Charlie Trotter’s on West Armitage is very expensive but also worth it: the epitome of New American gastronomy, punters are consistently dazzled by the freshness of the ingredients, the innovation of the daily changing menu, the exceptional wine cellar and the courteous and knowledgeable staff. It’s a touch over-formal but, after a few bottles, you’ll forget the stuffiness.

A tip: for the ultimate, sublime experience, get a reservation at the kitchen table. Also formal but utterly magical is TRU in Streeterville. A rather unique combination of gallery and eatery, this hip establishment houses two of Chicago’s most eminent chefs (Rick Tramanto and Gale Gand), sommelier Scott Tyree’s 1,400-bottle wine selection and an original Andy Warhol. From the moment you enter through the deliciously decadent black drapes, you’ll be stunned. Try the caviar, kobe beef and truffle-garnished scallops for a lasting memory. And don’t forget to wear a (louche) jacket.