$287 Cheap Flights from Winnipeg (YWG) to Port of Spain (POS)

View $287 flight on Fri, Oct 3, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at $287 for one-way flights and $550 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Sun, Nov 23 - Mon, Dec 8
YWG
Winnipeg
POS
Trinidad
$550 Roundtrip, found 6 days ago
$550
Roundtrip
found 6 days ago
Select Air Canada flight, departing Sun, Nov 23 from Winnipeg to Trinidad, returning Mon, Dec 8, priced at $550 found 6 days ago
Air Canada
Sat, Jan 24 - Mon, Feb 2
YWG
Winnipeg
POS
Trinidad
$561 Roundtrip, found 2 days ago
$561
Roundtrip
found 2 days ago
Select Air Canada flight, departing Sat, Jan 24 from Winnipeg to Trinidad, returning Mon, Feb 2, priced at $561 found 2 days ago
Air Canada
Mon, Nov 24 - Mon, Dec 8
YWG
Winnipeg
POS
Trinidad
$620 Roundtrip, found 6 days ago
$620
Roundtrip
found 6 days ago
Select Air Canada flight, departing Mon, Nov 24 from Winnipeg to Trinidad, returning Mon, Dec 8, priced at $620 found 6 days ago
Air Canada
Sun, Nov 23 - Tue, Dec 9
YWG
Winnipeg
POS
Trinidad
$635 Roundtrip, found 6 days ago
$635
Roundtrip
found 6 days ago
Select Air Canada flight, departing Sun, Nov 23 from Winnipeg to Trinidad, returning Tue, Dec 9, priced at $635 found 6 days ago
Air Canada
Fri, Nov 14 - Tue, Nov 25
YWG
Winnipeg
POS
Trinidad
$650 Roundtrip, found 6 days ago
$650
Roundtrip
found 6 days ago
Select Air Canada flight, departing Fri, Nov 14 from Winnipeg to Trinidad, returning Tue, Nov 25, priced at $650 found 6 days ago
Air Canada
Mon, Dec 29 - Wed, Jan 14
YWG
Winnipeg
POS
Trinidad
$657 Roundtrip, found 6 days ago
$657
Roundtrip
found 6 days ago
Select Air Canada flight, departing Mon, Dec 29 from Winnipeg to Trinidad, returning Wed, Jan 14, priced at $657 found 6 days ago
Air Canada
Sun, Dec 7 - Fri, Dec 26
YWG
Winnipeg
POS
Trinidad
$670 Roundtrip, found 6 days ago
$670
Roundtrip
found 6 days ago
Select Air Canada flight, departing Sun, Dec 7 from Winnipeg to Trinidad, returning Fri, Dec 26, priced at $670 found 6 days ago
Air Canada
Sun, Nov 23 - Fri, Dec 12
YWG
Winnipeg
POS
Trinidad
$671 Roundtrip, found 6 days ago
$671
Roundtrip
found 6 days ago
Select Air Canada flight, departing Sun, Nov 23 from Winnipeg to Trinidad, returning Fri, Dec 12, priced at $671 found 6 days ago
Air Canada
Sun, Nov 23 - Thu, Dec 11
YWG
Winnipeg
POS
Trinidad
$671 Roundtrip, found 6 days ago
$671
Roundtrip
found 6 days ago
Select Air Canada flight, departing Sun, Nov 23 from Winnipeg to Trinidad, returning Thu, Dec 11, priced at $671 found 6 days ago
United
Fri, Oct 3 - Fri, Oct 10
YWG
Winnipeg
POS
Trinidad
$970 Roundtrip, found 3 hours ago
$970
Roundtrip
found 3 hours ago
Select United flight, departing Fri, Oct 3 from Winnipeg to Trinidad, returning Fri, Oct 10, priced at $970 found 3 hours ago

Find the cheapest month to fly from Winnipeg (YWG) to Piarco (POS)

May is typically the cheapest month to fly

From $445 - $1,291 per traveler.
Flights from Winnipeg (YWG) to Port of Spain (POS)
Origin airport
Winnipeg James Armstrong Richardson Intl.
Destination airport
Piarco Intl.
Airlines serving
United
Roundtrip price
$549
Distance
3397 mi

Winnipeg to Port of Spain Flights

The cheapest times to fly from Winnipeg to Port of Spain

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

 

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

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

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 Port of Spain in 2025. You can also book with separate airlines for your outbound and return journeys, from $287 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 Port of Spain 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 Port of Spain 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 Piarco Intl. Airport (POS) cost?
Get a cheap one-way flight from $287 or cheap return flight from $550 from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Piarco Intl. Airport (POS) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Piarco Intl. Airport (POS)?
Traveling in November is a great way to save, as it's the cheapest month for flights between YWG and POS. You'll typically find the lowest prices during the off-season.
What is the cheapest airline that flies from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Piarco Intl. Airport (POS)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Customize the search to your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest YWG to POS flight.
How many flights per day from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Piarco Intl. Airport (POS)?
You'll have to take a flight with a layover if you're traveling from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Piarco Intl. Airport (POS). There are no daily direct flights on this route. However, simply filter your search to include one or more stops to discover the best option for your trip.
What day of the week has the most flights from YWG to POS?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during peak travel times or public holidays.*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 Piarco Intl. Airport (POS)?
To touch down at Piarco Intl. Airport (POS) without delays, book a flight that takes off from Winnipeg James Armstrong Richardson Intl. Airport (YWG) 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 Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Piarco Intl. Airport (POS) last-minute?
Waiting until right before your break to book your flight from YWG to POS generally means paying more. While you might find some last-minute offers, there's no guarantee. Keep your travel plans flexible for the best chance of getting a bargain.
Is it cheaper to book a YWG to POS flight and hotel package?
Compared with arranging flights and hotels separately, booking a YWG to POS flight and hotel package with Expedia could lead to significant savings. Better yet, managing everything in one place will take the hassle out of travel planning. Just secure your flights and choose from our wide range of hotels, then tailor your trip with other add-ons like tours and car rentals.
Can I cancel or change the date of my flight from Winnipeg James Armstrong Richardson Intl. Airport (YWG) to Piarco Intl. Airport (POS)?
In most instances, you're able to reschedule or cancel your YWG to POS flight. However, additional charges may apply, especially if your booking was made over 24 hours ago. Check your itinerary for the airline's fees and policies on flight changes, or if you want further information, visit our Customer Service portal.

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*Available to One Key members.