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Cocktail barDiner-bar hybrid
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.
DrinkWhiskey and a French dip
FoodFull Au Cheval menu
TipThe bar accepts walk-up only; sit there if you can't book. The single-with-egg cheeseburger is the menu's defining order.
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Cocktail barTiny historic cocktail bar
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.
DrinkOld fashioned, Gimlet
FoodNone
TipOrder an Old Fashioned. The slim bartender pour is the house standard; do not ask for it differently.
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Cocktail barJazz club and cocktail lounge
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.
DrinkBourbon old fashioned
FoodSnacks
TipThe Sunday night Uptown Poetry Slam (open mic, 21:00) is the original poetry slam since 1986, hosted by Marc Smith.
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Cocktail barCocktail bar with live music
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.
DrinkRotating cocktail menu
FoodSnacks
TipCover is $5 at the door for the back room music; the bar room is free. Wednesday is the strongest jazz night.
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Cocktail barJapanese-influenced cocktail bar
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.
DrinkToki highball
FoodKaiseki-leaning small plates
TipBook the chef's-counter omakase pairing if you have a long evening; otherwise the bar Toki highball is the showcase order.
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Cocktail barNeighbourhood cocktail bar
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.
DrinkRotating cocktail menu
FoodPop-up kitchens
TipThe back patio is the move from May through October. Walk-up; the indoor bar fills first on cold nights.