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
Chicago festivals
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
German-American Oktoberfest
Celebrate German heritage in all its forms, including dance, music, and food at the annual German-American Oktoberfest on September 5--7,2025, in the Lincoln Square neighborhood. The opening ceremony kicks off at 8 pm on September 5. Commemorating 100 years of German traditions, the German … [Read more...] about German-American Oktoberfest
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
Free Thirsty Ears Classical Music Fest
Enjoy the beautiful melodies, cultural traditions and welcoming community of Chicago's only classical music festival, the Thirsty Ears Festival on August 23-24, 2025. The 10th annual event supplies two days of classical music, food vendors, craft beer and kids' activities in the … [Read more...] about Free Thirsty Ears Classical Music Fest
Ravenswood ArtWalk
The Ravenswood Corridor community celebrates 21 years of the annual Ravenswood ArtWalk on September 13-14, 2025. The area's artists, manufacturers and brewers will welcome visitors during the ArtWalk for the first time in two years, with a host of fun and interactive … [Read more...] about Ravenswood ArtWalk
Free Chicago World Music Festival
The 25th annual World Music Festival Chicago is a city-wide, multi-venue festival presenting over 30 artists and ensembles from 22 countries around the globe, presented for free over 10 days from September 26 to October 5, 2025. Dance to the rhythms and melodies of musicians from all … [Read more...] about Free Chicago World Music Festival
Free Printers Row Lit Fest
The Midwest's largest literary festival returns to Chicago's historic Printer's Row neighborhood in the South Loop with the Printer's Row Lit Fest on September 6 and 7, 2025. Stretching out over five blocks, the Printers Row Lit Fest features more than 100 booksellers, interactive … [Read more...] about Free Printers Row Lit Fest
Hyde Park Jazz Festival
Venues across the Hyde Park, Kenwood and Washington Park neighborhoods will come alive with live jazz during the 18th annual Hyde Park Jazz Festival on September 27-28, 2025. Music lovers will enjoy 34 free performances of local, national and international artists at a varied assortment of … [Read more...] about Hyde Park Jazz Festival
