Questions to Ask a Chicago Contractor Before You Sign

The questions to ask a contractor before hiring in Chicago come down to six topics: license, insurance, permit, contract, payment and who actually shows up. You do not need to sound like a lawyer. You need to ask plainly and notice whether the answers are plain too. A contractor who is relaxed about being checked is usually the one you want.

Bring the estimate and a pen. If you want a version to print and check off, use our contractor hiring checklist.

What license covers this exact job?

Ask: "Which license do you hold for this work, and what is the business name on it?"

Chicago requires a general contractor license for most building construction, alteration, repair and demolition, including work that does not need a building permit (City of Chicago). Brick, concrete and stone work falls under the separate mason contractor license (City of Chicago). Roofing is licensed by the state, and it is unlawful to hold yourself out as a roofing contractor without that license (Illinois law).

A good answer gives you a name and a license type you can look up on the City's contractor license lookup in a few minutes. Then do it. Our guide to checking a Chicago contractor's license shows where each license is verified.

Follow-up: "Will your own crew do the work, or do you subcontract it?" Some work legitimately runs under a licensed general contractor's supervision (City of Chicago). That is fine when you know who is licensed and who is on your roof.

Who carries the insurance, and can I see the certificate?

Ask: "Can you email me a certificate of insurance today?"

Illinois law requires home repair businesses to maintain public liability and property damage insurance at set minimums, unless the business has a net worth of at least $1,000,000 (815 ILCS 513/25). You want the certificate, not a verbal "we are covered." Check that the business name on the certificate matches the name on the contract. Ask your own insurance agent if you are unsure what the certificate should show.

A good answer is a quick email with a PDF. A weak answer is a promise to "send it later," or a certificate for a different company.

Who pulls the permit?

Ask: "Does this job need a permit, and who pulls it and pays for it?"

Chicago requires a permit before most construction and repair work, with a limited list of exemptions (City of Chicago). Masonry permits require a licensed mason contractor (City of Chicago). An owner can act as their own contractor only in narrow cases: a primary residence, three stories or fewer, six units or fewer, with the owner taking on responsibility for worker safety, inspections and code compliance (City of Chicago).

So be careful with "just pull it yourself, it's cheaper." If you are the owner of a rental two-flat you do not live in, that route may not be open to you, and the risk moves to you either way. We cover this in who pulls the permit.

A good answer says the contractor handles the permit, names the line on the estimate that covers it, and tells you what the inspections will be. If the contractor says no permit is needed, ask which exemption applies and then confirm it with the Department of Buildings.

What does the written contract say?

Ask: "Can I see the contract before the day we start?"

For home repair or remodeling over $1,000 on a residence of one to six units, the contractor must give you a written contract or work order to sign before work starts. It must state the total cost, with parts and materials listed with reasonable particularity, and the business name and address (815 ILCS 513/15). The contractor must also give you the pamphlet "Home Repair: Know Your Consumer Rights," and on jobs over $1,000 you sign a dated acknowledgment (815 ILCS 513/20). The Act covers one to six units and excludes maintenance or repairs under $500 (815 ILCS 513/10).

Then read it. Make sure these are in writing:

• The scope: what is being repaired, replaced or rebuilt, elevation by elevation if it is masonry.
• Materials, by type and brand where it matters.
• Start and finish dates, and what happens if weather delays work.
• How change orders are approved and priced.
• Warranty terms, who gives them, and how long they last.

Our post on what your Illinois home repair contract must say goes line by line.

How do payments work?

Ask: "What is the payment schedule, and what does each payment buy?"

We are not going to name a magic deposit percentage, because we cannot point you to a City or State rule that sets one. What you can do is make payments follow work completed, in writing, and avoid paying the last amount before the work is finished and inspected where inspection is required. Pay by a method that leaves a record. See how much deposit is normal for how to think about it.

A good answer is a schedule tied to stages. A weak answer is a large amount up front for "materials" with no stages after it.

Who will be on my property, and for how long?

Ask: "Who is the person I call if something goes wrong, and who is on site every day?"

This is where good contractors separate from the rest. On a Chicago two-flat the work often runs across tenants, neighbors and the public way. Scaffolding, dumpsters and material storage in the street, alley or sidewalk need a separate permit from CDOT (City of Chicago), and a contractor who has done this before already knows that.

Ask also:

• How do you protect tenants' entrances, windows and belongings?
• What is the cleanup plan, and does the price include debris removal?
• What happens if you find something unexpected once the wall is open?
• Will you give me a few local references I can actually call?

Questions you do not have to ask in a hostile tone

It helps to treat this as an interview, not an interrogation. A good contractor answers all of these without friction. If you need a language other than English to understand the answers, say so, and ask for the contract in that language as well. For that angle, see hiring a Spanish-speaking contractor.

When the answers do not add up

If the license cannot be found, the insurance never arrives, or the contract keeps getting delayed, stop. Those are the patterns in our list of Chicago contractor red flags. Walking away costs you an afternoon. Signing costs you more.

Hiring for a Chicago building? Our full hiring guide covers the process, and our team will give you the exact business name, license and insurance information before you sign anything. Contact Akats for an estimate.

Common questions

This article explains general rules and common situations in Chicago. It is not legal advice, and City rules change. For a specific property, check with the Chicago Department of Buildings or a licensed professional.