Chicago's freeze-thaw cycle is hard on exterior paint. Water gets into small cracks, freezes, expands, and pushes the paint film away from the surface. By spring, a job that looked fine in October is peeling.
Good exterior paint starts with washing. Dirt, mildew, and road salt keep paint from bonding, so we power wash siding and trim before anything else and let it dry fully.
Next comes repair: scraping loose paint, replacing rotted wood, filling cracks, and repairing stucco. Bare wood gets primed. This step takes the most time and is the one most often skipped.
Timing matters too. Paint needs the right temperature range to cure, which in Chicago means planning exterior work from late spring through early fall. Paint applied in the right conditions over a properly prepped surface will hold its true color for years.