Cobbler Square Lofts | Loft Apartments in Old Town, Chicago
The Original Loft Living Made Modern
Located in the heart of Old Town, the renovated Cobbler Square Lofts blends historic charm with fresh, modern living. JDL Development is restoring and modernizing each classic Chicago-style loft to their design standard, adding sleek stainless-steel finishes and wide plank hardwood floors to the historic character of exposed brick and timber.
Find Your Home
With inviting amenity spaces and JDL’s signature commitment to service, Cobbler Square Lofts offers a stylish, boutique, and chic place to live. Learn more about the renovated finishes or discover the perfect floorplan for your lifestyle.
A Century of Character
Cobbler Square’s rich history adds to its charm. Built in 1880 as the headquarters for Dr. Scholl’s Manufacturing Company, the space originally spanned nearly 30 interconnected buildings. In 1985, the site was transformed into one of the first major examples of classic Chicago loft living. Today, JDL is breathing new life into the space, blending its historic character with fresh, elevated design.
An Oasis in Old Town
Cobbler Square is a calm escape from the city’s hustle. From the lush central courtyard to the relaxed rooftop deck, each space is designed for quiet moments and everyday ease. Experience the JDL lifestyle that brings a sophisticated approach to living, with an unwavering focus on quality and detail at each property.
Neighborhood
Welcome to Old Town — Chicago’s charming neighborhood on the near North Side. From relaxed, friendly corner pubs to elevated fine dining, there’s a little bit of everything just steps away from your front door.
