Chicago on the Cheap

The 27th annual Englewood Jazz Festival presents an exciting line-up of established and emerging Chicago musicians for three days in the Englewood community on September 17-19, 2026. Live the Spirit Residency at Hamilton Cultural Center educates and mentors the next generation of jazz musicians.  The free festival will open with the residency’s leader, Ernest Dawkins, […]

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Go back in time and enjoy oldies and throwback fashion at the 29th annual Retro on Roscoe festival on September 18-20, 2026, 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 the 70s, 80s and 90s with featured bands including The […]

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The Hyde Park neighborhood celebrates South Side jazz traditions with free outdoor concerts in Harper Court on the first Fridays of the summer months. Enjoy free live music in the heart of the historic community This year’s dates are June 5, 2026. July 10, 2026, August 7, 2026, and September 11, 2026.  Jazz in the […]

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What’s the forecast for bargain hunters and DQ fans? There’s a blizzard of savings at Dairy Queen this month! It’s just not summer without enjoying one of the ice cream shop’s signature (and iconic) menu items — the Blizzard Treat. Image: Dairy Queen And fans have just a few more weeks to enjoy the seasonal […]

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Looking for something fun to do this weekend in Chicago? There are tons of free and cheap events in the city. Here’s our list of the top free events, discounts, and deals to have fun around town on your Friday, Saturday, and Sunday. There are many diverse events, so choose your favorite.  Some events may […]

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