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Rated 4.9★ across 56 reviews, Henry & Sons Roof Repair is a top-tier roofing contractor serving the greater Chicago area. Focused on siding and gutters. One reviewer writes: "I am really pleased with the roofing job from Henry & Sons Roof Repair." The craftsmanship draws repeat praise from homeowners across the board. Tristan keeps homeowners updated without them having to chase for answers. Clients appreciate that timelines and budgets are respected, not estimates. Clients note the team cleans up thoroughly, leaving the home better than they found it. Based on reviewer data, typical projects fall in the $12,000 range. Familiar with the complexities of pre-war and mid-century Chicago homes.
Roofing projects typically cost $5K – $25K in Chicagoland
Diamond Garza
3 reviews
Chicago
No recurring concerns found across reviews. This contractor maintains a consistently positive reputation.
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“The whole process was smooth and professional, and I would definitely recommend this roofing company to anyone in Chicago looking for quality service.”
“I am really pleased with the roofing job from Henry & Sons Roof Repair.”
I am really pleased with the roofing job from Henry & Sons Roof Repair. On a hot day, the crew worked for hours without much shade to replace my entire roof in just one day. Tristan and the team were respectful, worked efficiently, and made sure everything was cleaned up nicely when they finished. I especially appreciated that even though they usually use Owens Corning materials, I wanted GAF shingles and they made it work for me at a great price. They made this big project feel easy and stress-free. I would definitely recommend them and would hire them again for any future roofing needs.
Colin Riggs
Jan 2026
“After searching for a trustworthy and dependable roofing company in Chicago for a couple of months,...”
After searching for a trustworthy and dependable roofing company in Chicago for a couple of months, I finally found Henry & Sons Roof Repair. Clinton was extremely honest, friendly, and knowledgeable from the start. He took the time to carefully inspect our 19-year-old home's original roof, both from the outside and in the attic, for a small fee. While other roofing companies only wanted to replace the whole roof for around $12,000, Clinton provided a detailed explanation and offered a much more affordable solution to repair the leak in our son's bedroom. The repair cost was just $685, and he assured us our roof would last another 7 to 10 years with this fix. It’s been several years since the repair, and our roof is still in great shape with no leaks or issues, even after some tough Chicago weather. We were so happy with the work that we recently had Clinton replace all our windows, and that was also done perfectly. I highly recommend their services for anyone needing honest, skilled roof repairs in the area. (And yes, Megan still jokes about wanting her coffee mug back!)
makenzie hardy
Jan 2026
“After looking into different roofing companies, I decided to hire Henry & Sons Roof Repair to take...”
After looking into different roofing companies, I decided to hire Henry & Sons Roof Repair to take care of two roofs on my commercial flat-roofed building, along with some brick repointing and stucco repairs. The roofs had been ignored for quite some time and needed all the old layers completely removed. The job turned out to be much bigger than expected, but Donovan stuck to the original price we agreed on and covered the extra costs himself, which really impressed me. Donovan was great to work with—always on time, honest, and very knowledgeable about roofing. The price was fair for the high quality of work provided, and there were no surprise charges along the way. The crew was flexible and made the whole process smooth and stress-free. I highly recommend their team if you need roof resurfacing, repairs, stucco work, or brick repointing. The finished roof looks fantastic, and now I have one less thing to worry about.
Roman W
Jan 2026
“After a big storm in Chicago, I was away from home dealing with a family emergency when a tree fell...”
After a big storm in Chicago, I was away from home dealing with a family emergency when a tree fell and damaged a large section of our roof. I called the roofing company early that morning, feeling really stressed. Clinton and the team quickly got to work, handling everything from helping me with the insurance claims to making sure my out-of-pocket costs stayed low. At first, I was unsure about having the repairs start while I was away, but they kept me updated every step of the way. The crew was fast and the quality of their roofing work exceeded what I was hoping for. Everyone I spoke with showed real care and concern for my situation, which meant a lot during such a tough time. This company is more than just a group of roofers—they really went above and beyond to help my family. I will definitely reach out to them again for any roofing or home repair needs in the future.
Bennett Choi
Jan 2026
“After a heavy storm in Chicago, the entire east side of my roof was damaged.”
After a heavy storm in Chicago, the entire east side of my roof was damaged. I reached out to a local roofing company early the next morning, not expecting a quick response. To my surprise, Jordan from their team arrived the very next day with a fair estimate and immediately put tarps on my roof to prevent any more damage. Even before my electricity was restored, the crew was already getting to work. I decided to upgrade to a metal roof, and was thrilled with how fast and smoothly everything went. My new roof was finished before many of my neighbors had even started the process. I was so happy with the results that I recommended this roofing company to everyone in my neighborhood—many of them ended up using their services as well! The whole experience, from the first estimate to the final payment, was handled with professionalism and care. If you need a roofer in Chicago, definitely give them a call—you won’t be disappointed!
Carson Walls
Jan 2026
“I highly recommend this roofing company.”
I highly recommend this roofing company! I recently had them install a new slate roof with copper accents, architectural shingles, and copper gutters on my home in Chicago. From start to finish, the entire team went above and beyond to deliver top-notch craftsmanship and outstanding customer service. The attention to detail on the copper work was truly impressive—it showed a level of skill I haven’t seen before. By the end of the project, they felt like family, and I trusted them completely. If you’re looking for reliable roofers in Chicago, you won’t find a better team!
Patrick Francis
Dec 2025
“Outstanding, trustworthy, and friendly roofing service is still out there.”
Outstanding, trustworthy, and friendly roofing service is still out there! I was pretty worried when I realized I needed roof repairs and wasn’t sure who I could rely on. As soon as I reached out to a local roofing company, my worries disappeared. Even though their team was away for training, I left a message expecting a long wait, but to my surprise, I got a call back the same day. The person on the phone was very friendly and quickly scheduled someone to come check out my roof within a week. I also received an email confirming my appointment and the scheduled time, which was reassuring. On the day of the inspection, Clinton from the roofing team arrived right on schedule. He took a thorough look at my roof, then explained all my repair options in a clear and honest way. Within just a couple of days, I received two detailed quotes by email, so I could easily compare my choices. Not only was their quote more affordable than another company’s, but it also included a warranty that lasted twice as long. I appreciated that they didn’t require any payment up front, which made me feel secure about the process. When I had a few follow-up questions about the quote, the woman who answered the phone was polite and tried to help right away. She quickly connected me to Clinton, who answered everything I needed to know. I always felt respected, and my questions were never brushed off. Since it was late in the season and the weather was getting colder, the team made sure to start work the very next day after I agreed to the repairs. They finished the whole roofing job in just two days and always arrived when promised. The crew was careful with my property and cleaned up thoroughly after themselves. I highly recommend this roofing company to anyone in need of reliable roof repairs or replacement!
robyn jennings
Nov 2025
“We are absolutely thrilled with our new roof.”
We are absolutely thrilled with our new roof! Our old roof was badly in need of repairs, so we decided to reach out after hearing about this roofing company on the radio. They got back to us right away and set up an appointment for a quote within the same week. The team was very flexible and worked around our busy work schedules. Their representative, Jordan, was extremely friendly and even showed up a little early, which was a nice surprise. Jordan made everything simple and stress-free from the start. When it came time to schedule the installation, Clinton was super helpful and easy to coordinate with. The roofers did an outstanding job—our property was even cleaner when they finished than before they started. The work was completed quickly and efficiently. We also decided to get covered gutters this time, and they made sure they were installed perfectly, unlike the previous ones we had. Now, every time I come home, I’m so happy to see our beautiful new roof and gutters. The whole process was smooth and professional, and I would definitely recommend this roofing company to anyone in Chicago looking for quality service.
Diamond Garza
Nov 2025
“I don’t usually leave reviews, but after working with Henry & Sons Roof Repair, I felt I needed to share my experience.”
I don’t usually leave reviews, but after working with Henry & Sons Roof Repair, I felt I needed to share my experience. From the start, I had a lot of questions about different roofing materials and options, and Donovan took the time to answer everything clearly. Their team really knows their stuff when it comes to roofing. The crew worked hard, put in long hours, and made sure my yard and property stayed protected throughout the job. Every day, they cleaned up the area before leaving, and were always patient with my questions. After the roof was finished, the follow-up and customer service were excellent. My new roof looks fantastic, and I feel confident it’ll stand up to Illinois weather. I highly recommend them to anyone looking for a reliable, high-quality roofer.
E Hurst
Nov 2025
“henry & sons roof repair did an outstanding job for us.”
henry & sons roof repair did an outstanding job for us! our first project with them involved fixing the original clay tile roof on an old house we were renovating. clinton went the extra mile to find just the right materials that not only matched the existing roof but also held up perfectly. the repairs look amazing! they also took care of the gutters and downspouts, and now our basement stays dry even after heavy rain—something we never thought possible in such an old home. clinton later replaced the roof on our front porch. we had tried a metal roof before, but it was much too noisy under the oak tree with all the acorns falling. now, our porch has a great-looking, solid roof that’s quiet and sturdy. the crew worked nonstop and their dedication was clear—they really put in the effort from start to finish. we’re so happy with their work that we’ve already asked for another estimate for the back porch roof, and we know exactly who we’ll call when it’s time for a full roof replacement in the future. highly recommend!
M Beard
Nov 2025
“We recently hired a local roofing company for both small repairs and a full roof replacement, and...”
We recently hired a local roofing company for both small repairs and a full roof replacement, and the experience was excellent from start to finish. I found them after reading many positive online reviews when our old roof, which really needed replacing, developed a leak. Jordan, the owner, was very understanding and quickly sent a team to investigate and repair the leak. This gave us time to plan the full roof replacement at our own pace, waiting for the best weather. Jordan was extremely thorough during the proposal phase. He brought different shingle samples—he works exclusively with top-quality brands—and explained all the options. He also took the time to talk about how to improve our attic ventilation and described all the layers that would be included in the new roofing system, like deck protection, leak barriers, starter strips, and ridge cap shingles. Jordan even provided a detailed list of roofs the company had completed in the area and took us to see some of their finished work. There was never any pressure to add extra services. When we decided not to replace our gutters and downspouts right away, Jordan respected our decision. Later, after our gutter specialist explained the benefits of doing both at once, Jordan kindly confirmed that it was a good idea but never pushed us. Jordan handled all the necessary permits and displayed them properly, so everything was up to code. The crew was punctual, arriving in the morning and finishing up in the evening each day. The whole process went smoothly and was surprisingly odor-free. At the end of the job, there was only a tiny bit of debris left—just a couple of nails and a water bottle—which was impressive considering the scale of the work. They were very careful with our property. Whenever I needed to talk to someone, whether it was Clinton, the foreman, or Frederick, one of the certified installers, they were always polite and helpful. Jordan also answered his phone personally whenever I had questions. The price was what you’d expect for a hassle-free experience, a long manufacturer’s warranty, a strong workmanship guarantee, and a beautiful new roof that really improved our home. I highly recommend this company for anyone needing roofing services.
Annabelle Cobb
Nov 2025
“One of the roofers, Jacob, came out to inspect our roof after we noticed a leak in one of our closets.”
One of the roofers, Jacob, came out to inspect our roof after we noticed a leak in one of our closets. He quickly found the source of the problem and explained exactly what needed to be fixed. Jacob also gave us helpful suggestions on how to prevent similar leaks in other parts of the house. He let us know that the rest of the roof is still in good shape and should last us quite a few more years. Communication with both the office staff and Jacob was excellent throughout the process. We’re very pleased with the repair work and the roofing crew. When it’s time for a full roof replacement, we’ll definitely call them again.
ann swanson
Oct 2025
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