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Holiday shopping is about to get a whole lot more interesting. The beloved Randolph Street Market Festival is returning to Chicago’s West Loop for two special Holiday Market weekends, Nov. 14-15 and Dec. 12-13, bringing its signature mix of vintage treasures, designer finds, handcrafted gift…

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I swear I could smell the pine trees the moment I walked into the Walnut Room at Macy’s State Street for its 119th Great Tree Lighting on the morning of Nov. 7. The historic dining room was packed with diners and onlookers, all eager to catch a glimpse of one of Chicago’s most beloved holida…

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Chicago’s holiday season will get a little extra Disney magic this year when Mickey Mouse and Minnie Mouse lead the 35th annual Wintrust Magnificent Mile Lights Festival on Saturday, Nov. 21. The beloved downtown tradition returns with a full day of free family activities, an evening parade,…

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As National Children’s Grief Awareness Day approaches, Rainbows for All Children is inviting the community to pick up a paddle and help bring greater attention to an issue that often goes unnoticed: the grief children experience when their families change or a parent is no longer present.The…

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WINGS raised a record $1.2 million to support domestic violence survivors at its 26th annual Purple Tie Ball held at the Renaissance Schaumburg Convention Center Hotel. More than 700 guests attended the grand masquerade-themed evening, which celebrated the organization’s work while raising c…

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As the weather chills and the leaves begin to change, Chicago says goodbye to another summer and welcomes in the autumn. While there are tons of activities to enjoy this fall, no holiday captures the seasonal spirit quite like Halloween, and this year, whether you're looking for family-frien…

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Music of the Baroque is giving Chicago’s summer fireworks season a classical twist with an elegant evening on Lake Michigan that pairs Handel’s triumphant music with dinner aboard a luxury cruise ship and a front-row view of Navy Pier’s fireworks.

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Chicago Bears legend Charles “Peanut” Tillman will take center stage in one of the city’s most cherished holiday traditions when he serves as Grand Marshal of the 92nd Chicago Thanksgiving Parade on Thanksgiving morning, Thursday, Nov. 26.

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Chicago’s Halloween fun isn’t just for humans. On Saturday, October 31, four-legged fashionistas will have their moment in the spotlight as three popular local destinations invite pets and their people to show off their most creative, cute and downright spooky costumes.

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Chicago’s lakefront is getting a seasonal makeover, and Navy Pier is giving visitors plenty of reasons to head east as temperatures cool. From free Halloween activities and indoor movies to live music, cultural celebrations and the return of a popular holiday attraction, the fall calendar of…

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Fashion, philanthropy and a whole lot of Chicago flair came together Oct. 2 in the Walnut Room for The Chicago Lighthouse’s 2026 FLAIR “Eye on Style” fashion show and luncheon. Nearly 300 of the city’s top fashionistas helped raise over $219,000 for this much-loved nonprofit.