Four of the Oldest Buildings in the Loop

By Alex Bean on March 30, 2016


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. Here are four of our favorites.

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 by the Chicago Architecture Foundation, 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.

If you’d like to know even more about it, the Pickwick Stable is a stop on our 1893 World’s Fair Tour.

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 can be seen in many of the oldest buildings in the Loop. The rows of adjacent arched windows and decorative cornices evoke the architecture of the Italian Renaissance.

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 the image of molten iron walls tumbling down amidst the flames meant that not too many were rebuilt.

The Berghoff moved into one of the buildings in the early 1900s, and then their business grew to other levels and buildings. These days, the Berghoff Buildings look like munchkins next to their towering neighbors. They give us a glimmer of what the landscape of downtown Chicago looked like in the 1870s. It’s tough to imagine, but little buildings like these once occupied much of the Loop.

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 Italiante 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. It 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

The Delaware Building might be the most heavily-used of the oldest buildings in the Chicago Loop. Completed in 1872, during the frenzied reconstruction of the Loop, this building is a spectacular time capsule. For anyone who has been on our Loop Interior Architecture Walking Tour, the Delaware was once a neighbor to the now-demolished McCarthy Building on Block 37.

Construction material sets the Delaware’s architecture apart from the other Italianate post-fire buildings written about here. The pre-cast concrete facade sets it apart from contemporaries. 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.

-Alex Bean, Office Manager and Tour Guide


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