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
outdoor
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
Free Sundays on State
State Street, that great street, will be closed to traffic and open for an interactive, fun-filled block party in the heart of the Loop. Sundays on State is scheduled this summer for September 7 and October 5, 2025. From 11 to 6 pm on the designated Sundays, State Street between Lake and … [Read more...] about Free Sundays on State
Free Lincoln Park Zoo Fall Fest
Celebrate the joys of autumn in the fun-filled setting of Lincoln Park Zoo during the ninth annual Lincoln Park Zoo Fall Fest, September 26-October 26, 2025. Step into the vibrant world of pumpkins, harvest mazes and fall photo ops during this family-friendly event. Admission to the zoo is … [Read more...] about Free Lincoln Park Zoo Fall Fest
Art on the Mart
Stroll through the Riverwalk for views of one of the world's largest digital art platforms. ART on THE MART displays contemporary art projections across the 2.5-acre facade of THE MART. The fall show features artists from Arts of Life on Thursdays and Fridays from September 11- October 5, 2025 … [Read more...] about Art on the Mart
