$79 Cheap American Airlines flights Chicago (ORD) to Fort Myers (RSW)

You can find budget-friendly return American Airlines flights from $119 from ORD to RSW by sorting your results from "Price (lowest to highest)" on Expedia. Or look for options from $79 for a one-way trip.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Look for affordable American Airlines flights from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW) one to three months before your departure date. Travelers who book domestic flights 34 to 86 days in advance can save 25% compared to those who book just 6 to 12 days ahead. No matter the fare type and journey, the best day to book a domestic flight is usually Sunday and the most expensive tends to be Monday. Passengers who book on a Sunday can save 6% on average compared to those who book on a Monday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.

The first American Airlines flight from ORD to RSW departs at 8:05AM UTC-6, arriving at 12:02PM UTC-5. If you prefer to head off later in the day, the last American Airlines flight leaves ORD at 12:42PM UTC-6 and lands at RSW at 4:39PM UTC-5. Flying before midday is generally a smart option as morning and mid-morning flights are least likely to face cancellations.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.