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.
Food program: Snacks
Tip: Cover is $5 at the door for the back room music; the bar room is free. Wednesday is the strongest jazz night.
Address: 2421 N Milwaukee Ave, Chicago, IL 60647
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.
