Neighborhoods · Central
Why people love it
Taylor Street, one of the few Chicago restaurant corridors that never had to reinvent itself.
What's drawing people
UIC and the medical district next door, which means tenant demand that does not follow the office market.
The value
The part of the Near West Side whose purchase prices never fully joined the West Loop run.
What people say about Little Italy
Little Italy is where I look on the Near West Side when someone wants a building rather than an address. The stock is older, the prices are lower, and the tenants are already there.
Taylor Street runs through the middle of it, and unlike a lot of Chicago restaurant corridors it never had to reinvent itself. The residential blocks around it hold a genuine supply of older two-flats and three-flats, plus rowhouses and some newer infill on lots cleared during the UIC expansion decades ago.
The university and the Illinois Medical District sit immediately west and south. That is the important part for an owner: tenant demand here comes from students, residents, nurses and hospital staff, and none of that follows the downtown office market. When the Loop has a bad year, this rental base does not.
Two to four unit buildings across the Near West Side ran a median near $681,000 in 2025. Little Italy generally sits below that community-area figure, because the West Loop pulls the average up.
Rents are the Near West Side numbers: $3,950 for a two-bedroom, $5,300 for a three-bedroom, both roughly flat over the year. Flat rents are a warning in the West Loop, where purchase prices assume growth. They are much less of a problem here, where you are buying at a lower basis to begin with.
The caution: a lot of this stock is old, and old buildings near a university have often been rented hard for decades. Budget for the systems, not just the finishes. That is true anywhere but it is especially true on these blocks.
Last updated August 2026.
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