Chicago bungalows were built tough, but they were built for a different climate. A few hours of winter prep in October can save you hundreds in heating bills and prevent the kind of damage (ice dams, burst pipes, drafty doors) that turns into a spring-time emergency call.
Start at the top: clear the gutters, especially the back ones that overlook the alley. A clogged gutter in November becomes an ice dam in January, and ice dams are how water ends up inside your plaster ceilings.
Walk every exterior door and check the weatherstripping. If you can see daylight at the threshold or feel a draft with the back of your hand, a $30 sweep and a $15 strip of foam will stop it. We can install both in under an hour.
Inside, look for hairline cracks where the wall meets the ceiling. Bungalows shift slightly with each freeze-thaw cycle, and small cracks invite cold air. A bead of paintable caulk seals it for a season.