$67 Cheap Flights from Chicago (ORD) to Fort Myers (FMY)

View $67 flight on Thu, May 22, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Page Field Airport (FMY)

Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Fort Myers (ORD-FMY)

Prices were available within the past 7 days and start at $67 for one-way flights and $134 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Oct 21 - Tue, Oct 28
ORD
Chicago
RSW
Fort Myers
$134 Roundtrip, found 1 hour ago
$134
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Oct 21 from Chicago to Fort Myers, returning Tue, Oct 28, priced at $134 found 1 hour ago
Spirit Airlines
Wed, Aug 27 - Sat, Sep 6
ORD
Chicago
RSW
Fort Myers
$140 Roundtrip, found 5 days ago
$140
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, Aug 27 from Chicago to Fort Myers, returning Sat, Sep 6, priced at $140 found 5 days ago
Spirit Airlines
Fri, May 30 - Mon, Jun 2
ORD
Chicago
RSW
Fort Myers
$154 Roundtrip, just found
$154
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, May 30 from Chicago to Fort Myers, returning Mon, Jun 2, priced at $154 just found
Spirit Airlines
Thu, May 22 - Sun, May 25
ORD
Chicago
RSW
Fort Myers
$157 Roundtrip, found 2 hours ago
$157
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Thu, May 22 from Chicago to Fort Myers, returning Sun, May 25, priced at $157 found 2 hours ago
Spirit Airlines
Wed, Aug 27 - Thu, Sep 11
ORD
Chicago
RSW
Fort Myers
$160 Roundtrip, found 5 days ago
$160
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, Aug 27 from Chicago to Fort Myers, returning Thu, Sep 11, priced at $160 found 5 days ago
United
Wed, Jul 2 - Fri, Jul 11
ORD
Chicago
RSW
Fort Myers
$164 Roundtrip, found 5 hours ago
$164
Roundtrip
found 5 hours ago
Select United flight, departing Wed, Jul 2 from Chicago to Fort Myers, returning Fri, Jul 11, priced at $164 found 5 hours ago
Spirit Airlines
Fri, May 30 - Wed, Jun 4
ORD
Chicago
RSW
Fort Myers
$166 Roundtrip, found 1 hour ago
$166
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Fri, May 30 from Chicago to Fort Myers, returning Wed, Jun 4, priced at $166 found 1 hour ago
Southwest Airlines
Sat, Aug 30 - Wed, Sep 3
ORD
Chicago
RSW
Fort Myers
$167 Roundtrip, found 8 hours ago
$167
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Sat, Aug 30 from Chicago to Fort Myers, returning Wed, Sep 3, priced at $167 found 8 hours ago
Delta
Tue, Jul 1 - Fri, Jul 11
ORD
Chicago
RSW
Fort Myers
$176 Roundtrip, found 3 hours ago
$176
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Jul 1 from Chicago to Fort Myers, returning Fri, Jul 11, priced at $176 found 3 hours ago
American Airlines
Sat, Aug 30 - Sun, Sep 7
ORD
Chicago
RSW
Fort Myers
$179 Roundtrip, just found
$179
Roundtrip
just found
Select American Airlines flight, departing Sat, Aug 30 from Chicago to Fort Myers, returning Sun, Sep 7, priced at $179 just found
Flights from Chicago (ORD) to Fort Myers (RSW)
Origin airport
O'Hare Intl.
Destination airport
Southwest Florida Intl.
Roundtrip price
$134
Distance
1122 mi

Chicago to Fort Myers Flights

The cheapest times to fly from Chicago to Fort Myers

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Fort Myers are during the month of October. You can find some of the cheapest flights from Chicago to Fort Myers with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Chicago to Fort Myers

Sunday is one of the best days to book for cheap flights from Chicago to Fort Myers: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Chicago to Fort Myers

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Fort Myers in 2025. You can also book with separate airlines for your outbound and return journeys, from $67 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Fort Myers flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Fort Myers airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Page Field Airport (FMY) cost?
Discover the latest flight deals from ORD to FMY by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from ORD to FMY?
The cheapest flights from ORD to FMY are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ORD to FMY?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from ORD to FMY. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from O'Hare Intl. Airport (ORD) to Page Field Airport (FMY)?
There are no daily nonstop flights from O’Hare Intl. Airport (ORD) to Page Field Airport (FMY). But you can book flights with layovers. Filter your search results on Expedia to include one or more stops, and you’ll be soaring above the clouds in no time.
What day of the week has the most flights from ORD to FMY?
Generally you’ll find the greatest selection of flight options on a Friday. Tuesdays are often the quietest.* But this can change based on the season, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Page Field Airport (FMY)?
To avoid potential delays on the O’Hare Intl. Airport (ORD) to Page Field Airport (FMY) route, fly before 3 PM. Flights after this time are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Fort Myers from O'Hare Intl. Airport (ORD)?
Southwest Florida Intl. Airport (RSW) is the only airport in Fort Myers with direct flights from O’Hare Intl. Airport (ORD). Check out your options and discover cheap fares on Expedia.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Page Field Airport (FMY) last-minute?
Last-minute fares from ORD to FMY are usually more expensive. To secure the best prices, start looking for flights ahead of time. That said, if you’re flexible with your travel plans, it’s possible to find a cheap fare right before you leave.
Is it cheaper to book an ORD to FMY flight and hotel package?
Opting for an ORD to FMY flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels in one place. Choose from our impressive range of hotels and then add car rentals, flights and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Page Field Airport (FMY)?
If you reserved your ORD to FMY flight in the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the fare type you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you want more information.

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*Available to One Key members.