Preservation Chicago harnesses the power of historic preservation to create healthy, dynamic, and vibrant communities — and over our 25-year history, we’ve directly advocated for many of the very hotels featured on this site.
From Impossible to Inevitable
In some cases, the buildings were highly endangered — facing imminent demolition — when we stepped in. Once-threatened structures have become treasured landmarks that are uniquely and authentically Chicago, delighting locals and visitors alike and anchoring economic development across the city’s neighborhoods.
The world’s first skyscraper rose in Chicago in 1885, designed by William Le Baron Jenney. His Home Insurance Building unleashed a wave of skyscraper construction that became the model for cities around the world. A century later, many of those same beautiful, significant towers stood shabby and vacant. At their most vulnerable moment, Preservation Chicago advocated — with urgency — to protect, preserve, and repurpose them, often by naming them to our annual “Chicago 7 Most Endangered” list to rally public attention before it was too late.
A Building Saved, Twice Over: The Gray Hotel
Consider the building that is now Kimpton’s The Gray Hotel at 39 S. LaSalle Street. Designed by Jenney himself — the “Father of the American Skyscraper” — the 1894 New York Life Insurance Building is one of three neighboring Jenney towers on LaSalle Street, rich with terracotta detailing and expansive marble. Like many early skyscrapers, it became vulnerable precisely because it was modest in size, and in 2005 a developer’s plan for a 52-story high-rise would have required partially demolishing it.
Working to save it, Preservation Chicago pushed the city to grant landmark protection and placed the building on our 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 restoration — exposing marble hidden beneath carpet and laminate, repairing hundreds of historic windows, and preserving the building whole rather than gutting it. Today its polished marble staircase and the law-library-lined Vol. 39 bar welcome guests into a genuine piece of Chicago history. As our executive director put it, “We are all very proud parents of a new Chicago treasure.”
A Second Life
As it turns out, these early skyscrapers make wonderful hotels. Today, many of Chicago’s most striking and historically important towers have been adaptively reused as hip, vibrant, and genuinely delightful places to stay.
These adaptive-reuse hotels join the ranks of Chicago’s grand historic hotels — the ones purpose-built during the city’s golden age. In their heyday, these large and elaborate hotels were the epitome of elegance and sophistication, and their lobbies and ballrooms still dazzle, connecting visitors tangibly to another era.
To avoid having to save them twice, we do what we can to help these beautifully restored buildings remain thriving businesses — ones healthy enough to keep investing in their own preservation. And the best way to do that is simple: choose a Chicago historic hotel for your stay.
Explore Chicago’s historic hotels
Every hotel we feature has been personally researched and recommended by our team.
From your friends at Preservation Chicago.
Love Your City Fiercely!