Chicago is a high cost-of-living market — pricing guide and permit rules below.
Chicago roofing rates: $10,000-$30,000 per roof. Always get 3 written quotes and verify IL licensing at Illinois IDFPR (idfpr.illinois.gov). Sales tax on materials: 10.25%.
Chicago requires permits when work exceeds $500 or involves full system replacement. Your licensed contractor pulls the permit — if they ask you to pull it, that's a red flag.