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Kimpton Gray Hotel rooftop with the Chicago skyline at night

Kimpton Gray Hotel (New York Life Insurance Building)

A marble-clad 1894 landmark — the New York Life Insurance Building —
turned chic boutique, with a glass-roofed rooftop lounge.

New York Life Insurance Building1894Chicago School 122 W. Monroe Street, in the heart of the Financial District

Kimpton Gray Hotel by IHG. New York Life Insurance Building, 1894, William Le Baron Jenney, 122 W. Monroe Street. Photo courtesy of Kimpton Gray Hotel by IHG.

Kimpton Gray Hotel's grand marble hall with twin staircases and coffered ceiling
Kimpton Gray Hotel's grand marble hall with twin staircases and coffered ceiling. Photo courtesy of Kimpton Gray Hotel by IHG.
Vol. 39 bar lined with vintage law encyclopedias and a leather Chesterfield
Vol. 39 bar lined with vintage law encyclopedias and a leather Chesterfield. Photo courtesy of Kimpton Gray Hotel by IHG.
Guest room at The Gray with skyline views and blue accents
Guest room at The Gray with skyline views and blue accents. Photo courtesy of Kimpton Gray Hotel by IHG.
Restored marble staircase and carved balustrade in the landmark lobby
Restored marble staircase and carved balustrade in the landmark lobby. Photo courtesy of Kimpton Gray Hotel by IHG.
Guest bathroom with patterned blue tile, soaking tub, and brass fixtures
Guest bathroom with patterned blue tile, soaking tub, and brass fixtures. Photo courtesy of Kimpton Gray Hotel by IHG.
Lounge with velvet chairs overlooking the LaSalle Street canyon
Lounge with velvet chairs overlooking the LaSalle Street canyon. Photo courtesy of Kimpton Gray Hotel by IHG.
The rooftop bar and restaurant at The Gray, lit at night beneath the skyline
The rooftop bar and restaurant at The Gray, lit at night beneath the skyline. Photo courtesy of Kimpton Gray Hotel by IHG.

Why this building matters

The New York Life Insurance Building is one of three neighboring towers on LaSalle Street designed by William Le Baron Jenney, the engineer-architect credited with inventing the metal-framed skyscraper. Like many of Chicago’s earliest high-rises, it grew vulnerable precisely because it was modest in size — too small for modern corporate floorplates. In 2005, a proposed 52-story tower would have required partially demolishing it. Preservation Chicago pressed the city for landmark protection and named the building to its “Most Endangered” list; the city designated it a Chicago Historic Landmark, and in 2014 Kimpton acquired the tower, investing more than $100 million in a careful, preserve-the-whole-building restoration rather than a gut renovation.

Read more on the National Trust for Historic Preservation → (booking directly with the hotel doesn't generate a referral fee that supports our preservation work — the button at right does)

What guests are saying

What guests love

  • The restoration is the star: original marble, hidden for decades beneath laminate and carpet, was exposed and cleaned; the brick and terracotta were tuckpointed; and hundreds of historic windows were removed, repaired, and reinstalled. A showpiece marble staircase rises to the second floor, and the rooftop bar and the law-library-lined Vol. 39 lounge — stocked with dog-eared legal encyclopedias salvaged from the building’s office days — give the hotel a distinctly authentic, of-another-era atmosphere.

What to keep in mind

  • Business-district setting is quieter on weekends
  • A historic tower — room sizes and layouts vary

Best for Travelers who want to sleep inside Chicago architectural history without sacrificing modern comfort — architecture enthusiasts, design-minded business travelers, and anyone who would rather stay in a meticulously restored 1894 landmark than a generic tower. Its Financial District location puts the Loop, the Riverwalk, and Millennium Park within an easy walk.

Summary of guest reviews. Sources: Kimpton Gray Hotel, Commission on Chicago Landmarks, Preservation Chicago. Photography courtesy of Kimpton Gray Hotel by IHG, used with permission. Details may change over time.