[1] The premise of this episode covers Michael Scofield and Lincoln Burrows' journey to Chicago with Sara Tancredi and Paul Kellerman.
At an Evansville, Indiana train station, Sara Tancredi (Sarah Wayne Callies) reunites with Michael Scofield (Wentworth Miller) and the two embrace.
When they let go of him, Kellerman tells the group that he recognizes Sara's key as being from a private cigar club in Chicago, Illinois.
In Ness City, Kansas, T-Bag (Robert Knepper) forces his hostages, Susan Hollander (K. K. Dodds) and her children, to pretend that they are a family.
In Benson, Minnesota, C-Note (Rockmond Dunbar) is at a diner with his daughter, Dede, where she is unable to digest her food and vomits in the bathroom.
C-Note attempts to defuse the situation by telling the hostages to stay in one corner and give the robber their money.
When Mahone says to let the Madison, Wisconsin FBI office handle Haywire and to continue focusing on the brothers, Wheeler tells him that he will report back to the headquarters.
Agent William Kim (Reggie Lee) phones Mahone and orders him to kill Haywire because he was Scofield's cellmate and there's no telling what he may know about the conspiracy.
Mahone returns to Fox River State Penitentiary where he tells Brad Bellick (Wade Williams) that since the prosecution violated his rights, the murder charge will be dropped upon a Habeas corpus hearing.
On an Algoma, Wisconsin shore, Haywire (Silas Weir Mitchell) tries to make his escape on his makeshift boat with his border collie.
Mahone arrives and is angry at a surprised Bellick for not stopping a large crowd from gathering to watch Haywire climb up the silo.
[2] The action sequence, which involved the train crashing into police cars, was also delayed to January 8, 2007 and was filmed in an area just north of Greenville.
Another Murdoch song, "Orange Sky", was played during the Prison Break episode "English, Fitz, or Percy".
A critic from UGO, Troy Rogers, gave "Chicago" a B grade, saying that "some aspects of the show are starting to feel tired".
"[6] Peter Brown from IFMagazine gave the episode a B+ grade, saying, "The serve of the week wasn’t as good as some of previous twists with the train jumpers but still continues a nice little tactic of giving the viewers something each week that stays true to what made this series good.
"[9] Jeff of TV Fodder reviewed the episode and also commented on the action sequence, stating, "The train escape was brilliant I think.