Vintage Chicago windows take a beating from condensation and lake-effect humidity. Here's how to repaint interior sills, casings, and sashes so they look sharp and still open.
Window casings and sills sit right at eye level and catch the daylight, so chipped, yellowed, or peeling paint stands out the moment a prospective tenant walks into a unit. In Chicago's vintage housing stock — the greystones of Lincoln Park, the brick two-flats of Logan Square, the courtyard buildings of Rogers Park — original wood windows are often close to a century old and have been painted a dozen times over. Landlords tend to spend their repaint budget on walls and ceilings and leave the trim alone, but tired window woodwork quietly drags down an otherwise clean unit. A crisp coat on the casing, stool, and apron makes a room read as cared-for, and it photographs far better for online listings. If you're turning a unit between tenants, the windows deserve a spot on the punch list.
Few surfaces in a Chicago apartment take more abuse than interior window trim. In winter, warm indoor air hits cold single-pane or aging double-pane glass and condenses, and that moisture runs straight down onto the wood sill. Over a few seasons it lifts the paint, swells the wood, and breeds mildew in the corners. Summers bring the opposite problem: lake-effect humidity off Lake Michigan keeps everything damp, so paint that never fully cured stays soft and prints. Buildings in Lakeview and Edgewater that sit close to the lake see this the most. Add decades of sun bleaching the south-facing sashes and you get the classic Chicago vintage-window look: yellowed, alligatored, and peeling at the nose of the sill. Knowing where the damage comes from tells you where to prep the hardest.
Any building put up before 1978, which covers most of the vintage stock in Wicker Park, Andersonville, and Old Town, likely has lead paint somewhere in the window layers. Window trim and sashes are the highest-risk spots because the friction of opening and closing creates fine lead dust. Dry-scraping or power-sanding that paint is both restricted under EPA RRP rules for paid work and genuinely hazardous, so prep has to be done wet and contained. Start by washing the trim with a degreaser to cut condensation grime, then wet-sand glossy areas to dull them. Scrape only the loose, flaking paint while misting with water, and bag the debris as you go. Fill gouges and old fastener holes with a hard wood filler, caulk the gap where the casing meets the wall, and prime any bare wood with a stain-blocking primer before the topcoat.
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