When the Legends discover a fugitive is hiding in 1970’s London, they realize he is part of a gang that is targeting the British Monarchy. Trying to stop the gang, they realize someone from the Legends must infiltrate them. Surprising everyone, Ray is the one to gain their trust after he is put through a series of tests with help from Sara and Rory. Meanwhile, Gary shows Nate the ropes at the Time Bureau, but it turns out to be anything other than an ordinary day at the office.

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.