Roof replacement cost and verified contractors in Chicago

This site helps Chicago homeowners:
- Understand the cost of roof replacement today
- Ask the contractor the right questions
- Compare offers from different companies
- Call prepared and get a fair price
Start with the cost calculator to understand the price of your roof.
The calculator is built without asking for your phone or email, so you are not exposed to unwanted calls.
Get your roof replacement cost
in 30 seconds
Free calculator. No signup, no obligation
Roof replacement cost calculatorNo phone • No email • No pressure
Why Chicago homeowners use this calculator
- Free to use
- No phone or email required
- Instant result in 30 seconds
- Real price breakdown: materials, permit, disposal
- Adjusted to your ZIP code and season
- Compare prices for different roof options
Then review the 12 questions worth asking a contractor. Call prepared, to compare offers and choose the best one
12 helpful questions for your call
- Are you properly licensed in Illinois?
- Will you take care of permits?
- Do you handle insurance claims?
See all 12 questions →Hide questions ↑
12 helpful questions for your call
- Are you properly licensed in Illinois?
- Will you take care of permits?
- Do you handle insurance claims?
Are you properly licensed in Illinois?
Preferred answer: Yes — and we can show you our license number right now.
Will you take care of permits?
Preferred answer: Yes — we handle the permit and it is included in the price.
Do you have liability insurance and workers' compensation?
Preferred answer: Yes — here is our certificate of insurance.
Do you handle insurance claims, and will you help prepare documents for the insurance company?
Preferred answer: Yes — we document everything before work begins.
Will your representative attend the meeting with the insurance adjuster?
Preferred answer: Yes — at no extra charge.
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.
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.
Does the estimate include debris removal, tear-off, and nail cleanup?
Preferred answer: Yes — including magnetic nail sweep of the entire property.
Do you guarantee the final cost will not exceed the estimate?
Preferred answer: Yes — fixed price. Any changes require your written approval.
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.
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.
Other questions you want to ask the contractor.
Now you are ready for the call. Remember, the consultation is absolutely free and comes with no obligation
Average project cost and timeline in Chicago today
This resource was created to help you choose the most convenient and reliable option for your roof replacement

Every contractor on our list holds an active Illinois roofing license. We check IDFPR records before any company makes the list.

Chicago has specific permit rules, climate demands, and flat roof requirements. We only include contractors who know this market.

Storm damage and insurance claims are common in Chicago. We prioritize contractors with documented experience navigating this process.

Roof replacement is a major investment. Our resource exists to inform, not to pressure. Call when you are ready.
Independent editorial resource. Companies do not pay for placement. Calls may be connected through a paid call service. Full disclosure →
We evaluate each contractor on active Illinois IDFPR license, Google rating and review volume, BBB accreditation, years in business, workmanship warranty length, and documented experience with Chicago building permits and insurance claims. Only companies that meet all criteria appear on our list.
Prices depend on roof size, pitch, and material. Here are typical ranges for Chicago homes in 2026.
All estimates include labor, materials, permits, and disposal. Full cost breakdown →
Storm damage, hail, wind, and fallen tree limbs. If a weather event caused the damage, your homeowner policy likely covers full replacement.
Normal wear, aging, and maintenance neglect. Insurance covers damage from events — not the natural end of a roof's life.
Illinois homeowners have 12 to 24 months from the storm date to file a hail damage claim. Document everything immediately after the storm.
Get a written contractor assessment before calling your insurer. Request that your contractor be present during the adjuster visit.
Not sure where to start?
One call connects you with a roofing advisor who can answer your questions about cost, materials, permits, and insurance. Free, no commitment
CALL NOW (844) 578-0719No obligation. Real answers. 7 days a week
Answers based on current Chicago market data, city permit requirements, and Illinois insurance regulations.