Must-See Chicago Concerts and Comedy Shows in October
The only thing frightening about the October concert and comedy calendar is how many scary good shows are taking place in Chicago. From a pair of Grammy-winning singers embarking on a collaborative co-headlining tour to our FAVORITE artist from this year’s Lollapalooza kicking-off a highly-anticipated run of shows right here in Chicago, here’s a look at some of the most exciting events happening in and around the city throughout the month of October.
Brandy & Monica – United Center – Oct. 18
This show is more than 25 years in the making! Brandy and Monica – who collaborated on the 1998 mega-hit “The Boy Is Mine” are joining forces for a headlining tour that is stopping by the United Center on Oct. 18. Kelly Rowland, Muni Long, and Jamal Roberts are also set to perform making this a sure-to-be unforgettable experience.
Alex Borstein – The Den Theatre – Oct. 14
You loved her in The Marvelous Mrs. Maisel and voicing Lois on Family Guy – Alex Borstein is set to bring her latest solo show Thirsty to The Den Theatre on Oct. 14. Being a mom and taking care of aging parents are just a few of the topics Borstein explores in this production.
Aly & AJ – The Salt Shed – Oct. 10


Rebellious Magazine favorites Aly & AJ are returning to Chicago to play a show at The Salt Shed on Oct. 10 on their Silver Deliverer Tour. Amanda Shires – whose new album Nobody’s Girl just came out on Sept. 26 – will be kicking off the evening so you’ll want to get there early to check out this fantastic double bill.
Doechii – The Aragon Ballroom – Oct. 14
When Doechii revealed that she would be kicking-off her Live From the Swamp Tour in Chicago during her Lollapalooza set, we couldn’t mark our calendars fast enough. She absolutely stole the show on a festival lineup of over 100 artists so you know this headlining tour is going to be a next-level experience. Don’t miss Doechii at the Aragon on Oct. 14.
Lucius – The Salt Shed – Oct. 18


Also happening on Oct 18 is a performance at The Salt Shed by the band Lucius, led by the incredible vocals of Jess Wolfe and Holly Laessig. This is another stacked bill, with Hurray for the Riff Raff and Jobi Riccio opening the show.
Elsewhere in October, Sir Chloe is performing at The Vic Theatre on Oct. 23 and Indigo De Souza will be playing Thalia Hall on Oct. 19. Neko Case is performing indoors at The Salt Shed on Oct. 16 and Purity Ring will be stopping by Metro on Oct. 24.
And if you’re looking for some Halloween season fun The Chicago Theatre is hosting a 50th Anniversary Tour stop for The Rocky Horror Picture Show on Oct. 19 with cast members Barry Bostwick, Nell Campbell, and Patricia Quinn set to be on-hand for the screening.
This month’s shows have us shivering with antici—pation.