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Pill Hill
Real Estate and Neighborhood Information

Pill Hill Overview

Pill Hill is a part of Calumet Heights.

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.

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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.

Pill Hill History

Located 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.

Dream Town Knows Pill Hill

As Chicago neighborhood experts, Dream Town has successfully sold properties in Pill Hill. Dream Town holds a well-earned reputation for its impressive sales volume and dedication to personal, attentive service. Benefit from the Dream Town advantage when selling your Pill Hill home. Utilizing state-of-the-art technology, Dream Town drives more sales than any other Chicago brokerage.

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The Sights of Pill Hill

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Schools In The Pill Hill Area

See grade levels, address, and scores for schools in the Pill Hill area.

School Type Grade Rating

Avalon Park Elementary School

8045 South Kenwood Ave - public

Preschool - Middle PK-8

Mann Elementary School

8050 South Chappel Ave - public

Preschool - Middle PK-8

Our Lady Of Guadalupe School

9050 South Burley Avenue - private

Elementary - Middle K-8

Sacred Heart School

2926 East 96th Street - private

Elementary - Middle K-8

Ami Kids Infinity Chicago

10211 South Crandon Avenue - private

High 9-12

Banner Academy South High School

2330 East 99th Street - private

High 9-12

Black Magnet Elementary School

9101 South Euclid Ave - public

Elementary - Middle K-8

Burnham Elementary Inclusive Academy

9928 South Crandon Ave - public

Preschool - Middle PK-8

Hoyne Elementary School

8905 South Crandon Ave - public

Elementary - Middle K-8

Mireles Elementary Academy

9000 South Exchange Avenue - public

Preschool - Middle PK-8

Shabazz International Chrtr Schls

7823 South Ellis Ave - charter

Elementary - High K-12

Sanders Academy of Excellence

115 15th S Prairie Ave - private

Preschool - Middle PK-8

Immaculate Conception School - Exchange

8739 South Exchange Avenue - private

Elementary - Middle K-8

Epic Academy High School

8255 South Houston Ave - charter

High 9-12

Butler College Prep

821 E. 103rd St. - charter

High 9

A Place Of Hope Christian Ministries

2434 East 87th Street - private

Preschool - Elementary PK-3


2647 East 88th Street - private

Elementary - High n/a

John Amos George College Preparatory

8736 South Blackstone Avenue - private

Preschool - High PK-12

Greater Pleasant Valley College Preparatory

910 East 83rd Street - private

Preschool - High PK-12

Caldwell Elementary Academy Of Math & Sci

8546 South Cregier Ave - public

Preschool - Middle PK-8

School data provided by GreatSchools.School service boundaries are intended to be used as reference only. To verify enrollment eligibility for a property, contact the school directly. GreatSchools Ratings provided by GreatSchools.org.

Surrounding Neighborhoods

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