$249 Many gourmets believe Spiaggia is the best Italian restaurant between the coasts. Its setting overlooking Lake Michigan is equally delicious. Tony Mantuano, a chef devoted to sourcing pristine ingredients from Italy, outdoes himself with a trio of appetizers: zucchini flowers stuffed with mozzarella di bufala and marinated in vintage Molise olive oil; Venetian cuttlefish eggs with osetra caviar from Lombardy; and a combination of Piedmontese white truffle and a tartare of aged prime strip steak. The wine is Franciacorta, Brut Saten from Ricci Curbastro. 980 N. Michigan Ave., Chicago (312-280-2750; Spiaggia)
$238 At 40th-floor Everest, chef Jean Joho prepares three more appetizers. He begins with Salt Point Pacific oysters and a half bottle of Josmeyer’s 2001 Pinot Gris, Hengst Grand Cru; follows up with braised pork cheeks with a mustard-bread-crumb coating and pickled veal tongue; and ends with hazelnut-crusted skate wing. 440 S. LaSalle St., 40th Floor, Chicago (312-663-8920; Everest)
$242 On to NoMI, located high above North Michigan Avenue, where chef Christophe David unveils a two-part main course of lamb: First, confit of neck and shoulder meat, baked in pastry with pistachios, dried apricots, and currants, is paired with Château de Beaucastel 2005. Next, salt-encrusted racks of lamb are carved and served with piquillo-pepper purée and smoked eggplant. Park Hyatt, 800 N. Michigan Ave., 7th Floor, Chicago (312-239-4030; NoMI)
$247 We finish our feast at Sixteen, on the 16th floor of the Trump International Hotel, where pastry chef Hichem Lahreche proffers a “pre-dessert” of pineapple and papaya cooked sous vide and anointed with yogurt cream and a cloud of green tea foam. The main dessert is a chocolate purse filled with chocolate cake and chocolate mousse and garnished with a scoop of bittersweet chocolate ice cream. Finally, a server sprays a mist of chocolate-steeped Cognac over everything. The wine capable of coping with these intense flavors is Banyuls Grand Cru 1995, Cave de L’Abbé Rous. Trump International, 401 N. Wabash Ave., 16th Floor, Chicago (312-588-8030; Sixteen)