These guys are fantastic! During a thaw after lots of snow, we had an ice jam that was causing water to flow into our house. I contacted Windy City Flat roof first thing on Monday morning and Eli called me back within minutes. They were swamped with calls due to the weather, but he had a crew out to our house within a couple hours. They cleared the snow and ice from our roof and diagnosed the problem. The water stopped, thankfully. And they came back 2 days later to do the recommended repairs. Roofing issues and repairs for me are like taking your car to the mechanic. They tell me what the issues are and what it will take to repair, but I have no clue what they are talking about. All I can say is Eli was SUPER patient with all of our questions and concerns. Roofing work is not cheap, not that it should be. It is dangerous work. And I do believe that you get what you pay for. So, yeah, we laid out some bucks, but the Windy City Flat Roof team was amazing from start to finish. Fast, efficient, and friendly. Can't ask for more than that! read more

never returned calls and 18 months after I spent $16k with them the roof has water pooling underneath it. Under no circumstances should you use them. read more

Windy City Flat Roof - Water pooling - Roofing Near Me - Chicago, Illinois

I worked with this company in 2023 to completely replace a flat roof on one of my rental properties. At the time all things were great. Shawn was very responsive, timely and they replaced my roof - a very expensive job. Less than a year later, I'm having the same and more water issues and leaking inside the building. I reach out to Shawn a number of times and never hear back. After digging up the owner, Ricky, I call him and he tells me an enormous story about how Shawn was acting on his own when he did my job and that Shawn had defrauded him. And because Shawn supposedly sent me the contract with multi-year warranty from a different email address that it was not covered! What am I going to do, take a small business owner with no assets, most likely, to court? No remedy at all. I reach back to Shawn with this info and he denies it all and claims that Ricky is running the business into the ground. There is clearly a lot not working well with this company. I won't bore anyone still reading this with the back and forth but this business is a disaster, did a terrible job on my roof costing me $6k extra to repair most of their entire job. Even if they had offered to fix the bad job(which they didn't) I wouldn't trust them to do it anyways. In many years of working with contractors and subs, this is the worst experience and outcome I've ever had. read more

They were super fast to respond when I reached out with a leaking roof. They came out very quick to inspect and let me know all of the options available. They focus on getting things done the right way and ensuring they completely fix the problem. The team to fix it then came out shortly after that. They were super communicative, transparent, clean, and professional. Would use them again; highly recommend! read more

Working on giving a house in Logan Square with 'good bones' some love, and attention turned to the roof! We talked to several roofers , and it was clear Shawn and Ricky were the right choice and we were not wrong! Professional, efficient, and communicative, they made smart recommendations for where we could save money, and places where some more cost (like enhanced insulation) would be a wise choice, without us ever once feeling 'upsold'. I could not recommend Windy City Flat Roof any more highly - 15 out of 10!! read more

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I recently used Windy City Flat Roof, Inc to replace my flat roof and do some masonry touch up work. Shawn was one of the owners that wrote the quote, answered all my questions, and was my point of contact prior to signing the proposal. After signing the proposal the other co-owner, Ricky, took over and made sure that the job was completed correctly. I shopped around multiple companies before deciding on Windy City and ultimately Windy City provided the best value. It has been two weeks since they did the work and so far everything is so good. Ricky made it very clear that if I ever have any issues that they stand by their work, so I just need to give them a call. read more

Fixed a damage area on my roof. Prompt service, quality workmanship, cleanliness, and very professional.

Ricky and his crew did a great job on repairing our garage roof. They were all very knowledgeable and pointed out the problem areas and areas of concern with specifically showing us those affected areas. Other roofers came out before him and just said to replace the entire roof without anymore discussion. We liked Ricky's honestly, expertise and responsiveness. Throughout the entire process we heard from Ricky at least once a day and then him being on-site when the job was performed. I'd recommend them for quality workmanship and honest assessments. We will definitely be working with them again in the future when needed. read more

Windy City Flat Roof - Garage roof - Roofing Near Me - Chicago, Illinois

100% recommend. Had a very complicated issue with the flat roof and the dog house and these guys were able to come up with a solution that 2 previous roofing companies could not do. They were able to adapt to the issues that came up along with way, as well as work with me on the cost (which was EXTREMELY helpful!). The crew was very skilled and easy to work with, and the materials they used were of the best quality. Windy City Flat Roof is now my "go to" roofing company, and I would recommend them to anyone. read more

I have literally worried about a leak on my residential 6k sf home! Live in suburbs. I am so thankful for Shawn coming out within 2 days. GETTING On the roof, taking photos and going over the issues with me. He was able to bring his foreman out the next day to show him what needed to be done. The next week his crew was there!!! I was out of town but he touched base with me via text multiple times during the week while job was happening. Sending me pictures of progress. Which was sooooo comforting after so many years of being bothered (stressed) about this. 100 percent clean up. And it was a messy job. Even came back out days later to touch up my metal gutter with special paint. At no charge. They did not have to do this. Highly recommend. Call them and ask that Shawn text or call you back. read more

Wow!! A professionally run company. Windy City Flat roofing provided an honest quote and delivered with excellent work. The owner was quick to respond to my request for a quote. Scheduled service for roof repairs the next day with his crew. The crew showed up on time and finished the job same day. The crew that worked on my roofs are experienced workers. They are efficient, professional(asked me questions), clean and kind! You will not be disappointed with this company!! I would highly recommend this company and suggest to get the work done now before the weather changes. read more

Wish I could give ZERO! I scheduled via text and since no initial response to me, I made up the appointment was accepted. While awaiting roofer's arrival, I realized they didn't confirm. I phoned & stated this revelation, then scheduled a day and time that would work. They even texted me their latest reviews for me to read before our meeting. On the confirmed day and exact confirmed time Shawn was to be physically standing at my place, I received a text that he wasn't coming due to the rain. I replied, "There's no rain where I live." Remember, this I'm-not-coming-text was sent at the EXACT TIME Shawn was to be PHYSICALLY PRESENT at my home. Yet, I was considerate and rescheduled. For this reschedule, I texted Shawn AFTER the time SHAWN CONFIRMED to be at my place. He TEXT-REPLIED 24 MINUTES LATE, which I quote: "We are going to have to set up a time in the late morning or afternoon. 9am I live too far....and I work in the office in the mornings . . . I'm working the office as we speak." Reminder - This text is 24 minutes AFTER THE TIME SHAWN PERSONALLY confirmed to be at my place, PLUS I ONLY GOT HIS TEXT AFTER I QUERIED ABOUT HIS LATE ARRIVAL TIME! TWO DAYS LATER Shawn sent me a new text and I quote: "My apologies about I missed appointments. I know your a busy person with a tight schedule. Me as well! (HOW ARROGANT SAYING - 'ME AS WELL') However..I'd like to come out and provide you with an inspection/writing quote. I would highly appreciate The opportunity." This text is written exactly as Shawn sent it to me minus my comment in parentheses. Lastly, another roofing contractor said to me up front, "You're out of our area." But Shawn instead, kept WASTING MY PRECIOUS TIME - EVENTUALLY SAYING "I LIVE TOO FAR" but still trying to waste more of my time by requesting another on-site estimate opportunity that at this point I could no longer trust he would honor. I ASK YOU AS THE READER OF THIS REVIEW - WOULD YOU STILL LET SHAWN COME AND GIVE YOU AN ESTIMATE AFTER HIS UNPROFESSIONALISM & WASTE OF YOUR TIME??? I already know your answer is NO WAY and my answer is the same. I didn't even bother to respond to Shawn's text. I'll just let my review of ZERO speak on my behalf. read more

Very good company they did very good job for us i called other company no one got back to me they called me back with in a hour came out the next day to look at the roof said they could start it that day thanks to WINDY CITY FLAT ROOF FOR VERY GOOD JOB read more

I had the pleasure of working with Shawn from Windy City Flat Roof. Shawn was awesome and very professional. I'm highly recommend dealing with Shawn if you need to contact them. Windy City was very efficient and helpGil in making sure our flat roof got fixed. They finished in one day and did an awesome job. They are super knowledgeable about roofs. Shawn explained everything in detail me along with how the process would go. Shawn was also quick to respond and very helpful during this entire process. The worked with me to make sure I got done what I needed. I would highly recommend them to friends and family and I would definitely use them again in the near future. They are awesome. read more

Windy City Flat Roof - Roofing Near Me - Chicago, Illinois

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Ricky and his team were prompt and very fair. As president of my HOA, we had to get at least 3 quotes to be able to move forward with one. While Ricky wasn't the least expensive (middle ground), he was about $1500 less expensive than the other bid (and $200 more than the lowest). Overall, they were fair, gave a thorough evaluation of the project, clearly laid out the project, and came out to give a free estimate the day after contacting them. I'd definitely recommend using them or at least contacting them for an estimate. read more

The owner of Windy Ciry contacted me, apologized for the time mix up and offered to reschedule to come out. He did come out a few days later, he was very professional, communicated in terms that gave me a clear understanding of what he and his team could do. I was quite impressed, and appreciated that told me about his credentials to do the job. Initially it was a misunderstanding and the owner was humble but professional enough to make it right, that is a business man with integrity. read more

Ricky , Shawn and Jonathan were totally professional. They analyzed the issue, gave me several solution options. They were quick to respond and arrived as scheduled and professionally completed the roof repair in one day. very satisfied. read more

Ricky and his team helped our HOA repair a damaged/leaky roof and completely waterproof our roof. Very responsive, professional, aand proactive in communication, with constant updates + pictures/videos. Prior to starting the work, Ricky provided several references. We called all of them and the feedback was positive. Pricing seemed to be fair and competitive. Our HOA was satisfied with his work. He just completed the work today so we'll see how things go after a year or so, but Windy City did include a 10 year warranty as part of their work read more

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I called WindyCity for an estimate on replacement roof on my garage and on my porch roof and matinance with repairs on my 2 flat building roof. When Shawn and his partner Ricky came out to evaluate the project, they gave me an great price. The crew was led by Johnathan the foreman, they did a fantastic job which took only 4 days with complete clean up and no inconvenience. This is the company that I will use and recommend for future projects for me & family and friends. Ricky and Shawn I appreciate you guys honestly and sincerness.THANK YOU MUCH!!! read more

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Quality work, honest/fair pricing, and flexible to our HOAs needs and scheduling. We highly recommend working with Windy City Flat Roofs!

Shawn and Ricky are honest and genuine. It's difficult to find quality vendors these days and I can assure you that Windy City Flat Roof is the best. They do more than just patch the problem they go all the way and correct the issue at its core. They are easy to work with and respond quickly and thoroughly. I would 100% use them again. Thanks. read more

We have nothing but good things to say about Ricky and his team - they have now done two jobs for us on our rental properties and we have been very happy with both. Ricky's professionalism and experience made us seek him out after his initial job for us, we found him very honest and easy to work with. Ricky's estimates were reasonable and he was true to his word regarding pricing. His team works fast and are very conscientious - everyone showed up on schedule and Ricky stayed in constant communication throughout the jobs, sending pictures and updates, he was a pleasure to work with! No question that we would work with him again if we had any roof issues at all - would not hesitate to recommend him to others! read more

I have nothing but great things to say about Windy City Flat Roof. We wrote in about our problem and got a quick response from one of the owners, Shawn. That was followed by an on-site inspection, a quick estimate, and a speedy but top notch repair and resurfacing of the entire roof. They replaced a large section of rotted wood and fixed some sloppy edging work by the original builder. The final product looks fantastic, and we appreciate the warranties! BTW, the estimate was one of the most thorough we've received from a contractor, breaking down all the issues to be repaired and noting what materials would be used. The price was fair for the extensiveness of the project. Highly recommended! read more

I needed a leak repair done, so I called this company for an estimate. the guy came out and convinced me to do the whole roof. saying how there were so many issues with it. like it was going to collapse. so I got scared. He seemed honest and trustworthy. so I handed him the job.A few months later the roof had multiple leaks. i quickly got in contact with him. he said he would come out to see what was the problem.but he never showed up. he kept giving me the runaround. so I decided to call another company. they came out and said he did a bad job he didn't put a whole new roof like he said he did. He overcharged me. And they also said I did not need a new roof. I was scammed !! would not recommend. Be aware!! read more

I moved into a condo a year ago and was told the roof had been replaced 3 years ago. It was done poorly. Windy City Flat Roof came in and noticed damage and did a partial replacement and maintenance on the rest. Shaw was responsive and clearly explained everything that needed to be done. He kept me up to date every step of the way. During the tear off, we found the joists to have rotted as well. Shawn helped me find solutions keeping budget in mind without sacrificing the integrity of the job. My roof looks beautiful and it was done in two days. They will be the only ones servicing my roof in the future. Can't recommend them enough read more

Windy City Flat Roof - After - Roofing Near Me - Chicago, Illinois

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We sustained some roof damage during a recent bad storm in Chicago, and the Windy City Flat Roof team helped us out. They were extremely responsive and communicative throughout the process, walking us through all of the relevant details. Would highly recommend them to anyone in need of roof repair! read more

We've called in WCFR twice in the last two years: first to restore the eastern half of our roof, second to restore the western half. They always do excellent work, and we know we can trust them. They take before/after photos. And Shawn gave us a deal to provide free coating for the western roof restoration. They also re-caulked our skylight and put down new membrane and proper flashing. Reasonable pricing for high-quality work that I don't have to worry about! read more

Needed a roofer in a hurry and these guys showed up quickly, diagnosed the problem, worked with me on price and got to work the next day! Great communication with Shawn and his foreman Jonathan was fantastic as well. Highly recommended! read more

My flat roof began leaking into my home during the heavy October rains. Ricky stopped by during a break to review and estimate repairs/replacement the same day I reached out to him. His communication was clear about my situation and options, and the estimates were very fair in comparison to others. His men showed up when he said they would, did their job and cleaned up. My roof looks more solid than ever and has not leaked since. Couldn't have asked for a better experience. Highly recommend!. read more

Outstanding work and great responsiveness from Shawn, Jonathan, and team. They were in contact with me right away regarding leaky skylights and roof problems, and they got the fixes done ahead of schedule. Competitive costs awesome customer service. Highly recommend! read more

Our Roof was damaged due to high winds and rain on a Tuesday Night. My wife found Windy City flat roofers on Yelp and contacted them. They responded immediately. Sean messaged my wife and even went as far to pull up satan it's imagery to see my roof to have a better idea of what was going on. Mind you this was 9pm on a Tuesday and he took at minimum an hour out of his night to address our problem. The next day Sean came out and evaluated the damage and was able to start the project on Friday. All repairs done in less than a full day. Ricky, Sean's boss was on top of everything to make sure we were satisfied. They took before and after photos so we could submit them to our insurance company. I highly recommend this company to anyone who is in need of roof work. Great guys! Up front and honest with no beating around the bush. Couldn't be happier with their service. Thank you Sean and Ricky for saving the day! Josh read more

After a storm I started to hear creaks and a potential leak inside the walls of my condo. Living on the top floor I was concerned about a problem with the roof. Windy City responded quickly to my Yelp quote request and came out the next day. The two of them were professional and walked me through the cracks and ponding that were occurring on my roof. They gave me a fair estimate and offered to get to work straightaway. I wish I had taken them up on that since it rained that night and I heard a leak from another spot, so the next day they agreed to come out and worked hard to get everything done in one day. They quickly cleaned the water off, recoated the problems areas, and sealed the cracks and I'm hopeful that the leaks will stop. read more

We had some water coming in from a leak in the roof. Ricky and his team were great and came over the same day I called to look at the roof and to give me various options to address the problem. They were very responsive, professional and pleasant to deal with. They fixed the problem that day and the leak was resolved. I would work with them again if I had any issues with my flat roof. Definitely recommended! read more

Friendly, efficiant and came out right away to fix hole raccoons made in my roof/ chimney. 100 percent guarantee! Highly recommend!

I'm fully aware everyone is short staffed given the climate we are living in however follow through and communicate can go a long way. After speaking with Windy City Flat Roof on Sunday for an estimate they tentatively scheduled an appointment for that day however it was pushed back to Monday which I was fine with...Monday came and went and nothing. Monday evening I reached out to see if they were available on Wednesday to complete an estimate on my roof and nothing, no response. I'm not ok with their lack of professionalism. read more

Shawn and his crew did an amazing job on our flat roof on our building! I would recommend them always!

Excellent, fast service from first contact through completed project, We needed a flat garage roof repaired and Shawn immediately got back to me the same day with a general estimate on repair and replacement if necessary. Ricky and his crew were out within 2 weeks and did an excellent job of patch, repair and sealing of the roof. Very professional and clean work was done within 1 day. Highly recommend this company. read more

We had a great experience with Ricky and his team! We noticed a leak in a skylight on a Wed night, and while looking for places to call in the morning, I sent a quick email over to Windy City, as the roof itself is flat, so the name seemed perfect. Ricky called me about an hour later and was able to come by the next day to take a look at things. He noticed that each of the four skylights needed work and offered different levels of repair, including a discount for doing all of the work at once. Not only did the crew come out on Saturday to get things taken care of, they removed an unsightly antenna from the roof that we had wanted to take down, and were able to add a coating to the entire roof for further weather protection. We will definitely be calling Ricky again for any future flat roof issues, and trust that he and his team will do a great job! read more

We had a ton of water seep in after that huge drop of snow in Feb 2021. Like many flat roofs, ice dams formed at the tops of the downspouts. And when the warmth from the house began to melt the snow, it found a way in where the ice had pulled apart the seams around the scupper boxes. After installing heating cables and inspecting the roof myself it was clear fixes were needed before this winter. Ricky's guys came out and gave me a couple of different options. His pricing was comparable to other quotes but Ricky's experience and attention to detail led me to book him for the job. It was one day's work to remove the boxes and reseal around the downspouts, but he got in extra guys to stay ahead of the rain that was forecast for later in the day. And they didn't skimp on the overlaying of materials in the trouble spots. He coated the entire roof too and gave me a five year warranty on the work. Obviously this is Chicago and you don't know how good roof work is until it's faced a full winter. So I will certainly repost if I have any problems in the next year. But for swift scheduling, getting the work done to a high standard and leaving everything tidy, Windy City Flat Roof get a well earned 5/5. read more

We called Windy City to provide an estimate to repair our flat roof on our 3 story condo building. They were super responsive, came out that day to provide a quote. After receiving 3 quotes, we chose Windy City because of Shane. Not only did they provide the best pricing but he provided clear information on the repair needed with pictures and all. The Crew that did the work on site were great. They worked quickly and effeciently. We would absolutely use Windy City in the future and HIGHLY RECOMMEND THEM! read more