Questions to Ask a Remodeling Contractor in Chicago

Most renovation disasters were predictable at the first meeting — the signals were there before any contract was signed. The questions below surface those signals early, and any contractor worth hiring will answer every one of them without flinching. We expect to be asked all seven.

What Should You Ask a Remodeling Contractor Before Hiring Them in Chicago?

Seven questions cover what matters most: license, insurance, the estimate, permits, payments, who’s on site, and recent references. Together they separate a contractor who runs a business from one who runs a truck. Here’s the short version — the answer you want to hear, and the one that should end the meeting.

1. Are You Licensed With the City of Chicago — and Can I Verify It?

The answer should be a license number, and you can check it yourself in about two minutes. Chicago licenses general contractors in five classes based on the size of a single project they can take on: Class A has no limit, Class B goes up to $10 million, Class C to $5 million, Class D to $2 million, and Class E to $500,000. Ours is Class D, License TGC132820. Search any contractor in the City’s contractor license lookup before you sign anything.

Trade work has its own licensing. In Chicago, electrical, plumbing, masonry, and sewer work is done by contractors licensed for that trade — so ask who performs it and under whose license. A general contractor who can answer that cleanly is coordinating real professionals. One who can’t is improvising.

Walk away if: there’s no number, the number doesn’t appear in the City’s lookup, or the plan is to work “under a buddy’s license.”

2. Can I See a Certificate of Insurance — Issued for My Project?

Yes — a certificate showing general liability and workers’ compensation, issued for your job. Illinois sets a floor: under the Home Repair and Remodeling Act, contractors must carry at least $100,000 per person and $300,000 per occurrence in bodily-injury coverage and $50,000 per occurrence in property-damage coverage, unless the company has a net worth of at least $1 million. Treat those numbers as the minimum, not the standard. Condo buildings routinely require more, and a contractor who works in them already carries it.

Workers’ comp is the coverage people forget to ask about, and the one that matters most. If an uninsured worker is hurt on your property, the claim can come looking for you.

Walk away if: you hear “we’re covered” but never see a certificate, or the certificate names a different company.

3. Will My Estimate Be Line-Item?

It should be — and in Illinois, any job over $1,000 requires a written contract anyway. The Home Repair and Remodeling Act requires a written contract for jobs over $1,000 that shows the total cost, including parts and materials, along with the contractor’s business name and address. Before you sign, the contractor must also give you the state’s “Home Repair: Know Your Consumer Rights” pamphlet. If you’ve never been handed one, that tells you something.

A line-item estimate goes further than the law requires: cabinets, counters, labor, permits, disposal, and contingency each priced separately, so you can compare bids honestly and see exactly what any change costs. Allowances need a grade attached — a “$5,000 tile allowance” means nothing until you know what product level it buys. Our kitchen remodel cost guide walks through how to read one.

Walk away if: the estimate is a single number, or the details are “we’ll figure that out as we go.”

4. Who Pulls the Permits?

The contractor, under their license. In Chicago, a general contractor overseeing permitted work has to be licensed and named on the permit. A contractor who asks you to pull the permit yourself is moving the liability for their work onto your name — and the property owner is the one responsible for making sure required permits exist. Moving plumbing, altering electrical, and changing walls all trigger permits; our Chicago renovation permits guide covers what else does, what permits cost, and how long review takes.

Walk away if: you hear “you don’t need a permit for that” about anything structural, plumbing, electrical, or gas.

5. How Do Payments Work?

Milestone payments tied to finished work: a deposit, progress payments as phases are completed or pass inspection, and a final payment at the walkthrough. The schedule belongs in the contract, and payments should never run far ahead of the work on site. Be cautious of anyone asking for half or more up front, cash-only pricing, or a large payment “to order materials” with nothing in writing. If you’re financing, ask how the lender pays out against the schedule — we offer financing through Hearth for clients who want it.

Walk away if: the payment terms aren’t written down, or most of the money is due before most of the work is done.

6. Who Is Actually On My Job Site?

A named project lead, a consistent crew, and a clear line between in-house trades and subcontractors. Ask who supervises the job day to day, which trades the company performs itself, and who you call when something goes wrong. A firm that self-performs its core trades — carpentry, tile, flooring, finish work — has fewer hand-offs, and hand-offs are where schedules slip and accountability disappears. Our answer: weekly photo updates, the same crew from demolition to punch list, and a direct line to the people running your job.

Walk away if: the answer is “depends who’s available that week.”

7. Can I See a Recent Project — or Talk to a Recent Client?

Yes — a real, recent, local reference, not just portfolio photos. Ask for a project from the last year, ideally similar in scope to yours, and ask that client how communication, cleanup, and changes were handled. Read online reviews too, including how the contractor replies to them. You can see our completed West Englewood gut rehab and Fuller Park ranch, documented room by room.

Walk away if: there are no references, or every reference is years old.

What Are the Red Flags When Hiring a Contractor in Chicago?

Pressure, vagueness, and missing paperwork. One is a reason to slow down; two are a reason to walk.

• Pressure to sign today. A discount that expires tonight is a sales tactic, not a price.
• No license number, or one that doesn’t appear in the City’s lookup.
• No written contract. For jobs over $1,000 in Illinois, that isn’t just bad practice — it’s required.
• Cash-only pricing, or a large deposit before any work starts.
• “You don’t need a permit for that” on structural, plumbing, electrical, or gas work.
• A bid far below everyone else’s. It usually means something is missing from the scope — and it comes back later as a change order.
• Door-to-door offers after a storm. For contracts signed at your home, you generally have three business days to cancel. Use them.

The cheapest bid usually becomes the most expensive project.

How Do You Compare Bids From Chicago Contractors?

Line them up item by item — same scope, same allowances, same exclusions — before you compare a single total. Two bids at $40,000 and $52,000 are often not the same job: one includes permits, debris removal, and a contingency, and the other leaves them out. Before comparing totals, check who pays the permit fees, whether disposal is included, how realistic each allowance is for the finishes you actually want, what’s excluded, and how change orders are priced. Then compare timelines, because a cheaper bid that runs six weeks longer is rarely cheaper once you count the disruption. Our kitchen guide lists what usually isn’t in a bid.

How Should You Communicate With Your Contractor During the Project?

One point of contact, a fixed update rhythm, and every change in writing. Settle these before demolition starts:

• Who you call — one named person, not whoever answers.
• How often you hear from them — weekly updates with photos are a reasonable standard.
• When decisions are due — late selections are the most common cause of delays, so get a list of what you need to choose and by when.
• How changes are priced — a written change order with its cost, signed before the extra work happens.

Keep a running list of questions for a weekly check-in instead of stopping the crew mid-task. Problems surface faster, and get solved cheaper, when both sides expect to talk on a schedule.

Should You DIY or Hire a Contractor in Chicago?

DIY the cosmetic work; hire licensed professionals for anything that touches structure, plumbing, electrical, or gas. Painting, trim, and hardware swaps are fair game. Permit-triggering work is different: Chicago generally requires licensed trades for electrical and plumbing, and permitted work is inspected at rough-in, before the walls close. Owners can act as their own general contractor, but then the scheduling, inspections, trade coordination, and liability are all theirs. Most people find the math changes the first time a sequencing mistake costs them a week.

Hiring a Contractor FAQs

What questions should I ask a remodeling contractor in Chicago? Ask about their City of Chicago license, a certificate of insurance for your project, a written line-item estimate, who pulls the permits, how payments are scheduled, who will be on site, and for a recent local reference.

How do I verify a contractor’s license in Chicago? Ask for the license number and search it in the City’s contractor license lookup. Chicago general contractor licenses come in five classes, A through E, based on the maximum value of a single project.

Does Illinois require a written contract for home remodeling? Yes, for jobs over $1,000. The Home Repair and Remodeling Act requires a written contract showing the total cost and the contractor’s business name and address, and the contractor must give you the “Home Repair: Know Your Consumer Rights” pamphlet before you sign.

What insurance should a contractor carry in Illinois? General liability and workers’ compensation, shown on a certificate issued for your project. Illinois sets minimums of $100,000 per person and $300,000 per occurrence for bodily injury and $50,000 for property damage, unless the contractor has a net worth of at least $1 million.

How much should I pay a contractor up front? Payments should follow milestones tied to completed work — a deposit, progress payments, and a final payment at the walkthrough. Be cautious of anyone asking for half or more before work begins.

What are the biggest red flags when hiring a contractor? Pressure to sign immediately, no license number, no written contract, cash-only pricing, advice to skip permits, and a bid far below the others. When you’re ready, get a free line-item estimate from us and compare it against the rest.