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Fort Myers

$162+ Cheap flights from Winnipeg (YWG) to Fort Myers (RSW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — RSW
Jun 10 — Jun 171
Wed 6/10
Wed 6/17
1 adult, Economy
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Cheap flight deals from Winnipeg to Fort Myers

Cheapest flights from Winnipeg to Fort Myers
Explore the most affordable flight options available from Winnipeg to Fort Myers. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 11, 2026.

This Mytrip deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:15 am
YWG
-
RSW
1 stop9h 25m
WestJet
Sun 10/2511:45 am
RSW
-
YWG
1 stop24h 50m
WestJet
Deal found 5/11$290
This United Airlines deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:00 am
YWG
-
RSW
2 stops13h 54m
United Airlines
Sat 8/224:41 pm
RSW
-
YWG
1 stop6h 52m
United Airlines
Deal found 5/10$313
This United Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/117:00 am
YWG
-
RSW
1 stop6h 36m
United Airlines
Fri 8/214:41 pm
RSW
-
YWG
1 stop6h 52m
United Airlines
Deal found 5/8$314
This United Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:00 am
YWG
-
RSW
1 stop7h 05m
United Airlines
Sun 10/259:00 pm
RSW
-
YWG
2 stops19h 59m
United Airlines
Deal found 5/11$389
This United Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/65:00 am
YWG
-
RSW
2 stops14h 34m
United Airlines
Wed 7/1511:59 am
RSW
-
YWG
2 stops11h 39m
United Airlines
Deal found 5/8$399
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/112:30 pm
YWG
-
RSW
1 stop9h 24m
Delta
Thu 1/218:10 am
RSW
-
YWG
2 stops16h 24m
Delta
Deal found 5/11$431
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:15 am
YWG
-
RSW
2 stops13h 57m
Delta
Sat 6/138:30 am
RSW
-
YWG
2 stops15h 59m
Delta
Deal found 5/6$474

Find flight deals from Winnipeg to Fort Myers

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Fort Myers (RSW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$290
(Mytrip)

One-way from

$162
(oojo)

Popular in

December

Cheapest in

September

Average price

$342
Provider with most accurate pricing for Winnipeg-Fort Myers SW Florida Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-Fort Myers SW Florida Intl flights.
Search Deals
From Winnipeg to Fort Myers SW Florida Intl
Search Deals
One-way flight from Winnipeg to Fort Myers SW Florida Intl
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Fort Myers that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 11, 2026.
Use the filters below to find and compare flights from Winnipeg to Fort Myers that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

WinnipegFort Myers

YWG - RSW

YWGRSW

Winnipeg

Tue 8/18

7:00 am-2:36 pm

1 stop6h 36m

Fort Myers SW Florida Intl

Sat 8/22

4:41 pm-10:33 pm

1 stop6h 52m

$313

WinnipegFort Myers

YWG - RSW

YWGRSW

Winnipeg

Tue 8/11

7:00 am-2:36 pm

1 stop6h 36m

Fort Myers SW Florida Intl

Fri 8/21

12:15 pm-10:33 pm

2 stops11h 18m

$313

WinnipegFort Myers

YWG - RSW

YWGRSW

Winnipeg

Thu 10/15

7:00 am-3:05 pm

1 stop7h 05m

Fort Myers SW Florida Intl

Sun 10/25

9:00 pm-3:59 pm

2 stops19h 59m

$389
Cheapest one-way

WinnipegFort Myers

YWG - RSW

YWGRSW

Winnipeg

Thu 10/15

6:15 am-4:40 pm

1 stop9h 25m

$162

WinnipegFort Myers

YWG - RSW

YWGRSW

Winnipeg

Sat 5/30

11:55 am-12:27 am

2 stops11h 32m

$214

WinnipegFort Myers

YWG - RSW

YWGRSW

Winnipeg

Sun 5/31

5:10 am-8:34 pm

2 stops14h 24m

$261

WinnipegFort Myers

YWG - RSW

YWGRSW

Winnipeg

Thu 10/15

7:10 pm-1:53 pm

2 stops17h 43m

$267

WinnipegFort Myers

YWG - RSW

YWGRSW

Winnipeg

Thu 5/28

6:40 am-9:37 pm

2 stops13h 57m

$336
Quickest one-way

WinnipegFort Myers

YWG - RSW

YWGRSW

Winnipeg

Tue 5/26

6:40 am-1:49 pm

1 stop6h 09m

$336

WinnipegFort Myers

YWG - RSW

YWGRSW

Winnipeg

Thu 10/15

4:55 pm-7:03 pm

3 stops25h 08m

$362

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/11

Showing 1-10 of 11 resultsSorted by cheapest first
1
2

Compare providers for flights from Winnipeg to Fort Myers

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Winnipeg to Fort Myers in May.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
Trip.comPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Winnipeg-Fort Myers flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-Fort Myers flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Winnipeg-Fort Myers flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Winnipeg-Fort Myers flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Winnipeg-Fort Myers flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Winnipeg to Fort Myers

Have a flexible travel schedule? Discover the best time to fly to Fort Myers from Winnipeg with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to Fort Myers

What is the cheapest month to book a flight from Winnipeg to Fort Myers?

Currently, September is the cheapest month in which you can book a flight from Winnipeg to Fort Myers (average of $305). Flying from Winnipeg to Fort Myers in December is currently the most expensive (average of $760). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Winnipeg to Fort Myers?

Reviews of airlines servicing Fort Myers

Get insights into the airlines that provide service to Fort Myers. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Fort Myers. Reviews last updated May 11, 2026.
Peruse reviews from past customers who have flown with Delta and WestJet from Winnipeg to Fort Myers to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,452 reviews

Overall

7.9

Boarding

8.1

Comfort

7.8

Crew

8.5

Food

7.2

Entertainment

7.8

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
Delta
7.9
Good
8,452 reviews
Delta
7.9
Good
8,452 reviews

Overall

7.9

Boarding

8.1

Comfort

7.8

Crew

8.5

Food

7.2

Entertainment

7.8

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
WestJet
7.2
Good
3,332 reviews
Delta
7.9
Good
8,452 reviews

Overall

7.9

Boarding

8.1

Comfort

7.8

Crew

8.5

Food

7.2

Entertainment

7.8

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Fort Myers. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Winnipeg to Fort Myers?

    United Airlines can get you from Winnipeg to Fort Myers in just under 6h 36m. Your travel time can differ by up to . The distance between Winnipeg and Fort Myers is about 1811 mi.

  • What are the cheapest airlines flying from Winnipeg to Fort Myers round-trip?

    WestJet, at $231, was found to be the cheapest airline from Winnipeg to Fort Myers. An alternate airline flying to your destination would be Delta. Users have found that WestJet is 50% cheaper than the other options available to this destination.

  • Can I find deals for flights from Winnipeg to Fort Myers that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Fort Myers flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Fort Myers?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Fort Myers.

  • Can I find deals for business class flights from Winnipeg to Fort Myers?

    Yes. Cheapflights offers flight deals from Winnipeg to Fort Myers by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Winnipeg to Fort Myers?

    Currently, September is the cheapest month in which you can book a flight from Winnipeg to Fort Myers (average of $305). Flying from Winnipeg to Fort Myers in December is currently the most expensive (average of $760). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Fort Myers?

Book flights to Fort Myers if you plan to visit one of these locations
North Fort Myers
Estero
Sanibel

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Alternative routes for Winnipeg to Fort Myers

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Winnipeg to Fort Myers

Discover the top 2 airlines that operate flights from Winnipeg to Fort Myers. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$231Average$306FlexibilityNo cancel feeOn-time60%
DeltaCheapest$306Average$506FlexibilityNo cancel feeOn-timeN/A

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