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
Chicago festivals
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
Lakeview Taco Fest
Munch your way through Southport Avenue and cast your vote for the best taco during the annual Lakeview Taco Fest on August 21-23, 2026. This popular three-day festival offers dozens of taco varieties and flavors all in one place. Celebrate the 13th year of the Lakeview … [Read more...] about Lakeview Taco Fest
Free Chicago World Music Festival
The 26th 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 25 to October 4, 2026. Dance to the rhythms and melodies of musicians from all … [Read more...] about Free Chicago World Music 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
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
Edgewater Music Fest
Visit the vibrant Edgewater community to experience a free, three-day festival of live music, food and elite vibes, during the annual Edgewater Music Fest from August 28-30, 2026. Enjoy two stages featuring over 35 local music acts, 100 vendors selling art, crafts, jewelry, and clothes and an … [Read more...] about Edgewater Music Fest
Free Chicago Jazz Festival
Since 1974, jazz fans from all over the globe have flocked to Chicago for the annual Chicago Jazz Festival, which showcases jazz legends as well as up-and-coming musicians. This year's four-day festival will run from September 3-6 2026. Celebrate jazz in all its forms in Millennium Park and … [Read more...] about Free Chicago Jazz Festival
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
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
West Loop Art Fest
Stroll into the trendy West Loop neighborhood for five blocks of eye-catching art for the sixth annual West Loop Music & Art Fest on August 22-23, 2026. The free event supplies a full weekend of fun in the Fulton Market district. Browse through art displays from over 100 … [Read more...] about West Loop Art Fest
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
