Italian beef at Al's, deep dish at Pequod's, pasta at Monteverde, pie at Bang Bang. Chicago is the show in microcosm: zero pretense, every plate huge.
8 places Phil ate at in Chicago, United States. Each spot below has its address, dishes Phil ate, and (where I could verify) booking + hours.
Open the Chicago map →Dinner & after
Also worth your time
Monteverde
€€€Pasta-driven Italian — central Pastificio rolling dough through service.
Phil ate: Tigelle with burrata and prosciutto
Booking: Book via Resy. Closed Sun–Mon.
When: Tue–Thu 17:00–22:00. Fri–Sat 17:00–22:30. Aperitivo Tue–Sat 14:30–16:30.
Virtue Restaurant
Upscale-casual American Southern by Erick Williams — James Beard winner, Bib Gourmand.
Phil ate: Southern cuisine
Booking: Reservations via the online system for 1–8+ guests.
Ebenezer Missionary Baptist Church
Phil ate: Sunday breakfast
Jim's Original
Phil ate: Polish dog, Deep-fried butterflied Polish dog, Deep-fried pork chop
Al's Beef
€Chicago classic since 1938 — Italian beef sandwiches.
Phil ate: Italian Beef sandwich
Pequod's Pizza
€Neighborhood deep-dish institution — caramelized-crust pan pizza.
Phil ate: Caramelized-crust deep dish
Booking: Online reservations recommended; walk-in expect 2hr+ at peak.
When: Mon–Sat 11:00–02:00. Sun 11:00–00:00.
Cindy's Rooftop
Phil ate: Hot dog, Soft pretzels