Gather

4539 N. Lincoln Ave., 773-506-9300
Best date-night dinner: This newcomer to the avenue makes sophisticated food that ranges from a solid burger to hamachi crudo. Nab a seat on the serene and inviting back patio.

Cafe Selmarie

4729 N. Lincoln Ave., 773-989-5595
Best dessert destination: Mobbed as a brunch destination but underrated as a dessert spot: The bakery cranks out masterpieces, from buttery cookies to European tortes and cakes.

Jeri’s Grill

4357 N. Western Ave., 773-604-8775
Best late-night junk food: Two words: The Mop—an inspired combination of biscuits and gravy over hash browns, topped with deep-fried bologna, served only from midnight to 6 a.m.