Despite obtaining one of the series' highest recorded audience, the episode received moderate responses from some critics. A critic from "UGO", Troy Rogers, gave "Chicago" a B grade, saying that "some aspects of the show are starting to feel tired". Similarly, Craig Blanchard of the "San Diego Union-Tribune" also gave the episode a B grade. Although Blanchard complimented on the characterization of Kellerman, describing him as "the man with a bottomless bag of tricks", he also commented on the character of Bellick, saying that "it's only a matter of time before Bellick is back to his role as a bottom-feeder. Talk about a riches-to-rags-to-riches story. He's even got a badge now." 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." The episode received an overall rating of 9.2/10 from "IGN"'s Ahsan Haque, who commented that "this episode continues the trend of bombarding viewers with extremely fast-paced and self-contained storylines for an ever-dwindling cast of characters".