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Bars, Cocktail bars River West/West Town
5 out of 5 stars
(3user reviews)
Photograph: Martha Williams Gimlet at Matchbox

If the thought of being crammed in this tiny boxcar of a bar makes you nervous, relax. The patio practically doubles the capacity of the place, and it’s the perfect spot to throw back one of its margaritas, made with fresh lemon and lime juice, top-shelf liquors and powdered sugar, and poured with a heavy hand. We’re also fans of the house-infused vodkas and the grub from the adjacent dining car (literally), Silver Palm.


Venue name: Matchbox
Address: 770 N Milwaukee Ave
Cross street: between Carpenter St and Ogden Ave
Opening hours: Mon–Thu 4pm–2am; Fri, Sun 3pm–2am; Sat 3pm–3am
Transport: El stop: Blue to Chicago. Bus: 56, 66.
Price: Average cocktail: $8.50
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Average User Rating

5 / 5

Rating Breakdown

  • 5 star:3
  • 4 star:0
  • 3 star:0
  • 2 star:0
  • 1 star:0
1 person listening

It's tiny but the drinks are good and strong and the garnishes are all hand prepared at the time each drink is ordered. In warmer weather the outdoor seating area is great for people watching at the corners of Chicago, Milwaukee and Ogden.


Hands down, the best gimlets you will find in Chicago. If they have passionfruit puree handy that day, order a passionfruit gimlet; it isn't explicitly on the menu but I think if they have the fresh puree of whatever flavor you are craving you can ask for it. This is the place to be in the summer/warmer months, especially 'cozy' if you are not a claustrophobic in the colder months when you can only sit inside. Every drink is phenomenal, and the staff is super down to earth. This is my favorite, 'just because I want a good cocktail' place!