Upscale in Chicago

Kumiko ★ 4.8

630 W Lake St, Chicago, IL 60661

Kumiko in Chicago is Julia Momose's West Loop Japanese cocktail bar on Lake Street, with a kaiseki-leaning food menu and a James Beard Outstanding Bar.

Tip: Book the chef's-counter omakase pairing if you have a long evening; otherwise the bar Toki highball is the showcase order.

The Loyalist ★ 4.8

177 N Ada St, Chicago, IL 60607

The Loyalist in Chicago is the wood-bar room downstairs from Smyth on Ada Street, an unfussy wine bar from John and Karen Shields with the cult dirty burger.

Tip: Walk up to the bar at 16:55. The dirty burger is on the bar menu from open; it leaves the kitchen rare and griddle-pressed.

The Office (at The Aviary) ★ 4.7

955 W Fulton Market, Chicago, IL 60607

The Office in Chicago is the speakeasy beneath The Aviary on Fulton Market: a 15-seat reservation-only basement room with rare-spirit flights and caviar.

Tip: Book six weeks out via the Tock system. The Pappy Van Winkle pour is the room's biggest draw.

Elske ★ 4.6

west-loop · 1350 W Randolph St, Chicago, IL 60607

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.

Tip: The Aquavit pairings are the room's secret weapon. Ask Anna for the by-the-glass walk.

The Publican ★ 4.6

west-loop · 837 W Fulton Market, Chicago, IL 60607

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.

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.

The Aviary ★ 4.6

955 W Fulton Market, Chicago, IL 60607

The Aviary in Chicago is the Achatz-Kokonas modernist cocktail bar above Next on Fulton Market, with edible-ice cocktails and a service script all its own.

Tip: Book the In the Rocks cocktail (cracked-ice presentation tableside); it is the room's defining drink and the value-per-dollar move.

Au Cheval (bar) ★ 4.6

800 W Randolph St, Chicago, IL 60607

Au Cheval in Chicago is the West Loop diner-bar on Randolph with one of the country's most-mentioned cheeseburgers, plus duck-heart hash and a bar-front.

Tip: The bar accepts walk-up only; sit there if you can't book. The single-with-egg cheeseburger is the menu's defining order.

Maria's Packaged Goods & Community Bar ★ 4.6

960 W 31st St, Chicago, IL 60608

Maria's Packaged Goods in Chicago is the Bridgeport corner store-and-bar on 31st Street: hybrid bottle shop, neighbourhood pub and Kimski Korean-Polish.

Tip: Kimski's kimchi pierogi and the Marz brewery beers on the back wall are the room's defining pairing.

avec ★ 4.5

west-loop · 615 W Randolph St, Chicago, IL 60661

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.

Tip: The communal seating means a walk-up at 17:00 usually beats waiting for a table. Bring a friend who likes elbows.

Monteverde ★ 4.5

west-loop · 1020 W Madison St, Chicago, IL 60607

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.

Tip: Sit at the pasta-counter seats if they're on offer. The kitchen rolls dough at eye level.

Boka ★ 4.5

lincoln-park · 1729 N Halsted St, Chicago, IL 60614

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.

Tip: Book the garden room in summer. It is one of the prettiest outdoor dining rooms in the city.

Girl & the Goat ★ 4.5

west-loop · 809 W Randolph St, Chicago, IL 60607

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.

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.

Billy Sunday ★ 4.5

3143 W Logan Blvd, Chicago, IL 60647

Billy Sunday in Chicago is Matthias Merges's Logan Square cocktail bar on Logan Boulevard, with a 100-bottle amaro back bar and Prohibition-era American.

Tip: Order off the amaro list, not the cocktail list, if you want the real value. The lesser-known Italians cost the same as a beer.

Longman & Eagle ★ 4.5

2657 N Kedzie Ave, Chicago, IL 60647

Longman & Eagle in Chicago is the Logan Square whiskey bar-and-restaurant on Kedzie Avenue, with a 250-bottle whiskey list, a Michelin Bib Gourmand and inn.

Tip: The Bib Gourmand dinner room is the right pairing for the whiskey list. Sit at the bar if walk-up and order the wild-boar sloppy joe.

The Green Mill ★ 4.5

4802 N Broadway St, Chicago, IL 60640

The Green Mill in Chicago is the Uptown jazz club on Broadway since 1907, an Al Capone hangout in the 1920s, with live jazz seven nights a week and a $10.

Tip: The Sunday night Uptown Poetry Slam (open mic, 21:00) is the original poetry slam since 1986, hosted by Marc Smith.

Frontera Grill ★ 4.4

river-north · 445 N Clark St, Chicago, IL 60654

Frontera Grill in Chicago is Rick Bayless's 1987 Clark Street Mexican dining room beside Topolobampo, the kitchen that brought regional Mexican.

Tip: Walk in at 17:00 on a weekday for the bar; the booths fill by 18:30 most nights.

Matchbox ★ 4.4

770 N Milwaukee Ave, Chicago, IL 60642

Matchbox in Chicago is the four-foot-wide West Town cocktail bar on Milwaukee Avenue, a 30-seat triangle serving stiff classic cocktails since 1995.

Tip: Order an Old Fashioned. The slim bartender pour is the house standard; do not ask for it differently.

Webster's Wine Bar ★ 4.4

2601 N Milwaukee Ave, Chicago, IL 60647

Webster's Wine Bar in Chicago is the long-running natural-wine bar that moved to Logan Square on Milwaukee Avenue in 2014, with a 200-bottle list.

Tip: The Monday-night flights are themed around a single region; the next-day discount on full bottles is a real value pull.

Gene & Georgetti ★ 4.3

river-north · 500 N Franklin St, Chicago, IL 60654

Gene & Georgetti in Chicago is the 1941 Italian-American steakhouse under the elevated tracks at Franklin and Illinois, opened by Michelotti and Federighi.

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.

Sportsman's Club ★ 4.3

948 N Western Ave, Chicago, IL 60622

Sportsman's Club in Chicago is Heisler Hospitality's Ukrainian Village bar on Western Avenue, with a rotating cocktail menu, pop-up kitchens and a tree-lined.

Tip: The back patio is the move from May through October. Walk-up; the indoor bar fills first on cold nights.

The Whistler ★ 4.3

2421 N Milwaukee Ave, Chicago, IL 60647

The Whistler in Chicago is the Logan Square cocktail bar on Milwaukee Avenue from Paul McGee, with nightly live music (jazz, soul) and rotating seasonal.

Tip: Cover is $5 at the door for the back room music; the bar room is free. Wednesday is the strongest jazz night.

Queen Mary Tavern ★ 4.2

2125 W Division St, Chicago, IL 60622

Queen Mary Tavern in Chicago is the Wicker Park cocktail bar on Division Street with a maritime theme, navy-blue panels and a fish-and-chips counter.

Tip: The fish-and-chips kitchen opens at 17:00 from the back room; the bar opens an hour earlier for cocktails only.

Rootstock Wine & Beer Bar ★ 4.2

954 N California Ave, Chicago, IL 60622

Rootstock in Chicago is Humboldt Park's neighbourhood natural-wine bar on California Avenue since 2011, with a small-producer list and a strong charcuterie.

Tip: The kitchen runs late; the burger and pork-rillette plate are the late-night moves once the cheese case thins.

Diversey Wine ★ 4.0

Logan Square · 3023 W Diversey Avenue, Chicago, IL 60647

Diversey Wine in Logan Square is the natural-wine shop and bar next door to Cellar Door Provisions on Diversey Avenue, with rotating skin-contact pours.