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
family friendly
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
Noche Caribena at Navy Pier
Celebrate the spirit of Puerto Rican culture during Noche Caribena, (Caribbean night) an evening of free Puerto Rican music and dance at Navy Pier's Polk Brothers stage, on August 22, 2026. Hosted by the Puerto Rican Arts Alliance , Noche Caribena features an array of traditional … [Read more...] about Noche Caribena at Navy Pier
Retro on Roscoe Festival
Go back in time and enjoy oldies and throwback fashion at the 29th annual Retro on Roscoe festival on September 18-20, 2026, in the Roscoe Village neighborhood. Groove to music on three stages, including a family stage, within a six-block stretch of Roscoe Village. Enjoy music from … [Read more...] about Retro on Roscoe Festival
Jazz in the Court
The Hyde Park neighborhood celebrates South Side jazz traditions with free outdoor concerts in Harper Court on the first Fridays of the summer months. Enjoy free live music in the heart of the historic community This year's dates are June 5, 2026. July 10, 2026, August 7, 2026, and September … [Read more...] about Jazz in the Court
Free Printer’s Row Art Fest
Head to the historic Printer's Row neighborhood in the South Loop to explore art and live music during the annual Printer's Row Art Fest on August 15-16, 2026. Browse through the original artworks of 95 juried artists, including paintings, ceramics, jewelry, woodwork, photography and fashion … [Read more...] about Free Printer’s Row Art Fest
Chicago Rubber Ducky Derby
Relive the childhood joy of floating rubber ducks and watch 60,000 rubber ducks get dumped into and race down the Chicago River during the annual Chicago Ducky Derby on August 6, 2026, at the Columbus Drive Bridge. The festivities include entertainment for the entire family, featuring … [Read more...] about Chicago Rubber Ducky Derby
Little Italy Festa
Celebrate Italian history and heritage in the historic Little Italy neighborhood at the annual Taylor Street Little Italy Festa on August 13-16, 2026. Savor the flavors, sounds and traditions of Italy at this beloved festival. Discover the vibrant essence of Italian culture while … [Read more...] about Little Italy Festa
Chalk Howard Street
The fun and creativity of chalk art will transform Rogers Park's Howard Street during the annual Chalk Howard Street on August 22, 2026. This free event hosts internationally renowned 2D and 3D artists from around the country Chalk Street Howard is Chicago's only chalk fest … [Read more...] about Chalk Howard Street
Taste of Greektown
Chicago's largest celebration of Hellenic culture returns for the 36th annual Taste of Greektown on August 28--30, 2026. Head to the historic Greektown neighborhood to savor Greek food, music and warm hospitality. The hallmark of Taste of Greektown is sampling dishes from the … [Read more...] about Taste of Greektown
