A flight from Illinois to Florida usually takes about 2.5 to 3.5 hours, depending on the cities and weather. For example, Chicago to Orlando or Miami is often just under three hours nonstop. I’ve done this route a few times, and it’s one of those flights that feels pretty quick—just enough time for a movie or a short nap. Delays or connections can add time, so nonstop flights are the fastest option. If needed, travelers sometimes for flight details.