$177 Cheap Flights from Winnipeg (YWG) to Fort Myers (RSW)

View $177 flight on Tue, Dec 2, 2025Opens in a new window

Popular airlines from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Southwest Florida Intl. Airport (RSW)

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Cheap Flights from Winnipeg to Fort Myers (YWG-RSW)

Prices were available within the past 7 days and start at $177 for one-way flights and $305 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

WestJet
Thu, Oct 23 - Tue, Nov 25
YWG
Winnipeg
RSW
Fort Myers
$305 Roundtrip, found 16 hours ago
$305
Roundtrip
found 16 hours ago
Select WestJet flight, departing Thu, Oct 23 from Winnipeg to Fort Myers, returning Tue, Nov 25, priced at $305 found 16 hours ago
WestJet
Sat, Nov 1 - Wed, Dec 17
YWG
Winnipeg
RSW
Fort Myers
$327 Roundtrip, found 3 days ago
$327
Roundtrip
found 3 days ago
Select WestJet flight, departing Sat, Nov 1 from Winnipeg to Fort Myers, returning Wed, Dec 17, priced at $327 found 3 days ago
Air Canada
Tue, Oct 28 - Tue, Nov 25
YWG
Winnipeg
RSW
Fort Myers
$329 Roundtrip, found 16 hours ago
$329
Roundtrip
found 16 hours ago
Select Air Canada flight, departing Tue, Oct 28 from Winnipeg to Fort Myers, returning Tue, Nov 25, priced at $329 found 16 hours ago
United
Sun, Oct 26 - Tue, Nov 25
YWG
Winnipeg
RSW
Fort Myers
$332 Roundtrip, found 16 hours ago
$332
Roundtrip
found 16 hours ago
Select United flight, departing Sun, Oct 26 from Winnipeg to Fort Myers, returning Tue, Nov 25, priced at $332 found 16 hours ago
United
Sun, Oct 26 - Fri, Nov 28
YWG
Winnipeg
RSW
Fort Myers
$340 Roundtrip, found 16 hours ago
$340
Roundtrip
found 16 hours ago
Select United flight, departing Sun, Oct 26 from Winnipeg to Fort Myers, returning Fri, Nov 28, priced at $340 found 16 hours ago
WestJet
Sat, Nov 1 - Wed, Dec 17
YWG
Winnipeg
RSW
Fort Myers
$351 Roundtrip, found 3 days ago
$351
Roundtrip
found 3 days ago
Select WestJet flight, departing Sat, Nov 1 from Winnipeg to Fort Myers, returning Wed, Dec 17, priced at $351 found 3 days ago
Air Canada
Wed, Oct 29 - Tue, Nov 25
YWG
Winnipeg
RSW
Fort Myers
$353 Roundtrip, found 16 hours ago
$353
Roundtrip
found 16 hours ago
Select Air Canada flight, departing Wed, Oct 29 from Winnipeg to Fort Myers, returning Tue, Nov 25, priced at $353 found 16 hours ago
Air Canada
Tue, Oct 28 - Mon, Dec 1
YWG
Winnipeg
RSW
Fort Myers
$357 Roundtrip, found 16 hours ago
$357
Roundtrip
found 16 hours ago
Select Air Canada flight, departing Tue, Oct 28 from Winnipeg to Fort Myers, returning Mon, Dec 1, priced at $357 found 16 hours ago
United
Sun, Oct 26 - Mon, Dec 1
YWG
Winnipeg
RSW
Fort Myers
$360 Roundtrip, found 16 hours ago
$360
Roundtrip
found 16 hours ago
Select United flight, departing Sun, Oct 26 from Winnipeg to Fort Myers, returning Mon, Dec 1, priced at $360 found 16 hours ago
Delta
Mon, Oct 27 - Sat, Nov 29
YWG
Winnipeg
RSW
Fort Myers
$365 Roundtrip, found 16 hours ago
$365
Roundtrip
found 16 hours ago
Select Delta flight, departing Mon, Oct 27 from Winnipeg to Fort Myers, returning Sat, Nov 29, priced at $365 found 16 hours ago

Find the cheapest month to fly from Winnipeg (YWG) to Fort Myers (RSW)

March is typically the cheapest month to fly

From $222 - $505 per traveler.

Graph displaying average flight prices per month

Flights from Winnipeg (YWG) to Fort Myers (RSW)
Origin airport
Winnipeg James Armstrong Richardson Intl.
Destination airport
Southwest Florida Intl.
Airlines serving
Air Canada, Delta, United, WestJet
Roundtrip price
$304
Distance
1812 mi

Winnipeg to Fort Myers Flights

The cheapest times to fly from Winnipeg 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 Winnipeg to Fort Myers are during the month of October. You can find some of the cheapest flights from Winnipeg to Fort Myers with Expedia's search tool and vast selection of airlines.

 

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

Sunday is one of the best days to book for cheap flights from Winnipeg 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 Winnipeg 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 Winnipeg to Fort Myers in 2025. You can also book with separate airlines for your outbound and return journeys, from $177 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 Winnipeg 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 Winnipeg 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 Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Southwest Florida Intl. Airport (RSW) cost?
Discover the latest flight deals from YWG to RSW 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 YWG to RSW?
The cheapest flights from YWG to RSW 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 YWG to RSW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from YWG to RSW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Southwest Florida Intl. Airport (RSW)?
Nonstop flights from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Southwest Florida Intl. Airport (RSW) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel dates and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from YWG to RSW?
Typically you'll find the greatest selection of flight options on a Friday. Tuesdays tend to be the quietest.* But this can change depending on the season, carrier 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 Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Southwest Florida Intl. Airport (RSW)?
To reach Southwest Florida Intl. Airport (RSW) without delays, book a flight that leaves from Winnipeg James Armstrong Richardson Intl. Airport (YWG) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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.
Is it cheaper to buy a plane ticket from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Southwest Florida Intl. Airport (RSW) last-minute?
Booking your flight from YWG to RSW just before your journey is generally more expensive. However, if you're flexible with your travel times and dates, you could score a cheap last-minute fare.
Is it cheaper to book a YWG to RSW flight and hotel package?
Securing a YWG to RSW flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels all in one place. Choose from our impressive range of stays and then add flights, car rentals 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 Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Southwest Florida Intl. Airport (RSW)?
In most instances, you can reschedule or cancel your YWG to RSW flight. However, additional fees may apply, especially if you booked more than 24 hours ago. Check your itinerary for the airline's fees and rules on flight changes, or if you'd like further information, head to our Customer Service portal.

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*Available to One Key members.