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 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 a blog post by the Chicago Architecture Foundation, this little structure near S. Wabash and E. Jackson 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 new 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 its occupied by the excellent Asado Coffee Company.

#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 has a cast iron facade. It was cheaper and easier than constructing it in brick.

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 this were once occupied much of 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 were constructed between 1875 and 1877. They sit on Jewelers Row along Wabash Avenue. 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.

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.

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 real 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.

I found that the biggest difference between the Delaware’s architecture and the other Italianate post-fire buildings written about here is its construction material. 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 shiny bright McDonald’s.

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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