I’ve never thought much of Chicago when big cities come up on my radar—even though it’s the US’s third-most populous city. (And I grew up only a few hours away.)
Chicago doesn’t have the scale and hustle of New York City, nor the liberal reputation of LA and San Francisco. It’s not known for its sexy beaches like Miami, nor its innovative tech industry like Seattle.
But that doesn’t mean this Midwestern metropolis doesn’t have big city swag and style.
In fact, it was voted as the #1 Big City in the US for six years in a row by Condé Nast. (That’s the parent company of The New York Times, Vogue, Glamour, Wired, and Vanity Fair, y’all.)
On top of it’s Condé Nast seal of approval, Chicago has all the key ingredients of an iconic big city.
It’s got history in spades (from mafia gangsters to precedent-setting court cases), a long-running relationship with all four Major Leagues, its own distinct culinary quirks, and a long list of proliferate artists (from Kanye West to Robin Williams. The city has also served as the backdrop for major motion pictures, from The Dark Knight to Ferris Bueller’s Day Off.
So you shouldn’t be surprised to learn that Chicago is home to some very stylish boutique hotels.
I’ve scoured the list of top boutique recs in Chicago – but not solely from a luxury standpoint. Instead, I’m on the hunt for one of the core characteristics of what makes Chicago so effortlessly cool: its love of stylish bars and its trust in professional mixologists.
(I’m not joking… the city is home to at least a dozen themed bars.)
Want a top-notch cocktail with your boutique hotel stay? Make sure to check out the hotels listed below—or, at least, their bars.
Longman & Eagle
Bar: Longman & Eagle
Located in the heart of Logan Square, this Chicago stay oozes austerity—and exclusivity. In terms of the hotel, it offers only six rooms, which are unique appointed and cozy.
On the grounds, you’ll also find the Longman & Eagle Restaurant—and that’s the main event here. The Longman & Eagle serves as an ode to Chicago’s drinking culture.
I have family members living in the city, and they’re all beer drinkers. But at the Longman & Eagle, you’ll see a strong emphasis on Chicago’s history in whiskey-making, along with plenty of love for its lesser-known hits—like locally sourced small-batch wine and seasonal cocktails.
With a shoutout from Michelin, it’s menu isn’t too shabby, either.
Freehand Chicago
Bar: Broken Shaker
If you’re on the hunt for a unique design, the Freehand has all the bespoke and quirky accents for a memorable trip.
From funky wallpaper to over-the-top textile features, it’s got spunk in spades.
But the Broken Shaker bar is also worth writing home about. Its focus is on craft cocktails—ones that require attention to detail, a daring approach to flavor, and a serious emphasis on character.
Chicago Athletic Association
Bar: Game Room
Welcome to one of the oddest projects from Hyatt that I’ve ever seen.
I mean odd in a good way, as the Chicago Athletic Association hotel delivers a seriously kitschy take on boarding school décor. As in, you’re going to leave this hotel with a hankering to find a Greek shipping magnate and change your last name to Onassis.
And like the bar’s name suggests, there’s a focus on gaming—but not in the digital sense. It’s all analog austerity here, from the green-felt pool billiards table to the sandy shuffleboard.
It’s how I imagine Victorian-era prep school kids hung out. Again, in a good way.
Viceroy Chicago
Bar: Pandan
The Viceroy is one of Chicago’s premier luxury stays.
There’s no reason to sell you on this location—from its views of the skyline to its opulent wallpaper to its location inside a landmark building, it’s worth every penny.
Best of all, guests also get direct access to its rooftop bar, Pandan. Pandan offers a panoramic view of the city from an 18th-floor roost. And it also excels in fusion foods, including South Asian and Western mashups.
The Robey
Bar: Cabana Club, The Up Room, & Clever Coyote
The Robey is renowned as a swanky boutique stay, blending modern and industrial designs. But you might have actually heard of The Robey if you visited Chicago thanks to its bars and location in the heart of Wicker Park.
There’s the Clever Coyote, a 90s-inspired bar where 30-somethings can frolic with the nostalgia of brightly colored cocktails. The Up Room, by contrast, is a slightly swankier rooftop bar that offers cocktails of all stripes. I’d probably head to the Cabana Club, located on the sixth floor and home to a seriously bougie pool setup.