Q1
What's your Illinois roofing contractor license number?
Why it matters
Illinois law requires every roofing contractor to hold an active state license issued by IDFPR. The license number is a public record. You can verify it in 60 seconds at idfpr.illinois.gov. Any contractor who refuses to provide the number, claims 'we're licensed in our home state,' or says 'I'll get that for you tomorrow' is disqualifying. Our license: IL Roofing Unlimited #104.010248.
Red flag: Refusal to provide a number, an out-of-state license, or a 'corporate license' that doesn't exist in Illinois.
Q2
Can you show me current general liability and workers' compensation certificates?
Why it matters
If a worker is injured on your property and the contractor doesn't carry workers' comp, you can be personally liable. If the contractor's general liability lapses, your homeowner's insurance becomes the backstop for property damage they cause. Both COIs should be dated within the last 12 months. Legitimate contractors send these to you immediately upon request.
Red flag: Hesitation, certificates more than 12 months old, or coverage amounts below $1M general liability.
Q3
Can you provide 3-5 references with addresses in my specific town?
Why it matters
Local references confirm the contractor has actually worked in your area. Storm-chasers who follow hail events can't produce local references because their local work began with the storm. A legitimate Chicagoland contractor with years of local work has these references easily. Call the references — ask what work was done, when, and whether the contractor responded after the project closed.
Red flag: References in other states only, vague offers to send references later, or contacts who don't pick up when called.
Q4
Will you waive my insurance deductible?
Why it matters
If the contractor says yes, walk away. Waiving deductibles is insurance fraud under Illinois law (215 ILCS 5/155.22) and violates essentially every homeowner insurance policy. The fraud benefits the contractor at your insurance carrier's expense AND puts you in legal jeopardy if the carrier audits the claim. The right answer is 'no, that's illegal in Illinois.'
Red flag: Any version of 'we'll take care of your deductible,' 'we have a relationship with insurance companies that lets us cover it,' or 'we can make sure you don't pay anything out of pocket.' All variations on the same illegal practice.
Q5
Will I need to sign an Assignment of Benefits (AOB) agreement?
Why it matters
An AOB transfers your insurance rights to the contractor. Once signed, the contractor controls communication with your insurance company, negotiates the claim scope, and receives the insurance payment directly. AOBs in roofing are frequently used to extract higher payouts than the homeowner would have agreed to, and disputes get resolved between the contractor and insurance company without your input. No legitimate Illinois roofer requires an AOB.
Red flag: An AOB requirement, especially when bundled with the project contract. Refuse to sign the AOB even if you sign the project contract.
Q6
What's included in the written estimate — and what's not?
Why it matters
A legitimate Chicagoland roofing estimate spells out: tear-off scope, decking inspection with per-sheet replacement allowance, ice-and-water shield coverage (minimum: eaves + valleys + all penetrations), underlayment type, shingle brand and product line, ridge vent linear footage, ALL flashing work (step, chimney, pipe boots), haul-away and cleanup, permit fees, manufacturer warranty term and tier, and contractor workmanship warranty. A one-page quote with a single number on it is a red flag — either the contractor is hiding scope or doesn't know what they're doing.
Red flag: Single-line numbers without scope detail, missing ice-and-water shield, vague 'permit fees may apply' language, or refusal to itemize.
Q7
What's the brand and product line of the materials you're proposing?
Why it matters
'Standard architectural shingles' is not a brand. A real estimate names the manufacturer (GAF, Owens Corning, CertainTeed, Atlas) and the specific product line (Timberline HDZ, Duration, Landmark Pro, StormMaster). The product line determines warranty terms, wind rating, hail resistance, and lifespan. If the contractor can't or won't name the specific product, they're either using whatever's cheapest at the warehouse that day or planning to substitute mid-project.
Red flag: Generic descriptions like 'name-brand shingles,' 'premium architectural,' or 'we use whatever the customer prefers without specifying defaults.'
Q8
What's your workmanship warranty and how is it backed?
Why it matters
The manufacturer warranty covers material defects. The workmanship warranty covers installation errors — which are the source of the majority of roof problems. Ten years on workmanship is reasonable. Lifetime workmanship warranties from a brand-new company aren't worth the paper they're printed on. The right answer is a specific term (typically 10-15 years) backed by a contractor with the operating history to actually honor it.
Red flag: 'Lifetime' warranties from new companies, no written warranty terms, or warranty terms shorter than 5 years.
Q9
How long has your business operated in Illinois?
Why it matters
Storm-chasers come and go. The roofer you want to hire is the one who'll still be answering the phone in 15 years when a warranty issue comes up. Years in business is a proxy for whether the contractor will be around to honor commitments. Leaders Roofing: 30 years in Mount Prospect since 1996. Same family, same address.
Red flag: Less than 5 years in business in Illinois, especially if they appeared in your area within days of a recent storm event.
Q10
Will the same crew that gives me the estimate do the actual work?
Why it matters
Some contractors operate as estimating-only fronts that subcontract the actual install to other crews. This creates accountability gaps — the person who promised the scope isn't on the roof to enforce it. Legitimate established contractors have direct relationships with their installation crews and can put a foreman on your project who's been with the company for years.
Red flag: Vague answers about who does the work, references to 'our network of installers,' or unwillingness to introduce you to the foreman who'll run your project.
If you already got an estimate that fails one of these tests
The most common scenario: you've already had 2-3 contractors out and one of them is pressuring you to sign. Step back. Use this checklist on the estimates you already have. Any contractor that fails questions 1-5 (license, insurance, references, deductible-waiving, AOB) is disqualifying — don't sign with them regardless of price or schedule pressure.
If you want a third opinion from a 30-year family-owned Chicagoland contractor who'll tell you honestly whether the existing estimates are reasonable, we'd welcome the conversation. Free assessment, no pressure, no AOB. Call (708) 847-5418 or use our contact form.
If your existing estimate is for hail damage replacement specifically, our hail damage roof replacement page walks through what an honest scope looks like vs the storm-chaser playbook. Our full storm-chaser red flags article covers the broader pattern.