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.
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.