There are few guarantees in this world, and yet one can confidently assert that there is no better way to experience the Windy City than with a bona fide tiki legend as your guide. Kevin Beary, beverage director of Chicago’s Three Dots and a Dash, is up to the task.
A modern great with an old island soul, Beary is the charming presence that keeps the ship’s legendary bar program running tightly (but with an unwaveringly chill vibe, in true tiki fashion). And it goes without saying that a man whose suit game is as strong as his Hawaiian shirt collection knows how to both button up and let loose. Here is a Bartography guide to Chicago, as told by Kevin Beary, master of high-low balance.
My go-to order at this quintessential dive bar in River North (near Three Dots and a Dash) is a cheap blended Scotch served neat and a tall boy. It’s also a great escape from the Loop if you just want a casual drink. Location.
The vintage spirits selection that The Office has is incredible. The composed cocktails in The Aviary are terrifyingly well executed, in both balance and presentation. A must if you are in the West Loop. Location.
Three Dots and a Dash
When hanging out at Three Dots and a Dash, you have access to an incredible rum selection that can’t be found easily in Chicago. For me, the best part is bringing friends in to try rum cocktails that would normally be outside their comfort zone. Location.
Sparrow (in Gold Coast)
Sparrow has great service and well-made Daiquiris. Split-base Daqs are encouraged. Location.
This new West Loop restaurant has a vibrant scene, especially in the summer. The bar has well-made classic and modern cocktails by Liz Pearce, too. Location.
Kingston Mines in Lincoln Park is a Chicago staple. It’s a 1968 blues bar, and a must for late-night music. Location.
This is a historic seafood spot on 95th Street. My advice here is to grab a friend, a 6-pack, and a car. The move is to grab a whole bunch of items and head over to the park near Lake Michigan and have a smoked fish and beer picnic. The smoked whitefish, salmon steaks, and shrimp are not to be missed. Location.
My favorite dishes at Proxi in the West Loop are the fried skate wing and roasted baby potato “carbonara.” The wine list changes concepts every few months; when I went they were only featuring offerings from the Loire Valley, which were insanely good. Location.
Roister is an open-kitchen restaurant concept centered around primal cooking techniques. My absolute go-to here is the whole chicken and aged cheddar rillettes, and I never ever order chicken at a restaurant. Roister’s chicken is the only exception I make. Location.
The Langham in the Loop is the swankiest hotel room in town. The location offers easy access to plenty of great eating and drinking, and the high tea game is fierce (if you’re into that kind of thing). Location.
The Robey is located in Wicker Park, making it a great alternative to hotels located in downtown Chicago. Being there gives you easy access to all of the great cocktail bars in Logan Square and Wicker Park. Location.
As you can tell from my recommendations, a lot of my favorite spots are some of the newer dining options in the West Loop neighborhood. Logan Square has had a ton of intriguing bars and restaurants that opened up this summer, so is definitely an up-and-coming area worth checking out. I tend to not stick to one neighborhood, but I generally avoid the Loop, as there is not much eating and drinking to be done.
If you are visiting Chicago in the summer, don’t miss Grant Park across from Lake Michigan and Buckingham Fountain. The Art Institute and Museum of Contemporary Art are also absolutely worth checking out.