Hotel-and-gallery district just north of the river. Tourist-heavy but holds Gene & Georgetti, Bavette's, Gilt Bar and the original Pizzeria Uno on Ohio Street.
Bavette's Bar & Boeuf in Chicago is the dimly-lit River North steakhouse on Kinzie, French bistro paintings overhead, with a bone-in ribeye that anchors.
OrderThe bone-in ribeye with hash browns; the lobster gnocchi for non-beef eaters.
TipBook at 21:00 on a weeknight if you want the back booths. The earlier seating is mostly business dinners.
Gene & Georgetti in Chicago is the 1941 Italian-American steakhouse under the elevated tracks at Franklin and Illinois, opened by Michelotti and Federighi.
OrderThe Garbage Salad; the bone-in ribeye; a Negroni at the bar before sitting down.
TipAsk for one of the back-room booths under the photo wall. The lighting is the same warm gold it has been for eighty years.
RPM Steak in Chicago is the marble-and-leather River North steakhouse on Kinzie from the Melman family of Lettuce Entertain You, with A5 Wagyu sliders.
OrderA5 Wagyu sliders to start, the dry-aged ribeye for two, popovers as the side.
TipSit at the bar if you cannot land a booth. The bar menu is the same and the cocktails arrive faster.
Topolobampo in Chicago is Rick Bayless's Michelin-starred Mexican fine-dining room beside Frontera on Clark, with regional menus that rotate every six weeks.
OrderWhichever mole is on the current tasting menu; Bayless has been cooking them in Chicago since 1989.
TipReservations open 60 days out and the Friday slot goes in an hour. Set a calendar alarm.
Frontera Grill in Chicago is Rick Bayless's 1987 Clark Street Mexican dining room beside Topolobampo, the kitchen that brought regional Mexican.
OrderCarne asada with handmade tortillas; the cochinita pibil if the Yucatan menu is running.
TipWalk in at 17:00 on a weekday for the bar; the booths fill by 18:30 most nights.
Ramen-san in Chicago is Lettuce Entertain You's River North ramen room on Hubbard, with a tonkotsu base and a spicy garlic bowl that pulls the regulars back.
OrderThe spicy garlic ramen; the chashu pork bun on the side.
TipLunch is faster than dinner. The 12:30 rush clears by 13:15.
Pizzeria Uno in Chicago is the original deep-dish pizza shop, opened by Ike Sewell on Ohio Street in 1943, where the city's pan-baked pizza was invented.
OrderThe Numero Uno, the canonical deep-dish from the original menu.
TipThe pies bake 45 minutes; order on arrival. The nearby Due (Pizzeria Due) is the same kitchen if Uno is full.
Portillo's in Chicago is the Ontario Street flagship of the chain founded 1963 by Dick Portillo, with Chicago hot dogs, Italian beef and the chocolate cake.
OrderA Chicago dog, an Italian beef dipped, a small chocolate cake shake.
TipDrive-thru is faster than the counter. The chocolate cake shake is a chocolate shake with a slice of chocolate cake blended into the cup.
Mr. Beef on Orleans in Chicago is the no-frills Italian-beef counter that inspired The Bear, opened by Joe Zucchero in 1979, with a sandwich line out past.
OrderItalian beef, dipped, hot peppers. The combo if you want sausage on top.
TipCash only and counter only. Closes by 16:30 on weekdays, earlier on weekends.
Spybar in Chicago is the River North underground house and techno room that runs late every Friday to 04:00 and Saturday to 05:00 with a 240-capacity rig.
TipLate weekends only, doors typically open at 22:00. Table reservations through the site; the booth and dance floor share one room downstairs.
Prysm in Chicago took over the old Crobar warehouse on Kingsbury Street and runs a 1,400-capacity main room with LED ceiling and weekend EDM bookings.
TipFriday and Saturday open at 22:00 and close at 04:00 and 05:00 respectively. Table reservations through Discotech are the easier path past the line.
Watershed in Chicago tucks beneath Pops for Champagne at State and Ohio. A staircase marked with a large W drops to a basement of stone walls and seasonal cocktails.
TipWalk-in only, no reservations. The cocktail menu rotates by season; ask the bartender about the rotating themed list pulled from TV shows.
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