Many Chicago streets are named after the people who once lived here, but we also have quite a few named after U.S. presidents. According to the book Streetwise Chicago: A History of Chicago Street Names, I counted at least 20 roadways possibly named after former presidents and their homes in the city. I included Thomas Jefferson’s Monticello and Andrew Jackson’s Hermitage, but excluded the Kennedy and Eisenhower Expressways. I was surprised to learn that Cleveland Avenue is named after 19th century subdivider Franklin A. Cleveland, and not 22nd (and 24th) president Grover Cleveland (although there is Grover Street in Jefferson Park), and Pierce Street honors the Pierce Brothers land development firm instead of Franklin Pierce. So let’s explore some properties for sale located on streets that preserve the memory of past commanders-in-chief.

3325 N Lincoln Ave APT 402, $995,000

Let’s start with Abraham Lincoln, a name that is hard to escape in the state of Illinois. The historic Brundage Lofts, prominently located where Lincoln and Marshfield Avenue meet School Street, was originally built as the Marshfield Trust and Savings Bank in 1924. The pie-shaped building is now home to 10 residential units, including this bright and airy four-bedroom, three-bathroom penthouse. On sale at a reduced price, the 2,600-square-foot interior features two primary bedroom suites. The property has $542 monthly HOA fees and also comes with an off-site parking space — and it’s only one block from the Paulina L stop.

812 W Van Buren St #6HI, $1,499,000

The West Loop is one of the city’s hottest housing markets and it’s filled with streets named after America’s earliest presidents: Washington, Madison, Monroe, and Van Buren. Westgate Lofts, once home to the Pontiac Engraving & Electrotype Company, was among the earliest residential conversions in the neighborhood, in 1990. This corner duplex penthouse with three bedrooms and three bathrooms has 12-foot ceilings and a custom-built fireplace. The property also includes a 500-square-foot private roof deck with stunning views and side-by-side parking spaces.

161 W Harrison St UNIT 1203, $559,000

In Printer’s Row, you’ll find streets honoring a somewhat forgotten president, James K. Polk, along with the president with the shortest term in history, William Henry Harrison. The Patten Building was designed by local architect Christian Eckstrom in 1904. This particular unit for sale has 1,800 square feet of living space spread over three floors. It’s made more interesting by the angled walls and prominent staircase. Not only does the loft come with its own private roof deck, but it is conveniently located right next to the LaSalle Street train station. 

565 W Quincy St UNIT 512, $359,000

A block south of Adams Street is one of only two ‘Q’ streets in Chicago. Quincy (and possibly Adams itself) is named after America’s sixth president, John Quincy Adams. Located right next to Union Station, 565 West Quincy is a World War II-era building that was converted into lofts in 2008, with an additional 11 floors added as tower units. This two-bedroom condo with its own large terrace and private storage space, which is already contingent, caught my eye. Besides an eighth-floor common area and a game room, this high-rise is the only residential building in Chicago with its own bowling alley.

910 W Madison St APT 904E, $1,650,000

Let’s return to the West Loop to take a look at a prime property located on one of the city’s major east-west thoroughfares, named after the fourth U.S. president. This three-bedroom, three-bathroom penthouse loft was created by combining two separate units to form 2,500 square feet of custom-designed living space. I personally love the wet bar hidden behind a walnut pocket door. The $1 million-plus price tag makes sense when you consider all the luxurious amenities and high-end finishes, in addition to the 1,500-square-foot L-shaped wraparound terrace that includes 20 self-irrigating planters.