The architecture here is varied enough that experience with your kind of house matters more than experience in general.
Verify before you admire the portfolio
Licence, general liability insurance and workers compensation. Ask for all three, look at the certificates, and check the dates. This takes ten minutes and eliminates a whole category of risk.
Workers compensation is the one people skip. If a trade is injured on your property and the contractor does not carry it, the exposure can land on your homeowner policy.
Match the contractor to the house
Chicago-area housing runs from pre-war brick through mid-century ranches to recent construction, and they fail in completely different ways. Knob-and-tube wiring, galvanised supply lines, balloon framing and settled foundations are all specific problems with specific solutions.
Ask what they have worked on that resembles your house. A firm that does forty new-build kitchens a year is excellent at new-build kitchens.
Ask what the company turns down. A builder who says yes to everything has told you how attention gets divided.
What a real estimate looks like
Labour and materials separated. Allowances stated with numbers you can test. Exclusions written down. A payment schedule tied to completed stages rather than calendar dates.
If an estimate is one page and one number, it is not an estimate. It is a guess that both of you will be renegotiating in month three.
- Labour and materials as separate lines.
- Allowances you can check against real showroom prices.
- Written exclusions, including permits, dumpsters and final clean.
- Stage-based payments, never date-based.
Ask how they communicate
Who do you call, how often will you hear from them, and what happens when the schedule moves. A renovation is weeks of small decisions, and the companies that run well are the ones that make those decisions easy to make.
Ask for a blank change order form. A contractor who has one has already thought about the part of the project that generates the most disputes.
Two references, one question
Ask for the last two projects finished, not a curated list. Then ask each one what went wrong and how it was handled.
Every renovation has a bad week. The answer to that question is the most honest signal you will get about what yours will be like.