851 N. Ashland Ave., 312-624-8509
Best date-night dinner: Weekend wait times are long. But slip into this 32-seat BYO on a weeknight and indulge in progressive white-tablecloth-worthy dining in an utterly chill enviroment.

Black Dog Gelato

859 N. Damen Ave., 773-235-3116
Best dessert destination: Intriguing flavors such as sea salt caramel and coconut thyme are the reason to visit Jessie Oloroso’s dessert mecca, still the most inventive in West Town.

Pie-Eyed Pizzeria

1111 W. Chicago Ave., 312-243-3735
Best late-night junk food: After a Saturday night bender, one of these floppy oversize slices—with creamy, piquant cheese spread over sweet tomato sauce—will be your life raft to sobriety.