While the Legends contemplate how to get to New York City, Behrad discovers Hoover has train tickets to DC and Sara and Ava come up with a plan. With the help of Gary, Nate will have to impersonate Hoover, but he soon learns it is harder being Hoover than he expected. Since Zari is stuck without the internet, she is forced to take a digital detox and becomes obsessed with figuring out who blew up the Waverider. Meanwhile, Astra and Spooner have stayed behind in Texas and are dealing with the aftermath of Astra's special spell.

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.