Cocktail barNeighbourhood cocktail bar$$$Daily 17:00-02:00
Sportsman's Club in Chicago is Heisler Hospitality's Ukrainian Village bar on Western Avenue, with a rotating cocktail menu, pop-up kitchens and a tree-lined.
Signature drink: Rotating cocktail menu
Food: Pop-up kitchens
Tip: The back patio is the move from May through October. Walk-up; the indoor bar fills first on cold nights.
Cocktail barAmaro and bitters cocktail bar$$$Mon-Tue 17:00-23:00; Wed-Thu 17:00-00:00; Fri-Sat 17:00-02:00; Sun 12:00-23:00
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.
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.
Cocktail barModernist cocktail tasting$$$Tue-Thu 17:00-23:00; Fri 17:00-01:00; Sat 16:30-01:00; Sun-Mon closed
The Aviary in Chicago is the Achatz-Kokonas modernist cocktail bar above Next on Fulton Market, with edible-ice cocktails and a service script all its own.
Signature drink: In the Rocks (cracked-ice cocktail)
Food: Small bites with the cocktail menu
Tip: Book the In the Rocks cocktail (cracked-ice presentation tableside); it is the room's defining drink and the value-per-dollar move.
Cocktail barSpeakeasy beneath The Aviary$$$Tue-Thu 17:00-23:00; Fri 17:00-01:00; Sat 16:30-01:00; Sun-Mon closed
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.
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.
Cocktail barCocktail bar with nautical theme$$$Mon-Thu 17:00-01:00; Fri-Sun 15:00-01:00
Queen Mary Tavern in Chicago is the Wicker Park cocktail bar on Division Street with a maritime theme, navy-blue panels and a fish-and-chips counter.
Signature drink: Pisco-and-vermouth highball
Food: Fish-and-chips bar snacks
Tip: The fish-and-chips kitchen opens at 17:00 from the back room; the bar opens an hour earlier for cocktails only.
Cocktail barWhiskey bar and restaurant$$$Mon-Thu 11:00-23:00, Fri 11:00-01:00, Sat 09:00-01:00, Sun 09:00-23:00
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.
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.