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 Legends and Gwyn finally time travel, the time machine goes haywire leaving them stranded in a lush forest with no idea when or where they are. Seeing that Sara and Ava are noticeably stressed, Nate takes over and gives everyone tasks to set up camp to keep everyone occupied. Meanwhile, unbeknownst to The Legends, someone keeps trying to destroy the anomalies that keep popping up which could create bigger ripples throughout history.