Five Ways to Appreciate Chicago’s Historic Buildings

Chicago’s historic buildings are a three-dimensional manifestation of our city’s history and culture. If these buildings could talk, they would have endless stories to tell about the city and the many people that have passed through. Read here to learn how to better understand the architecture around you, and imagine, if Chicago’s buildings were among the guests at your Thanksgiving dinner, the stories they would tell!

As an architectural historian, I’m always on the look-out for those stories. With the Thanksgiving season upon us, I’d like to give thanks to the beautiful architecture of Chicago. So I’ve compiled a list to jump start your understanding and appreciation architecture. When I look at a building for a professional project (or even just my own curiosity!), I often look for the same things to gain a basic understanding of what I’m seeing. If you’re exploring architectural history in Chicago, whether you’re a local or a visitor, here is a list of five ways you can appreciate Chicago’s historic buildings.

Chicago's historic Buildings Reliance Building
The Reliance is a classic among downtown Chicago’s historic buildings.

#1. Architectural Style

The style of Chicago’s historic buildings is one of the most fun things to look at and talk about. From Classical Revival to modernism, Chicago has had a national and even world-wide influence since the nineteenth century. Of course, discussions of style often get complicated very quickly (though that just means there’s all the more to talk about. Cue Thanksgiving dinner discussions!). Like any trend, style reflects not just the current tastes, but the opinions and budget of the people behind the building, including the owner, the architect, and the builder.

The 1893 World’s Columbian Exhibition in Chicago began a resurgence of the Classical Revival style rippling across the country. The Prairie School of architecture has its roots in Chicago, thanks in part to Frank Lloyd Wright’s work in area like Hyde Park and Oak Park.

Chicago's historic buildings Robie House Frank Lloyd Wright
Wright’s Robie House is a masterpiece of the Prairie School.

Mies van der Rohe, another architect active in Chicago in the twentieth century, pioneered a very different style of Modernism: the International School. You can find his trademark glass skyscrapers in downtown Chicago, on many university campuses, and along the shore of Lake Michigan.

That isn’t all! Chicago has many well-recognized local-only styles to appreciate as well. Generally, local styles of architecture (or the lack thereof) are called vernacular architecture. Several vernacular styles can be easily recognized among Chicago’s historic buildings, including the Chicago bungalow and courtyard apartment buildings. Chicago even has its own window type, the Chicago window: a large single pane with two narrow double-hung windows, one on either side.

This Thanksgiving, we can be grateful for an amazing variety of architectural eye candy around Chicago, coming in the form of countless ages and styles.

#2. Materials

The materials used to build a building can tell you so many things (and besides, some of them are just really fun to look at up close). Materials can tell you a lot about the technology and materials available, particularly in the days before trains and trucks made nationwide transportation viable. For example, out in the lumber-rich and time-short Pacific Northwest, pioneers built primarily wood houses.

Chicago's historic buildings Lincoln Park
Italiante-style brick is a dead giveaway that you’re looking at some of the oldest of Chicago’s historic buildings.

Meanwhile, the pioneers on the Great Plains found materials were few and far between. So many settlers constructed houses made of sod. Laura Ingalls Wilder briefly lived in a sod house in the children’s classic, On the Banks of Plum Creek. Materials can tell you more locally-rooted stories as well.

In Chicago, the Great Fire of 1871 led to an uptick in the use of non-flammable materials (hello, brick!). The Italianate style dominated post-fire construction. These post-fire buildings can be seen in many parts of the city and were almost always built with bricks. They reflect the changing nature of post-fire style and material preferences.

#3. Look around the corners to appreciate all sides!

It is easy to just look at the front of one of Chicago’s historic buildings. I get it. The front door is there and there may be a lot of details to take in. I had a professor that liked to tell us, you don’t truly get to know a building until you’ve been in the basement and the attic.

Chicago's historic buildings corners side walls
There’s often a pretty big contrast between the front and side.

The same thing should be said of the sides and back of a building. Looking around the corner can reveal the actual construction of the building. Nicer bricks frequently adorn facades in places like the historic Pullman, on the far South Side, and even on Chicago bungalows. But take a peek down the sides and you might spot Chicago common brick. You’d never know if you didn’t peer around the corner.

#4. Property Appraisers

I may be an architectural historian, but just admiring architecture from the street is one of my favorite pastimes. That said, if I really want to learn about a building from a deeper perspective, I have to hit the books. Luckily, a lot of information is online these days. Appraisers vary by county and state. In Cook County, you can view properties online and get a quick rundown of facts.

It’s important to keep in mind that the property appraiser records can be incorrect, but they are generally close. If you’ve already looked at the style, materials, and construction, you will likely have a good sense of whether the listed construction date fits. Need a more precise record? Head to the property appraiser’s office to track back the sales of the property.

Chicago's historic buildings Mies van der Rohe Lincoln Park
Downtown business district or residential neighborhood? Hard to tell!

#5. Appreciate the local history of  Chicago’s historic buildings

Nothing pulls the story together like a little knowledge. The context of what was going on during the time that your building was built. You can dig into political events, economic booms and busts, and immigration of new communities. Most any Chicago building, whether they are suburban bungalows or urban skyscrapers, are part of local trends that reflect bigger cultural shifts. Learning about the Great Chicago Fire is key to understanding what the building owners were thinking at the time. Right after 1871 they were likely thinking, let’s build something that won’t burn!

The best part about Chicago architectural history is that it’s an inexhaustible source of intrigue, stories, and learning. Not only is there always something new to explore, but there’s something for everyone. Chicago’s skyline is etched with disasters, triumphs, technological advances, and shifting cultural tastes. Just look closely and you’ll start to see snippets of the buildings’ stories that you can appreciate on any day of the year!

– Susan Trexler, Guest Blogger


Share on facebook
Share on twitter
Share on pinterest
Share on linkedin

be a



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

Book a chicago event

Let’s Connect!