Matchbox is a bar in Chicago.
Editorially verified May 18, 2026 by Elliot Marsh, TableJourney editor. Source.
Food program: None
Water activity · 1.5 hours
Climb aboard a 90 passenger historic riverboat & sip cocktails while cruising the Chicago River! Relax and learn about the history & architecture of the city via live ...
2 hours
Unleash your creativity with a fun paint and sip experience in Chicago. Enjoy a relaxed atmosphere with music, drinks, and plenty of laughs as you create your own masterpiece.
Guided tour · 2 hours
Discover Chicago's Ukrainian Village on a Mid-Century Cocktail Bar tour. Visit three hidden bars, enjoy craft cocktails & beers for you to purchase, and maybe experien...
Address: 770 N Milwaukee Ave, Chicago, IL 60642
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.
DrinkBourbon old fashioned
FoodSnacks
TipThe 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.
DrinkRotating cocktail menu
FoodSnacks
TipCover is $5 at the door for the back room music; the bar room is free. Wednesday is the strongest jazz night.
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.
DrinkToki highball
FoodKaiseki-leaning small plates
TipBook 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.
DrinkRotating cocktail menu
FoodPop-up kitchens
TipThe 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.
DrinkAmaro-forward cocktail menu
FoodSmall plates
TipOrder 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.
DrinkIn the Rocks (cracked-ice cocktail)
FoodSmall bites with the cocktail menu
TipBook the In the Rocks cocktail (cracked-ice presentation tableside); it is the room's defining drink and the value-per-dollar move.
