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Gary Krist…comic but sneakily affecting novel about Chicago politics…[Simon] is clearly infatuated with Chicago, and the zeal with which he celebrates the city, warts and all, is hard to resist. His book is larded with insider bonus features that hard-core Chicago aficionados will delight in, whether it's a blow-by-blow description of how Mexican chilaquiles are made or a knowing dissertation on the agony of the long Chicago winter…Windy City, for all its emphasis on the sausage-factory venality of big-city politics, seems intended mainly as a big, sloppy valentine to the cultural jambalaya that is 21st-century Chicago. The Second City has taken a lot of abuse in its day, from writers as various as Rudyard Kipling, Oscar Wilde, Norman Mailer and Dave Barry. It's good to see the old place shamelessly flattered for a change.
—The Washington Post