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.
Food program: Pop-up kitchens
Tip: The back patio is the move from May through October. Walk-up; the indoor bar fills first on cold nights.
Address: 948 N Western Ave, Chicago, IL 60622
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.
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 rooms.
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.
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 whiskey row.
Signature drink: Whiskey and a French dip
Food: Full Au Cheval menu
Tip: The bar accepts walk-up only; sit there if you can't book. The single-with-egg cheeseburger is the menu's defining order.
