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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.
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Cocktail barAmaro and bitters cocktail bar
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.
DrinkAmaro-forward cocktail menu
FoodSmall plates
TipOrder off the amaro list, not the cocktail list, if you want the real value. The lesser-known Italians cost the same as a beer.
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Cocktail barModernist cocktail tasting
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.
DrinkIn the Rocks (cracked-ice cocktail)
FoodSmall bites with the cocktail menu
TipBook the In the Rocks cocktail (cracked-ice presentation tableside); it is the room's defining drink and the value-per-dollar move.
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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.