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.
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.