What Questions Should I Ask a Roofing Contractor in Chicago, IL?

Before signing any agreement in Chicago, run through this checklist with each provider you're considering. The answers — and how they're answered — reveal more than the quoted price.

Start with the basics: Are you licensed in Illinois? Can I see your general liability and worker's compensation certificates? Who will be on site — your own crew or subcontractors? If subs, how are they vetted? These questions weed out roughly half of marginal providers before you get to scope.

Next, ask about scope in writing: What's included, what's excluded, what's a change order? Who pulls permits and when? What's the exact payment schedule and what triggers each milestone? What's the warranty — on both labor and materials — and what voids it?

For roofing contractors specifically, dig into the project-level details that drive cost and quality: material choices (asphalt, metal, tile), manufacturer certifications, workmanship warranty vs material warranty. A pro should be able to explain each factor in plain language and how their approach handles it.

Ask for three recent references from Chicago-area projects similar to yours — not a generic list from anywhere. A legitimate provider will have these ready and won't hesitate to share contact information. When you call the references, ask about timeline adherence, change orders, cleanup, and whether they'd hire the provider again.

Close with the deal-breakers: Do you guarantee the start date in writing? How do you handle weather delays or material backorders? If something goes wrong after the job, who do I call? Clear answers here separate professional operators from providers who'll disappear the moment final payment clears.

20 listed providers serve Chicago with an average 4.8-star Google rating. A short conversation and a written answer to each question is cheap insurance compared to a bad hire.