Cocktails, wine bars and dives: drinking in Chicago for grown-ups.
Cocktail bars, wine bars, dive bars and gastropubs: drinking in Chicago for grown-ups.
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 program win.
Signature drink: Toki highball
Food: Kaiseki-leaning small plates
Tip: Book the chef's-counter omakase pairing if you have a long evening; otherwise the bar Toki highball is the showcase order.
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 patio.
Signature drink: Rotating cocktail menu
Food: Pop-up kitchens
Tip: The back patio is the move from May through October. Walk-up; the indoor bar fills first on cold nights.
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 spirits.
Signature drink: Amaro-forward cocktail menu
Food: Small plates
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.
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.
Signature drink: In the Rocks (cracked-ice cocktail)
Food: Small bites with the cocktail menu
Tip: Book the In the Rocks cocktail (cracked-ice presentation tableside); it is the room's defining drink and the value-per-dollar move.
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 service.
Signature drink: Rare-spirit flights
Food: Caviar service, snacks
Tip: Book six weeks out via the Tock system. The Pappy Van Winkle pour is the room's biggest draw.
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 at the back.
Signature drink: Pisco-and-vermouth highball
Food: Fish-and-chips bar snacks
Tip: The fish-and-chips kitchen opens at 17:00 from the back room; the bar opens an hour earlier for cocktails only.
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 rooms.
Signature drink: Whiskey-flight menu
Food: Pub-elevated full kitchen
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.
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 whiskey row.
Signature drink: Whiskey and a French dip
Food: Full Au Cheval menu
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.
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, cash only.
Signature drink: Old fashioned, Gimlet
Food: None
Tip: Order an Old Fashioned. The slim bartender pour is the house standard; do not ask for it differently.
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 cover.
Signature drink: Bourbon old fashioned
Food: Snacks
Tip: The Sunday night Uptown Poetry Slam (open mic, 21:00) is the original poetry slam since 1986, hosted by Marc Smith.
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 cocktails.
Signature drink: Rotating cocktail menu
Food: Snacks
Tip: Cover is $5 at the door for the back room music; the bar room is free. Wednesday is the strongest jazz night.
Peak food season in Chicago is year-round.
Local dining hours: lunch around 12:30, dinner from 19:30.
service is typically included; small extra is welcome but not expected.
Ask the next local you meet what they would order. Chicago rewards trust.