The Matchbox

$ $
770 N Milwaukee Ave
Chicago, IL 60642
4:00pm - 2:00am
4:00pm - 2:00am
4:00pm - 2:00am
4:00pm - 2:00am
4:00pm - 2:00am
4:00pm - 3:00am
4:00pm - 2:00am



  • Drink this: Matchbox's excellent cocktails, such as its margaritas, come with powdered sugar.
  • get a sidecar
  • The original "cocktail bar" in Chicago. If you're not cool to the staff, they'll mock you publicly - so be nice.
  • Congratulations, you've found one of Esquire's Best Bars in America. We'd recommend getting a lemon drop, but you can't go wrong with whatever the bartender's in the mood for.
  • Ask for the French 75, it's divine.
  • Every drink tastes like a classic cocktail should, replete with a healthy dose of booze. The margaritas and gimlets are still the draw: smooth, delicious and sweet:
  • Best Gimlet I've ever had, the powdered sugar on the rim made it even better. Gotta come back soon.
  • The cosmos r off da chain.....
  • Gin gimlets, extra sugar, please.
  • It's not on the menu, but it's the best kept secret in Chicago. Order a French 75, they'll know what you're talking about.
  • Gin gimlets, extra sugar, please. -FS
  • The Kentucky Tiki is the play here. It tastes like the beaches of Hawaii and the backwoods of Kentucky at the same time.
  • Those looking for a no-nonsense cocktail joint probably won't find a bar with fewer frills than The Matchbox.
  • Great classic drinks. Try the gimlets.
  • Named for its tiny size, this place is huge on personality!
  • Order an old school gentleman's drink. They make cocktails right.
  • Must haves: Margarita, Sidecar and Brandy Manhattan.
  • Pretty much can't go wrong with any of the cocktails. The music is always good and the beer list is always strong.
  • Only gin gimlet in the city worth drinking
  • Pineapple gimlet FTW

Nearby places

501 N Ogden Ave (at Grand Ave)
1424 W Chicago Ave (at Bishop St.)
1531 N Damen Ave (at N Wicker Park Ave)