I lived in Cobbler Square Lofts for three years and thoroughly enjoyed my time here. The building has unmatched character in its common spaces and in the units themselves. Friends and family were always impressed with the charm of the building. Front desk staff were always kind, friendly, and helpful. Maintenance team was responsive to issues and able to fix problems quickly. Common spaces were well maintained. There’s a great sunroof with communal grills, a fire pit, and great views of the north side.

There are, of course, some downsides to the building. The walls and floors are quite thin, so you’ll hear any loud music or conversations in your neighbors’ units. I rarely experienced “disruptive” noise from neighbors – more just general awareness of TVs, music, or phone calls. External brick walls can be a bit drafty, so I usually requested maintenance each fall/spring to seal up gaps in mortar.

Overall, I definitely recommend living here. It’s a great location and a unique building. Get yourself a unit with a view of the internal courtyards and you should find it very comfortable.

– Sean McNelis

My Cobbler Square Loft Experience Revue:

Since first setting out on a vast apartment search in late July 2024, the building at Cobbler Square Lofts was relatively unassuming to me. I walked around the building once upon an initial visit to Old Town, nor suspected I would be living here a few weeks after that point in time.

From the initial property management tours with both Alyssa DeSimone and Alisa Kadic to a very easy move in process, my overall experience with the people, residents and newly renovated loft space life has been quite enjoyable! While the blunt Chicago real estate sticker shock of all overall property costs did raise my eyebrows and debt load all at once, I've found this comes with the territory of all large metropolitan areas (LA, NYC, CLE, even hipster city.. Madison, Wisconsin).

The historical charm of Old Town and the unique architecture of the former Dr. Scholl's building (via the original bike factory this property originally was built for in the late 1800's) is what really what ultimately sold me. I love history. The westward facing, bright apartment I presently occupy in the G building is great and connects to inner city charms such as the changing trees (Fall colors) outside, to the passing elevated train that is right out of the 1990 'Dick Tracy' film by Warren Beatty.

Neighbors are for the most part friendly and easy to connect with. The maintenance and security staffers are also friendly, helpful and often strike up fun conversations in passing. It's a welcoming space for a brief moment in time.

I moved here specifically due to the proximity to The Second City and Zanies comedy clubs as I am in the process of planning and producing a live sketch comedy show called "The Weather Crew ™" for the Summer of 2025. The ease of walking to SC, area grocery stores, restaurants, book shops and close proximity to Lake Michigan for beach walks or jogs cannot be topped.

Between the 18 individual apartments I looked at in the West Loop, Gold Coast and Old Town in a two week span in early August 2024; from sky rises, vintage buildings to luxury lofts, the historical Cobbler Square Lofts remains by far my favorite. Sure there are areas to improve upon, and it would be fantastic to have the original meditative water fountains restored in the main courtyard per the 1985 Chicago Tribune articles on the original building renovation, but one thing at a time! 🙂

Thank you for providing this property, services and for the friendly connections made in the short time living here!

Feel free to share my thoughts and viewpoints with your management team!

All the best,

Blake Naftel

– Blake Naftel

Today I had a maintenance emergency in my unit. The maintenance crew was not available but Nick C. (Leasing agent and Service Ambassador) went above and beyond and came to the rescue. Thank you Nick and this is a good example of empathy and teamwork.

– Sandra George