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Pill Hill

The south side bedroom community of Pill Hill was once a prime living destination for a number of Chicago doctors and healthcare industry professionals. We have the nearby South Chicago Hospital to thank for that. As M.D.’s began trickling in to this subdivision of Calumet Heights, the area was quickly tagged with its witty name – Pill Hill. Over the years, the population of Pill Hill has shifted and now the neighborhood is home to many middle-class workers and business professionals.

Lots of attractive characteristics have drawn homeowners to Pill Hill – rows of houses sit on well-manicured lawns, spacious properties and leafy trees adorn the blocks, and intricate landscaping and impeccable maintenance provide a sense of community caring that is hard to find in the typical big city neighborhoods. Most homes here have something else you’ll be hard-pressed to find in the thick of Chicago; built-in garages (usually for one car) and private yards. Like a mini suburban oasis, Pill Hill residents are accustomed to having their very own yard to grow a garden, host a barbeque or let the kids play in a protected comfort. And that garage provides handy extra storage space.

What you won’t find in Pill Hill is a ton of commercial businesses. The tiny eight-block wide neighborhood has a sparse strip of quick bite restaurants on 95th Street (the southern border of Pill Hill), but that’s about it. When in need of a little retail therapy or more dining selection, there are plenty of shops and restaurants located in the area’s surrounding neighborhoods. The way Pill Hill residents see it – the lack of commercial development is just another subdued element that makes the neighborhood a safe and secure spot to raise a family in the city.

Because it is so small, there are a finite number of properties for sale in Pill Hill. So, you’ve got to be lucky to score a home in this petite pocket of residential real estate. The architectural styles here vary widely from bungalows to townhomes to ranches, with a few condominiums dotting the blocks. Non-conforming houses are a large part of Pill Hill’s charm. Frame houses with front porches sit next door to redbrick bungalows and mid-century split-levels. To match its diverse housing market, the neighborhood offers a widespread pricing scale where a two- or three-bedroom detached house can run anywhere from $75,000 to $280,000.