2119 N. Clark St., 773-549-0038
Best date-night dinner: Lively and easygoing, Riccardo has an authentic Italian menu and a seductive la dolce vita ambiance. You’re having grappa with dessert? Live it up.
2536 N. Clark St., 773-883-7220
Best dessert destination: These cupcakes are so good they’re practically fadproof, and the rest of the menu—homemade ice creams, pies, brownies, cookies—is also stellar.
Taco Burrito Palace #2
2459 N. Halsted St., 773-248-0740
Best late-night junk food: Ignore the fool who fell asleep on his nachos and order any of the delicious classics—tacos al pastor, enchiladas, flautas, or tamales—all available until 5 a.m.