Building file · Old Town
A whole Old Town block that built bicycles, then shoes — Western Wheel Works, then Dr. Scholl's — converted in 1985 into one of Chicago's defining early loft communities. One important note: these lofts are rentals, not condos.
In the 1890s Western Wheel Works was one of the largest bicycle makers in the world, and this was its factory. When the bicycle boom ended, the complex found its second industry: Dr. Scholl's made its foot-care products here for decades, until the plant closed in 1981.
The conversion came fast — completed in 1985 by a venture led by Sam Zell, it became one of the buildings that taught Chicago what a loft community could be: a maze of brick wings, timber interiors and interior courtyards filling most of a city block on Wells Street.
Cobbler Square is an apartment community of roughly 292 lofts — it is not a condominium, so you rent here rather than buy. For loft hunters that makes it two things: the easiest way in Chicago to live the Old Town loft life before committing to a purchase, and a reminder to read listings carefully — “Cobbler Square” on a search result is a lease, not a deed.
We track the buildings, not just the listings. If Cobbler Square is on your list — or you want the honest comparison against its neighbors — ask.
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