Dovetail Brewery and Begyle Brewing serve up their annual fall street festival with Oktoberfestiversary on October 11-12, 2025. Enjoy brews, live music and food in the Ravenswood neighborhood. Sip on special tappings from Beglye and Dovetail while munching on sausages, lobster rolls and … [Read more...] about Oktoberfestiversary
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Chicago Architecture Biennial
The city's most anticipated architecture event, the Chicago Architecture Biennial, unfolds this year with the theme, "SHIFT: Architecture in Times of Radical Change," featuring exhibits, panel discussions, films, performances, activations and events across the city through February 28, … [Read more...] about Chicago Architecture Biennial
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
Lincoln Square Ravenswood Apple Fest
Enjoy Fall fun with apple-inspired food, drinks and artisan goods at the Lincoln Square Ravenswood Apple Fest, October 3-5, 2025. 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 food … [Read more...] about Lincoln Square Ravenswood Apple Fest
Reeling International Film Fest
The second-oldest LBTGQ+ film festival in the country kicks off with an exciting line-up of international features, documentaries and shorts with the 43rd annual Reeling International Film Festival on September 19-28, 2025. The rich diversity of the queer community is showcased during the … [Read more...] about Reeling International Film 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
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 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
St. Alphonsus Oktoberfest Chicago
It's that time of year when Chicagoans welcome the autumn season with polka, lederhosen and lots and lots of beer. St. Alphonsus Church celebrates its 21st annual Oktoberfest Chicago in the west Lakeview neighborhood with Bavarian food, live music and craft beer tasting on September 26-28, … [Read more...] about St. Alphonsus Oktoberfest Chicago
West Loop Art Fest
Stroll into the trendy West Loop neighborhood for five blocks of eye-catching art for the fifth annual West Loop Music & Art Fest on September 20-21, 2025. The free event supplies a full weekend of fun in the Fulton Market district. Browse through art displays from over … [Read more...] about West Loop Art Fest
Chicago Live! at Navy Pier
Witness the excitement of Chicago's extensive performing arts scene during the fifth annual Chicago Live! festival on September 20-21, 2025. Navy Pier will host free, non-stop performances featuring Chicago dance, theater, music and more during the two-day event. The breadth of Chicago's … [Read more...] about Chicago Live! at Navy Pier
Englewood Jazz Fest
The 26th annual Englewood Jazz Festival presents an exciting line-up of established and emerging Chicago musicians for three days in the Englewood community on September 18-20, 2025. Live the Spirit Residency at Hamilton Cultural Center educates and mentors the next generation of … [Read more...] about Englewood Jazz Fest
