Arts in the Dark
Photograph: Neal O'Bryan

October 2023 events calendar for Chicago

Plot out your October in Chicago with our calendar of things to do, including the best festivals and Halloween parties.

Jeffy Mai
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The official start of fall in Chicago might be in September, but the season doesn't really hit its stride until October—a month replete with crisp air, colorful fall foliage and a heaping helping of spooky fun. Take advantage of everything autumn has to offer by exploring the best pumpkin patches near Chicago, attending an apple-themed neighborhood fest, getting lost in corn mazes or staring up at the changing leaves at your local park or garden. And of course, celebrate Halloween in Chicago with spooky pop-ups, haunted houses, horror movie marathons and even more ghoulish events. Ready to embrace autumn? Check out the rest of the best things do to in Chicago this October. 

RECOMMENDED: Events calendar for Chicago in 2023

Featured events in October 2023

  • Music
  • Folk, country and blues
  • United Center

Tennessee country singer/rapper Jelly Roll rocks up at the United Center for the Chicago leg of his 'Beautifully Broken' tour. Expect tracks from his latest, 7th studio album 'Whitsitt Chapel', as well as his bigger hitters, 'Need a Favor' and 'Son of a Sinner'.

  • Music
  • United Center

After the success of his Super Bowl halftime show, R&B smoothie Usher Raymond IV brings his loverman soul-pop show back to the masses for his 'Past Present Future’ world tour. Gird your loins for plenty of libidinous tracks from his hefty back catalog, which features hits such as 'Yeah!', 'DJ Got Us Fallin' In Love' and 'Love In This Club'.

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  • Music
  • Pop
  • United Center

A consummate pro, J.T. mixes Sinatra’s swagger and charisma with the airtight funk of Michael Jackson at his peak. Though the former NSYNC member’s last few albums haven’t quite lived up to the rest of his catalog, he’s still adept at making magic on stage night after night (especially when with an accompanying big band). 

GYG Chicago TTD

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