$395 Cheap Flights from Port of Spain (POS) to Winnipeg (YWG)

View $395 flight on Sat, Nov 8, 2025Opens in a new window

Popular airlines from Piarco Intl. Airport (POS) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)

Cheap Flights from Port of Spain to Winnipeg (POS-YWG)

Prices were available within the past 7 days and start at $395 for one-way flights and $786 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Caribbean Airlines
Mon, Nov 10 - Sun, Nov 23
POS
Trinidad
YWG
Winnipeg
$786 Roundtrip, found 3 days ago
$786
Roundtrip
found 3 days ago
Select Caribbean Airlines flight, departing Mon, Nov 10 from Trinidad to Winnipeg, returning Sun, Nov 23, priced at $786 found 3 days ago
Air Canada
Fri, Nov 14 - Sun, Nov 23
POS
Trinidad
YWG
Winnipeg
$805 Roundtrip, found 9 hours ago
$805
Roundtrip
found 9 hours ago
Select Air Canada flight, departing Fri, Nov 14 from Trinidad to Winnipeg, returning Sun, Nov 23, priced at $805 found 9 hours ago
Air Canada
Fri, Nov 14 - Tue, Nov 18
POS
Trinidad
YWG
Winnipeg
$812 Roundtrip, found 4 days ago
$812
Roundtrip
found 4 days ago
Select Air Canada flight, departing Fri, Nov 14 from Trinidad to Winnipeg, returning Tue, Nov 18, priced at $812 found 4 days ago
Caribbean Airlines
Wed, Nov 12 - Fri, Nov 28
POS
Trinidad
YWG
Winnipeg
$812 Roundtrip, found 4 days ago
$812
Roundtrip
found 4 days ago
Select Caribbean Airlines flight, departing Wed, Nov 12 from Trinidad to Winnipeg, returning Fri, Nov 28, priced at $812 found 4 days ago
Caribbean Airlines
Sat, Jan 24 - Fri, Jan 30
POS
Trinidad
YWG
Winnipeg
$826 Roundtrip, found 14 hours ago
$826
Roundtrip
found 14 hours ago
Select Caribbean Airlines flight, departing Sat, Jan 24 from Trinidad to Winnipeg, returning Fri, Jan 30, priced at $826 found 14 hours ago
Caribbean Airlines
Tue, Jan 27 - Thu, Jan 29
POS
Trinidad
YWG
Winnipeg
$828 Roundtrip, found 4 days ago
$828
Roundtrip
found 4 days ago
Select Caribbean Airlines flight, departing Tue, Jan 27 from Trinidad to Winnipeg, returning Thu, Jan 29, priced at $828 found 4 days ago
Caribbean Airlines
Sat, Jan 24 - Fri, Jan 30
POS
Trinidad
YWG
Winnipeg
$832 Roundtrip, found 14 hours ago
$832
Roundtrip
found 14 hours ago
Select Caribbean Airlines flight, departing Sat, Jan 24 from Trinidad to Winnipeg, returning Fri, Jan 30, priced at $832 found 14 hours ago
Caribbean Airlines
Tue, Nov 25 - Tue, Dec 2
POS
Trinidad
YWG
Winnipeg
$845 Roundtrip, found 5 days ago
$845
Roundtrip
found 5 days ago
Select Caribbean Airlines flight, departing Tue, Nov 25 from Trinidad to Winnipeg, returning Tue, Dec 2, priced at $845 found 5 days ago
Air Canada
Wed, Dec 3 - Thu, Dec 25
POS
Trinidad
YWG
Winnipeg
$845 Roundtrip, found 5 days ago
$845
Roundtrip
found 5 days ago
Select Air Canada flight, departing Wed, Dec 3 from Trinidad to Winnipeg, returning Thu, Dec 25, priced at $845 found 5 days ago
United
Mon, Aug 17 - Mon, Aug 24
POS
Trinidad
YWG
Winnipeg
$3,542 Roundtrip, found 2 days ago
$3,542
Roundtrip
found 2 days ago
Select United flight, departing Mon, Aug 17 from Trinidad to Winnipeg, returning Mon, Aug 24, priced at $3,542 found 2 days ago

Alternative airports near Winnipeg

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Winnipeg Intl. YWG. Cheapest and Closest option available. Average driving time to city center is 15 minutes. Flights from $878
YWG
Winnipeg Intl.
CheapestClosest
Average driving time to city center15 min
Flights from $878
Flights from Port of Spain (POS) to Winnipeg (YWG)
Origin airport
Piarco Intl.
Destination airport
Winnipeg James Armstrong Richardson Intl.
Airlines serving
Air Canada, United
Roundtrip price
$786
Distance
3397 mi

Port of Spain to Winnipeg Flights

The cheapest times to fly from Port of Spain to Winnipeg

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

 

The best time to book a flight from Port of Spain to Winnipeg

Sunday is one of the best days to book for cheap flights from Port of Spain to Winnipeg: 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 Port of Spain to Winnipeg

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 Port of Spain to Winnipeg in 2025. You can also book with separate airlines for your outbound and return journeys, from $395 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 Port of Spain to Winnipeg 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 Port of Spain to Winnipeg 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 Piarco Intl. Airport (POS) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) cost?
Snag a cheap one-way flight from $395 or cheap return flight from $786 from Piarco Intl. Airport (POS) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Piarco Intl. Airport (POS) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
The cheapest month to fly from POS to YWG is November, when there's less demand. Off-peak months are usually when you'll find lower airfares between these airports.
What is the cheapest airline that flies from Piarco Intl. Airport (POS) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
To find the cheapest airline flying from POS to YWG, use Expedia's filter tool. Tailor your search based on what matters most to you, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Piarco Intl. Airport (POS) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
Nonstop flights from Piarco Intl. Airport (POS) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filters. Enter your travel details and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from POS to YWG?
Typically you'll find the widest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* But this can change depending on the airline, season 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 Piarco Intl. Airport (POS) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
To arrive at Winnipeg James Armstrong Richardson Intl. Airport (YWG) on schedule, opt for a flight that leaves from Piarco Intl. Airport (POS) before 3 PM. The chance 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 Piarco Intl. Airport (POS) to Winnipeg James Armstrong Richardson Intl. Airport (YWG) last-minute?
Holding off until just before your trip to book a flight from POS to YWG often results in higher prices. While you may find some last-minute offers, they aren't always guaranteed. Be flexible with your itinerary to maximize your chances of landing a bargain.
Is it cheaper to book a POS to YWG flight and hotel package?
You'll typically save money by booking a POS to YWG flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one convenient place. After choosing your ideal flights and accommodations, consider adding extras including activities, tours and car rentals.
Can I cancel or change the date of my flight from Piarco Intl. Airport (POS) to Winnipeg James Armstrong Richardson Intl. Airport (YWG)?
In most cases, you're able to reschedule or cancel your POS to YWG flight. However, there may be additional charges, especially if you booked over 24 hours ago. Check your itinerary for the airline's guidelines and fees on flight changes, or if you'd like further information, go to our Customer Service portal.

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*Available to One Key members.