Five Cool Chicago Hotels – A Little Leopard Five Cool Chicago Hotels – A Little Leopard
Five Cool Chicago Hotels – A Little Leopard Five Cool Chicago Hotels – A Little Leopard

Five Cool Chicago Hotels – A Little Leopard Five Cool Chicago Hotels – A Little Leopard

June 6, 2016 // Chicago· travel

Is a Windy City visit in your future (Lollapalooza next month, maybe)? And are you the type of person who insists on staying only in the hippest of the hip hotels when you travel? Chicago may not have an Ace Hotel yet, but never fear. I’ve got you covered with these five cool Chicago hotels.

Image: Curbed Chicago

The Freehand

The Freehand is a combination hotel/hostel with both private and shared rooms, and it’s quite possibly the coolest hostel you’ll ever see. Located in the buzzy River North neighborhood, it has the added benefit of being home to one of my favorite bars in the city, The Broken Shaker. Grab coffee and breakfast from Cafe Integral in the lobby on your way out to explore the city.


ACME Hotel Company

Literally next door to the Freehand is the ACME Hotel Company, with another of my favorite bars, the Berkshire Room. You don’t need to be staying here to go downstairs and order a “Dealer’s Choice” for one of the best drinks you’ll ever have. But if you do stay here, expect trendy digs with high-tech amenities like free hotspots and fast wifi.


Chicago Athletic Association

A relative newcomer to the Chicago hotel scene, the Chicago Athletic Association is in a historic building overlooking Millennium Park. The rooms are a funky throwback with nods to the building’s history, but what really makes this place hip is the food and beverage program. There’s a Shake Shack downstairs, Cindy’s rooftop upstairs, and a couple of dining and drinking outlets from Land and Sea Dept. and master mixologist Paul McGee in between.

Soho House Chicago

Staying at Soho House is one of the few ways to swing access to all their amenities as a non-member…like the killer rooftop pool. Between that and the hip West Loop locale steps from some of Chicago’s hottest restaurants, what more do you need? Well, if you do need more, Soho House has it, from posh rooms to fabulous dining and a gym complete with boxing ring. The downstairs restaurants and spa are open to the public — The Allis is fabulous for both daytime coffee + tea and nighttime drinks while waiting for your table at Au Cheval. Try the avocado toast!

(Seriously….anyone out there want to sponsor my membership application? $1000 a year seems worth it for the rooftop pool alone, no?)

Image: Kinfolk

Longman & Eagle

Did you know this Logan Square hot spot restaurant and whiskey bar is also a tiny bed and breakfast? Well, now you do. Longman & Eagle is the perfect home base for exploring Chicago’s most hipster neighborhoods, like Logan Square itself and nearby Bucktown and Wicker Park. Heck, if it’s in Kinfolk, you know it’s hip.