Four of the Oldest Buildings in the Loop

The oldest buildings in the Loop can be hard to find. Downtown Chicago is justly famous for its wealth of modern skyscrapers. Behemoths like the Willis Tower dominate the skyline and our attention. It always makes me feel like everything in the Loop sprang up in the middle of the 20th century. However, there are a surprising number of buildings from the 1800’s scattered around downtown Chicago. We’ve learned all about these oldest buildings as tour guides in Chicago. Here are four of our favorites.

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Pickwick Stable Asado Coffee Chicago oldest buildings in the loop
The charming Pickwick Stable was rumored to be the oldest building in the Loop, but it probably isn’t. Photo Credit: Alex Bean

#1. The Pickwick Stable

According to an old blog post, this little structure on Jackson just west of Wabash was once a horse stable and may have been built as early as 1857. However, more recent research has uncovered that it dates back to 1892. An English chophouse served Beef Wellington here during the 1893 World’s Fair.

A succession of much larger buildings loom around it. They have boxed the three-story brick building into a small alley. These days it’s occupied by the excellent Hero Coffee Bar.

#2. The Berghoff Buildings

The three distinct buildings that now house the Berghoff restaurant were constructed in 1872. That’s only a year after the Great Chicago Fire destroyed most of the Loop. These buildings are an example of the Italianate architecture that’s among the oldest buildings in the Loop. The rows of adjacent arched windows and decorative cornices evoke the architecture of the Italian Renaissance. The Berghoff moved into one of the buildings in the early 1900s, and then their business grew to other levels and buildings. 

I find it fascinating that one section of the building, its western third, has a cast iron facade. Covering an entire building in precast iron was cheaper and easier than constructing it in brick. Cast iron facades were all the rage before 1871, though not many were used afterwards. The image of molten iron walls melting down amidst the inferno will do that to ya.

These days, the Berghoff Buildings look like munchkins next to their towering neighbors. It’s tough to imagine, but little buildings like these once occupied much of the Loop. They give us a glimpse of what the landscape of downtown Chicago looked like in the 1870s. Because Berghoff sold their beer at the 1893 World’s Columbian Exposition, we also used to visit this building on our 1893 World’s Fair Tour with Bars. We’d be thrilled to show it to you on a custom private tour these days!

Berghoff Restaurant oldest buildings in the Loop
The Berghoff Restaurant inhabits three distinct buildings from the 1870’s. Photo Credit: Pawel Skrabacz

#3. The Haskell, Barker, and Atwater Buildings

This trio of buildings went up on Wabash between 1875 and 1877. They sit on Jewelers Row, between Monroe and Adams. Just like the Berghoff Buildings, they demonstrate the heavy masonry and Italianate architecture that is so common among the oldest buildings in the Loop. The three buildings are most notable for their association with famed Chicago architect Louis Sullivan. He redesigned the lower two levels of the Haskell Building in 1896. His signature cast iron ornamentation on the facade is visible from clear across the street.

oldest building in the Loop Louis Sullivan Jewlers Row Haskell Barker Atwater Buildings
The Haskell, Barker, and Atwater Buildings are still standing on Jewelers Row. Photo by Alex Bean

Amazingly, metal sheeting covered up one of those designs in the 1920s. Restoration workers discovered this lost Sullivan work in 2008. I am a huge fan of Sullivan’s work, so it’s a treat to see his work here and connect it with his more famous work on the Sullivan Center facade a block away on State Street. Speaking of, many Chicagoans have likely been in these historic buildings by virtue of grocery shopping at the State Street Target. That store stretches back and occupies the upper floors on Wabash.

Dearborn Building Chicago oldest buildings in the Loop
The Delaware Building, at Lake and Dearborn, dates to right after the Great Chicago Fire. Photo Credit: Alex Bean

#4. The Delaware Building

Completed in 1872, during the frenzied reconstruction of the Loop, the Delaware Building is a spectacular time capsule. For anyone who came on our old Loop Interior Architecture Walking Tour, the Delaware was once a neighbor to the now-demolished McCarthy Building on Block 37.

Stylistically, the Delaware is similar to the other Italianate post-fire buildings written about here. It’s building materials were quite unique for the time though. The facade of arched windows was built with concrete. That’s one of the most common materials in construction today, but was ahead of its time in 1872.

The Delaware Building sits on prime real estate at Randolph and Dearborn. It’s in the midst of the Loop Theater District and is kiddy-corner from Daley Plaza. You may recognize it as the old-looking building with a bustling McDonald’s. As of 2019, the old owners were foreclosed upon, so the Delaware may be getting a facelift very soon.

Many other 1800’s buildings dot downtown. These four stand out as easily located and notable landmarks. You can use them as a starting point on your own quest for the oldest buildings in the Loop or give us a call for a custom tour or more original Chicago content.

-Alex Bean, Office Manager and Tour Guide


In business since 2010, Chicago Detours is a passionate team of educators, historians and storytellers. We applied a decade of experience as one of Chicago’s top-rated tour companies to become a virtual event company in 2020. We bring curious people to explore, learn and interact about Chicago’s history, architecture and culture through custom tours, content production, and virtual events.


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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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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.
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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.

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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.
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