Southern American$$andersonville
Big Jones in Chicago is Paul Fehribach's Andersonville Southern kitchen on Clark Street, with shrimp-and-grits and buttermilk biscuits that anchor the brunch menu.
Signature: Buttermilk biscuit, Shrimp and grits, Fried chicken
Order: Buttermilk biscuit with sorghum butter, plus the shrimp and grits.
Tip: Sunday brunch tables go on the books two weeks out. The bar takes walk-ups if you arrive at 11:00.
Italian, handmade pasta$$$west-loop
Monteverde in Chicago is Sarah Grueneberg's Italian dining room on Madison Street in the West Loop, a pasta-led menu with all the dough rolled in the open kitchen.
Signature: Cacio whey pepe, Handmade tortelloni
Order: The cacio whey pepe; the kitchen ferments its own pecorino whey for the sauce.
Tip: Sit at the pasta-counter seats if they're on offer. The kitchen rolls dough at eye level.
Modern American$$$lincoln-park
Boka in Chicago is Lee Wolen's Michelin-starred dining room beside Alinea on Halsted, with a quiet garden courtyard and a roast-chicken-for-two worth the table.
Signature: Roasted chicken for two, Garganelli pasta
Order: The roasted chicken for two, brined two days; it leaves the kitchen carved.
Tip: Book the garden room in summer. It is one of the prettiest outdoor dining rooms in the city.
American, wood-fire$$$west-loop
Girl & the Goat in Chicago is Stephanie Izard's Randolph Street wood-fire kitchen since 2010, with the pig face plate that came back when Bravo's Top Chef did.
Signature: Wood-fire pig face, Green beans with cashews
Order: The wood-fire pig face; the green beans with cashews and fish sauce vinaigrette.
Tip: If the dining room is fully booked, walk up to the bar at 17:00 for the same menu and no wait most weeknights.
Steakhouse, French$$$$river-north
Bavette's Bar & Boeuf in Chicago is the dimly-lit River North steakhouse on Kinzie, French bistro paintings overhead, with a bone-in ribeye that anchors the room.
Signature: Bone-in ribeye, Hash browns
Order: The bone-in ribeye with hash browns; the lobster gnocchi for non-beef eaters.
Tip: Book at 21:00 on a weeknight if you want the back booths. The earlier seating is mostly business dinners.
Steakhouse, classic American$$$$gold-coast
Gibsons in Chicago is the Rush Street steakhouse since 1989 with its own USDA Prime stamp, packed nightly with politicians, athletes and conference traffic.
Signature: W.R.'s Chicago Cut, Twin lobster tails
Order: The Chicago Cut, a 22-ounce bone-in ribeye. The au jus is on by default.
Tip: The cake slices are large enough for four. Order one for the table and ask for four forks.