Chicago on the Cheap

Deals, discounts and free events in Chicago

Expired

West Loop Art Fest

Stroll into the trendy West Loop neighborhood for five blocks of eye-catching art for the fifth annual West Loop  Music & Art Fest on September 20-21, 2025.  The free event supplies a full weekend of fun in the Fulton Market district.  Browse through art displays from over … [Read more...] about West Loop Art Fest

Chicago Live! at Navy Pier

Witness the excitement of Chicago's extensive performing arts scene during the fifth annual Chicago Live! festival on September 20-21, 2025. Navy Pier will host free, non-stop performances featuring Chicago dance, theater, music and more during the two-day event. The breadth of Chicago's … [Read more...] about Chicago Live! at Navy Pier

Englewood Jazz Fest

  The 26th annual Englewood Jazz Festival presents an exciting line-up of established and emerging Chicago musicians for three days in the Englewood community on September 18-20, 2025. Live the Spirit Residency at Hamilton Cultural Center educates and mentors the next generation of … [Read more...] about Englewood Jazz Fest

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

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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

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