Modernist American$$$$lincoln-park
Alinea in Chicago is Grant Achatz's three-Michelin-star tasting menu at 1723 N Halsted, the dining room that codified American modernist fine dining since 2005.
Signature: Edible balloon, Painted-tablecloth dessert
Order: Whichever course needs your two hands; the kitchen is unsentimental about it.
Tip: Book the Gallery flow if you want the full theatre; Salon is the quieter, three-course-less option.
Modern American$$$$west-loop
Smyth in Chicago is John and Karen Shields's two-Michelin-star tasting menu on Ada Street, with produce from their own farm 90 minutes south of the city.
Signature: Egg yolk in sea-buckthorn, Smoked sturgeon and caviar
Order: The yolk in sea-buckthorn vinegar; it has been on the menu since 2016 for a reason.
Tip: The companion bar downstairs, The Loyalist, runs an excellent burger if you can't land the upstairs seats.
Modern American$$$$west-loop
Oriole in Chicago is Noah Sandoval's two-Michelin-star room on Walnut Street in the West Loop, a quiet 28-seat tasting menu with a strong caviar service.
Signature: Hokkaido scallop with caviar, Quail with mole
Order: The opening caviar course; the kitchen treats it as the focal pivot, not a bookend.
Tip: The wine pairings are unusually well-judged at the German-and-Austrian end. Ask for them by region, not by tier.
Modern American$$$$west-loop
Ever in Chicago is Curtis Duffy's two-Michelin-star Fulton Market tasting menu, opened 2020 after Duffy left Grace, with rigorous service and quiet plating.
Signature: Foie gras with brioche, Wagyu with mushroom
Order: The foie gras course; it is the dish that follows Duffy across his career.
Tip: Sit at the chef's counter if it is on offer at booking. The view of the pass is the room's best seat.
Modern Scandinavian$$$west-loop
Elske in Chicago is David and Anna Posey's Danish-influenced Michelin-starred Randolph Street kitchen, a married chef-team plate with restraint and clean wood.
Signature: Duck-liver tart, Smoked beets with brown butter
Order: The duck-liver tart, an opening course that has stayed on the menu since 2016.
Tip: The Aquavit pairings are the room's secret weapon. Ask Anna for the by-the-glass walk.
Filipino, modern$$$$ukrainian-village
Kasama in Chicago is Tim Flores and Genie Kwon's Filipino bakery by day, Michelin-starred tasting menu by night, in the Ukrainian Village on Winchester.
Signature: Filipino breakfast plate, Lechon
Order: The morning ube cruffin, which sells out by 10:30 most weekends.
Tip: The bakery has no reservations; the tasting menu books out 60 days ahead. Treat them as two different visits.
American, pork-forward$$$west-loop
The Publican in Chicago is Paul Kahan's Fulton Market mead-hall, opened 2008, anchored by the heritage pork chop and a daily oyster list of 20 to 30 varieties.
Signature: Heritage pork chop, Country ham, Oysters
Order: Publican-style pork chop for the table, with one of the ham flights.
Tip: The walk-in counter at the bar is first-come, first-served and turns over fast. Aim for 17:30 if you cannot book.
Mediterranean$$$west-loop
avec in Chicago is the cedar-walled Mediterranean wine bar next to Blackbird's old space, with the dates-wrapped-in-bacon plate that has run since 2003.
Signature: Chorizo-stuffed bacon-wrapped dates, Wood-oven flatbreads
Order: The chorizo-stuffed bacon-wrapped dates; on the menu since opening for good reason.
Tip: The communal seating means a walk-up at 17:00 usually beats waiting for a table. Bring a friend who likes elbows.
American, farm-to-table$$logan-square
Lula Cafe in Chicago is Jason Hammel's 1999 Logan Square dining room and breakfast counter, anchored by a Monday farm-dinner menu the neighbourhood books out fast.
Signature: Farm dinner Monday, Pasta with brown butter
Order: Monday's farm dinner if you can book it; brown-butter pasta with sage on walk-in nights.
Tip: Brunch is walk-up only on weekends; aim for 09:30 to skip the worst of the queue.
American, fried chicken$$avondale
Honey Butter Fried Chicken in Chicago is the Avondale counter from Christine Cikowski and Joshua Kulp, with the honey-butter biscuit that named the place.
Signature: Fried chicken with honey butter, Sides board
Order: Two-piece dark plate with the honey butter biscuit and the corn salad.
Tip: Order online from your phone before you walk in. The counter line is twice as long as the screen-pickup one most evenings.
Southern American$$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$$$west-loop
Girl & the Goat in Chicago is Stephanie Izard's Randolph Street wood-fire kitchen since 2010, with the pig face plate that came back when Bravo's Top Chef did.
Signature: Wood-fire pig face, Green beans with cashews
Order: The wood-fire pig face; the green beans with cashews and fish sauce vinaigrette.
Tip: If the dining room is fully booked, walk up to the bar at 17:00 for the same menu and no wait most weeknights.
Steakhouse, French$$$$river-north
Bavette's Bar & Boeuf in Chicago is the dimly-lit River North steakhouse on Kinzie, French bistro paintings overhead, with a bone-in ribeye that anchors the room.
Signature: Bone-in ribeye, Hash browns
Order: The bone-in ribeye with hash browns; the lobster gnocchi for non-beef eaters.
Tip: Book at 21:00 on a weeknight if you want the back booths. The earlier seating is mostly business dinners.
Steakhouse, classic American$$$$gold-coast
Gibsons in Chicago is the Rush Street steakhouse since 1989 with its own USDA Prime stamp, packed nightly with politicians, athletes and conference traffic.
Signature: W.R.'s Chicago Cut, Twin lobster tails
Order: The Chicago Cut, a 22-ounce bone-in ribeye. The au jus is on by default.
Tip: The cake slices are large enough for four. Order one for the table and ask for four forks.
Italian-American steakhouse$$$river-north
Gene & Georgetti in Chicago is the 1941 Italian-American steakhouse under the elevated tracks at Franklin and Illinois, opened by Michelotti and Federighi.
Signature: Garbage salad, Bone-in ribeye
Order: The Garbage Salad; the bone-in ribeye; a Negroni at the bar before sitting down.
Tip: Ask for one of the back-room booths under the photo wall. The lighting is the same warm gold it has been for eighty years.
Modern steakhouse$$$$river-north
RPM Steak in Chicago is the marble-and-leather River North steakhouse on Kinzie from the Melman family of Lettuce Entertain You, with A5 Wagyu sliders at the bar.
Signature: A5 Wagyu sliders, Dry-aged ribeye
Order: A5 Wagyu sliders to start, the dry-aged ribeye for two, popovers as the side.
Tip: Sit at the bar if you cannot land a booth. The bar menu is the same and the cocktails arrive faster.
Mexican, fine dining$$$$river-north
Topolobampo in Chicago is Rick Bayless's Michelin-starred Mexican fine-dining room beside Frontera on Clark, with regional menus that rotate every six weeks.
Signature: Suckling pig in mole, Tasting-menu ceviches
Order: Whichever mole is on the current tasting menu; Bayless has been cooking them in Chicago since 1989.
Tip: Reservations open 60 days out and the Friday slot goes in an hour. Set a calendar alarm.
Regional Mexican$$$river-north
Frontera Grill in Chicago is Rick Bayless's 1987 Clark Street Mexican dining room beside Topolobampo, the kitchen that brought regional Mexican to the Midwest.
Signature: Carne asada, Cochinita pibil
Order: Carne asada with handmade tortillas; the cochinita pibil if the Yucatan menu is running.
Tip: Walk in at 17:00 on a weekday for the bar; the booths fill by 18:30 most nights.
Italian, pasta$$logan-square
Daisies in Chicago is Joe Frillman's Logan Square pasta-and-vegetable dining room on Milwaukee Avenue, with grain and produce sourced directly from Illinois farms.
Signature: Cavatelli with ragu, House-made focaccia
Order: Cavatelli with whatever ragu is current; the focaccia first, while you wait.
Tip: Brunch is the underrated meal here. The same pasta program with eggs and patio seating in summer.
Japanese, ramen$$river-north
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.
Signature: Spicy garlic ramen, Hong Kong beef noodle
Order: The spicy garlic ramen; the chashu pork bun on the side.
Tip: Lunch is faster than dinner. The 12:30 rush clears by 13:15.
American barbecue$$irving-park
Smoque BBQ in Chicago is the Irving Park no-frills counter on Pulaski Road since 2006, with brisket and St Louis ribs smoked over apple and hickory in-house.
Signature: Brisket, Pulled pork, St Louis ribs
Order: A sliced brisket plate with the St Louis ribs split. Half-rack rather than full.
Tip: Closed Mondays. Closes at 21:00 sharp and meat sells out from 19:30 on weekends.