฿4,215 Cheap Flights from Chicago (ORD) to Fort Myers (RSW)

View ฿4,215 flight on Sun, 5 Oct 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at ฿4,215 for one-way flights and ฿8,430 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sun, 5 Oct - Thu, 9 Oct
ORD
Chicago
RSW
Fort Myers
฿8,430 Return, found 5 days ago
฿8,430
Return
found 5 days ago
Select American Airlines flight, departing Sun, 5 Oct from Chicago to Fort Myers, returning Thu, 9 Oct, priced at ฿8,430 found 5 days ago
United
Sun, 5 Oct - Thu, 9 Oct
ORD
Chicago
RSW
Fort Myers
฿8,430 Return, found 5 days ago
฿8,430
Return
found 5 days ago
Select United flight, departing Sun, 5 Oct from Chicago to Fort Myers, returning Thu, 9 Oct, priced at ฿8,430 found 5 days ago
United
Sun, 5 Oct - Thu, 9 Oct
ORD
Chicago
RSW
Fort Myers
฿8,725 Return, found 5 days ago
฿8,725
Return
found 5 days ago
Select United flight, departing Sun, 5 Oct from Chicago to Fort Myers, returning Thu, 9 Oct, priced at ฿8,725 found 5 days ago
American Airlines
Sun, 5 Oct - Thu, 9 Oct
ORD
Chicago
RSW
Fort Myers
฿9,050 Return, found 5 days ago
฿9,050
Return
found 5 days ago
Select American Airlines flight, departing Sun, 5 Oct from Chicago to Fort Myers, returning Thu, 9 Oct, priced at ฿9,050 found 5 days ago
United
Sun, 5 Oct - Thu, 9 Oct
ORD
Chicago
RSW
Fort Myers
฿10,445 Return, found 5 days ago
฿10,445
Return
found 5 days ago
Select United flight, departing Sun, 5 Oct from Chicago to Fort Myers, returning Thu, 9 Oct, priced at ฿10,445 found 5 days ago
American Airlines
Sun, 5 Oct - Thu, 9 Oct
ORD
Chicago
RSW
Fort Myers
฿10,670 Return, found 5 days ago
฿10,670
Return
found 5 days ago
Select American Airlines flight, departing Sun, 5 Oct from Chicago to Fort Myers, returning Thu, 9 Oct, priced at ฿10,670 found 5 days ago
United
Sun, 5 Oct - Thu, 9 Oct
ORD
Chicago
RSW
Fort Myers
฿10,965 Return, found 5 days ago
฿10,965
Return
found 5 days ago
Select United flight, departing Sun, 5 Oct from Chicago to Fort Myers, returning Thu, 9 Oct, priced at ฿10,965 found 5 days ago
American Airlines
Sun, 5 Oct - Thu, 9 Oct
ORD
Chicago
RSW
Fort Myers
฿11,280 Return, found 5 days ago
฿11,280
Return
found 5 days ago
Select American Airlines flight, departing Sun, 5 Oct from Chicago to Fort Myers, returning Thu, 9 Oct, priced at ฿11,280 found 5 days ago
Delta
Sun, 5 Oct - Thu, 9 Oct
ORD
Chicago
RSW
Fort Myers
฿12,000 Return, found 5 days ago
฿12,000
Return
found 5 days ago
Select Delta flight, departing Sun, 5 Oct from Chicago to Fort Myers, returning Thu, 9 Oct, priced at ฿12,000 found 5 days ago
United
Sun, 5 Oct - Thu, 9 Oct
ORD
Chicago
RSW
Fort Myers
฿12,295 Return, found 5 days ago
฿12,295
Return
found 5 days ago
Select United flight, departing Sun, 5 Oct from Chicago to Fort Myers, returning Thu, 9 Oct, priced at ฿12,295 found 5 days ago

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

January is typically the cheapest month to fly

From ฿2,197 - ฿7,694 per traveller.
Flight from Chicago to Fort Myers route information
Origin airport
O'Hare Intl.
Destination airport
Southwest Florida Intl.
Return price
฿8,430
Distance
1796 km

Perfect flights from Chicago to Fort Myers

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from Chicago to Fort Myers. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
 
Picture yourself strolling through the streets of , surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
 
Our flexible O'Hare Intl. to Southwest Florida Intl. ticket options cater to your travel preferences, with incredible one-way fares from ฿4,215 and roundtrip prices from ฿8,430. Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
 
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at Southwest Florida Intl. and explore and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
 
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your to travel arrangements today and embark on the journey of a lifetime in Fort Myers.

Frequently asked questions

How much is a flight from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport?
If you're travelling between O'Hare Airport and Southwest Florida Intl. Airport (RSW), round-trip flights start from ฿8,430. This figure is based on fares quoted within the last 7 days on Expedia for flights departing within the next year, so don't delay. Book now and save yourself money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from ORD to Southwest Florida Intl. Airport (RSW)?
We get that life can throw the odd curveball, so we've made it as hassle-free as possible for you to cancel your flight online. Just visit the Customer Service Portal and follow the instructions.
How do I find cheap flights from O'Hare Airport to Southwest Florida Intl. Airport (RSW) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for ORD to Southwest Florida Intl. Airport (RSW) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from ORD to RSW?
The flight distance between O'Hare Intl. Airport (ORD) (ORD) and RSW (RSW) is 1,800 kilometres. Listen to some music or finish that novel and the journey will zip by.
Which airlines fly direct from ORD to RSW?
There are several airlines that travel directly from O'Hare Intl. Airport (ORD) to RSW. United Airlines (UA) is a popular choice, offering 121 flights every month. Operating 73 flights a month along this route, American Airlines (AA) is another good option.
Are ORD to Southwest Florida Intl. Airport (RSW) flight tickets cheaper when they're purchased at the last minute?
Late planners can occasionally nab a bargain, with some of the cheapest fares from O'Hare Intl. Airport (ORD) to Southwest Florida Intl. Airport surfacing a few weeks before the departure date. If you'd rather plan ahead of time, Expedia compares and updates the best flight deals regularly — as early as a year in advance in some cases. It does depend on the carrier though, as not all airlines quote prices that far in advance.

Explore a world of travel with Expedia

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