4000-4006 N. Sheridan Road and 1002-1016 W. Irving Park Road, c.1915, Uptown. A three-story red brick apartment block wrapping the corner above a continuous white terra cotta storefront, longtime home of the Holiday Club. Demolished August 2026. Photo credit: Google MapsTHREATENED: Demolition Looms for Ornate Terra Cotta Holiday Club Building (Chicago 7 2023); Preservation ChicagoFull Permit Issued For 91 Units At 4006 North Sheridan, But Demolitions Still Pending, Daniel Schell, Chicago YIMBY, 8/16/26
3619 N. Magnolia Avenue, 1906, Lake View. A greystone two-flat, the second of two adjacent greystones lost on this block within six months. Demolished August 2026. Photo credit: Daniel Schell / Chicago YIMBYLake View Greystone Next To Demolished Greystone Will Be Demolished, Daniel Schell, Chicago YIMBY, 7/13/261910 Wrigleyville Greystone To Be Demolished, Replaced With Two Dwelling Units, Daniel Schell, Chicago YIMBY, 3/2/26
909 W. Webster Avenue, c.1888, Lincoln Park. A three-story rusticated brownstone with raised English basement, arched third-floor window and a wood entry porch with turned columns. Demolished August 2026. Photo credit: Peter Fynmere
2121 W. Cortland Street, c.1890, Bucktown. A brick residence with a steep front gable and decorative bargeboard, two-story canted bay and contrasting stone banding. Demolished August 2026. Photo credit: Google Maps
1736 W. Farragut Avenue, c.1910, Andersonville. A buff brick two-flat with a projecting three-sided bay, bracketed metal cornice and a full-width porch with ornamental ironwork. Demolished August 2026. Photo credit: Redfin
1113 W. Drummond Place, c.1890, Lincoln Park. A two-story brick two-flat with a projecting bay, bracketed cornice, stone lintels and a wood entry porch with turned posts. Demolished August 2026. Photo credit: Google Maps
2438 N. Burling Street, c.1890, Lincoln Park. A two-story rock-faced limestone residence with an arched art glass window, stone stoop and projecting wood entry portico. Demolished August 2026. Photo credit: Redfin
32 W. 111th Street, c.1915, Roseland. A two-story brick two-flat with a corbelled and stepped parapet, projecting bay, stone accent panels and a carved stone entry hood. Demolished August 2026. Photo credit: Google Maps
4143 W. 21st Street, c.1900, North Lawndale. A two-story brick two-flat with a projecting three-sided bay, pressed metal cornice and pedimented parapet. City-owned. Emergency demolition, August 2026. Photo credit: Google Maps
5749 S. Laflin Street, c.1900, Back of the Yards. A two-story buff brick two-flat with a projecting three-sided bay, corbelled brick cornice and a wood entry porch. City-owned. Emergency demolition, August 2026. Photo credit: Google Maps
634 W. Aldine Avenue, c.1910, Lake View. A two-story red brick residence with a bracketed and dentiled porch cornice, brick porch piers and a raised entry. Demolished August 2026. Photo credit: Google Maps
4019 W. Monroe Street, c.1900, West Garfield Park. A two-story frame two-flat with clapboard siding, a full-height projecting bay, an octagonal attic window and a metal entry canopy. Demolished August 2026. Photo credit: Google Maps
1308 W. Nelson Street, c.1890, Lake View. A frame gable-front cottage with fish-scale shingles in the gable, a pedimented entry hood on turned brackets and a boxed bay window. Demolished August 2026. Photo credit: Google Maps
10627 S. May Street, c.1925, Washington Heights. A brick cottage with a steep hipped roof, corbelled brick chimney and a raised entry. Emergency demolition, August 2026. Photo credit: Google Maps