Furnace or boiler service by October, gutter cleaning after leaf-drop, exterior faucet shutoff and hose-bib draining, weatherstripping, and a roof scan before snow hides everything. Chicago punishes late fall procrastination specifically.
Ice dams form where attic heat leaks — watch eaves after snows, and fix the insulation cause, not just the symptom. Keep walks clear (liability is real), watch for frozen-pipe signs in exterior walls, and never let a vacant unit's heat fail silently.
Freeze-thaw writes its report every spring: masonry cracks, spalled brick, lifted flat-roof seams, foundation seepage in April rains. Walk the building top to bottom, then book tuckpointing and sealing while contractors still have calendar.
Porch repairs (the city cares), exterior painting, AC service, and any concrete work. Chicago's building trades compress into the warm months — schedule early.
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