[5][6][8][9] Characters from the Vampire mythos are woven into real-life Chicago, including their involvement with landmarks such as Meigs Field, the Biograph Theater, and the UIC campus, as well as how the Kindred have influenced the history of the city and its geography.

[7] Crow describes the cover art by an uncredited Mitchell as "a 'Watchman'-like shot [...] of a vampire plunging to his death from a skyscraper window.

[19] At the same time, a goal was to create a book that was universal and could be used by storytellers to construct other city settings for their own Vampire: The Masquerade campaigns.

[23] Klara Horskjær Herbøl, one of the writers on the book, took inspiration from Grigori Rasputin for the Lasombra vampire Aleksandr Malenkov, portraying him as a charismatic but "filthy" and unlikable person.

[25] The book was produced to match the visual format of previous V5 books, something new for Onyx Path Publishing, who did not have a photography or costuming department; they ended up using illustrations, with a modified photograph as the cover art used as a segue into their take on the visual format, created by the art director Tomas Arfert at series owner Paradox Interactive.

[11] The third edition of Chicago by Night was announced at the gaming convention Gen Con in August 2018, as Onyx Path Publishing's first V5 book.

[45] By 1999, Casus Belli still considered Chicago by Night the most important Vampire: The Masquerade supplement, and recommended new players to begin with it.

[4][47] Arcane found the cast of characters strong, and enjoyed how their complex relations together with the political intrigue opened possibilities for stories to tell and mysteries for players to explore; they wished that the Chicago Chronicles reprint would have corrected the errors in it and updated it for Vampire: The Masquerade's second edition, considering the supplement otherwise "perfect".

[48] The Games Machine found the first edition "very interesting";[35] Computer + Videogiochi called it a masterful work that continues to surprise, with well crafted stories and situations in a detailed setting.

[9] Casus Belli called it a model work, praising the detail of the characters, plots, and maps, and particularly recommended it to French players due to how most Vampire: The Masquerade materials published in French at the time were set around the Chicago region; they thought it would be particularly useful together with the supplements The Succubus Club and Ashes to Ashes.

[49] Dragon was more critical, considering the first edition's visuals to look "borderline amateur" in retrospect, compared to later supplements like Constantinople by Night (1996), but still found the writing highly imaginative.

[50] Nerdist considered the third edition brilliantly written, and thought that its writing and amount of content made it "no wonder" that the crowdfunding campaign was as successful as it was.