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
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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
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
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
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
Glenwood Avenue Arts Fest
The Rogers Park neighborhood will host the highly anticipated Glenwood Avenue Arts Fest on August 14-16, 2026. Chicago's most diverse community will showcase free live music, art, creative performances, food and crafts by an eclectic array of artists and artisans. Over 120 … [Read more...] about Glenwood Avenue Arts Fest
Bud Billiken Parade
Head to Chicago's Bronzeville neighborhood to witness the second-largest parade in the U.S. after the Rose Bowl; the historic Bud Billiken Parade celebrates 97 years of African American music, pageantry and community on August 8, 2026. Filled with over 200 elaborate marching bands, drill … [Read more...] about Bud Billiken Parade
