Why We Built This

The Chicago Historic Hotels: Embrace Authenticity website is a lovingly curated guide to Chicago’s most authentic and architecturally significant hotels, presented by Preservation Chicago: Love Your City Fiercely!

Chicago is a world-class city and a top-rated tourist destination. Chicago has won the “Best Big City in the U.S.” 9 years in a row by Condé Nast Traveler readers!

Chicago welcomed 56.8 million visitors in 2025, who spent a record $21.5 billion. Visitors enjoy Chicago’s world-class architecture, incredible parks and lakefront, renowned museums, outstanding theaters, and vibrant restaurants and neighborhoods. Authenticity is the trait that connects them all.

A Virtual Concierge

ChicagoHistoricHotels.org offers heritage travelers high-quality, well-researched guidance from local architectural historians and preservation advocates. Think of us as your virtual concierge: our goal is to provide you with the information and recommendations to enable a marvelous stay. We love this city and its buildings, and we’re thrilled to share that energy with you.

Your hotel is more than a place to sleep — it’s your home base, your launching-off point for the city’s restaurants, museums, architecture, and neighborhoods. With over 500 hotels in Chicago, it’s a challenge for heritage tourists to find one that is genuinely special and that fits your own interests, priorities, and budget.

After years of informally steering friends and family toward great places, we decided to harness our collective expertise in Chicago’s historic hotels into a website that would reach a wider audience and help them find a great place to stay for their Chicago visit.

How Hotels Are Selected

This is a lovingly curated selection of approximately 70 of Chicago’s most delightful and authentic historic hotels that meet our criteria. We hope that this site will make it easy to find Chicago hotels based on their unique value propositions, including quality, authenticity, uniqueness, and historic interest.

These are hotels we treasure and have long recommended to the people closest to us — and now we’re sharing those recommendations with you. Every hotel is personally reviewed and documented so that each is a place we’d genuinely recommend. Many of these hotels we know intimately, having helped save them from demolition and working alongside developers and city officials to reimagine them as hotels.

The list spans the full range: purpose-built grand hotels and recent adaptive-reuse conversions, decadent luxury and hip energy, top-dollar suites and affordable hostels, and everything in between. They sit across a variety of prices and neighborhoods, though most cluster in and around the Loop.

Hotels cannot buy their way onto this site. To qualify, a hotel must occupy a historic building at least 50 years old, must be unique and authentic, and must be charming enough to enhance a visit to Chicago. The test we apply is simple: would we send an old friend here on their first trip to the city? If the answer is an enthusiastic yes, the hotel makes the list.

In fact, many are so special that we encourage you to visit even if you’re staying elsewhere — step into their glorious lobbies, have a drink in their beautiful bars, linger over a meal in their restaurants. As we like to say, everything is just a little bit better in a historic building.

Who We Are

Preservation Chicago: Love Your City Fiercely! 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 hotels featured on this site.

In a large city like Chicago, it’s surprising that one small advocacy nonprofit can have such an oversized impact. Yet we have a remarkable track record of hundreds of successful outcomes. Many buildings would have been demolished if not for our direct intervention and advocacy.

Vibrant communities seem an impossible dream when standing among vacant buildings and empty store fronts. But transforming “Impossible to Inevitable” is our specialty. Preservation Chicago is the catalyst behind an unprecedented surge of high-profile, transformational efforts to revitalize long-neglected historic assets into dynamic neighborhood anchors. We leverage the power of historic preservation to create healthy, vibrant, diverse and sustainable communities.

When historic buildings were endangered and facing demolition, we engaged directly at critical inflection points to deliver decisive wins through our innovative “Leveraged Impact Advocacy” strategy. 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.

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. We’ve successfully used this strategy to catalyze hundreds of millions of dollars of public and private investment in restoring and revitalizing historic buildings throughout Chicago.

A Building Saved, Twice Over: The Kimpton Gray Hotel

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.

Consider the building that is now the Kimpton 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 annual Chicago 7 Most Endangered list. Eventually, 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 — named for the building’s LaSalle Street address — 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: Adaptive Reuse from Office to Hotel

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.

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.

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 Kimpton 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 on our website. Learn more at PreservationChicago.org.

Support for the Effort

Choosing a historic hotel is itself an act of advocacy. Every booking through the guide generates a small referral fee that supports Preservation Chicago’s work — at no additional cost to you.

From your friends at Preservation Chicago.

Love Your City Fiercely!