From Glamor to Gloom at the Pittsfield

In the 100 years of its history, the Pittsfield Building is a big art deco skyscraper that has gone through an incredible transformation. Despite being located adjacent to the bustling Millennium Park, this 37-story skyscraper was once practically empty. From the outside, the Pittsfield appears to be your typical 1920s building, constructed in a throne shape. No one would guess inside one will find a soaring, 5-story atrium draped in gilded exotic Spanish Gothic details. And no one would guess, the story this building holds.

The Pittsfield Building exists in a beguiling balance. Visual clues to its rich past remain, despite it present with an uncertain future. Walking inside is like stepping through a time warp. It’s a fascinating example of how Chicago architecture can elegantly age, even while time passes it by.

We research stories from Chicago history, architecture and culture like this while developing our live virtual tours, in-person private tours, and custom content for corporate events. You can join us to experience Chicago’s stories in-person or online. We can also create custom tours and original content about this Chicago topic and countless others.

Pittsfield building atrium cafe
The gorgeous Spanish-influenced atrium of the Pittsfield, where the beloved eponymous café is located. Photo by Alex Bean.

History of the Pittsfield Building

Located just next to the landmark district of the Loop’s Jewelers Row, the Pittsfield Building opened in 1927 as a mixed-use office and retail skyscraper. It’s right across the street from more-familiar landmarks like the Cultural Center and Marshall Field’s.

The Estate of Marshall Field constructed the Pittsfield Building, trying to capitalize on the building boom of the Roaring 20s. The prolific architecture firm of Graham, Anderson, Probst & White, which was the successor to the famous D.H. Burnham and Co. designed the tower. The Field Estate constructed other office towers in this era, including the Burnham Center in 1913 and the Field Building in 1934. All three towers were funded by the wealth left laying around by Field when he passed away. Quite a bit of loot!

Pittsfield Building Exterior Street Level
The Pittsfield soars 37 stories above Jeweler’s Row. Photo by Alex Bean.

Architecture of the Pittsfield

The tower, despite its gleaming terra cotta facade, is a bit hidden on the skyline. Tucked a block back from Michigan Avenue, it looms over the adjoining ‘L’ tracks, rather than the lakefront parks. Due to its ongoing development issues, detailed below, one has had to enter the building by going under gloomy construction scaffolding. Finding which door on Washington Street will even open is sometimes a challenge in and of itself.

One cannot help but wonder what lies hidden behind such an uninviting entrance. Just past the doors, a sleepy security guard flips through his phone at a cheap table set across the lobby hall. The light is dim and indirect, making one feel almost like a trespasser. Once your eyes adjust, though, the opulence is awe-inspiring.

The coffered ceiling above the elevators thrums in a maze-like hexagonal pattern. An ostentatious mailbox, bedecked with a metallic eagle, arrests your attention as you pass into the building’s heart. There, a central atrium soars five floors above, crowned with a gigantic chandelier. Marble covers every spare surface in the lobby and atrium, though much of the space is lost in dim shadows.

The effect of all the architectural ornamentation is stunning in its opulence and aesthetic appeal – no wonder it’s been rented out for weddings. The architects called their style “Spanish Gothic Revival,” but a careful eye can spot hints of the burgeoning Art Deco aesthetic. Of course, that fits right into the flashy architectural approach that Marshall Field pioneered at his store, as any of our Loop Interior Architecture Walking Tour guests can attest. It’s easy to see why the building was declared a Chicago Historic Landmark in 2002.

The dazzling coffered ceiling of the Pittsfield’s elevator lobby. Photo by Alex Bean

Contemporary Hurdles for the Pittsfield

Two different commercial uses dictated the design patterns of the Pittsfield Building. The upper floors, from 5 to 37, were professional offices for lawyers, dentists, and doctors. The lower levels, from the basement to the 5th, were for small retailers such as jewelers, restaurants, tobacco stores, and newsstands.

The architectural plan for the Pittsfield Building suited its time, but it faces some contemporary hurdles. Medical professionals and their patients prefer sparkly new facilities, meaning a loss of tenants and office rentals. The Pittsfield has made up for that loss by renting several of the floors to nearby universities as dorms. Another plan wants to turn some of the floors into a new hotel, but a legal battle between developers has that currently on hold.

The mysteriously decrepit basement arcade of the Pittsfield sits only one floor below the beguiling atrium. Photo by Alex Bean.

A building this old also presents a challenge for contemporary retailers. The architects’ original plan put most of the shops and cafes in the atrium or basement. The ground-floor spaces still look beautiful, but most are vacant and seemingly forgotten, giving the Pittsfield a haunted feeling. Only Pittsfield Café patrons searching for the restroom visit the basement arcade, pictured above. Its faux storefronts, empty display windows, and hallways to nowhere are hauntingly strange.

Strange Vibes and An Uncertain Future

To be frank, there’s little else in downtown Chicago with a vibe as strange as the Pittsfield’s. Nearby historic skyscrapers, like the Reliance, have been reborn as beautiful hotels. Others, like the aforementioned Field Building and Burnham Center, are still bustling office spaces. All of them have seen significant upgrades and preservation efforts. The Pittsfield is unique in its obsolescence.

Magnificent architecture litters Chicago’s past. Many of those works, like the Pittsfield, outlived their original architectural design. Some, like Louis Sullivan’s old Stock Exchange, met the wrecking ball. Others, like the Chicago Athletic Association, are thriving after being revitalized and repurposed. I’d prefer the latter for the Pittsfield Building, of course, but it will take a developer with big ambitions and deep pockets to see it all the way through.

– Alex Bean, Chicago Detours’ Content Manager


Chicago Detours is a boutique tour company passionate about connecting people to places and each other through the power of storytelling. We bring curious people to explore, learn and interact with Chicago’s history, architecture and culture through in-person private group tourscontent production, and virtual tours.


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Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

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Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

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With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.


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Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.


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Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

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Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
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Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

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Amanda Scotese

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I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
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