Gallo clashes with the new lieutenant temporarily filling in for Casey. Severide closes in on a dangerous and deadly arsonist.

When the Legends arrive in Chicago, they come across a speakeasy that caters to a diverse crowd, however their presence results in upsetting a mob who in turn burn down the club. Wanting to make things right, Zari demands they help to fix the club by throwing a party, with a special performance by The Bullet Blondes, to help raise money to rebuild it. Coincidentally, Astra, Spooner and Gideon are also in Chicago and feel compelled to help a female musician sever ties to the mob, while also trying to reach the Legends. Meanwhile, Gary points out something that Nate never realized about his relationship track record.

When the Muldoons push to close the investigation, Ambrose refuses, pushing Sonya to the brink.

Jimmy asks The Roots to improvise songs about audience members on the spot in a new Freestylin’ with The Roots, then catches up with Kristen Stewart and Bad Bunny before enjoying a standup performance from Joyelle Nicole Johnson.