Standing twenty-three stories above the intersection of Milwaukee, North, and Damen Avenues — the crossroads Chicagoans simply call the six corners — a terra-cotta-clad Art Deco tower built in 1929 by Perkins, Chatten & Hammond gives The Robey its entire architectural argument. The building's stepped crown, visible for blocks across Wicker Park's low-rise grid, was designed as an office tower and spent decades as such before its 2016 conversion into a 69-room hotel under the direction of développeur firm Grupo Habita, whose sensibility runs to adaptive reuse with a spare, design-forward hand. The interiors honor the building's geometry without retreating into period pastiche. Rooms are fitted with low-slung platform beds in dark-stained oak, marble-topped nightstands cantilevered from lacquered red steel brackets, and frosted glass partition walls — details visible in the images that draw a clear line to the Bauhaus tradition rather than 1920s Deco ornament. Marcel Breuer's Cesca chair appears at corner tables where black-trimmed casement windows frame rooftop views over the neighborhood's Victorian two-flats. Downstairs, the all-day restaurant deploys deep crimson leather banquettes against herringbone oak floors and pendant Edison fixtures suspended from a graphite ceiling — industrial warmth calibrated to the neighborhood rather than the Loop. The rooftop pool deck, modest in scale, turns the building's height into its main amenity, the Chicago skyline and the steeples of Wicker Park's older churches visible in every direction.

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