Pill Hill

This relatively affluent, middle-class neighborhood on Chicago's south side offers spacious homes in a quiet, pocketsize residential setting. Near enough to the highway to allow easy transportation into the heart of the city, without all the hubbub of being right on top of a freeway. Pill Hill was at one time the prime address for area doctors who worked at the nearby South Chicago Hospital (hence the name Pill Hill — as in prescription pills). These days the neighborhood welcomes a variety of residents.

Pill Hill Facts

Location: About 13 miles south of the Loop
Boundaries: 92nd Street to the north, Paxton Avenue to the east, 94th Street to the south and Cregier Avenue to the west
Bordering Neighborhoods: Calumet Heights, Jeffrey Manor

Then and Now

Pill Hill Real EstateLocated in the middle of the south side of Chicago community known as Calumet Heights, the tiny eight-block by two-block Pill Hill is a well-to-do middle-class neighborhood that attracts residents of all walks of life. Of course, like all things, it wasn’t always this way.

Unlike much of the surrounding area, the small nook where Pill Hill now exists was first settled by farmers looking for a good place to sow their crops. The swampy nature of the land removed farming as an option, so it remained undeveloped for quite a while. It really wasn’t utilized at all until the 1870s when a number of industrial businesses (such as the Calumet and Chicago Canal and Dock Company and Pullman Railcars) built factories nearby. As workers from the factories needed places to live, residential development finally began in the Pill Hill area. Eventually the population of the neighborhood was high enough for Chicago to take notice, and it incorporated the tightly-packed enclave into the city in 1889.

Moving along into the 1940s, the entire Calumet Heights region (of which Pill Hill is a part) started to see a demographic shift. As the once-important factories began closing down, the old blue-collar factory laborers moved out and young white-collar workers moved in. Pretty soon the area became solidly middle-class and gained a reputation for affluence and nice houses.

In the midst of this prosperous area, an interesting trend sprung up in the 1970s. A large number of doctors from the nearby South Chicago Hospital moved into a small enclave within Calumet Heights. Due to the concentration of medical professionals living here, people then began referring to this little region as 'Pill Hill.' As you might have guessed, the name stuck and the little neighborhood continues to be known as Pill Hill to this day. Although some doctors do live in Pill Hill, it’s no longer the majority occupation of neighborhood residents. These days, all manner of middle-class workers and business people call Pill Hill home.

Pill Hill Real Estate

Today, Pill Hill retains a subtle charm from the days of being the sought-after neighborhood for south side doctors. The rows of houses sit on green lots that are nicely landscaped and surrounded by towering, leafy trees. On a whole, properties in Pill Hill are relatively good-sized and well maintained. The majority have built-in garages (though most are for only one car), and the private yards offer a decent amount of space for gardens and flowerbeds. Backyards are sizable, and most of them are home to large trees that shade the homes and provide a sense of maturity and stability.

Down any Pill Hill neighborhood street you’ll find a considerable range of architectural designs, from bungalows and split-levels to town homes and ranches, with a few condos thrown in for good measure. One-story frame houses with cute front porches sit next to redbrick bungalows with stone stoops. Some sections of Pill Hill even have stately new-construction two stories that bring all the amenities of downtown living to this outlying suburb-like south side neighborhood.

The variety of Pill Hill home styles can be further seen in the pricing. The average sale price for a two- or three-bedroom detached house in the neighborhood is about $164,000; however, there are a handful of properties of this size that sell for $150,000 or less—the low end being $75,000. Some of the newer homes here can go for as high as $280,000. Despite the lack of commercial developments (as the community is a purely residential area) Pill Hill offers much in the way of quality housing and a pleasant place to live.

Getting Around

Pill Hill is pretty easy to get around using your own two feet; there are sidewalks everywhere and, honestly, it’s not very big. Now this may be a fine way to head over to the neighbor’s for a weekend barbeque, but our guess is, you’d probably need a bit of help getting to work everyday. Luckily, transportation out and about is fast and convenient, especially thanks to Chicago’s stellar public transit system (the CTA).

The CTA has buses running all over Chicago, and Pill Hill is no exception. Grabbing one of the buses that run through the neighborhood can take you anywhere you want to go within city limits (though you’ll probably have to make a couple transfers). Say you’re trying to get to work in downtown. We recommend a particularly scenic route. First grab the #95E bus off of 93rd Street. Transfer at Commercial Avenue to the #6 bus, which runs along Lake Shore Drive up to the Loop. This gives you a great view of both the lake and an up-close look at the buildings that make up Chicago’s famed skyline.

If bus transfers seem a bit tricky to you, driving in and out of Pill Hill is a perfectly viable alternative to public transport. About six blocks east of the neighborhood sits the Chicago Skyway (I-90), which runs right into Chicago’s busy city center. This provides a quick and easy route into the heart of downtown by car, so it’s a great way to deal with your work commute. And owning a vehicle in Pill Hill is rather secure and hassle-free thanks to the majority of homes having garages, which allows you to keep your car off the streets at night.

School’s in Session

Though Pill Hill only has a single school within its tight boundaries, the surrounding area offers a number of education options. In addition to the following Pill Hill public elementary, you can find more information on Chicago area schools at our Chicago Guide Schools page.

Joseph Warren Elementary School 9239 S Jeffery Ave - (773) 535-6625

Basic Needs

We’ve assembled a handful of places in the Pill Hill neighborhood to fulfill your basic needs, from food to fill the fridge to books to fill your head.

Chicago Transit Authority - (888) 968-7282


Jeffery Manor Branch 2401 E 100th St - (312) 747-6479

Post Office

9308 S South Chicago Ave (800) ASK-USPS

Emergency Rooms

University of Chicago Comer Children’s Hospital (Hyde Park) - 5721 S Maryland Ave - (773) 702-6249

Sometimes it makes more sense to view the city of Chicago as a bunch of separate neighborhoods—especially when it comes to real estate. Whether you are in the market for a loft, condo, townhome, or house, it is just as important to inspect the surrounding area as it is to inspect the home’s foundation. Pill Hill neighborhood is just one Chicago community with an abundance of residential properties, and a life all its own. From where you send your kids to school to where you dine at night, the information we provide is an essential piece of the puzzle when you’re trying to decide whether or not to buy that beautiful loft or adorable house in Pill Hill.