Prepare your Chicagoland home for winter with this fall maintenance checklist. Roof, gutters, windows, doors, and siding inspection guide.
Illinois winters are brutal on homes. Spending an afternoon on fall maintenance can prevent expensive repairs and emergency situations. Here's your checklist.
Roof
- Look for missing, curling, or damaged shingles from summer storms
- Check flashing around chimneys, vents, and valleys for gaps or rust
- Look for granule accumulation in gutters (sign of aging shingles)
- Schedule a professional roof inspection if your roof is 15+ years old — our inspections are free
Gutters
- Clean all gutters and downspouts of leaves and debris
- Check for sagging sections, loose hangers, and leaking seams
- Verify downspouts direct water at least 4 feet away from the foundation
- Consider gutter guards if you're tired of cleaning every fall — gutter guard comparison →
Windows
- Check weatherstripping around all windows — replace if cracked or compressed
- Test all windows for smooth operation and proper locking
- Look for fog between panes — seal failure means replacement is needed
- Check caulk around exterior window frames — re-caulk any gaps
Doors
- Check weatherstripping on all exterior doors
- Test door operation — sticking or gaps indicate problems that worsen in cold weather
- Verify deadbolts and locks engage smoothly
Siding
- Walk the perimeter and look for cracks, loose panels, or gaps
- Check caulk around all penetrations (vents, faucets, outlets)
- Look for signs of moisture damage or mold near the foundation line
Found issues? Call (331) 250-3726 for a free assessment before winter arrives.
A ten-minute walk around the house
Twice a year, walk the outside slowly. Look up at the roof edges for lifted shingles and sagging gutters. Look at the siding for cracks, gaps and soft spots near the ground. Check caulk around windows and doors. Look down at the foundation for soil that has settled toward the house and downspouts that have come loose. Photograph anything that has changed since last time. Small problems caught in a walk-around are cheap; the same problems found by a leak are not.
What to schedule early
Exterior contractors book up before each season. Windows and doors are built to order and take weeks to arrive, and roofing calendars fill after every storm. If you want work finished before winter, start the estimates in late summer; for spring work, start in winter. Planning ahead also gives you time to compare products instead of taking whatever is available.
Where exterior money goes furthest
For how a house looks from the street, the front door, garage door and siding color do the most. For comfort, windows and air sealing. For protecting the building, roof, gutters and flashing. For resale, national cost-versus-value surveys consistently put entry doors, siding and windows near the top for the share of cost recovered. A good plan fixes anything leaking first, then spends on what you will see and feel every day.
Plan the whole house, then phase it
Even if you will do one project a year, decide the end result first: roof color, siding color, trim and window finish. Then each phase fits the next and nothing has to be redone. Tell your contractor the full plan. We keep measurements, product lines and colors on file so that the windows installed next year match the ones installed this year.
Common questions
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