12 questions to ask before you hire a roof replacement contractor in Chicago

1. Are you properly licensed in Illinois?

   Preferred answer: Yes — and we can show you our license number right now.

2. Will you take care of permits?

   Preferred answer: Yes — we handle the permit and it is included in the price.

3. Do you have liability insurance and workers' compensation?

   Preferred answer: Yes — here is our certificate of insurance.

4. Do you handle insurance claims, and will you help prepare documents for the insurance company?

   Preferred answer: Yes — we document everything before work begins.

5. Will your representative attend the meeting with the insurance adjuster?

   Preferred answer: Yes — at no extra charge.

6. Do you offer a warranty on labor and a separate warranty on materials?

   Preferred answer: Yes — minimum 5 years on labor in writing, plus manufacturer warranty on materials.

7. If it rains or wind picks up off the lake while my roof is open — what is your protocol?

   Preferred answer: We have tarps on site and a clear plan for any weather emergency.

8. Does the estimate include debris removal, tear-off, and nail cleanup?

   Preferred answer: Yes — including magnetic nail sweep of the entire property.

9. Do you guarantee the final cost will not exceed the estimate?

   Preferred answer: Yes — fixed price. Any changes require your written approval.

10. Do you offer a free on-site inspection before the estimate?

    Preferred answer: Yes — we inspect the roof, attic, and flashing at no charge before any commitment.

11. Is your crew local to Chicago — or do you bring in out-of-state teams?

    Preferred answer: We are a local Chicago company. Our crew lives and works here year-round.

12. Other questions you want to ask the contractor.

Want to understand why these questions matter and what to do when a contractor answers poorly? Read our full expert guide with preferred answers, red flags, and action steps for each question.