• Winnetka’s Trusted Roofing Experts

Premier Roofing Contractor in
Winnetka, IL

Expert roof repair, replacement & storm restoration for Cook County’s North Shore. Serving Hubbard Woods, Indian Hill & all Winnetka neighborhoods with pride.

★★★★★5.0 Google Rating
IL Licensed #104.019069

Free Inspections Roofing · Siding · Gutters

GAF CertifiedFactory-Certified Installer

BBB A+ RatedBetter Business Bureau

Owens CorningPreferred Contractor

AngiSuper Service Award
Google5.0 ★ Rating
Our Services

Winnetka Roofing & Exterior Services

From emergency roof repairs to full exterior remodels, we deliver North Shore-quality craftsmanship on every project.

Roof Replacement

Complete asphalt shingle, cedar shake & slate roof replacement for Winnetka’s historic and modern homes. We handle all Village permits.

Roof Repair

Fast, reliable roof repair for leaks, missing shingles, and storm damage. Emergency services available for North Shore homeowners.

Storm Restoration

Hail damage & wind damage specialists. We work directly with your insurance company to maximize your claim coverage.

Siding Installation

Premium James Hardie fiber cement & treated wood siding built to withstand Lake Michigan’s humidity and Illinois freeze-thaw cycles.

Gutter Replacement

Seamless gutter systems with leaf guards to protect your Winnetka home from heavy Illinois rainfall and ice dam formation.

Cedar Shake Maintenance

Specialized preservation and maintenance for Winnetka’s many cedar shake roofs. Protect your investment with expert care.

Completed roof replacement




500+ Roofs

Protected in Winnetka

The Face Behind the Brand

Meet Roman—Your Neighbor, Your Roofer

At Roman Roofing, we aren’t a faceless corporation with a distant call center. We’re your neighbors. I started this company because Winnetka families deserved a roofer who understands the unique character of North Shore homes—from the historic estates of Hubbard Woods to the classic colonials along Indian Hill.

When you work with us, you’re getting a crew I’ve personally vetted and trained to treat your roof like it’s their own. Whether we’re working near the Elm Street shops or along Green Bay Trail, our team is dedicated to honest advice and high-quality craftsmanship. You’ll get the personal touch of a local business with the collective expertise of a crew that genuinely loves what they do.


IL Licensed

Fully Insured

Family Owned

Transparent Pricing

How Much Does Roof Repair Cost in Winnetka?


2026 Average Cost
$350 – $2,000
This is what most roof repair Winnetka IL homeowners typically pay. Winnetka’s larger homes and premium materials can push costs above the Chicago metro average.

For larger projects, a full roof replacement in Winnetka IL may be more cost-effective. We provide a detailed report during every roof inspection for hail damage in Winnetka to help you decide if a repair or replacement is right for you.

Minor Repairs

$350 – $750

Replacing damaged shingles or fixing a small leak around a vent or skylight.

Moderate Repairs

$750 – $2,000

Repairing valley flashing, addressing wind damage, or resealing chimney masonry on North Shore homes.

Full Re-Roof Replacement

$9,500 – $23,000

Complete tear-off and new roof installation with premium architectural shingles, new underlayment, and full warranty coverage.

Pro Tip from Roman:

“After a hailstorm, always get an inspection before filing a claim. Winnetka’s larger roofs often have hidden damage from Lake Michigan wind patterns. What looks like minor damage is sometimes more extensive—and catching it early saves you thousands down the road.”

Why Choose Us

Why Winnetka Trusts Our Team

Your North Shore home deserves a roofing contractor that understands the area’s unique architecture, weather challenges & building codes.

Winnetka Local

We know Cook County codes, Village permits & the Landmarks Commission process inside out.

Fully Licensed & Insured

IL License #104.019069 & #105.009446. Bonded and insured for your complete peace of mind.

5-Star Rated

Consistently rated 5 stars by Winnetka homeowners on Google, Angi & the BBB.

24/7 Emergency Service

Storm damage doesn’t wait. Our emergency crews are available around the clock for North Shore homes.

Family Owned

A family-run business that treats every Winnetka home like our own. No corporate shortcuts.

Insurance Claim Experts

We navigate the insurance process for you, maximizing coverage on storm & hail damage claims.

Areas We Serve

Serving Every Winnetka Neighborhood

From Hubbard Woods to Indian Hill, we’re the local roofers Winnetka, IL homeowners call first. Cook County proud.

Hubbard Woods

Historic district homes with cedar shake & slate roofs needing expert preservation.

Indian Hill

Large estate properties requiring premium roofing materials and custom solutions.

Elm Street District

Mixed residential & commercial properties near the vibrant shopping corridor.

West Winnetka

Family homes with aging asphalt shingle roofs ready for quality replacements.

East Winnetka

Lakefront-adjacent homes exposed to Lake Michigan winds and moisture.

Green Bay Trail Area

Charming bungalows and colonials along the historic trail corridor.

FAQ

Frequently Asked Questions

Everything Winnetka homeowners need to know about roofing & exterior services.

 

Yes. The Village of Winnetka requires a building permit for all roof replacements. If your home is in a designated Historic District or is an “Architecturally Significant” property, you may also need approval from the Winnetka Landmarks Commission. We handle all permit filings with the Village Hall on Green Bay Road to ensure your project meets local code.
In the North Shore, “freeze-thaw” cycles can cause cheaper vinyl siding to crack and wood siding to rot due to moisture trapped behind ice dams. We recommend James Hardie Fiber Cement or treated wood siding for Winnetka homes to withstand Lake Michigan’s humidity and extreme temperature swings.
Most residential roof replacements in Winnetka are completed in 1-3 days, depending on the size and complexity of your home. Historic homes with cedar shake or slate roofs may take longer due to specialized materials and techniques required.
Absolutely. As Winnetka storm restoration contractors, we work directly with all major insurance providers. We document hail and wind damage thoroughly, meet with your adjuster on-site, and ensure you receive fair coverage for your claim.
For Winnetka’s climate and architectural styles, we recommend GAF Timberline HDZ or Owens Corning Duration asphalt shingles for most homes. For historic properties, we specialize in cedar shake restoration and natural slate repair to maintain your home’s character.
Yes, we are fully licensed, bonded, and insured to perform roofing and exterior work throughout Cook County, including all Village of Winnetka requirements. We carry $2M in general liability coverage and full workers’ compensation insurance.

GET IN TOUCH

Request Your Free Consultation

Ready to protect your home with premium roofing and siding? Fill out the form and our team will contact you within 24 hours to schedule your free assessment.

Email

romanroofingil@gmail.com

Website

RomanRoofingIL.com


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    Ready to Protect Your Winnetka Home?

    From Yorktown to Lilacia Park, Roman Roofing IL is the roofing company Lombard families trust. Get your free roof inspection today—no obligation, just honest answers about your roof’s condition.

    Mon–Fri 7AM–6PM | Sat 8AM–2PM
    Serving Winnetka & the North Shore since 2005