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October 2019 events calendar for Chicago

Plot out your October in Chicago with our calendar of things to do, including the best theater and concerts

Arts in the Dark
Photograph: Courtesy Arts in the Dark

The spookiest month of the year has arrived and there's no better time to make the most of fall in Chicago. In October, you can cheer on tireless runners along the Chicago Marathon course, catch some at the Chicago International Film Festival or explore skyscrapers during Open House Chicago. It's also one of the best months for concerts, especially if you're a fan of Nine Inch Nails, Gorillaz or Christina Aguilera. And don't forget about beer festivals, Chicago Ideas Week, Bloody Mary Fest and tons of spooky Halloween celebrations. If you're looking for things to do in October, let us guide the way.

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Concerts in October 2019

Madonna brought her Rebel Heart tour to the United Center on September 28, 2015.
Photograph: Chris Sullivan
Music, Pop


icon-location-pin Chicago Theatre | Chicago, IL, Loop

Madame X, the 14th studio album from Madonna, casts the 60-year-old Queen of Pop as a secret agent, taking on different guises and identities as she travels across the world—a concept that will undoubtably serve as an excuse for a cavalcade of costume changes during live performances. Crafted in the wake of Madge's recent move to Lisbon, Portugal, her latest record oozes with the trendy sounds of Latin pop, including the sultry lead single "Medellín" featuring Columbian singer Maluma. Collaborations with rappers Quavo and Swae Lee suggest that Madonna will also be dabbling in some trap-tinged tunes, which seem destined to rank among her most desperate attempts at cultural relevancy (remember the EDM bangers from her last few records?). Thank goodness that she has multiple decades worth of classic pop songs to fall back on.