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Cocktail barSpeakeasy beneath The Aviary
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.
DrinkRare-spirit flights
FoodCaviar service, snacks
TipBook six weeks out via the Tock system. The Pappy Van Winkle pour is the room's biggest draw.
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Cocktail barCocktail bar with nautical theme
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.
DrinkPisco-and-vermouth highball
FoodFish-and-chips bar snacks
TipThe fish-and-chips kitchen opens at 17:00 from the back room; the bar opens an hour earlier for cocktails only.
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Cocktail barWhiskey bar and restaurant
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.
DrinkWhiskey-flight menu
FoodPub-elevated full kitchen
TipThe 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.
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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.