Chicago on the Cheap

Deals, discounts and free events in Chicago

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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

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Free Chicago World Music Festival

The 25th annual World Music Festival Chicago is a city-wide, multi-venue festival presenting over 30 artists and ensembles from 22 countries around the globe, presented for free over 10 days from September 26 to October 5, 2025. Dance to the rhythms and melodies of musicians from all … [Read more...] about Free Chicago World Music Festival

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

Hyde Park Jazz Festival

Venues across the Hyde Park, Kenwood and Washington Park neighborhoods will come alive with live jazz during the 18th annual Hyde Park Jazz Festival on September 27-28, 2025. Music lovers will enjoy 34 free performances of local, national and international artists at a varied assortment of … [Read more...] about Hyde Park Jazz Festival

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

Posted by Rosalind Cummings-Yeates Filed Under: Expired Tagged With:

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

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