Chicago runs on deadlines that start the day you move in, and none of them send you a reminder. Illinois gives you 90 days to trade your out-of-state driver's licence, but only 30 for the plates — and the city gives you 30 for the vehicle sticker, after which the ticket starts at $200 and can be written again every day until you comply.
This list is ordered by how soon each thing bites, not by how important it feels. The three vehicle deadlines come first, then the parking rules that catch new arrivals in their first winter, then the free cards and accounts worth having.
Every step links to the agency that sets the rule rather than to a summary of it, because these change. Checked against the official pages on 19 September 2026. If you are reading this much later, follow the link — the deadline is the thing to trust, not the date on this page.