Chicagoland winters present a unique set of challenges to hardy Midwesterners. Whether it’s snow, ice, freezing temperatures or even Thundersnow - remember that crazy winter? - Midwest winters can be tough on your home's exterior. We want to provide our best advice on how to prepare your home for Chicago winter, ensuring that your home is safe and warm this winter, and the time to start preparing is NOW!
We encourage homeowners to look for missing, curling or damaged shingles, flashing problems, and signs of previous leaks. Chicago’s freeze/thaw cycles; snow and ice can turn relatively minor roof vulnerabilities into water problems.
Clean gutters and downspouts will move melting snow and rain away from your home, ensuring that water will not seep into your basement or damage your interior foundation walls. Check for clogged gutters, loose sections, leaks, and downspouts that are not directing water far enough from the foundation. If you’re not currently using some kind of leaf guard protection, it’s something you might want to consider. They keep debris out of your drainage system, allowing rain and snow melt to flow freely into the downspouts. Additionally, the leaves, pine needles and debris being kept out of your gutters, means less of your time devoted to cleaning your gutters.
Walk completely around your home's exterior. Look for cracked, loose, warped or damaged siding, deteriorated caulk and openings around penetrations. Siding isn’t just about curb appeal; it’s part of your home’s protective envelope. Whether your home is covered with fiber cement or vinyl siding, they each provide a protective, insulated layer keeping the cold outside, where it belongs.
We suggest using the Candle Test. Turn off all fans, air conditioners, and heaters to keep the room air still. Light a candle, and slowly move it along the edges, corners, and frame of the window. If the flame flickers and dances, you have found an air leak. Check for drafts, deteriorating seals, and any condensation between the windowpanes, windows that don’t close or lock properly and visibly damaged frames. If you find drafts or identify any of the problems identified above, it might be time to think about window replacements. Modern windows can improve comfort and energy performance. In addition, many are Energy Star Certified, meeting the most stringent standards, keeping your home comfortable year-round.
Check your weatherstripping, caulk, and the seal around your entry doors. These are the various materials used around the inside of your door frame, to block air, rain, snow, dust, insects, and street noise. Together they should stop heated or cooled air from escaping your home, lowering your energy costs. If you can see daylight or feel air moving around your closed door, it’s definitely worth addressing.
This is something homeowners often overlook. Look for peeling paint, rot, gaps, animal damage and moisture staining. Soffits and fascia protect your home’s roof structure, improve attic ventilation and support your gutter system.
Wood decks should be inspected for loose boards, deteriorating wood and failed finishes, which is the protective coating (usually a poly stain) that has broken down, peeled off, or stopped repelling water.
Composite decks require less seasonal maintenance, but homeowners should still clear debris and inspect railings, stairs and fasteners.
After a heavy rainfall, walk around your property and notice where the water goes. Look for pooling near the foundation, overflowing gutters, poor downspout placement and any drainage towards your house rather than away from it. Water, whether from rain or melting snow, can cause serious structural damage to your foundation and the potential for mold inside your walls.
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A little preventive attention this fall can make a big difference when Chicagoland winter weather arrives. If you discover aging siding, drafty windows, roofing concerns or other exterior issues during your inspection, now is the time to address them – before freezing temperatures, snow and ice make small problems bigger for you.
Not sure where to start? Cobblestone Exteriors can help you evaluate your home’s exterior and identify areas that may need attention. From siding, windows and doors, to roofing, gutters and more, our experienced team can help you prepare your home for the season ahead.

We work with the very best manufacturers of Exterior products, from James Hardie fiber cement siding, ProVia & Mastic insulated vinyl siding, Marvin, Pella and ProVia windows, TimberTech and Zuri composite & PVC decking, ThermaTru, Marvin and ProVia doors, GAF, Ownes Corning, Certainteed and Alsco roofing.
With over 35 years successfully transforming the Exterior of our customer’s homes, we bring experience, quality craftsmanship and products, and we are proud of our A+ Rating from the Better Business Bureau.