Affinity Design & Build

This will be answered when you ask if all employees are licensed. The only way to obtain a legitimate tradesman's license is to be a legal or naturalized citizen of the US. The company may employ people in positions that don't require a license, however, so it's wise to inquire.

Some companies may require a 10% deposit, some may not require any. For larger projects, you'll almost always need to give a deposit, and it's good to ask how much the deposit will be before going forward with a project. The Chicago contractor will know how much they need for a deposit when they've given you the estimate, so ask early.

You'll certainly want to ask them this. Steer clear of any company that is not insured in Illinois, because that means that any incidental damage they may do on your property will be a real hassle to recover compensation for. It is never wise to work with uninsured tradesmen of any kind. Most states also require that someone have insurance in order to be issued a trade license. If they say they're licensed but not insured, they're being less than truthful.

Always ask for references, and always check them. Keep in mind though that the only references you'll get are people who the contractor is certain will give him a good review. You'd also be well advised to check online review sources in Chicago as well, which will give you a broader view of customer satisfaction for a given company.