$349 Cheap Flights from Winnipeg (YWG) to Key West (EYW)

View $349 flight on Sat, Aug 15, 2026Opens in a new window

Popular airlines from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Key West Intl. Airport (EYW)

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Cheap Flights from Winnipeg to Key West (YWG-EYW)

Prices were available within the past 7 days and start at $349 for one-way flights and $739 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Fri, Jul 24 - Fri, Jul 31
YWG
Winnipeg
EYW
Key West
$739 Roundtrip, found 3 days ago
$739
Roundtrip
found 3 days ago
Select United flight, departing Fri, Jul 24 from Winnipeg to Key West, returning Fri, Jul 31, priced at $739 found 3 days ago
United
Fri, Jul 24 - Fri, Jul 31
YWG
Winnipeg
EYW
Key West
$747 Roundtrip, found 3 days ago
$747
Roundtrip
found 3 days ago
Select United flight, departing Fri, Jul 24 from Winnipeg to Key West, returning Fri, Jul 31, priced at $747 found 3 days ago
United
Fri, Jul 24 - Fri, Jul 31
YWG
Winnipeg
EYW
Key West
$749 Roundtrip, found 3 days ago
$749
Roundtrip
found 3 days ago
Select United flight, departing Fri, Jul 24 from Winnipeg to Key West, returning Fri, Jul 31, priced at $749 found 3 days ago
United
Fri, Jul 24 - Fri, Jul 31
YWG
Winnipeg
EYW
Key West
$757 Roundtrip, found 3 days ago
$757
Roundtrip
found 3 days ago
Select United flight, departing Fri, Jul 24 from Winnipeg to Key West, returning Fri, Jul 31, priced at $757 found 3 days ago
WestJet
Fri, Jul 24 - Fri, Jul 31
YWG
Winnipeg
EYW
Key West
$763 Roundtrip, found 3 days ago
$763
Roundtrip
found 3 days ago
Select WestJet flight, departing Fri, Jul 24 from Winnipeg to Key West, returning Fri, Jul 31, priced at $763 found 3 days ago
United
Fri, Jul 24 - Fri, Jul 31
YWG
Winnipeg
EYW
Key West
$770 Roundtrip, found 3 days ago
$770
Roundtrip
found 3 days ago
Select United flight, departing Fri, Jul 24 from Winnipeg to Key West, returning Fri, Jul 31, priced at $770 found 3 days ago
WestJet
Thu, Jul 23 - Thu, Jul 30
YWG
Winnipeg
EYW
Key West
$772 Roundtrip, found 2 days ago
$772
Roundtrip
found 2 days ago
Select WestJet flight, departing Thu, Jul 23 from Winnipeg to Key West, returning Thu, Jul 30, priced at $772 found 2 days ago
WestJet
Thu, Jul 23 - Thu, Jul 30
YWG
Winnipeg
EYW
Key West
$779 Roundtrip, found 2 days ago
$779
Roundtrip
found 2 days ago
Select WestJet flight, departing Thu, Jul 23 from Winnipeg to Key West, returning Thu, Jul 30, priced at $779 found 2 days ago
United
Fri, Jul 24 - Fri, Jul 31
YWG
Winnipeg
EYW
Key West
$780 Roundtrip, found 3 days ago
$780
Roundtrip
found 3 days ago
Select United flight, departing Fri, Jul 24 from Winnipeg to Key West, returning Fri, Jul 31, priced at $780 found 3 days ago
Delta
Fri, Jul 24 - Fri, Jul 31
YWG
Winnipeg
EYW
Key West
$909 Roundtrip, found 3 days ago
$909
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Jul 24 from Winnipeg to Key West, returning Fri, Jul 31, priced at $909 found 3 days ago

Frequently asked questions

How much does a flight from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Key West Intl. Airport (EYW) cost?
Grab a cheap one-way flight from $349 or cheap return flight from $739 from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Key West Intl. Airport (EYW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Key West Intl. Airport (EYW)?
Traveling in July is a good way to save, as it's the cheapest month for flights between YWG and EYW. You'll often find the lowest prices during the off-season.
What is the cheapest airline that flies from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Key West Intl. Airport (EYW)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll fly you from YWG to EYW. Then, sort your results by "Price (lowest to highest)" to pick up a good deal.
How many flights per day from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Key West Intl. Airport (EYW)?
There aren't any daily direct flights available from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Key West Intl. Airport (EYW). But you can book flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be soaring above the clouds before you know it.
What day of the week has the most flights from YWG to EYW?
Typically you'll find the most flight options available on a Friday. Tuesdays are often the quietest.* However, this can change based on the time of year, airline 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 Key West Intl. Airport (EYW)?
Choose a flight from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Key West Intl. Airport (EYW) that takes off before 3 PM to reduce the likelihood of delays and cancellations. Departures after this time have a 22% higher chance of being canceled, on average.**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 Key West Intl. Airport (EYW) last-minute?
Booking your flight from YWG to EYW right before your getaway is usually more expensive. But if you're flexible with your itinerary, you could land a cheap last-minute fare.
Is it cheaper to book a YWG to EYW flight and hotel package?
Compared with arranging hotels and flights separately, booking a YWG to EYW flight and hotel package with Expedia could result in significant savings. Better yet, having it all in one place takes the hassle out of travel planning. Simply secure your flights and choose from our wide range of stays, then customize your trip with other add-ons like activities and car rentals.
Can I cancel or change the date of my flight from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Key West Intl. Airport (EYW)?
In most instances, you can cancel or reschedule your YWG to EYW flight. However, additional fees may apply, especially if you booked more than 24 hours ago. Check your itinerary for the airline's guidelines and fees on flight changes, or if you want more details, go to our Customer Service portal.

Travel information

Origin airport
Winnipeg James Armstrong Richardson Intl.
Destination airport
Key West Intl.
Airlines serving
WestJet
Roundtrip price
$738
Distance
1938 mi

Book with confidence

Winnipeg to Key West Flights

The cheapest times to fly from Winnipeg to Key West

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 Key West are during the month of July. You can find some of the cheapest flights from Winnipeg to Key West with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Winnipeg to Key West

Sunday is one of the best days to book for cheap flights from Winnipeg to Key West: 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 Key West

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 Key West in 2025. You can also book with separate airlines for your outbound and return journeys, from $349 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 Key West 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 Key West 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.

 

Winnipeg to Key West Flights

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*Available to One Key members.