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.