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.
Food program: Caviar service, snacks
Tip: Book six weeks out via the Tock system. The Pappy Van Winkle pour is the room's biggest draw.
Address: 955 W Fulton Market, Chicago, IL 60607
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.
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, cash only.
Signature drink: Old fashioned, Gimlet
Food: None
Tip: Order an Old Fashioned. The slim bartender pour is the house standard; do not ask for it differently.
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 cover.
Signature drink: Bourbon old fashioned
Food: Snacks
Tip: The Sunday night Uptown Poetry Slam (open mic, 21:00) is the original poetry slam since 1986, hosted by Marc Smith.
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.
Signature drink: Rotating cocktail menu
Food: Snacks
Tip: Cover is $5 at the door for the back room music; the bar room is free. Wednesday is the strongest jazz night.
