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Heritage Contractors has a loyal client base as a roofing contractor serving the greater Chicago area, carrying 112+ reviews at 5.0★. Focused on siding and gutters. One reviewer writes: "My husband, I recently moved into our first home, and were put in touch with Charlie at Heritage Contractors." Clients describe the work as "workmanship was exceptional". John gets consistent marks for keeping things organized and on track. Clients appreciate that timelines and budgets are respected, not estimates. They consistently leave the job site clean — a point of pride for the team. Value for money comes up repeatedly in client feedback. They stay engaged with past clients through review responses. Has worked on enough vintage Chicago homes to understand what they demand.
Roofing projects typically cost $5K – $25K in Chicagoland
Terry Gavin
4 reviews
Chicago
No recurring concerns found across reviews. This contractor maintains a consistently positive reputation.
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“From their professionalism and attention to detail, this company exceeded my expectations in every way.”
“I had a great experience using Heritage for my roofing needs.”
I had a great experience using Heritage for my roofing needs. They project managers were very responsive, professional, timely and took the time to explain the project, making several trips to show me pictures and explain the process. Heritage was contracted to replace my roof but went above the call and ensured that my gutters were properly secured. I would recommend their services.
LaShawn Murray
Nov 2025
“Had a wonderful experience with heritage.”
Had a wonderful experience with heritage. I got my siding, trim around my windows, new OSB, weatherproofing, and insulation where needed. The quality of work was stellar. Everything they did looks beautiful and professional. John and Mary were extremely informative throughout the whole process. I’d recommend their company to anybody!
Tom Small
Nov 2025
“I usually don't write reviews but in this case i'm making an exception, heritage contractors and...”
I usually don't write reviews but in this case i'm making an exception, heritage contractors and their team are the best I've ever met and I've been in the trades business for 50 years. I'd like to thank John , mary ,charlie ,and matt and they're incredible crew. An unbelievable job from the time I received the estimate to the final cleanup. We could not be happier.A special shut out to charlie you made this so incredible effortless for us. Thank you,
Mark Schneider
Oct 2025
“Heritage Contractors is top notch.”
Heritage Contractors is top notch! The incredible customer service, professionalism, and quality of work cannot be beat. We are thrilled to have worked with such a wonderful and local company. We will be contacting Heritage for all of our roofing needs over the years. Thank you Heritage for all your hard work!
Pamela Capouch
Oct 2025
“Could not be happier with our new roof and gutters provided Heritage Contractors.”
Could not be happier with our new roof and gutters provided Heritage Contractors. From start to finish they were wonderful. After providing a very competitive quote (beating three other contractors) and addressing all of our questions and concerns we moved forward and boy are we glad we did. John , Charlie and Matt and crew were very professional every step of the way. I don’t think the ground our home has ever been cleaner with each and every piece of roof, scrap and nail meticulously picked up and cleaned. A very minor repair was suggested and we agreed to their proposal but only after everything was explained to us in great detail and a quote was provided to explain and describe the additional work needed. It’s always a good feeling when you can choose a local , family owned and operated company to do business with and be pleasant surprised when the job is completed. Bill and Beth Hickey
William Hickey
Oct 2025
“My husband and I recently moved into our first home and were put in touch with Charlie at Heritage Contractors.”
My husband and I recently moved into our first home and were put in touch with Charlie at Heritage Contractors. It can be uncomfortable entering unfamiliar territory getting work done on your house as a first time homeowner. However, from the initial message to the completion of our garage roof, we were highly impressed. Charlie was able to come inspect our roof the same day we reached out to him. He gave us a transparent and highly competitive price for our project. We needed some time to get settled in but promised Charlie we would call him back when we were ready to start. A few months later, Charlie and I reconnected and he was able to review the pricing with me and help get our project scheduled within the next couple of weeks based on our combined schedules. He was able to put me in touch with a point of contact for day of work, Matt, who to my surprise was just as great as Charlie. He was respectful and periodically came back to the house throughout the project to ensure it was on track and met his standards. His team of contractors were hard workers and treated myself and my home with respect. They worked diligently through the day and even left my backyard looking better than when they got there! Our roof came out awesome and we are so happy our paths crossed with Charlie, Mary, John, Matt and their team. From top to bottom, this company was a pleasure to work with and we’d highly recommend to anyone who’s looking for a reliable and trustworthy company to get their job done right. Thank you all & we look forward to working with you on our next job when the time comes!
Carly O’Sullivan
Oct 2025
“Over the past few months, we've had Heritage install a standing seam metal roof, replace a curved...”
Over the past few months, we've had Heritage install a standing seam metal roof, replace a curved picture window, and replace a flat roof. All three teams that have done the work have been great. The first window that was installed was the wrong color. I asked John to replace it, and he did without fighting me on it. John is a great communicator and how he resolved the window gave us the confidence to have Heritage do the flat roof as well. I won't hesitate to refer people to Heritage.
Timothy Catanzaro
Sep 2025
“Honest and reliable contractors are hard to find, but you truly cannot go wrong with Heritage Contractors.”
Honest and reliable contractors are hard to find, but you truly cannot go wrong with Heritage Contractors. If you need a new roof, gutters, siding, or windows—call John. I first met John 9 years ago when I bought my home. He inspected the roof and told me it still had a few years left, so we held off—and ended up getting 9 more years out of it. Recently, our gutter guy pointed out it was finally time for a new one, and while we knew it was coming, replacing a roof is never something you’re excited to spend on. It’s a big expense without the “wow factor” of a kitchen or bathroom renovation—it’s just an evil necessity. When John came out, I initially asked him to just patch a few spots since we were considering selling within the next year. He had no problem with that and was happy to help us despite it being what most businesses would consider a small job that wasn’t worth their time. But our plans quickly changed, and we decided to move forward with a full replacement. John’s estimate wasn’t only fair—it was the best we received. In fact, it came in $9,000 less than the next lowest bid, and unlike others, he didn’t try to upsell us on things we didn’t need. He listened to what we wanted and delivered a straightforward, honest quote. From the start, we had a great feeling about John. He’s honest, trustworthy, responsive, and genuinely cares about his clients. His wife Mary is just as kind, and his foreman Matt was fantastic. They scheduled us within 2 weeks, and even when a small mishap with fascia occurred, John and Matt immediately owned it, apologized, and made it right—something you don’t see often in this industry. We have two homes, and while we can’t update everything all at once, Heritage Contractors will absolutely be our first call for any future exterior work. Thank you, John, Mary, and Matt—you’re truly the best!
Ashley Perisee
Sep 2025
“We had a great experience with Heritage Contractors.”
We had a great experience with Heritage Contractors! As a local family business, they treated us like neighbors. They were professional, friendly, and communicative from start to finish. The crew worked efficiently, cleaned up perfectly, and the new roof and gutters looks fantastic. Highly recommend!
Amy Taylor
Sep 2025
“John at Heritage Contractors has gone above and beyond for us.”
John at Heritage Contractors has gone above and beyond for us. They repaired our roof and recently were able to figure out why we had a leak in our dining room ceiling. He repaired the window that was causing the leak promptly. John is always quick to respond and the company does excellent work, highly recommend.
Jennifer White
Aug 2025
“Heritage was very easy to work with got a quote for a roofing job, very fair price.”
Heritage was very easy to work with got a quote for a roofing job, very fair price. This was a smaller job but Heritage was very professional, did quality work had a supervisor on site work was very nice. Job was finished quickly, clean up was excellent very satisfied with the work Heritage completed. Heritage is also easy to communicate with and I appreciate that as well!
Edward Wolf
Aug 2025
“I recently noticed a small leak from the living room ceiling.”
I recently noticed a small leak from the living room ceiling. I've been in my house for 10yrs and had no idea of the condition of the roof as the house was purchased as a short sale. I called Heritage and John came out to inspect in a timely fashion. Heritage was respectful of my home and honest about the repairs that needed to be done. They made the necessary repairs the same day and went above and beyond what was quoted! A definite call for quality, affordability, and customer service.
Rahsaan Metcalf
Aug 2025
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