The large number of all-ages festivities make Jack's one of the most popular fall excursions. … [Read more...] about Jack’s Pumpkin Pop Up
