€77 Cheap Flights Chicago to Fort Myers (ORD-RSW)

View €77 flight on Wed, 17 Dec 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at €77 for one-way flights and €171 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Fri, 5 Dec - Sun, 7 Dec
ORD
Chicago
RSW
Fort Myers
€171 Return, found 2 days ago
€171
Return
found 2 days ago
Select American Airlines flight, departing Fri, 5 Dec from Chicago to Fort Myers, returning Sun, 7 Dec, priced at €171 found 2 days ago
JetBlue Airways
Fri, 5 Dec - Sun, 7 Dec
ORD
Chicago
RSW
Fort Myers
€185 Return, found 2 days ago
€185
Return
found 2 days ago
Select JetBlue Airways flight, departing Fri, 5 Dec from Chicago to Fort Myers, returning Sun, 7 Dec, priced at €185 found 2 days ago
Delta
Fri, 5 Dec - Sun, 7 Dec
ORD
Chicago
RSW
Fort Myers
€188 Return, found 2 days ago
€188
Return
found 2 days ago
Select Delta flight, departing Fri, 5 Dec from Chicago to Fort Myers, returning Sun, 7 Dec, priced at €188 found 2 days ago
United
Fri, 5 Dec - Sun, 7 Dec
ORD
Chicago
RSW
Fort Myers
€214 Return, found 2 days ago
€214
Return
found 2 days ago
Select United flight, departing Fri, 5 Dec from Chicago to Fort Myers, returning Sun, 7 Dec, priced at €214 found 2 days ago
American Airlines
Thu, 30 Oct - Mon, 3 Nov
ORD
Chicago
RSW
Fort Myers
€216 Return, found 10 hours ago
€216
Return
found 10 hours ago
Select American Airlines flight, departing Thu, 30 Oct from Chicago to Fort Myers, returning Mon, 3 Nov, priced at €216 found 10 hours ago
American Airlines
Wed, 17 Dec - Mon, 22 Dec
ORD
Chicago
RSW
Fort Myers
€219 Return, found 6 days ago
€219
Return
found 6 days ago
Select American Airlines flight, departing Wed, 17 Dec from Chicago to Fort Myers, returning Mon, 22 Dec, priced at €219 found 6 days ago
American Airlines
Wed, 17 Dec - Mon, 22 Dec
ORD
Chicago
RSW
Fort Myers
€227 Return, found 6 days ago
€227
Return
found 6 days ago
Select American Airlines flight, departing Wed, 17 Dec from Chicago to Fort Myers, returning Mon, 22 Dec, priced at €227 found 6 days ago
American Airlines
Wed, 17 Dec - Mon, 22 Dec
ORD
Chicago
RSW
Fort Myers
€228 Return, found 6 days ago
€228
Return
found 6 days ago
Select American Airlines flight, departing Wed, 17 Dec from Chicago to Fort Myers, returning Mon, 22 Dec, priced at €228 found 6 days ago
United
Fri, 31 Oct - Sun, 2 Nov
ORD
Chicago
RSW
Fort Myers
€231 Return, found 5 days ago
€231
Return
found 5 days ago
Select United flight, departing Fri, 31 Oct from Chicago to Fort Myers, returning Sun, 2 Nov, priced at €231 found 5 days ago
American Airlines
Fri, 31 Oct - Sun, 2 Nov
ORD
Chicago
RSW
Fort Myers
€235 Return, found 5 days ago
€235
Return
found 5 days ago
Select American Airlines flight, departing Fri, 31 Oct from Chicago to Fort Myers, returning Sun, 2 Nov, priced at €235 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 €57 - €187 per traveller.
Chicago to Fort Myers route information
Origin airport
O'Hare Intl.
Destination airport
Southwest Florida Intl.
Return price
€170
Distance
1796 km
Average flight time
4 hours 38 mins

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 Fort Myers, 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 €77 and roundtrip prices from €171. 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 Fort Myers 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 ORD to RSW 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 €171. 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.

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