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 19 to November 1, 2026. 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
fall events
Lincoln Square Ravenswood Apple Fest
Enjoy Fall fun with apple-inspired food, drinks and artisan goods at the beloved Lincoln Square Ravenswood Apple Fest, October 2-4, 2026. Celebrate the new season with a bounty of edible goodness. Midwest farms will be serving up fresh apples and related dishes and local restaurants and … [Read more...] about Lincoln Square Ravenswood Apple Fest
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
St. Benedict’s Oktoberfest
Get ready for the welcoming traditional German toasts of "Prost!" to echo throughout the courtyard during the 60th annual St. Benedict Oktoberfest on October 2-4, 2026. St. Benedict parish celebrates its German roots with a family-friendly fest that includes German food and … [Read more...] about St. Benedict’s Oktoberfest
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 19- October 31, 2026. Enjoy autumn festivities like hay rides on the river, pumpkin patches and eating apple cider donuts along … [Read more...] about Riverwalk Fall Fest
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
Adults Night Out Howl-o-ween at Lincoln Park Zoo
Get ready for spooky animal shenanigans at Adults Night Out Howl-o-ween at Lincoln Park Zoo. Visitors 18 and over can stroll the zoo after dark, sip cocktails and have a fang-tastic time on October 24, 2025. Pop-up bars, corn hole, Jenga and free rides on the AT&T Endangered Species … [Read more...] about Adults Night Out Howl-o-ween at Lincoln Park Zoo
Super Horror Rama Film Fest
Dive into the creepiness of the scary season with two nights of obscure horror films at Super-Horror-Rama Film Fest on October 10-11, 20245 in the Lakeview neighborhood at the Music Box Theatre. Prepare to have petrified fun with a showcase of horror film oddities with the theme of … [Read more...] about Super Horror Rama Film Fest
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
Free Time Out Market Fifth Anniversary Party
Join the all-day celebration for five years of food, drinks and events during the Fifth Anniversary Celebration of Time Out Market, on November 16, 2024. Enjoy food and drink specials and live DJs in the West Loop neighborhood. Head to Time Out Market for festivities filled … [Read more...] about Free Time Out Market Fifth Anniversary Party
Andersonville Viking Pub Crawl
The Andersonville neighborhood's historic Swedish roots will be on full display during the sixth annual Viking Pub Crawl down Clark Street on November 17, 2024. Hundreds of revelers will don viking gear and grab a commemorative glass as they visit a dozen bars and restaurants offering specials … [Read more...] about Andersonville Viking Pub Crawl
