Cocktails in Chicago, Illinois

The Windy City impresses, especially during cocktail hour.

(It’s always 5 o’clock somewhere, right?)

Story by Julia Bayly

Whether you prefer your cocktails be shaken, stirred, muddled, served on the rocks, neat or straight up, the Windy City has you covered.

Throughout my recent trip to Chicago, Illinois, I was consistently impressed at cocktail hour.

Much of that is due to the talents of bartenders—though calling them “bartenders” is a bit like referring to Michelangelo as a doodler. They are true artists with spirits and fruits (their paints) and glasses (their canvases).

That’s certainly the case at 20 East, located at the Talbot Hotel, where the Purple Matter gets my vote for the prettiest cocktail ever. It’s also the most complicated drink prepared at the bar, according to D., the bartender who prepared mine when I ordered it.

A really great bourbon is just the beginning for the Purple Matter. Lemon and dry curaçao are added in a series of complicated mixing and layering steps followed by two rounds of shaking—a dry, iceless shake followed by a good shake with ice. After it’s poured into a wide glass, a layer of frothy egg whites is carefully poured on top and, for the final flourish, two spoons of Malbec are drizzled over the top to create a unique floral pattern. On sunny days 20 East opens up its outdoor terrace seating and there is arguably no better place to enjoy a picture-perfect cocktail like the Purple Matter on such a picture-perfect Chicago afternoon.

But there’s no reason to consider that the end of your cocktail tour of Chicago!

If whiskey is your thing, I recommend heading over to Eduardo’s Enoteca. Ask Angel behind the bar to prepare his “Floatin’ Sky Rye,” made with rye, domaine de canton, lemon and a splash of pinot noir.

“Angel’s cocktails are the most interesting by far,” says his fellow bartender Byrd Jasper. “He plays around with flavors and textures and pays a lot of attention to detail.”

If nothing on the restaurant’s cocktail menu strikes your fancy, which seems unlikely, no worries: Angel has you covered. “He’s always willing to make a custom drink depending on what you are in the mood for,” Jasper says.

Over at Chicago’s Old Town institution Orsos Restaurant the Manhattan Nights cocktail proved to be everything a great Manhattan should be: sweet and bitter in perfect balance. The cocktail features Bulleit Bourbon and Zucca Rabarbaro Amaro and is served on the rocks. By my palate, it’s a drink that is perfect any time of day or night.

Speaking of bourbon, the Peach Old Fashioned at Patio at Cafe Brauer at Lincoln Park Zoo is a refreshing choice to enjoy alfresco. The patio overlooks a pond and walking trails; it’s a great spot for both bird and people watching. The drink combines Makers Mark Bourbon with a simple peach syrup and peach bitters.

Tavern On Rush has a patio setting, too, and is consistently voted as home of the city’s best outdoor seating. I now consider it a personal favorite spot. The Strawberry Blondie Martini is like drinking a grown-up slushie made with your grandmother’s best strawberry preserves. In actuality, the mixologists create the drink with Stoli Raspberry Vodka, fresh strawberry puree, pineapple juice and sour mix. It’s a perfect cooler on a warm day.

Peaches seem to be “in” this year when it comes to cocktails and at 3 Arts Club Cafe, located at Restoration Hardware Chicago, peach juice is added to prosecco to create a delicious Bellini (think peachy mimosa).

Of course, sometimes you want something clear, something fresh. For me the drink that fills that set of requirements so well it feels like an old friend is the tried-and-true gin and tonic. At the Waldorf Astoria in Chicago the G&T is everything it should be: crisp, light and perfected with a squeeze of fresh lime.

On my short visit I was barely able to dip into the punch bowl that is Chicago’s cocktail scene. There is much more to sip and savor, but trust me: It’s a city that belongs on any libation lover’s must-go travel list.

“Yes, we have a lot of great beer and wine bars,” says Byrd Jasper at Eduardo’s Enoteca. “But the feedback I get from the tourists we get is they love coming back [to Chicago] for cocktails because those are the best experiences.”

Plan A Trip

Julia Bayly


Julia Bayly, an award-winning journalist based in Maine, writes about traveling with her sidekick Chiclet the rescue dog at