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Southern AmericanAndersonville
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.
OrderButtermilk biscuit with sorghum butter, plus the shrimp and grits.
TipSunday brunch tables go on the books two weeks out. The bar takes walk-ups if you arrive at 11:00.
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ItalianWest 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.
OrderThe cacio whey pepe; the kitchen ferments its own pecorino whey for the sauce.
TipSit at the pasta-counter seats if they're on offer. The kitchen rolls dough at eye level.
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Modern AmericanLincoln 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.
OrderThe roasted chicken for two, brined two days; it leaves the kitchen carved.
TipBook the garden room in summer. It is one of the prettiest outdoor dining rooms in the city.
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New AmericanWest 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.
OrderThe wood-fire pig face; the green beans with cashews and fish sauce vinaigrette.
TipIf the dining room is fully booked, walk up to the bar at 17:00 for the same menu and no wait most weeknights.
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SteakhouseRiver 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.
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.
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New AmericanGold 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.
OrderThe Chicago Cut, a 22-ounce bone-in ribeye. The au jus is on by default.
TipThe cake slices are large enough for four. Order one for the table and ask for four forks.