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This really only matters if you have a preference, but it is good to ask. If you have a strong ideological belief about unions or nonunions, it's perfectly acceptable to make a decision based on the preference.
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.
Though a standard question, it's important to ask. Most contractors will tell you how long they expect the job to take without you asking. If they don't volunteer that information, be sure to ask. It's also helpful to ask if that's a hard finish date, meaning that it's the definite finish date. If it's a soft finish date, it may be extended for any number of reasons.
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 West Chicago contractor will know how much they need for a deposit when they've given you the estimate, so ask early.