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The Sipping Point: Four Chicago Cocktails You Have to Try

The Porthole Cocktail at The Aviary Cocktail Bar in Chicago

There’s something about Chicago that makes you feel… well, a little thirsty. You can blame the myriad of world-class cocktail bars crammed into the city—oftentimes, it seems you can’t turn a corner without running into another one-of-a-kind drink that you just have to try.

That’s where this list comes in handy. While it can be difficult to choose a favorite, these are five must-haves on your next trip to the Windy City.

The Porthole Cocktail

The Aviary

This is no ordinary cocktail, and it’s served at no ordinary cocktail bar. The Aviary is owned by Grant Achatz (the chef behind one of the best restaurants in the world, Alinea), and the cocktails are as inventive and unbelievable as it gets. While the menu changes regularly, there’s always one constant: a cocktail that comes in a porthole.

It’s served in a piece designed by Martin Kastner of Crucial Detail specifically for The Aviary, and the porthole allows the spirits to become infused with different flavors.
The Porthole Cocktail at The Aviary
+ Photo: Christian Seel; The Aviary

It’s served in a piece designed by Martin Kastner of Crucial Detail specifically for The Aviary, and the porthole allows the spirits to become infused with different flavors. (The most recent was called Barrel Depletions and featured hibiscus, black Canadian ice wine elixir, gooseberries, and thyme, and the next one will be called Bunker Pants and feature Thai chilies, lime, raspberry, shochu, rum, and lemongrass.)

Margarita

Big Star

Big Star Margarita - Photo by Edouard Pierre
+ Photo: Edouard Pierre; Big Star

When the weather is nice, one thing is guaranteed: The front patio at Big Star in Wicker Park is going to be packed. The tacos are a big draw, but so are pitchers of the classic margaritas. The only warning: They go down way too easily. Get there early, grab a spot, order a pitcher, and settle in for some of the best people-watching and guacamole in town. 

Frozen Negroni

Parson’s Chicken & Fish

Head over to Logan Square, find the restaurant with the red-and-white circular sign out front, and make your way to the big back patio. That’s the ideal spot to sidle up to the outdoor bar and order a frozen negroni. It’s a grown-up slushie that’s bitter and refreshing—basically everything you want in a hot-weather cocktail.

It’s a grown-up slushie that’s bitter and refreshing—basically everything you want in a hot-weather cocktail.
Parson's Negroni - Photo by Clayton Hauck
+ Photo: Clayton Hauck; Parson's Chicken & Fish

The Bronze Italian

The Barrelhouse Flat

Barrelhouse Flat - photo credit Brandie Armento
+ Photo: Brandie Armento; The Barrelhouse Flat

Tucked into a random corner of Lincoln Park is a cocktail bar that would be at home in any of the swankest hoods in the country. Its menu is packed with cocktails featuring every kind of liquor, but The Bronze Italian, highlighting rum, is made special for the summer. You can credit the charred, pineapple-infused Campari for how easy it goes down.

Featured Photo Credit: Christian Seel; The Aviary

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