Chicago on the Cheap

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 6, 2026,  at the Columbus Drive Bridge. The festivities include entertainment for the entire family, featuring face painting, games, and appearances by several sports mascots.  […]

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Celebrate Italian history and heritage in the historic Little Italy neighborhood at the annual Taylor Street Little Italy Festa on August 13-16, 2026. Savor the flavors, sounds and traditions of Italy at this beloved festival. Discover the vibrant essence of Italian culture while enjoying traditional food, music and traditions. Dance and sing along to live entertainment […]

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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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Stroll into the trendy West Loop neighborhood for five blocks of eye-catching art for the sixth annual West Loop  Music & Art Fest on August 22-23, 2026.  The free event supplies a full weekend of fun in the Fulton Market district.  Browse through art displays from over 100 artists representing a range of mediums, including […]

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The fun and creativity of chalk art will transform Rogers Park’s Howard Street during the annual  Chalk Howard Street on August 22, 2026.  This free event hosts internationally renowned 2D and 3D artists from around the country Chalk Street Howard is Chicago’s only chalk fest and it returns live in and in person in Rogers Park. […]

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