S$193 Cheap Flights from Chicago to Fort Myers

View S$193 flight on Sat, 3 Jan, 2026Opens 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 S$193 for one-way flights and S$335 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, 3 Jan - Wed, 7 Jan
ORD
Chicago
RSW
Fort Myers
S$335 Return, found 5 days ago
S$335
Return
found 5 days ago
Select Delta flight, departing Sat, 3 Jan from Chicago to Fort Myers, returning Wed, 7 Jan, priced at S$335 found 5 days ago
Delta
Sat, 3 Jan - Wed, 7 Jan
ORD
Chicago
RSW
Fort Myers
S$349 Return, found 5 days ago
S$349
Return
found 5 days ago
Select Delta flight, departing Sat, 3 Jan from Chicago to Fort Myers, returning Wed, 7 Jan, priced at S$349 found 5 days ago
Delta
Sat, 3 Jan - Wed, 7 Jan
ORD
Chicago
RSW
Fort Myers
S$363 Return, found 5 days ago
S$363
Return
found 5 days ago
Select Delta flight, departing Sat, 3 Jan from Chicago to Fort Myers, returning Wed, 7 Jan, priced at S$363 found 5 days ago
Delta
Sun, 4 Jan - Thu, 8 Jan
ORD
Chicago
RSW
Fort Myers
S$376 Return, found 5 days ago
S$376
Return
found 5 days ago
Select Delta flight, departing Sun, 4 Jan from Chicago to Fort Myers, returning Thu, 8 Jan, priced at S$376 found 5 days ago
United
Sat, 3 Jan - Wed, 7 Jan
ORD
Chicago
RSW
Fort Myers
S$376 Return, found 5 days ago
S$376
Return
found 5 days ago
Select United flight, departing Sat, 3 Jan from Chicago to Fort Myers, returning Wed, 7 Jan, priced at S$376 found 5 days ago
Delta
Sat, 3 Jan - Wed, 7 Jan
ORD
Chicago
RSW
Fort Myers
S$386 Return, found 5 days ago
S$386
Return
found 5 days ago
Select Delta flight, departing Sat, 3 Jan from Chicago to Fort Myers, returning Wed, 7 Jan, priced at S$386 found 5 days ago
American Airlines
Sat, 3 Jan - Wed, 7 Jan
ORD
Chicago
RSW
Fort Myers
S$388 Return, found 5 days ago
S$388
Return
found 5 days ago
Select American Airlines flight, departing Sat, 3 Jan from Chicago to Fort Myers, returning Wed, 7 Jan, priced at S$388 found 5 days ago
United
Sat, 3 Jan - Wed, 7 Jan
ORD
Chicago
RSW
Fort Myers
S$389 Return, found 5 days ago
S$389
Return
found 5 days ago
Select United flight, departing Sat, 3 Jan from Chicago to Fort Myers, returning Wed, 7 Jan, priced at S$389 found 5 days ago
Delta
Sun, 4 Jan - Thu, 8 Jan
ORD
Chicago
RSW
Fort Myers
S$397 Return, found 5 days ago
S$397
Return
found 5 days ago
Select Delta flight, departing Sun, 4 Jan from Chicago to Fort Myers, returning Thu, 8 Jan, priced at S$397 found 5 days ago
American Airlines
Sat, 3 Jan - Wed, 7 Jan
ORD
Chicago
RSW
Fort Myers
S$402 Return, found 5 days ago
S$402
Return
found 5 days ago
Select American Airlines flight, departing Sat, 3 Jan from Chicago to Fort Myers, returning Wed, 7 Jan, priced at S$402 found 5 days ago

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

January is typically the cheapest month to fly

From S$76 - S$218 per traveller.
Chicago to Fort Myers route information
Origin airport
O'Hare Intl.
Destination airport
Southwest Florida Intl.
Return price
S$334
Distance
1796 km
Average flight time
3 hours 55 mins

Perfect flights from Chicago to Fort Myers

Your Journey from Chicago to Fort Myers

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to Fort Myers caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta, United, American Airlines. Our selection of flights from O'Hare Intl. to Southwest Florida Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Chicago to Fort Myers Flights

Experience the joy of finding cheap flights from O'Hare Intl. to Southwest Florida Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$193 and roundtrip prices from S$335*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to Fort Myers with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Fort Myers

Picture yourself stepping off the plane in Fort Myers and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Chicago to Fort Myers Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Chicago to Fort Myers.
 

Beyond the Flight – Exploring Fort Myers

With Expedia, your adventure extends beyond the flight. Explore Fort Myers at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Chicago to Fort Myers with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Chicago to Fort Myers with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

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 S$335. 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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