Must-See Concerts and Comedy Shows in October 2026
Fall is here, the air is crisp, and spooky season is upon us with a Chicago-area concert and comedy show calendar that is scary good. From one of the biggest and brightest pop stars on the planet to a genre-bending R&B innovator, here’s a look at some of the incredible artists performing in and around Chicago this October.
Kelela – The Vic Theatre – Oct. 6
Rebellious Magazine favorite Kelela is back with a new album and a new tour. The genre-bending R&B innovator is bringing the New Avatar Live Tour, with keiyaA, to The Vic Theatre on Oct. 6. Be sure to wear your dancing shoes for this one.
Olivia Rodrigo – United Center – Oct. 11 & 12
Fresh off the success of her charitable Daisy Chain Fields Festival, Olivia Rodrigo is bringing The Unravelled Tour to the United Center on Oct. 11 & 12. As if two nights with Olivia in Chicago wasn’t good enough, Wolf Alice is set to open both shows with their irresistible brand of rock music.
Suki Waterhouse – Aragon Ballroom – Oct. 17
Suki Waterhouse must have had a good time in Chicago during Lollapalooza this summer because she’s already making her triumphant return to the city. The Loveland Tour, with support from Rochelle Jordan, will hit the Aragon Ballroom on Oct. 17.
Robby Hoffman – The Vic Theatre – Oct. 7 & 9
Hacks scene-stealer Robby Hoffman will be performing three shows of stand-up across two evenings at The Vic Theatre on Oct. 7 & 9. Can’t make it to the shows? The comedian’s special Wake Up is currently streaming on Netflix.
Muna – The Salt Shed – Oct. 9
Muna is one of those bands that you think can’t get any better, but each time you see them perform you are blown away even further by their musicianship and infectious energy. When they play outdoors at The Salt Shed on Oct. 9 a portion of the proceeds will go to The Ally Coalition and their work supporting LGBTQ youth and queer migrants across the US.
Elsewhere in October, Tedeschi Trucks Band will be performing at The Chicago Theatre Oct. 23, 24, 26, 27 and Allison Russell is bringing The In The Hour of Chaos Tour to The Vic on Oct. 31. Sienna Spiro will be performing at The Riv on Oct. 27 and Doja Cat, with very special guest Latto, will be taking the stage at the United Center on Oct. 3. Maria Bamford will be at the North Shore Center for the Performing Arts in Skokie on Oct. 24 and Taylor Tomlinson will be trying out new ideas at The Den Oct. 27, 28, 30.
And that’s not all, Digable Planets will be at Metro on Oct. 18, but if you prefer hilarity over hip-hop Amy Poehler is bringing her Good Hang podcast to The Vic that very same evening. Nice As Fuck is set to perform an early show and a late show at Outset on Oct. 24 and Tinashe will be performing inside the Salt Shed on Oct. 16.
Forget the tricks, it’s all about the treats for fans of live entertainment in Chicago this October.
