Cocktail barWhiskey bar and restaurant$$$Mon-Thu 11:00-23:00, Fri 11:00-01:00, Sat 09:00-01:00, Sun 09:00-23:00
Longman & Eagle in Chicago is the Logan Square whiskey bar-and-restaurant on Kedzie Avenue, with a 250-bottle whiskey list, a Michelin Bib Gourmand and inn.
Signature drink: Whiskey-flight menu
Food: Pub-elevated full kitchen
Tip: The Bib Gourmand dinner room is the right pairing for the whiskey list. Sit at the bar if walk-up and order the wild-boar sloppy joe.
Cocktail barDiner-bar hybrid$$$Mon-Sat 10:00-23:15, Sun 10:00-22:15
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.
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.
Cocktail barTiny historic cocktail bar$$$Mon-Fri 15:00-02:00; Sat 15:00-03:00; Sun 15:00-02:00
Matchbox in Chicago is the four-foot-wide West Town cocktail bar on Milwaukee Avenue, a 30-seat triangle serving stiff classic cocktails since 1995.
Signature drink: Old fashioned, Gimlet
Food: None
Tip: Order an Old Fashioned. The slim bartender pour is the house standard; do not ask for it differently.
Cocktail barJazz club and cocktail lounge$$$Daily 17:00-04:00
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.
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.
Cocktail barCocktail bar with live music$$$Tue-Wed 18:00-01:00; Thu-Fri 18:00-02:00; Sat 18:00-03:00; Sun 18:00-01:00; Mon closed
The Whistler in Chicago is the Logan Square cocktail bar on Milwaukee Avenue from Paul McGee, with nightly live music (jazz, soul) and rotating seasonal.
Signature drink: Rotating cocktail menu
Food: Snacks
Tip: Cover is $5 at the door for the back room music; the bar room is free. Wednesday is the strongest jazz night.
Cocktail barJapanese-influenced cocktail bar$$$Wed-Sun 16:00-22:00
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.
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.