A Proper Cocktail Travel Guide to Chicago

A Proper Cocktail Travel Guide to Chicago

Choosing our favorites from Chicago’s robust bar scene became a Herculean task we were humbled to take on. In a town where the mighty Aviary exists just around the corner from the exquisite Kumiko, and veteran bartenders from Violet Hour and Billy Sunday staff neighborhood taverns across the city, it’s difficult to decide where to drink.

We narrowed it down to a few gems, both old and new, from the city where grabbing a Margarita at the Matchbox brings the same amount of joy as exploring the creative depths of tiki mixology at Three Dots and a Dash. Expect a Chicago Handshake and a balance of genuine respect for the oldies, plus tons of heartfelt originality.


Best Intentions
Neighborhood: Logan Square
What’s Good: Come for the well made classics, stay for a shot of Angostura Bitter from the tap, a smash burger, and a malted Wondermint shake. 
Worth Noting: Darts, arcade games, and a sweet patio take this corner dive to legend status.

Neighborhood: Albany Park
What’s Good: Warm and cozy neighborhood bar brings serious swank at this LGBTQ-owned tavern. Lengthy menu of creative cocktails zhuzhed up with dramatic, yet effective, presentation. 
Worth Noting: Try on point versions of the Daiquiri, French 75, and other textbook faves for cheap at Happy Hour. 

Duck Inn
Neighborhood: Bridgeport
What’s Good: Yes, this South-sider’s got Hamm’s on tap, but you can also trust the barkeep to stir up a strong Batanga (the OG rum and coke) and more retro faves. 
Worth Noting: A Chicago-style duck fat dog (sans ketchup) will make you feel right at home. 

Neighborhood: West Town
What’s Good: The newest fancy cocktail bar feels just right. A straightforward menu board of thought provoking classics lists gems like the Clover Club and the Corpse Reviver #1.
Worth Noting: When’s the last time you had a Clover Club??

The Meadowlark
Neighborhood: Logan Square
What’s Good: Carefully researched, intricately themed menus plus a well-stocked back bar in a vintage library setting.
Worth Noting: Make a reservation for relaxed lounge-y seating, or walk-in to sit at the bar. 

Neighborhood: Gold Coast
What’s Good: Drinking sugar cane spirits in this art deco setting will transport you to an early 20th century Caribbean hotel lobby bar. 
Worth Noting: Their rum collection is second to none. 

The Whistler
Neighborhood: Logan Square
What’s Good: Great spot to call out your favorite cocktail, but the pros behind the bar create custom tipples that are worth trusting. Original drinks like the Milk Maid (blanco tequila, coco lopez, lime) will convince you.
Worth Noting: Jazz, DJ’s, and art installations are all on regular rotation.

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