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You already know you can walk the Lakefront Trail, visit Millennium Park and take a selfie at “The Bean” without spending a dime. But Chicago has a much more interesting list of free things to do if you know where to look.

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There’s something about fall in Chicago that makes even the most devoted city dweller want to trade skyscrapers for apple orchards, swap sidewalks for pumpkin patches and spend a Saturday searching for the perfect pumpkin. Add a little cider, a hayride, a corn maze and perhaps a caramel appl…

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If Halloween is your excuse to get dressed up, get a little wild and see Chicago from a whole new perspective, this may be your last chance to experience one of the city’s most dazzling parties. Illumination: A Halloween Gala of Light, Life, and Hope celebrates its 10th anniversary and final…

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Chicago sports fans, wine collectors and whiskey aficionados have until Friday evening to bid on what could be one of the city’s most unforgettable dining experiences: a private dinner inside the Chicago Blackhawks locker room with Blackhawks legends, exceptional wine, rare whiskey and a men…

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If you’re looking for an excuse to break out the lederhosen, grab a giant pretzel and raise a stein, Oktoberfest Nation is bringing six weeks of Bavarian-style fun to Fulton Market this fall. Billed as Chicago’s largest Oktoberfest, the celebration returns September 17 through October 26, 20…

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Art and shopping meet along one of Chicago’s most iconic streets when Amdur Productions presents the Magnificent Mile Art Festival Sept. 19-20 at 875 North Michigan Avenue.

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Labor Day is getting a little more exciting at Darvin Furniture & Mattress, where shoppers can score major savings on furniture and mattresses while also getting the chance to turn a purchase into a getaway. Now through Sept. 7, Darvin’s Labor Day Sale is offering up to 55% off, plus an …

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Chicago will once again come together this fall for an event centered on hope, remembrance and the belief that suicide can be prevented. The 2026 Out of the Darkness Chicagoland Walk, presented by Happiness Project and the American Foundation for Suicide Prevention (AFSP) Illinois, takes pla…

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Six Flags Great America says Fright Fest is back for its 35th year, turning the Gurnee park into a Halloween destination with haunted attractions, roaming monsters, live shows and nighttime rides. The event runs select nights from Saturday, Sept. 19 through Sunday, Nov. 1, according to the p…

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Chicago will celebrate the global reach of House music with a four-day festival and conference from Thursday, Aug. 27, through Sunday, Aug. 30, as the city’s Department of Cultural Affairs and Special Events (DCASE) brings back the Chicago House Music Festival and Conference. The free event …