$34 Cheap Flights from Chicago (ORD) to Fort Myers (RSW)

View $34 flight on Sat, Jan 10, 2026Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)

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Today's featured flight deals from Chicago O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)

Nonstop
Carry-on included
Lower price than typical

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

Prices were available within the past 7 days and start at $34 for one-way flights and $85 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Jan 6 - Sat, Jan 10
ORD
Chicago
RSW
Fort Myers
$85 Roundtrip, found 1 hour ago
$85
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Jan 6 from Chicago to Fort Myers, returning Sat, Jan 10, priced at $85 found 1 hour ago
Frontier Airlines
Sat, Jan 10 - Sun, Jan 11
ORD
Chicago
RSW
Fort Myers
$90 Roundtrip, just found
$90
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Jan 10 from Chicago to Fort Myers, returning Sun, Jan 11, priced at $90 just found
Spirit Airlines
Sun, Nov 16 - Thu, Nov 27
ORD
Chicago
RSW
Fort Myers
$100 Roundtrip, found 16 hours ago
$100
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Sun, Nov 16 from Chicago to Fort Myers, returning Thu, Nov 27, priced at $100 found 16 hours ago
Frontier Airlines
Sat, Jan 10 - Wed, Jan 14
ORD
Chicago
RSW
Fort Myers
$104 Roundtrip, found 1 hour ago
$104
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Jan 10 from Chicago to Fort Myers, returning Wed, Jan 14, priced at $104 found 1 hour ago
Frontier Airlines
Sat, Feb 14 - Fri, Feb 20
ORD
Chicago
RSW
Fort Myers
$107 Roundtrip, found 2 days ago
$107
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Feb 14 from Chicago to Fort Myers, returning Fri, Feb 20, priced at $107 found 2 days ago
Spirit Airlines
Wed, Dec 31 - Sat, Jan 10
ORD
Chicago
RSW
Fort Myers
$109 Roundtrip, just found
$109
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Dec 31 from Chicago to Fort Myers, returning Sat, Jan 10, priced at $109 just found
Spirit Airlines
Sat, Jan 10 - Sun, Jan 11
ORD
Chicago
RSW
Fort Myers
$112 Roundtrip, just found
$112
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Jan 10 from Chicago to Fort Myers, returning Sun, Jan 11, priced at $112 just found
United
Tue, Jan 6 - Sat, Jan 10
ORD
Chicago
RSW
Fort Myers
$114 Roundtrip, found 1 hour ago
$114
Roundtrip
found 1 hour ago
Select United flight, departing Tue, Jan 6 from Chicago to Fort Myers, returning Sat, Jan 10, priced at $114 found 1 hour ago
Southwest Airlines
Fri, Jan 9 - Sat, Jan 10
ORD
Chicago
RSW
Fort Myers
$129 Roundtrip, found 7 hours ago
$129
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Fri, Jan 9 from Chicago to Fort Myers, returning Sat, Jan 10, priced at $129 found 7 hours ago
American Airlines
Fri, Dec 12 - Sat, Jan 10
ORD
Chicago
RSW
Fort Myers
$133 Roundtrip, found 3 days ago
$133
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Dec 12 from Chicago to Fort Myers, returning Sat, Jan 10, priced at $133 found 3 days ago

Find the cheapest month to fly from Chicago (ORD) to Fort Myers (RSW)

January is typically the cheapest month to fly

From $67 - $220 per traveler.

Alternative airports near Fort Myers

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Southwest Florida Intl. RSW. Cheapest option available. Average driving time to city center is 22 minutes. Flights from $204
RSW
Southwest Florida Intl.
Cheapest
Average driving time to city center22 min
Flights from $204

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW) cost?
Get a cheap one-way flight from $34 or cheap return flight from $85 from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
The cheapest month to fly from ORD to RSW is January, when demand is low. Off-peak months are typically when airlines offer better prices between these airports.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
You can pick from 4 airlines that fly direct from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW). Including:

  • United Airlines
  • American Airlines
  • Spirit Airlines

What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
While prices may vary depending on when you travel, Frontier Airlines and Spirit Airlines are go-to choices for flights between O'Hare Intl. Airport (ORD) and Southwest Florida Intl. Airport (RSW). You can also compare carriers on Expedia and use the "Sort by" filter to find the cheapest ticket for your ORD to RSW flight.
How many flights per day from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
When flying out of O'Hare Intl. Airport (ORD), you can take your pick from an average of 8 daily direct flights to Southwest Florida Intl. Airport (RSW).
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
Flights between ORD and RSW are busiest at 8 AM. If you're after a less crowded experience and potentially cheaper tickets, look for a time when demand is lower.
What day of the week has the most flights from ORD to RSW?
Sunday offers the most flights from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW). Consider jetting off on this day and you'll have a greater chance of finding a schedule that works for you.
What is the earliest flight from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
The earliest flight taking off from O'Hare Intl. Airport (ORD) is at around 5:35AM UTC-6. Hop on this flight and you'll land at Southwest Florida Intl. Airport (RSW) at approximately 9:29AM UTC-5. The overall travel time is 2h 54m.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
Typically, it takes 3 hours to cover the 1,100 mi from ORD to RSW.
What airline has the least delays from ORD to RSW?
Consider traveling with Frontier Airlines if you'd like to fly straight from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW) without any delays. This airline has the best track record for punctuality, with an on-time performance of 100%. Want to be notified if anything changes? You can check your flight status using the Expedia App.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW)?
To avoid potential delays on the O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW) route, travel before 3 PM. Later flights have a 22% higher chance of being 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)?
If you're traveling on a direct flight from O'Hare Intl. Airport (ORD) to Fort Myers, Southwest Florida Intl. Airport (RSW) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport (RSW) last-minute?
Waiting until just before your departure to book a flight from ORD to RSW generally means paying more. Although you may find some last-minute discounts, they aren't always guaranteed. Allow some flexibility in your schedule for a better chance of getting a bargain.
Is it cheaper to book an ORD to RSW flight and hotel package?
Securing an ORD to RSW flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Select from our extensive range of hotels and then add flights, car rentals and activities to your booking. Bundle it all 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 Southwest Florida Intl. Airport (RSW)?
If you booked your ORD to RSW flight within the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you want more information.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Southwest Florida Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United
Roundtrip price
$85
Distance
1122 mi
Average flight time
3 hours 56 mins

Book with confidence

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 January. 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 $34 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.

 

Chicago to Fort Myers Flights

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*Available to One Key members.