$90 Cheap American Airlines flights Fort Myers (RSW) to Chicago (ORD)

Scoring cheap one-way American Airlines flights from RSW to ORD from $90 on Expedia couldn’t be easier — just filter by “Price (lowest to highest).” Or check out our affordable return fares from $157 for your next adventure.**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.

American Airlines flights to Chicago are generally more affordable in the low-season months of January and February. Whether you need a round-trip or one-way ticket, you could land a better deal then.

Search for cheap American Airlines flights from Southwest Florida Intl. Airport (RSW) to O’Hare Intl. Airport (ORD) one to three months ahead of your departure. 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. Regardless of fare type and journey, the best day to book a domestic flight is generally 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 their travel 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.

Book a seat on one of American Airlines’s 14 direct weekly flights from Southwest Florida Intl. Airport (RSW) to O’Hare Intl. Airport (ORD). To see your choices, enter your dates, destination and origin and hit search. Next, apply the “Nonstop” and “Airline” filters.

It takes approximately 3h 15m to travel nonstop from Southwest Florida Intl. Airport (RSW) to O’Hare Intl. Airport (ORD) with American Airlines.

Thursday has the most American Airlines flights from Southwest Florida Intl. Airport (RSW) to O’Hare Intl. Airport (ORD). With 2 daily departures, this is the best day of the week to book something that will work for your schedule.

Taking off from RSW at 12:38PM UTC-5, the first American Airlines flight to ORD arrives at 2:50PM UTC-6. Traveling early means you’re less likely to experience cancellations.* Not a morning person? The last American Airlines flight from RSW to ORD departs at 5:29PM UTC-5 and touches down at 7:45PM UTC-6.*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.

O’Hare Intl. Airport (ORD) is the main gateway for American Airlines flights from Southwest Florida Intl. Airport (RSW) to Chicago. But this airline also flies to Midway Intl. Airport (MDW). Be sure to choose the “All Airports” option for your destination to see all available choices for your escape in Chicago.

You’ll likely be on a Boeing 737-800 or an Airbus A319 when flying American Airlines from Southwest Florida Intl. Airport (RSW) to O’Hare Intl. Airport (ORD). However, keep in mind that a different plane could be assigned to your route depending on operational requirements.

Changes are typically free within 24 hours of making your booking, but your airline may charge a fee after that time. For more details about altering your flights, check out your “Trips,” select your flight and click on “Manage Booking.” If you’d like the flexibility to update your itinerary without being charged, apply the “Changes included” and “No cancel fee” filters when organizing your next break.