Nobody could ever accuse the Kimpton group of not throwing its weight behind Chicago. Located in the former New York Life Insurance Building – now practically dwarfed by the surrounding skyscrapers – the newly opened The Gray is the San Francisco-based outfit’s fifth property in the Windy City, and the eighth in the Midwest alone.

Interior designers Beleco have been respectful in its reimagining of William le Baron Jenney’s 1894 pile. While the brick and terracotta façade retains its elegant symmetry, the interiors pay subtle homages to Chicago, past and present – the blues in each of the 293 guestrooms hint of the city’s flag, the public spaces are sprinkled with artwork by local artists, and the original Georgia Gray marble in the lobby still glimmers.

The Kimpton’s trademark playful youthfulness is evident at every turn – pets are welcome, a mini-bar in each room stocks a tie, lapel pin and pocket square from The Tie Bar, while specialized rowing classes and lifestyle coaching are just what the doctor ordered. 

On the 15th floor, rooftop lounge Boleo blends Argentinian and Peruvian street snacks with pisco sours, while the ground floor Steadfast – lined with banquettes, a charcuterie room, shaved ice crudo bar, and a zinc bar – serves butter poached lobsters, and ribeye and caviar. 

In other words, The Gray is an all-round treat.