MostBest Chicago | Cocktail Bars

There are 435 cocktail bars in Chicago. Feeling overwhelmed? MostBest knows the Top 3.

Whether you like it dirty, shaken, or stirred, these spots serve up expertly mixed cocktails that will have you planning your next visit after just one sip.


via Flickr user Sam Howzit

via Flickr user Sam Howzit

Tucked away in an alley, Three Dots and a Dash is a hidden gem that’s always poppin’. The staff is excellent, the bartenders make lethal drinks, and the atmosphere attracts the likes of some of Hollywood’s biggest celebs. Masterful mixologist Paul McGee (of Lost Lake) created the cocktails, and he delivered what you would expect of a world-renowned specialist.

We Love Their: Puka Puka Punch

435 N. Clark St
(312) 610-4220


via Flickr star5112

via Flickr star5112

Take a journey into The Violet Hour, located in the heart of Wicker Park. This is truly a hidden gem that has perfected the art of artisanal cocktails while emitting an elegant ambiance. When you walk in, you’ll notice that it is mostly candle-lit, making it the perfect place for an intimate date night.

We Love Their: The Boss

1520 N Damen Ave
(773) 252-1500


via Flickr user Sam Howzit

via Flickr user Sam Howzit

Scofflaw is essentially a gin lover’s fantasy, but if you don’t like gin or don’t know anything about it, the expert mixologists will take the time to customize something that is sure to make you a fan. This spot is elegant, with a fireplace, antique furniture, and candlelight. It’s both vintage and romantic. At midnight, be on the lookout, because that’s when they hand out free homemade cookies straight out the oven!

We Love Their: Cloister

3201 W Armitage Ave
(773) 252-9700