5 Tips to Choose the Best Roofing Contractor in Naperville, IL

If you’re a homeowner in Naperville, IL, or the surrounding area, you've probably noticed how many local roofing contractors are making similar claims. Whether you’re dealing with a surprise leak or preparing for a full roof replacement, choosing the right roofer can make or break your home’s protection and your peace of mind. With dozens of roofing contractors to choose from, how do you know which one you can trust with your next roofing project? 

At Happy Roofing, we’ve worked with hundreds of Naperville homeowners facing all kinds of roofing concerns, from storm damage and leaks to full replacements. We've seen firsthand how overwhelming the contractor search can feel, especially when every company sounds the same. And no, we're not here to give you our sales pitch; we’re here to help. Whether you choose to partner with us or someone else, we want you to feel informed and confident in your decision because we genuinely believe every homeowner deserves guidance when making a decision as important as who to trust with their home.

This guide will walk you through exactly what to look for when comparing roofing contractors. Our goal is to help you avoid the common pitfalls homeowners face and feel fully informed and confident when it’s time to make your decision.

If you're exploring your options in Naperville, here are five important things to consider during your search.

1. Check Licensing & Insurance

Any contractor who sets foot on your roof must have the proper licensing and insurance. Roofing is high-risk work, and without proper credentials, you could be held responsible for damage to your home or injuries on your property. That's a liability no homeowner wants, so what are some questions you could ask to ensure your roofing contractor is properly licensed and insured? 

What to Ask:

• Are you licensed to operate in Illinois? Licensing verifies that the contractor is legally allowed to perform roofing work in the state. It also means they’ve met the required standards for knowledge and safety. Without it, there’s no guarantee they’re qualified or that you’ll have any legal recourse if an accident were to occur during construction on your property.
• What is your license number, and can I verify it online? A legitimate contractor will readily provide their roofing license number when asked, and many include it on their website. Once you get the number, you can verify it through the Illinois Department of Financial and Professional Regulation (IDFPR) License Lookup tool. This added step ensures that their license is active and in good standing.
• Do you carry both general liability and workers’ compensation insurance? Active insurance and a workers' compensation package ensure that any accidents, injuries, or property damage that occur during the project are covered by the contractor’s policy, and you won't be held liable. These give you peace of mind and protect you from unexpected legal or financial issues. Always ask for proof of coverage, and don’t hesitate to verify it with their provider if you want additional reassurance.

As the homeowner, you must be confident that the contractor you choose is experienced and has the right safety equipment to perform the roofing task. A reputable roofing company will have no problem showing documentation of its credentials. If they hesitate, that’s a red flag.

2. Check Recent Ratings and Reviews

For a more complete picture of a roofing contractor’s reliability, check review platforms like Google, Facebook, and Yelp. These sites feature real feedback from local homeowners who've worked with that contractor in the past, and they often highlight important details that can make or break your experience. Comments providing insight into factors like how well the company communicated, whether their crews kept the job site clean, and the quality of their work can help you determine if they would be a good fit for you and your home.

Look for consistent patterns in reviews, not just star ratings. Do customers mention professionalism, punctuality, cleanliness, and consistent follow-through? Are recent reviews positive? Do they respond to their reviews? Seeing how a contractor handles both praise and criticism can give you valuable insight into what it’s really like to work with them.

3. Look at Examples of Completed Work

One of the best ways to evaluate a roofing contractor’s reliability is by reviewing examples of their past projects. Don’t just settle for a few “after” shots taken from far away with a drone; those don’t tell you much about how the job was actually done. Reputable contractors will often provide progress photos during their projects that show the full scope of their work, including preparation, installation, and cleanup. If they haven't publicly posted these, you can ask for a portfolio of past work on roofs similar to yours. 

This level of documentation signals transparency and pride in craftsmanship. It also allows you to see whether they follow proper installation practices and maintain clean, safe job sites. Looking for green flags, like covering siding and windows during construction, can indicate that a contractor takes pride in their work and the safety of your home. Contractors who are hesitant to share past work or only provide vague before-and-after photos may not have the same level of accountability.

If possible, ask for local references you can drive by or customer testimonials that include photos. Seeing their work up close helps you feel more confident in the quality and reliability of the contractor you’re considering.

Here's an example of a progress photo showing how the windows and siding are protected from debris during the project: 

4. Ask About Warranties and Certifications

A solid workmanship warranty is one of the clearest signs that a contractor is confident in their work. The real value of a warranty depends on the company offering it, which is why you should always ask for the details in writing. Understanding what’s covered after installation, and for how long, helps ensure there are no surprises if an issue arises later.

It’s also worth checking if the contractor holds manufacturer's certifications from top shingle manufacturers such as GAF, Malarkey, or CertainTeed. These certifications indicate that the contractor has completed advanced training and meets rigorous installation standards. In many cases, this not only improves the long-term durability of your roof but also gives you access to stronger manufacturer-backed warranties that non-certified contractors can’t offer.

Together, a clear workmanship warranty and verified manufacturer certifications provide peace of mind that your contractor is committed to both quality installation and long-term customer support.

5. Get a Detailed Estimate

Before signing anything, make sure you receive a detailed, written estimate that breaks down materials, labor, and costs by line item. A trustworthy contractor won’t give you vague numbers or rush you into a decision. Seeing a generic quote like "roof replacement - $15,750" doesn't tell you much about what you're getting for the cost. By understanding the details around why each line item is important, or what brand of materials are being used, you'll be able to do accurate research on these specific factors before agreeing to the work. 

Find a contractor that will take the time to walk you through the proposal, explain each line item and why they've included it, and answer all of your questions without making you feel pressured. Transparency in this stage is critical. The more open and thorough a contractor is with their estimate and communication, the more confident you can feel about both the project and the partnership. If a roofer hesitates to provide details or avoids your questions, it’s a strong signal to keep looking.

Here's an example of a roof estimate that doesn't provide clear insight into the scope of the project or the quality of materials that will be used:

By contrast, here is an example of a detailed roof estimate providing more detail into each line item and specific costs:

Choosing the Right Roofing Company for You

Choosing a roofing contractor in Naperville doesn’t have to feel overwhelming. By asking the right questions prioritizing the factors we've outlined in this article, you’ll be able to separate the trustworthy professionals from the ones you’re better off avoiding.

If you’re still comparing your options, we recommend checking out our guide: Who Are the Best Roof Replacement Companies in Naperville? It’s designed to give you an unbiased look at the top local roofing companies so you can make the most informed choice for your home.

Looking for honest answers about your roof? Our team at Happy Roofing offers no-commitment consultations to help you assess your roof’s condition and answer any questions you have without any added pressure or expectations.