Chicago Cocktail Bars Overview

The Whistler - Cocktail Bar | Live Music Venue | Lounge in Chicago

Chicago basically invented prohibition-era chicanery with a plethora of illegal speakeasies and hidden drinking dens popping up throughout the city in the 1920s. Today, those drinking traditions remain (although now legally) with a wide array of artisanal cocktail joints and mixology masters concocting new creations on a nightly basis.

There are so many great cocktail bars in Chicago that it can be hard to know where to start. Just know that no matter what neighborhood you’re in, chances are there’s a cocktail bar waiting for you.

One of the best Chicago cocktail bars is The Barrelhouse Flat in Lincoln Park. Here, an extensive list of cocktails as well as signature punches keep a diverse clientele boozed up in the most unique ways possible.

Three of Chicago’s finest whiskey bars are Longman & Eagle, Big Star, and Delilah’s. Longman’s motto is “Eat, Sleep, Whiskey” which is fitting since there’s Michelin star cuisine, perfectly crafted cocktails, and 6 guest rooms above the bar to sleep it all off in. Big Star, meanwhile, serves up out-of-this-world Mexican fare with their whiskey, whereas Delilah’s carries over 400 types of the brown stuff to mix and match in whichever way you want.

Prohibition is long gone and the art of drinking is in full force in Chicago. And while there are still crazy laws regarding happy hour, it’s easy to find one-of-a-kind cocktail bars to serve up artisanal libations any time of day and any day of the week.

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