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.

After Sara, Ava, Behrad and Gary arrive in New York City, they track down Dr. Gwyn Davies, who isn't the scientist they expected. Astra, Spooner, and Gideon are still trying to stop the Legends from using the time machine, but they run into some more setbacks along the way. Meanwhile, in the pocket dimension Nate and Zari work together on the Hoover situation as well how to make their future together work.

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.