In this episode of OpenHouse Chicago, Cortney Hall guides us through a dynamic and elevated look at adaptive reuse in the city’s most iconic neighborhoods and begins a home tour journey that celebrates the intersection of preservation, design, and contemporary living.
We begin 550 feet above the Loop, in the Gothic Revival crown of the Pittsfield Building, located at 55 E Washington Street. Once the tallest building in Chicago and home to the world’s largest collection of medical offices, this 1927 architectural treasure is being transformed into upscale residential apartments by developer Tom Roszak, known online as @SkyscraperGuy. With sweeping views of the skyline and painstaking attention to its historic detailing, the project embodies adaptive reuse at its highest level—both literally and figuratively. Roszak’s vision preserves the building’s soul while reimagining its purpose in a post-office era.
Next, Cortney joins top-producing real estate broker Carrie McCormick and mortgage expert Ben Cohen in the heart of Wicker Park, at 1849 N Hermitage Ave, #301, where a former 1905 convent has been converted into a modern three-bedroom, two-bathroom residence spanning approximately 1,829 square feet. Located just across from St. Mary of the Angels Church, the property juxtaposes its ecclesiastical roots with fresh, modern interiors curated by PS Lehman Staging. With soaring ceilings, curated tiles, and a charming terrace that's accessible from both the hallway and primary suite, this home offers sanctuary in every sense of the word.
In the third and final stop, Cortney visits Laura Tribbett, owner and principal designer of Outline Interiors, in her personal home: a converted bicycle factory penthouse in the Fulton Market District. What was once an industrial workspace is now a tailored family residence with city views as its central artwork. Laura, who designed the space herself, offers a masterclass in layering function, personality, and bold design. Her kitchen, wrapped in navy cabinetry and topped with Calcutta quartzite, seamlessly connects to an open living and dining area accented with a Mitzi light fixture hung thoughtfully to preserve skyline views. Custom French doors by Wayward Machine Co. enclose a guest lounge wrapped in kid-friendly shibori-inspired vinyl wallpaper, blending durability with refined taste.
Laura also shares thoughtful and practical design insights throughout the tour, offering recommendations on how to balance bold choices with livable luxury. One of her key tips is to create an open concept layout while still delineating functional zones—she achieves this by anchoring her living space with a large broadloom area rug, defining it as a casual lounge and gathering area. She emphasizes the importance of not obstructing a breathtaking skyline view, opting for a minimalist chandelier hung slightly higher than usual to preserve the openness. She also infuses personality into her personal space with rich blue cabinetry, brass hardware, and a striking Calacatta quartzite countertop — unique pairings she chose with confidence, showing that bold design can still feel timeless. Durability is central to her approach as a parent, seen in her choice of easy-to-clean, whimsical dining chairs and a vinyl wall covering with a shibori-style print in the guest lounge. Moreover, she cleverly converted what was once open space into a glass-enclosed guest room with custom French doors fabricated by Wayward Machine Co., highlighting how intentional architecture can enhance both function and style.
Throughout the episode, Ben Cohen offers insight into navigating home purchases while simultaneously selling your existing property, which proves to be a frequent challenge in Chicago’s competitive housing market. From the importance of getting pre-approved to the logistics of same-day closings, Ben and Carrie share actionable advice to help prospective buyers stay one step ahead. Additionally, Chicago Title and Trust’s Greg Kenner and Dell from Land Trust Company provide critical homeowner tips. This time, they address issues of privacy, asset protection, and estate planning, reminding viewers that a land trust is not just for celebrities or high-net-worth individuals, but for anyone seeking peace of mind.
Overall, this episode of Open House: Chicago is a celebration of transformation—of spaces, of uses, of lifestyles. From repurposed skyscrapers to reimagined sanctuaries and refined lofts, OpenHouse Chicago shows us that the city’s most inspiring homes often come with a past as rich as their present.
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