The Story Behind Chicago’s Downtown Office Space

We are currently in the market for Chicago downtown office space because we must leave Chicago Detours’ home for the past 5 years. We’ve been in the historic Bennett Brothers Building at Adams and Wabash. I’ve always like this cool retro ceiling in the lobby.

downtown office space 30 E Adams
Retro ceiling in 30 E. Adams (Bennett Building) Photo Credit: Amanda Scotese

Time for a New Space

We have to move because of the changing real estate market in downtown Chicago. The Bennett family has sold their building – one of the last family-owned high-rises in the Loop – to a developer called CEDARst Companies. They plan to convert the 12-story building into luxury apartments for millennials, particularly college students. Now that people are willing to live in downtown Chicago again, apartment buildings are the great new way for developers to profit from downtown space.

It’s sad to go, but there are greener pastures! I’ve been shopping around for a new downtown office space to rent, since a small business like ours cannot lease or buy, and have found it fascinating. The work environment worlds differ so much between the the skyscrapers of the Loop that I’ve stepped into.

Touring Interesting Old Buildings

It’s been fun to enter some interesting buildings I hadn’t gone into before! Have you ever noticed the Singer Building at 120 S. State Street? We walk past it on the 1893 World’s Fair Tour, but I’d rarely given it much notice. Designed by Mundie and Jensen in the 1920’s, this skinny little skyscraper was built for the headquarters of Singer Corporation, the makers of sewing machines. Today it is full of lawyers clustered in cubicles. The office has lovely high ceilings and exposed brick walls, but it looks out on a dark alley. That might be tough after getting to look down at the ‘L’ for five years.

The bonus is that the lawyer who showed me around had a super gruff voice and a “horseshoe mustache,” aka the ’80s biker ‘stache. (This isn’t a picture of him here, but I shared it so you know what I’m talking about.) There’s a giant book about Harleys on his desk. I suspect he’s got a lawyer-in-a-suit-by-day and motorcycle-dude-by-night lifestyle! Lawyers never really surprise me, though. The lawyer that shares our office rollerblades from Pilsen to downtown just about everyday. Rain, snow, you name it, he sticks to his rollerblading commute. I’m not making this up!

chicago architecture skyline view
A fire escape view of downtown skyscrapers Photo credit: Amanda Scotese

Discovering Who Works Where

I looked at a quiet floor on skyscraper mostly used by psychotherapists. It’s right on Michigan Avenue, close to where most of our public architecture tours start. Unfortunately the office had those drop ceilings that were all the rage for, well, decades. I’d rather have the ducts exposed with more space to breathe. At that building, I snuck out on a fire escape to take this shot.

I went into the CNA Building for another downtown office space. Signature Offices has smaller spaces divided, and they have killer views over Grant Park and Lake Michigan. We are a small business though, and can’t really splurge on such a luxury. But wow, could you imagine how serene the world would be looking out at that everyday?

On the more historic side of downtown office space, the Mallers Building on S. Wabash has a lovely patina to its interiors. You may know it for its “Jeweler’s Center” sign. I was happy to hear that it is a family-owned building. Constructed in 1912, the 21-story building houses the largest collection of jewelry in the Midwest. You can peak in on jewelers within the natural habitat of their workshops while walking down the glass-paneled hallways. Some of these small businesses have been here for generations, others are new immigrants from India, Africa or China. The office spaces range from sparkly bright and new, and others are time-capsule-style, with awesome mid-century furniture or cherry wood walls of the ’80s. The office I looked at even has the set-up for working with chemicals and metals.

jewelery history chicago office
A jewelry-making set-up. Photo credit: Amanda Scotese

The Remnants of Little Cheyenne

Last and certainly not least is a building that I really hope still exists two years from now. (I say this because it will likely be torn down.) Hidden behind the Board of Trade, this 2-story dinosaur has bypassed downtown development, especially since it’s next door to the Federal Prison. The owner of the old-school Boni Vino’s, making pasta and pizza since ’67, owns the building. I walked into to a stairwell of wood paneling a la ’70s, and the faint, stale smell of cigars. I could only imagine some of the few guys left here from the days of the trading floors might be stashing a flask in their desks.

This office is really one of the most livable I’ve seen. The high ceilings and big windows on a corner are great. Check out the bars over the windows though! It’s on the second floor and it’s got this kind of security. It’s like the rough downtown Chicago of the ’80s. Well, and it is next door to the Federal Prison, let’s not forget. This corner here is one of my favorites. Preservation Chicago has put this block, aka “Little Cheyenne,” on its “Endangered List” of historic architecture that needs to be preserved.

chicago downtown office space by board of trade
Old-time office space Photo Credit: Amanda Scotese

Do you know of any office space downtown? We are a creative business. We are up for shared spaces, too! Please let us know at We have to make a decision by May 31 at the very latest.

Chicago is a city that works! And its downtown office space, both the spectacular and less spectacular, shares a fascinating dimension of the Chicago’s people, industries and architecture.

— Amanda Scotese, Executive Director


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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.

“Our guide Ellen was exceptional and gifted with a great personal touch.”


Tour Guide

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.

“Jen was a perfect storyteller and kept us spellbound for hours.”


Tour Guide

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.


Tour Guide

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.


Operations Coordinator and Tour Guide

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.

“Marie was a bubbling fountain of information and contagious enthusiasm.”


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.
“Sonny was extremely knowledgeable about all things Chi-town.”
Wade K


Content Manager and Tour Guide

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.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
Katie K

Amanda Scotese

Executive Director and Tour Guide

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.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
Shelby F

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