Our Services
Full-service roofing contractor in Flanagan — from asphalt shingle roof replacement and emergency hail damage repair to metal roofing, flat roof systems, and gutter installation. Every project is installed by manufacturer-certified crews with workmanship warranties.
Trusted by homeowners and businesses across Flanagan.
We get on the roof, take photos, and give you an honest assessment. If you don't need work, we'll tell you. No charge, no obligation, no high-pressure sales pitch.
We've been roofing Flanagan homes since before half these companies had a website. 12 years means we know the local codes, the weather patterns, and the materials that hold up here.
Storm damage? We work with your insurance company directly. Free inspection, Xactimate documentation, adjuster meeting on-site. We fight for full replacement when your roof qualifies.
Fully licensed, bonded, and insured in Illinois. We carry $2M in general liability. Workers' comp on every crew member. Your property is protected if anything goes sideways.
Simple Process
Our inspector walks the roof looking at shingle condition, flashing integrity, vent function, and signs of moisture underneath. 30-45 minutes for most Flanagan homes.
We email or text the proposal so you can review it at home. Questions? Call us. No pressure, no expiration date tricks, no "today-only" pricing.
Dumpster arrives at 7 AM. Tarps on the landscaping. Tear-off starts immediately. New ice and water shield, underlayment, drip edge, shingles, ridge vent. All in sequence.
Before we leave: magnetic nail sweep across the entire yard, driveway, and walkways. Dump trailer hauled off. Gutters cleaned out. Your property looks better than when we arrived.
Verified Reviews
"Couldn't believe how clean the job site was when they left. Three passes with the magnet, swept the driveway, cleaned the gutters out. My wife said the yard looked better than before they showed up."
"Got three quotes for a roof replacement. Flanagan Roofing & Maintenance was the middle price but the only one who actually got on the roof and showed me photos. Everyone else just eyeballed it from the driveway."
"The crew showed up at 7:30 and was done by 4. Old roof off, new one on, yard cleaned up. I watched from the window. These guys don't mess around."
Meet the Owner
Owner & Lead Contractor
Jason has been serving Flanagan for over 12 years, building a reputation on honest work, fair pricing, and crews that treat every home like their own. What started as a one-truck operation has grown into a full-service Roofing company — but the values haven't changed.
"We don't cut corners. Every job gets the same attention to detail whether it's a small repair or a complete replacement. That's how you earn 348+ five-star reviews."
