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 Zari 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.

With Astra, Spooner and a now-human Gideon trying to save the Legends, Gideon becomes overwhelmed by her new human choices sending her into a catatonic state. Astra and Spooner combine their powers to enter Gideon's mindscape and discover that a virus is trying to erase all of Gideon's memories. Acting fast, they devise a plan to defeat the virus before it's too late. Meanwhile, the Legends are about to go up against a powerful new foe.

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.

When the Legends crash land in 1940s Seattle, they find themselves right in the middle of WWII with a surprise guest. Needing replacement parts to fix the time machine, Sara, Ava, Astra, Spooner and Gideon find themselves working in different sections of an airplane factory alongside "Rosies." With Astra frustrated with inequality in the workforce, she takes matters into her own hands. Meanwhile, Behrad offers to play host and help teach Nate about Persian culture and etiquette.

Sara starts to realize her team is making questionable choices when it comes to the timeline. Trying to figure out who is behind everything, Sara discovers some harsh truths.

When Gideon jumps the time machine into the Manor Dimension, which lands in Hell, Astra realizes that a damned 90's reality show crew sneaks into the manor. With the reality show crew causing emotions to spike, Sara and Ava share their true feelings about their roles as Co-Captains. Behrad seeks advice about Astra from Nate and Zari but Behrad finds that his past is put on display instead.

With the Legends tired of being chased by an evil A.I. and her robo-soliders, Sara decides to create an aberration that will allow the team to take back the Evil Waverider. However, they find themselves in a bar for time-travelers and quickly learn that this "fixed point" is popular with time-travelers, leaving Sara questioning her odds at winning. With Behrad and Astra growing closer, Zari and Spooner are forced to awkwardly interact with each other as the rest of the Legends are paired up on the mission. Meanwhile, Ava hears Gwyn's plan to save his boyfriend, and is forced to remind him of the consequences in he succeeds.

With some help from an unexpected person, the Legends break a fixed point, creating an aberration that will attract the Evil Waverider. The Legends are soon shocked at who has been hunting them and Sara tries to negotiate which doesn't go as planned. Seemingly out of options, Gwyn rises to the occasion by using his military experience and hatches a stealth plan. Meanwhile, Gary helps Astra realize what she is side lining Gideon from the mission.

With Gideon hurt, the Legends only have one way to save her. Once Evil Gideon is active, she continues to try to destroy the Legends, until Gideon reminds her of a certain protocol she must follow. Trying to help, Gideon negotiates a deal to save the Legends but to get them to agree, she breaks a major rule. Meanwhile, the Legends come up with another plan that could potentially solve all their problems.

The Legends are all disappointed and hurt by Gideon's actions, but Gideon is horrified when AI Gideon tells her about Gary. Itching to get back to doing what they love best, they realize that Gwyn has broken the treaty and must find him. Meanwhile, Sara keeps an important secret from Ava because she doesn't know how she will react.