Chicago on the Cheap

One of the most beloved events of the early summer season is Chicago’s signature open-air market, the Randolph Street Market Festival. Filled with vintage treasures, live bands, food and fun, the market opens on May 23-24, 2026, in the West Loop. Celebrating 23 years, the Randolph Street Market Festival features an intriguing mix of vintage […]

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The annual Chicago Memorial Day Parade and Wreath Laying Ceremony honors all men and women who made the ultimate sacrifice in defense of our country. This year’s parade is scheduled for May 23, 2026.   Head to Daley Plaza in the Chicago Loop to witness the moving Wreath Laying Ceremony at 11 am at the Eternal […]

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For many neighborhood festival fans, the Summer fest season officially kicks off with the cover band glory of the Belmont-Sheffield Music Festival, set for May 22-24, 2026.   The 40th annual celebration of community and local musicians draws enthusiastic crowds to the streets near the Belmont Red Line station in the Lake View neighborhood. Noted […]

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Beer, food and cover bands are the hallmarks of the city’s first festival of the summer, Chicago Mayfest. This year’s 29th annual edition continues the tradition from May 15-17, 2026, in the Lincoln Park neighborhood.   This year’s fest will kick off at Armitage and Sheffield and feature an impressive offering of street food, cocktails […]

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There’s no Chicago market more iconic than Maxwell Street Market. This year, the market runs on select Sundays, May 17 through October 4, 2026, 10 am -3 pm.  Open since 1912, this bustling marketplace is much more than just a place to shop; it’s a Chicago cultural mecca. Maxwell Street was where Chicago Blues was […]

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