Celebrate Hispanic Heritage Month along with Latino theater and dramatic creativity at the ninth annual Destinos: Chicago International Latino Theater Festival for three weeks from September 14 to October 11, 2026, at theaters across the city. The Chicago Latino Theater Alliance … [Read more...] about Destinos Chicago Latino Theater Festival
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Hyde Park Jazz Festival
Venues across the Hyde Park, Kenwood and Washington Park neighborhoods will come alive with live jazz during the 20th annual Hyde Park Jazz Festival on September 26-27, 2026. 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
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
Ravenswood ArtWalk
The Ravenswood Corridor community celebrates 24 years of the annual Ravenswood ArtWalk on September 12-13, 2026. The area's artists, manufacturers and brewers will welcome visitors during the ArtWalk with a host of fun and interactive activities. Unfolding from Lawrence to Irving Park St.. … [Read more...] about Ravenswood ArtWalk
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 12 and 13, 2026. Stretching out over five blocks, the Printers Row Lit Fest features more than 100 booksellers, interactive … [Read more...] about Free Printers Row Lit Fest
German-American Oktoberfest
Celebrate German heritage in all its forms, including dance, music, and food at the annual German-American Oktoberfest on September 11- 13, 2026, in the Lincoln Square neighborhood. The opening ceremony kicks off at 8 pm on September 11. Commemorating 100 years of German traditions, the … [Read more...] about German-American Oktoberfest
Taste of Polonia
Celebrate Polish culture at the largest Polish festival in the country, Taste of Polonia, scheduled for September 4-7- 2026. The 44th-anniversary festival brings four days of traditional Polish food, music and crafts. The Taste of Polonia festival serves up live music on four stages, art … [Read more...] about Taste of Polonia
World Dumpling Fest
Explore Chicago's diverse cultures with music, dance and samples of all the variations of ethnic dumplings during the annual World Dumpling Fest on September 19-20, 2026, in the Lincoln Park neighborhood. The Chicago Cultural Alliance hosts the sixth annual World Dumpling Fest to support and … [Read more...] about World Dumpling Fest
Free Lincoln Park Zoo Fall Fest
Celebrate the joys of autumn in the fun-filled setting of Lincoln Park Zoo during the tenth annual Lincoln Park Zoo Fall Fest, September 25-November 1, 2026. 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
Randolph Street Market Festival
One of the most beloved events of the fall season is Chicago's signature open-air market, the Randolph Street Market Festival. Filled with vintage treasures, live bands, food and fun, the market opens on September 26- 27, 2026, in the West Loop. Celebrating 23 years, the Randolph Street … [Read more...] about Randolph Street Market Festival
Englewood Jazz Fest
The 27th annual Englewood Jazz Festival presents an exciting line-up of established and emerging Chicago musicians for three days in the Englewood community on September 17-19, 2026. Live the Spirit Residency at Hamilton Cultural Center educates and mentors the next generation of jazz … [Read more...] about Englewood Jazz Fest
