10 Questions to Ask a Roofer Before You Sign the Contract

Why These Questions Matter

A roofing contract is a big commitment — typically $10,000 to $30,000 for a full replacement. Yet most homeowners in Chicago, Hinsdale, Oak Brook, and the surrounding suburbs sign contracts after asking just one or two basic questions. These 10 questions will protect you from hidden fees, shoddy work, and contractors who disappear after cashing your check.

1 "Are you licensed, bonded, and insured?"

This is non-negotiable. Ask to see their certificate of insurance — not just hear them say yes. You need both general liability and workers' compensation. If an uninsured worker gets hurt on your property, you could be liable.

2 "Can I see your certificate of insurance?"

Saying "yes we're insured" is different from showing you proof. A legitimate contractor will email you their certificate within minutes. If they stall or make excuses, walk away.

3 "Who is actually doing the work — your crew or subcontractors?"

Many roofing companies are just sales operations — they sell the job and then subcontract it to the cheapest crew available. You want a company whose own crew does the work. That's how quality and accountability are maintained.

4 "What exactly is included in this price?"

Get specifics: How many layers are being torn off? What brand and type of shingles? Is ice and water shield included in valleys and eaves? What about starter strip, ridge vent, pipe boots, flashing? Is cleanup and haul-away included? The more detail, the less room for surprise charges.

5 "What happens if you find damage to the decking?"

Rotted plywood under old shingles is common in Chicago homes. A good contractor will tell you upfront: "We charge $X per sheet of plywood if replacement is needed, and we'll show you the damage before proceeding." A bad contractor either hides this cost or surprises you mid-job.

6 "What's your warranty — both workmanship and materials?"

There are two warranties: manufacturer (covers the shingles) and workmanship (covers the installation). Ask how long each lasts, what's covered, and what would void them. A contractor who stands behind their work will give you clear, specific answers.

7 "Will you pull the building permit?"

Most Chicago suburbs require a permit for roof replacement. The contractor should handle this — not you. If they suggest skipping the permit, that's a red flag. Unpermitted work can cause problems when you sell your home.

8 "What's your payment schedule?"

A reasonable structure is a small deposit (10-30%) with the balance due upon completion. Never pay 100% upfront. Never pay cash without a receipt. And never pay the final balance until you've done a walkthrough of the completed work.

9 "Can you provide references from jobs in my area?"

Ask for 2-3 references from recent jobs in your suburb. A contractor with a strong reputation in Hinsdale, Elmhurst, or Oak Brook will happily connect you with past clients. Also check their Google reviews — look for specific, detailed reviews rather than generic ones.

10 "Do you handle insurance claims?"

If your roof has storm damage, the right contractor will inspect for free, document the damage, meet with your insurance adjuster, and manage the claims process. This is a major differentiator — some contractors just hand you an estimate and leave you to fight with insurance alone.

How GSKI Answers These Questions

We're licensed, bonded, and insured — certificates available on request. Our own crews do the work. We provide detailed written estimates with no hidden fees. We pull all permits. We warranty every job for the life of the roof. And we manage the full insurance claims process for storm damage. Serving Chicago, Hinsdale, Oak Brook, Elmhurst, Highland Park, Park Ridge, Wilmette, Glencoe, Northbrook, and Oak Park.