Subway: Red to Grand(312) 521-5100 mastrosrestaurants.com41.891054 -87.629804 520 N Dearborn St (at Grand Ave) River North, Chicago
DinnerAverage main course: $43
Vodka martini: $18. Crab cakes: $14 each. Sixteen-ounce New York strip: $49. Before you shake your head and huff off to the Rock and Roll McDonald’s, hear us out: If you’ve got these kinds of funds at your disposal, Mastro’s is the place to blow them. The martini is shaken with dry ice so that it bubbles like a cauldron when poured tableside. Steaks come out perfectly medium-rare on the hottest plates you’ve ever accidentally touched, and the signature side of lobster mashed potatoes—listed for “market price”—is comically indulgent. Just remember: If you have to ask, you can’t afford it.