Drink, Sleep, and Be Merry: Chicago’s Best Boutique Hotels with Bars

I’ve never thought much about Chicago when big cities pop up on my radar, even though it’s the third most populous city in the U.S. (And I grew up just a few hours away.)

Chicago doesn’t have the size and bustle of New York City, nor the liberal reputation of LA and San Francisco. It’s not known for its sexy beaches like Miami, nor for its innovative tech industry like Seattle.

But that doesn’t mean this Midwestern metropolis isn’t lacking in big-city swag and style.

In fact, it was voted the #1 major city in the U.S. six years in a row by Condé Nast. (That’s the parent company of The New York Times, Vogue, Glamour, WiredAnd Vanity Fairall.)

In addition to the Condé Nast seal of approval, Chicago has all the key ingredients of an iconic big city.

The city has a rich history (from mafia gangsters to precedent-setting lawsuits), a long-standing relationship with all four Major Leagues, its own culinary quirks, and a long list of proliferating artists (from Kanye West to Robin Williams. The city has also served as the backdrop for major films, from The dark knight Unpleasant Ferris Bueller’s Day Off.

So it won’t surprise you to learn that Chicago is home to a number of terribly stylish boutique hotels.

I’ve been perusing the list of Chicago’s best boutique recommendations, but not just from a luxury perspective. Instead, I’m on the hunt for one of the core attributes that makes Chicago so effortlessly cool: a love of stylish bars and a trust in professional mixologists.

(I’m not kidding… the city is home to at least a dozen theme bars.)

Fancy a top-notch cocktail while staying at a boutique hotel? Then definitely check out the hotels below, or at least their bars.

Longman & Eagle

Bar: Longman & Eagle

Located in the heart of Logan Square, this Chicago residence exudes sobriety and exclusivity. As for the hotel, it offers only six rooms, which are uniquely decorated and cozy.

Also on the property is the Longman & Eagle Restaurant, which is the main event here. The Longman & Eagle serves as an ode to Chicago’s drinking culture.

I have family members who live in the city and they’re all beer drinkers. But at Longman & Eagle, you see a strong emphasis on Chicago’s whiskey-making history, along with a lot of love for the lesser-known hits, like locally produced small-batch wines and seasonal cocktails.

Thanks to a Michelin mention, the menu isn’t bad either.

Book here

Freehand Chicago

Bar: Broken Shaker

Looking for a unique design? The Freehand has all the bespoke and quirky touches for an unforgettable journey.

From funky wallpaper to extravagant textile elements: it exudes courage.

But the Broken Shaker bar is also worth writing home about. The focus is on craft cocktails, cocktails that require attention to detail, a bold approach to flavor, and a serious emphasis on character.

Book here

Chicago Athletic Association

Bar: Playroom

Welcome to one of the strangest Hyatt projects I’ve ever seen.

I mean weird in a good way, because the Chicago Athletic Association hotel delivers a seriously kitschy take on boarding school decor. As in, you’re going to leave this hotel yearning to find a Greek shipping magnate and change your last name to Onassis.

And as the bar’s name suggests, the focus is on gaming, but not in the digital sense. It’s all analog sobriety here, from the green felt pool table to the sandy shuffleboard.

This is how I imagine the kids at Victorian prep schools hung out. Again, in a good way.

Book here

Viceroy Chicago

Bar: Pandan

The Viceroy is one of the most luxurious hotels in Chicago.

There’s no reason not to recommend this location: from the skyline views to the lavish wallpaper and location in a landmark building, it’s worth every penny.

Best of all, guests also get direct access to the rooftop bar, Pandan. Pandan offers panoramic views of the city from an 18^and-floor grill. And it also excels in fusion food, including South Asian and Western mashups.

Book here

The Robey

Bar: Cabana Club, The Up Room and Clever Coyote

The Robey is known as a chic boutique retreat that combines modern and industrial designs. But you may have heard of The Robey if you’ve visited Chicago, thanks to its bars and location in the heart of Wicker Park.

There’s the Clever Coyote, a 90s-inspired bar where thirtysomethings can revel in the nostalgia of brightly colored cocktails. The Up Room, on the other hand, is a slightly more upscale rooftop bar that serves cocktails of all kinds. I’d probably head to the Cabana Club, which is on the sixth floor and has a seriously bougie pool.

Book here