Celebrate German heritage in all its forms, including dance, music, and food at the annual German-American Oktoberfest on September 5--7,2025, in the Lincoln Square neighborhood. The opening ceremony kicks off at 8 pm on September 5. Commemorating 100 years of German traditions, the German … [Read more...] about German-American Oktoberfest
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Free Thirsty Ears Classical Music Fest
Enjoy the beautiful melodies, cultural traditions and welcoming community of Chicago's only classical music festival, the Thirsty Ears Festival on August 23-24, 2025. The 10th annual event supplies two days of classical music, food vendors, craft beer and kids' activities in the … [Read more...] about Free Thirsty Ears Classical Music Fest
Cinnabon celebrates 40th birthday with $1.25 cinnamon rolls for one day only
You always know a Cinnabon is nearby because of the sweet scent wafting in the air. And the bakery shop has been pulling fresh, hot cinnamon rolls out of the oven for 40 years. This year marks Cinnabon’s 40th birthday and they’re celebrating by taking customers back to 1985 with a sweet deal on its … [Read more...] about Cinnabon celebrates 40th birthday with $1.25 cinnamon rolls for one day only
Free Printers Row Lit Fest
The Midwest's largest literary festival returns to Chicago's historic Printer's Row neighborhood in the South Loop with the Printer's Row Lit Fest on September 6 and 7, 2025. Stretching out over five blocks, the Printers Row Lit Fest features more than 100 booksellers, interactive … [Read more...] about Free Printers Row Lit Fest
Harper Court Summer Music Series
Hyde Park sizzles in the summer and the neighborhood will get even more energized during the Harper Court Summer Music Series, set for August 7 and September 4, 2025. A summer tradition since 2015, the free outdoor concerts feature local musicians and bring a festive sense of community … [Read more...] about Harper Court Summer Music Series
Glenwood Avenue Arts Fest
The Rogers Park neighborhood will host the highly anticipated Glenwood Avenue Arts Fest on August 15-17, 2025. 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 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
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
