Eight questions to ask before signing with any Chicago contractor

Choosing a contractor for a six-figure home renovation is one of the largest purchasing decisions most homeowners ever make — and it is usually made with less information than buying a car. Here is the short list of questions that catch 90% of the red flags.

1. "Can I see your Illinois general contractor license and certificate of insurance?"

Both documents should be provided on request within 24 hours. No documents, no contract. Verify the license number at the Illinois Department of Financial and Professional Regulation website. The insurance certificate should list your address as a certificate holder — this is your proof of coverage during the job.

2. "What is your payment schedule?"

A typical healthy schedule is 10% at contract signing, then draws tied to measurable milestones (framing complete, drywall complete, etc.), with the final 10% held until punch list is finished. Run from anyone who asks for 50% upfront.

3. "Who is the project manager, and how often will they be on site?"

You want one person — a named individual — who owns the project and is on site at least twice a week. Large firms that rotate project managers or run 10 jobs per manager deliver worse outcomes.

4. "Can I walk an active job site?"

Yes, within reason. Any contractor who refuses a site visit is hiding something. Check for: tidy site, dumpster, port-a-john, workers wearing hard hats and steel-toe boots, protected floors inside the home.

5. "What is your change order process?"

The right answer: any change is written up, priced, and signed by both parties before work proceeds. The wrong answer is a hand-wavy "we'll figure it out at the end."

6. "What warranty do you offer?"

Industry minimum is one year on workmanship. Good contractors offer three to five years. A five-year warranty is a strong signal because warranty claims are expensive, and a contractor would not extend the term if they were not confident in their crew.

7. "Can I call three references from the last 12 months?"

Not testimonials on a website — direct phone numbers. Ask the references: was the project on time, on budget, and how did the contractor handle problems that came up?

8. "What is not in the bid?"

This catches the largest surprise charges. Any cost not in the written bid is either excluded or will come as a change order. Ask explicitly: "Is demolition, dumpster, port-a-john, permit, and final cleanup all included?"

A final note on price

The lowest bid is almost never the best deal. If you are choosing between a $78,000 bid and a $95,000 bid for the same scope, the $17,000 difference usually reflects either a weaker cabinetry spec, inexperienced crew, or a contractor bidding a job they do not intend to finish at that price. Itemize both bids line by line and the difference becomes visible.