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.
Our advocacy at work
Since our founding in 2001, Preservation Chicago has published an annual “Chicago 7 Most Endangered” list — naming threatened buildings to mobilize public attention before demolition becomes irreversible. We push for Chicago Historic Landmark designations, testify before city bodies, and generate media coverage to buy time for investors to discover the latent potential in these buildings. Several of the hotels on this guide are direct outcomes of that sustained advocacy.
Saved from demolition: The Pendry Chicago
The Carbide & Carbon Building at 230 N. Michigan Avenue — a 1929 masterwork by the Burnham Brothers, clad in dark-green terra-cotta and crowned in 24-karat gold leaf — spent decades as offices before falling into an uncertain twilight. Preservation Chicago strongly advocated for its Chicago Historic Landmark designation, helping secure the protection that made a careful hotel conversion possible. Today it operates as Pendry Chicago, its dazzling Art Deco lobby, bronze detailing, and gilded crown intact — one of the most spectacular historic interiors in the city, and one guests can now sleep inside.
The same story — threat, advocacy, landmark protection, adaptive reuse — has played out across Chicago’s architectural landscape. The Kimpton Gray Hotel on LaSalle Street (detailed above) was saved from partial demolition when Preservation Chicago named it to the Most Endangered list and pressed the city for landmark designation in 2005. The Chicago Athletic Association, InterContinental Chicago, the Blackstone, and dozens of other landmark hotels across the city all benefited from the broader preservation climate that Preservation Chicago has helped build over 25 years — one in which the default answer to “what do we do with this old building?” has shifted from demolition to reimagination.
Our innovative “Leveraged Impact” model — amplifying awareness, securing landmark protections, and catalyzing public and private investment — has produced outcomes that once seemed impossible. As our executive director has said of victories like The Gray: “It looks impossible at the start and inevitable once complete — but the advocacy is lengthy, difficult, and never guaranteed.”
We document our ongoing campaigns and victories at PreservationChicago.org/advocacy. To read more about the specific hotels on this guide and why we champion them, visit our Guide to Historic Chicago Hotels on PreservationChicago.org.
Support the work
Choosing a historic hotel is itself an act of advocacy. Every booking through this guide generates a small referral fee that supports Preservation Chicago’s work — at no cost to you. And if you’d like to do more, we are a Candid Platinum-rated, Charity Navigator 4-star nonprofit that makes every dollar count.
Explore Chicago’s historic hotels
Every hotel we feature has been personally researched and recommended by our team.
From your friends at Preservation Chicago.
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