Windward Roofing & Construction
About Windward Roofing & Construction
Established in 1984, Windward Roofing & Construction is a family-owned business providing commercial roofing solutions across Illinois, Wisconsin, Michigan, Indiana, and Florida. They specialize in various commercial roofing systems, including TPO, EPDM, metal roofing, and more. Our roofing crews install and repair asphalt shingles, metal roofing, tile, flat roof systems, and commercial roofing. We handle storm damage assessment, insurance claim assistance, gutter installation, fascia and soffit repair, and attic ventilation. Every roof we install comes with a manufacturer warranty plus our own workmanship warranty. We provide free drone-assisted roof inspections so you can see the condition of your roof from the ground without anyone climbing up. Serving Chicago and the greater Chicagoland area. Licensed Illinois contractor. We understand the extreme temperature swings from subzero winters to hot summers that challenge every home system in the Midwest.
13 years in business
Services
Roof Inspection
FeaturedComprehensive roof inspection with photo documentation. Identifies leaks, damage, and remaining lifespan.
Starting at $500 / visit
Roof Repair
FeaturedPatch leaks, replace damaged shingles, fix flashing, and seal penetrations. Emergency repairs available.
Starting at $400 / per repair
Full Roof Replacement
Complete tear-off and replacement with new underlayment, shingles/tile, flashing, and ridge vents. Includes permits.
Starting at $6950 / per roof
Gutter Installation
Seamless aluminum gutter installation with downspouts and leaf guards. Custom color matching.
Starting at $1150 / per home
Storm Damage Assessment
Insurance-ready storm damage assessment with detailed report. Help with insurance claim filing.
Starting at $500 / visit
Location
919 S Sacramento Blvd, Chicago, IL 60612
Chicago, IL 60601
Typical Roofing Costs in Chicago
$5,000–$15,000
Costs vary based on project scope, materials, and complexity. Get a free quote from Windward Roofing & Construction to compare pricing in Chicago.
Hours of Operation
Services Offered
Roof Inspection
Comprehensive roof inspection with photo documentation. Identifies leaks, damage, and remaining lifespan.
$500
starting at
Roof Repair
Patch leaks, replace damaged shingles, fix flashing, and seal penetrations. Emergency repairs available.
$400
starting at
Full Roof Replacement
Complete tear-off and replacement with new underlayment, shingles/tile, flashing, and ridge vents. Includes permits.
$6,950
starting at
Gutter Installation
Seamless aluminum gutter installation with downspouts and leaf guards. Custom color matching.
$1,150
starting at
Storm Damage Assessment
Insurance-ready storm damage assessment with detailed report. Help with insurance claim filing.
$500
starting at
Reviews
4.8
10 reviews
10 reviews
Connie M.
Commercial flat roof replacement on our warehouse. They worked around our operating hours and the install was clean and professional. Trusted commercial roofing service. (Chicago)
Response from Windward Roofing & Construction
Thank you for trusting us with your roof! We stand behind our work 100%.
Brenda F.
Added two skylights to our living room during a roof replacement. Natural light is incredible now. Clean install with no leaks. Quality roofing and skylight work. (Chicago)
Response from Windward Roofing & Construction
Thank you so much for the kind words! We take pride in our work and it means a lot when customers notice.
Frank T.
Several cracked tiles replaced without damaging surrounding tiles. Not easy work but they made it look effortless. Specialists in tile roofing repair. (Chicago)
Response from Windward Roofing & Construction
Thank you for trusting us with your roof! We stand behind our work 100%.
Ashley W.
Got a full reroof - tear off old shingles and new architectural shingles. Crew of 5 guys knocked it out in 2 days. They were on the roof by 7am both days. Clean job, hauled everything away.
5 people found this helpful
Response from Windward Roofing & Construction
What a wonderful review! We are honored to have earned your loyalty and look forward to serving you for years to come.
Connie M.
Commercial flat roof replacement on our warehouse. They worked around our operating hours and the install was clean and professional. Trusted commercial roofing service. (Chicago)
Response from Windward Roofing & Construction
We really appreciate you taking the time to leave this review. Your satisfaction is our top priority!
Natasha B.
A friend recommended Windward Roofing & Construction after I had a bad experience with another company. Night and day difference. These guys actually care about doing a good job.
8 people found this helpful
Victor S.
Complete tear-off and new shingle roof installed in two days. Crew was professional, cleaned up everything, and the new roof looks fantastic. Best roofing service near me. (Chicago)
Response from Windward Roofing & Construction
Thank you so much for the kind words! We take pride in our work and it means a lot when customers notice.
Connie M.
Commercial flat roof replacement on our warehouse. They worked around our operating hours and the install was clean and professional. Trusted commercial roofing service. (Chicago)
Response from Windward Roofing & Construction
What a wonderful review! We are honored to have earned your loyalty and look forward to serving you for years to come.
Oscar U.
Restored our cedar shake roof instead of replacing it. Cleaned, treated, and replaced damaged shakes. Looks brand new. Specialist roofing craftsmanship. (Chicago)
Response from Windward Roofing & Construction
Thank you for trusting us with your roof! We stand behind our work 100%.
Glenn E.
Other roofer said we needed full replacement. These guys came out and said repairs would be sufficient for another 5 years. Honest roofing company that does not upsell. (Chicago)
Response from Windward Roofing & Construction
Thanks for choosing us! We will keep working to earn that fifth star.
Service Area
Serves Chicago and surrounding areas
Frequently Asked Questions
Last updated April 2026
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