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.[src]
According to the sign on the door of Chicago's Chapeaux, the events of this episode occur in the week of the 3rd to 9th of a month, with the back of a sign advertising an event taking place on a Monday the 24th.
The only month of 1925 with a Monday the 24th was August, placing this episodes events in early August.
This is somewhat consistent with the dating of "The Bullet Blondes", as those events presumably occurred in either April or July, with the July dating seeming more consistent.
However, this is vastly inconsistent with the dating provided in "The Need for Speed", which states that the events of said episode concluded on October 24, 1925.
The Legends get upset when Gary tips their waitress $20, due to the fact that it's overly generous and nearly a quarter of their entire budget ($93.65). While Gary feels a $20 tip is fitting for what they'd ordered (by 2021 standards), $20 in 1925 would be equal to $301.13 in 2021.