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
family friendly
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
Jazz ‘N on The Steps
Take in the smooth rhythms of jazz during Summer evenings at the Jazz' N on the Steps free event on July 26, August 28 and September 27, 2026, at St. Moses the Black Parish. Hosted by the Southside Jazz Coalition, this popular community concert features well-known jazz … [Read more...] about Jazz ‘N on The Steps
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
Free Chicago Air and Water Show
One of the most anticipated events of the Summer is the thrilling Chicago Air and Water Show. For over six decades, Chicagoans have witnessed the exciting spectacle of pilots and parachutists performing daring tricks over Lake Michigan. The largest show of its kind in the U.S., this … [Read more...] about Free Chicago Air and Water Show
Free Chicago Museum Days for Summer
Summertime Chicago supplies so many non-stop activities and adventures that it's easy to overlook excursions that are available all year round. But Chicago's world-class museums are popular at any time, so it's helpful to consider Chicago museum free days during the summer months. Check out these … [Read more...] about Free Chicago Museum Days for Summer
