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
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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
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 27-30, 2026. The four days of free events will feature live … [Read more...] about Chicago House Music Festival and Conference
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 SummerDance
One of the city’s most beloved dance traditions, Chicago Summerdance, returns to the Spirit of Music Garden in Grant Park as well as neighborhood parks for open-air dancing, live music and dance lessons all summer long, through August 29, 2026. Every Wednesday through Saturday of each week, … [Read more...] about Chicago SummerDance
Northalsted Market Days
The largest street festival in the Midwest returns to the bustling Lakeview neighborhood for a three-day celebration of music, pride and community. Northalsted Market Days is scheduled for August 7-9, 2026. The 44th annual festival kicks off with over 250 vendors, five stages and all-day … [Read more...] about Northalsted Market Days
Free Obama Center Activities
The Obama Presidential Center has drawn visitors from all over the world who want to discover the history and legacy of the country's first Black President. The museum and its interactive exhibits capture a lot of attention but the campus also hosts free events open to the public. … [Read more...] about Free Obama Center Activities
