"A gutted mid-century office tower reborn as Uptown apartments — great bones, loft-style feel, and a rooftop pool that earns its keep."
Ratings Breakdown
Upper Level's exclusive rating for Chicago winter survivability — indoor parking, pedway access, CTA proximity, and wind exposure.
The Rundown
The Draper is a 12-story, 354-unit apartment building at 5050 N Broadway in Uptown — the result of a complete gut renovation of a 1964 mid-century office building that once served as the headquarters of Combined Insurance Company (later Aon). Booth Hansen led the renovation, completed in 2019, preserving the building's distinctive floor-to-ceiling glass curtain wall while adding a rooftop pool, fitness center, and all-season lounge.
The loft-style layouts are a genuine differentiator: high ceilings, large windows, and open floor plans that feel more like converted lofts than typical apartment units. The Argyle Red Line stop is literally steps from the front door, making this one of the best-connected buildings in Uptown for transit riders. The Asia on Argyle dining district — one of Chicago's most vibrant ethnic dining corridors — is right outside.
The trade-offs: converted office floor plates mean some units have awkward proportions and limited natural light. Online ratings are low (1.4/5 on Apartments.com), with most complaints focused on management responsiveness. Studios are very small (356–400 sq ft). The building is managed by Greystar.
Who Lives Here
Transit-dependent young professionals, Uptown locals who want new construction amenities without downtown prices, and renters attracted by the building's distinctive mid-century aesthetic. The Asia on Argyle location draws residents who are serious about food.
The Neighborhood
The Draper sits at the corner of Broadway and Argyle — the heart of the Asia on Argyle district, one of Chicago's most vibrant ethnic dining corridors. Vietnamese, Thai, and Chinese restaurants are literally steps from the front door. The Argyle Red Line stop is steps away. Uptown's entertainment district (Aragon Ballroom, Riviera Theatre) is walkable. Montrose Beach is a 15-minute walk.
What You Get
Elevator Experience
Upper Level Intel
Former Aon Headquarters
The building was originally the headquarters of Combined Insurance Company, which later became Aon. The mid-century modern bones are why Booth Hansen's renovation works — the floor plates and window lines were designed for offices, which is why some units feel oddly proportioned.
Ask for Upper Floors
Upper floor units get significantly better views and more natural light. The building is only 12 stories but the surrounding Uptown streetscape is low-rise, so even the 8th floor gives you decent sightlines.
Argyle Red Line Is Steps Away
The Argyle Red Line stop is literally steps from the front door. You're 20 minutes from the Loop and 35 minutes from O'Hare. For transit-dependent residents, this is a genuine win.
Low Online Ratings
The building has a 1.4/5 rating on Apartments.com from 7 reviews, with most complaints focused on management responsiveness. Greystar manages the property — verify current management quality before signing.
Rooftop Pool Is Seasonal
The rooftop pool is outdoor and closes in winter. The all-season rooftop lounge with kitchenette is the winter substitute — it's a decent space but not the same as the pool terrace.
The Good & The Not-So-Good
Wins
- ✓Argyle Red Line is literally steps from the front door
- ✓Rooftop pool and terrace with grills and fire pits
- ✓Loft-style layouts with high ceilings and large windows
- ✓Asia on Argyle dining district right outside
- ✓All-season rooftop lounge with kitchenette
- ✓In-unit washer/dryer
Watch Out
- ✗Low online ratings (1.4/5 on Apartments.com) — management complaints
- ✗Converted office floor plates — some units have awkward layouts
- ✗Studios are very small (356–400 sq ft)
- ✗Some units have limited natural light
- ✗Uptown still has safety concerns on some blocks
The Verdict
The Draper is a solid mid-tier Uptown rental with a genuinely interesting backstory (former Aon HQ) and a good amenity package for the price. The loft-style layouts and high ceilings are a real differentiator from cookie-cutter new construction. The location — Argyle Red Line steps away, Asia on Argyle dining right outside — is excellent for transit-dependent residents. The main risks are management quality (low online ratings) and the inherent awkwardness of converted office floor plates. For renters who want a distinctive building with good transit access and don't need the newest finishes, The Draper is worth a look.
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