$$$$New AmericanLincoln Park
Alinea in Chicago is Grant Achatz's three-Michelin-star tasting menu at 1723 N Halsted, the dining room that codified American modernist fine dining.
OrderWhichever course needs your two hands; the kitchen is unsentimental about it.
TipBook the Gallery flow if you want the full theatre; Salon is the quieter, three-course-less option.
$$$$Modern AmericanWest Loop
Smyth in Chicago is John and Karen Shields's two-Michelin-star tasting menu on Ada Street, with produce from their own farm 90 minutes south of the city.
OrderThe yolk in sea-buckthorn vinegar; it has been on the menu since 2016 for a reason.
TipThe companion bar downstairs, The Loyalist, runs an excellent burger if you can't land the upstairs seats.
$$$$Modern AmericanWest Loop
Oriole in Chicago is Noah Sandoval's two-Michelin-star room on Walnut Street in the West Loop, a quiet 28-seat tasting menu with a strong caviar service.
OrderThe opening caviar course; the kitchen treats it as the focal pivot, not a bookend.
TipThe wine pairings are unusually well-judged at the German-and-Austrian end. Ask for them by region, not by tier.
$$$$FilipinoUkrainian Village
Kasama in Chicago is Tim Flores and Genie Kwon's Filipino bakery by day, Michelin-starred tasting menu by night, in the Ukrainian Village on Winchester.
OrderThe morning ube cruffin, which sells out by 10:30 most weekends.
TipThe bakery has no reservations; the tasting menu books out 60 days ahead. Treat them as two different visits.
$$$$Tasting menu
Alinea in Chicago is Grant Achatz's three-Michelin-star Lincoln Park dining room, the original American modernist tasting menu since 2005 at 1723 N Halsted.
TipSalon is the shortest flow and the easiest to book; Kitchen Table is the deepest dive into the menu.
$$$$Modern AmericanWest Loop
Ever in Chicago is Curtis Duffy's two-Michelin-star Fulton Market tasting menu, opened 2020 after Duffy left Grace, with rigorous service and quiet plating.
OrderThe foie gras course; it is the dish that follows Duffy across his career.
TipSit at the chef's counter if it is on offer at booking. The view of the pass is the room's best seat.
$$$$Tasting menu
Smyth in Chicago is the two-Michelin-star West Loop tasting menu from John and Karen Shields, paired with The Loyalist downstairs and produce from their own.
TipAsk for the wine-pairing 'reserve' option if you have a long evening; the cellar lists a deep run of Burgundy.
$$$$Tasting menu
Oriole in Chicago is Noah Sandoval's two-Michelin-star tasting menu room at 661 W Walnut Street, a 28-seat West Loop room with strong caviar service.
TipThe wine pairings lean Germanic and Austrian. Ask by region, not by tier; the value is on the long-pour bottles.
$$$$SteakhouseRiver North
Bavette's Bar & Boeuf in Chicago is the dimly-lit River North steakhouse on Kinzie, French bistro paintings overhead, with a bone-in ribeye that anchors.
OrderThe bone-in ribeye with hash browns; the lobster gnocchi for non-beef eaters.
TipBook at 21:00 on a weeknight if you want the back booths. The earlier seating is mostly business dinners.
$$$$Modern MexicanRiver North
Topolobampo in Chicago is Rick Bayless's Michelin-starred Mexican fine-dining room beside Frontera on Clark, with regional menus that rotate every six weeks.
OrderWhichever mole is on the current tasting menu; Bayless has been cooking them in Chicago since 1989.
TipReservations open 60 days out and the Friday slot goes in an hour. Set a calendar alarm.
$$$$Filipino
Kasama in Chicago is Tim Flores and Genie Kwon's Michelin-starred Filipino tasting menu at 1001 N Winchester in Ukrainian Village, doubling as a daytime.
TipDay-room bakery and evening tasting menu run separate book-and-pay flows. Plan to come for both, on different days.
$$$$Tasting menu
Ever in Chicago is Curtis Duffy's two-Michelin-star Fulton Market tasting menu, opened in 2020 after he left Grace, with rigorous service and quiet plating.
TipSit at the chef's counter if it is offered at booking; the view of the pass is the room's best seat.
$$$$New AmericanGold Coast
Gibsons in Chicago is the Rush Street steakhouse since 1989 with its own USDA Prime stamp, packed nightly with politicians, athletes and conference traffic.
OrderThe Chicago Cut, a 22-ounce bone-in ribeye. The au jus is on by default.
TipThe cake slices are large enough for four. Order one for the table and ask for four forks.
$$$$Mexican
Topolobampo in Chicago is Rick Bayless's Michelin-starred Mexican fine-dining room at 445 N Clark Street, with menus that rotate every six weeks by region.
TipFriday slots open 60 days out and disappear inside an hour. Set a 09:00 alarm for the exact 60-day mark.
$$$$Nordic
Elske in Chicago is David and Anna Posey's Michelin-starred Randolph Street dining room with Danish influences, restrained plating, and a small front-yard.
TipThe Aquavit pairings are the room's secret weapon. Ask Anna for the by-the-glass walk.
$$$$Modern SteakhouseRiver North
RPM Steak in Chicago is the marble-and-leather River North steakhouse on Kinzie from the Melman family of Lettuce Entertain You, with A5 Wagyu sliders.
OrderA5 Wagyu sliders to start, the dry-aged ribeye for two, popovers as the side.
TipSit at the bar if you cannot land a booth. The bar menu is the same and the cocktails arrive faster.
$$$$Tasting menu
Next in Chicago is the Achatz-Kokonas Fulton Market tasting menu that changes theme every season, from Childhood to Sicily to Vegan to Trio.
TipTickets, not reservations: you buy by season on Tock, and they sell out the morning they drop.
$$$$Japanese sushi
Mako in Chicago is B.K. Park's Michelin-starred 22-seat omakase counter at 731 W Lake Street in the West Loop, with fish flown twice weekly from Toyosu.
TipSit at the wood corner of the counter, closest to the rice cooker; the timing of the nigiri is sharpest there.
$$$$New American
Boka in Chicago is Lee Wolen's Michelin-starred dining room beside Alinea on Halsted, with a quiet garden courtyard and a brined whole-roast chicken for two.
TipBook the garden room in summer. It is one of the prettiest outdoor dining rooms in the city.
$$$$Tasting menu
Esmé in Chicago is Jenner Tomaska's Michelin-starred Lincoln Park tasting menu, themed seasonally around a guest artist whose work runs on the plates.
TipSit at the chef's counter for the longer between-course explanations of the current theme.
$$$$Middle Eastern
Galit in Chicago is James Beard winner Zachary Engel's Michelin-starred Middle Eastern dining room on Lincoln Avenue in Lincoln Park, with a choose-your-own.
TipOrder the laffa straight off the hearth as your opening course; the warm bread is the anchor for every spread on the meze list.