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 96 years of African American music, pageantry and community on August 9, 2025. Filled with over 200 elaborate marching bands, drill … [Read more...] about Bud Billiken Parade
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Retro on Roscoe Festival
Go back in time and enjoy oldies and throwback fashion at the 28th annual Retro on Roscoe festival on September 5-7, 2025, 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
Eataly Prix Fixe Deal: Sicilian Nights
Travel to the sun-splashed coast of Sicily and indulge in the fresh produce and seafood that the Italian region is known for, at Eatly Chicago's special prix fixe menu, Sicilian Night, through August 31, 2025. Taste the luscious ingredients of Sicilia, including eggplants, pistachios, … [Read more...] about Eataly Prix Fixe Deal: Sicilian Nights
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 7, 2025, at the Columbus Drive Bridge. The festivities include entertainment for the entire family, … [Read more...] about Chicago Rubber Ducky Derby
Jeff Fest Arts and Music Festival
The Jefferson Park neighborhood on Chicago's Northwest side will come alive with music and creative arts during the 24th annual Jeff Fest, on August 1-2, 2025. The sprawling seven acres of Jefferson Memorial Park will host this beloved community event, which features tribute bands, … [Read more...] about Jeff Fest Arts and Music Festival
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 August 28 -31, 2025. Celebrate jazz in all its forms in Millennium Park and … [Read more...] about Free Chicago Jazz Festival
Northalsted Market Days
The largest street festival in the Midwest returns to the bustling Lakeview neighborhood for a two-day celebration of music, pride and community. Northalsted Market Days is scheduled for August 8-10, 2025. The 43rd annual festival kicks off with over 250 vendors, five stages and all-day … [Read more...] about Northalsted Market Days
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
Chicago House Music Festival and Conference
As the birthplace of house music, Chicago always celebrates and honors this influential art form. The Chicago House Music Festival and Conference will bring the music, history and culture of house music into focus on August 21-24, 2025. The four days of free events will feature … [Read more...] about Chicago House Music Festival and Conference
Southport Art Fest
Chicago's bustling Southport Corridor will fill with even more activity during the annual Southport Art Festival on July 13 and 14, 2025. This two-day event features an eclectic assortment of art and crafts as well as food and drinks. Stroll down the leafy streets and check out paintings, … [Read more...] about Southport Art Fest
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 27, 2025, at St. Moses the Black Parish. Hosted by the Southside Jazz Coalition, this popular community concert features well-known jazz vocalists and musicians performing on the … [Read more...] about Jazz ‘N on The Steps
Wrigleyville Night Market
Summer nights just got more exciting with the start of the weekly Wrigleyville Night Markets at Gallagher Way, kicking off on July 10, 2025, through September 18, 2025. Enjoy strolling through over 50 vendors displaying vintage clothing, jewelry, home goods and lots of unexpected finds. … [Read more...] about Wrigleyville Night Market
