Roofing in Chicago, IL
Roofing in Chicago, IL from Pro House Maintenance starts with a free, fixed-price estimate from a licensed, insured local crew. Typical Roofing projects run $8,000–$22,000 per project. We handle the work end to end, keep the job site clean, and don't consider it done until you're satisfied.
Serving Lincoln Park, Wicker Park, Hyde Park, Andersonville and nearby Illinois communities.
Matched with a vetted roofing specialist in Chicago, IL.
Every roofing job goes to a licensed, insured, background-checked professional from our own crews or hand-vetted local network, never a random subcontractor.
- Licensed & insured, background-checked pros
- Free, fixed-price written estimate before work begins
- Top-rated local specialists matched to your job
Roofing statistics: what the data says
Current industry and government data on roofing, with every figure linked to its source. These national benchmarks help Chicago homeowners judge a fair roofing quote before hiring a pro.
- A new asphalt shingle roof averages about $15,439 for a 2,000-square-foot home, ranging from roughly $6,885 to $23,993 (This Old House).
- Asphalt shingles last 20 to 30 years, metal 40 to 70 years, and slate 75 to 200 years (This Old House).
- Over 47% of homeowners who replaced a roof chose asphalt shingles, more than any other material, in a 2026 survey of 1,000 homeowners (This Old House).
- About one in 35 insured homes files a wind or hail claim each year, the most common homeowners claim (Insurance Information Institute).
From Lincoln Park, Wicker Park and Hyde Park to the rest of Chicago, Pro House Maintenance connects the area's roughly 2,696,555 residents with vetted roofing pros. The work is licensed and insured, priced up front at a typical $8,000–$22,000 per project, and backed by a free written estimate before anything starts.
What does roofing include in Chicago?
A roofing project in Chicago typically covers 6 core areas, starting with full tear-off of existing shingles and underlayment. Pro House Maintenance handles the full scope with a licensed, insured local crew and a free, fixed-price written estimate before any work begins.
- Full tear-off of existing shingles and underlayment
- Decking inspection and replacement of damaged boards
- Ice-and-water shield in valleys and eave zones
- Synthetic underlayment across the full roof deck
- Architectural shingle installation
- Ridge cap, flashing, and proper ventilation
How does roofing work in Chicago?
Roofing in Chicago follows 4 clear steps, from free inspection and estimate to a final walkthrough. A vetted local pro manages the schedule, keeps the site clean, and does not consider the job done until you are satisfied.
Free inspection and estimate
We inspect your roof from the deck up, document any decking damage or ventilation issues, and provide a written estimate the same day.
Material ordering and scheduling
You choose shingle color and style; we order materials, schedule the crew, and handle any HOA or permit requirements.
Tear-off and deck prep
Old roofing is stripped, debris is contained and removed daily, and all damaged decking is replaced before new materials go down.
Install and inspect
New roofing system is installed to manufacturer spec, and we do a final debris sweep with magnets for loose nails around the property.
How much does Roofing cost in Chicago?
Roofing in Chicago typically runs $8,000–$22,000 per project, based on scope and materials. Pro House Maintenance gives every Chicago homeowner a free, fixed-price written quote before any work begins.
| Detail | What to expect |
|---|---|
| Typical cost | $8,000–$22,000 per project |
| Estimate | Free, fixed-price written quote |
| Crews | Licensed & insured, vetted local pros |
| Service area | Chicago, Illinois and nearby communities |
Roofing in Chicago: questions answered.
How much does roofing cost in Chicago?
In Chicago, roofing typically runs based on scope and materials. Pro House Maintenance gives every Chicago homeowner a free, fixed-price written quote before any work begins, so there are no surprises.
How do I know if I need a full replacement or just a repair?
Roofs under 15 years old with isolated damage are often good candidates for repair. Roofs over 20 years old, with granule loss or multiple failing areas, typically need full replacement. We assess honestly and never push a replacement when a repair makes financial sense.
Will you work with my homeowner's insurance for storm damage?
Yes. We document storm damage thoroughly with photos and measurements, provide a written scope-of-loss report, and can meet your insurance adjuster on-site to walk through the findings together. Insurance claim work is a significant part of our business and we understand how to document legitimate damage correctly so your claim accurately reflects the full scope of repairs needed.
What homeowners say about roofing.
"Full tear-off and new architectural shingles in two days, with the yard cleaned of every nail."
"Fair quote, no upsell games, and the new roof has held through two major storms. Exactly what we hoped for."
"The crew tarped everything overnight when weather rolled in. Careful and professional."
Other services in Chicago
Attic Finishing
Transform wasted attic space into a bedroom, office, or bonus room.
Basement Renovation
Turn an unfinished basement into living space you'll actually use.
Bathroom Remodeling
Spa-worthy bathrooms built on time and within budget.
Cabinet Installation
Custom, semi-custom, and stock cabinets installed level, plumb, and built to last.
Concrete and Masonry
Foundations, flatwork, steps, and walls built to carry loads for generations.
Deck Building
Custom decks designed and built to complement your outdoor living space.
Door Installation
New interior and exterior doors installed plumb, level, and properly weathersealed.
Roofing in nearby cities
Key takeaways
- Roofing in Chicago from Pro House Maintenance starts with a free, fixed-price estimate and no obligation.
- Typical roofing projects in Chicago, IL run $8,000–$22,000 per project.
- All crews are licensed, insured, and vetted local professionals.
- All crews are licensed and insured.
- Financing is available for qualified homeowners.
- Pro House Maintenance serves Chicago, Illinois and surrounding communities.