Cobbler Square Lofts | Renovated 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.
Frequently Asked Questions
Learn more about life at Cobbler Square Lofts
Cobbler Square Lofts is a renovated historic loft-style apartment community in Chicago’s Old Town, known for timber ceilings, exposed brick, and large courtyard living with modern renovations.
Cobbler Square Lofts stands out for its true loft character—timber beams, brick accents, and unique layouts — combined with large private courtyards, a pool and hot tub (coming Summer 2026), and a central Old Town location.
Cobbler Square Lofts is located at 1350 N Wells Street in the Old Town neighborhood of Chicago, just north of downtown and within walking distance of Lincoln Park and North Avenue Beach.
Cobbler Square Lofts offers studios, studio lofts, convertibles, one-bedroom, and two-bedroom apartments, with layouts designed to maximize space and natural light.
Amenities include two large interior courtyards, a swimming pool and hot tub (Coming Summer 2026), rooftop terrace, fitness center, co-working spaces, lounge and game areas, and a dedicated dog run.
Yes! Cobbler Square Lofts is pet-friendly and includes a dog run along with access to pet services such as grooming, walking, and boarding.
Cobbler Square Lofts is within walking distance of the Sedgwick Brown and Purple Line station (about 5 minutes) and the Clark/Division Red Line station (about 8 minutes), along with multiple CTA bus routes.
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.
