What Should I Look for in a Roofing Contractor to Avoid Bad Installs and Future Leaks in Chicago?

This is one of the most important questions a homeowner can ask before replacing a roof. A bad install can lead to years of leaks, frustration, and expensive repairs. The first step is doing a real online deep dive. Look beyond a contractor’s website and check reviews on Google, Yelp, Facebook, and other platforms where customers can leave honest feedback. Read both the good and the bad. Patterns matter more than a single review, and consistent complaints are usually a red flag.

Licensing and insurance are non-negotiable in Chicago. Any contractor performing roofing work must have a valid Illinois roofing license. If the project is in the City of Chicago, the contractor must also hold a City of Chicago general contractor license. Without both, they cannot legally pull a permit. It is also critical that the contractor carries active workers’ compensation insurance. If a roofer does not have workers’ comp, their Illinois roofing license is automatically invalid until it is reinstated. Always ask for a copy of their insurance certificate and request to be listed as additionally insured. This protects you if there is an injury or property damage during the project.

It is also worth asking how the company staffs its jobs. For flat roof work especially, experienced W-2 employees matter. Flat roofing requires more technical detailing and consistency than many pitched roof installations. Meeting with contractors in person, asking questions, and paying attention to communication style is important. Ask yourself how responsive this company would be three years from now if an issue comes up. Do they return calls promptly, explain things clearly, and stand behind their work, or do they feel rushed and transactional?

Finally, look at the overall professionalism of the company. Lettered trucks, branded uniforms, proper permits, and organized documentation are often signs of a contractor who plans to be around long term. Fly-by-night operators tend to cut corners, skip permits, and disappear when problems arise. While there are many factors that go into choosing the right roofer, following these basics will dramatically reduce the chances of bad installs and future leaks. A little extra diligence up front can save you a lot of stress later.

If you’d like to learn more about avoiding bad roofing installs, check out our video here: https://youtu.be/YwW6nDPsA88?si=rO6TkE5ammAB4uXs

Service provided: Roof Replacement

Location: Chicago, IL