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Cheap flights from Winnipeg to Port of Spain from C$ 685

YWG — POS
10 Oct — 17 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Port of Spain

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Port of Spain

Sat 3/101:30 p.m. -
2 stops33h 45m
Mon 5/101:20 a.m. -
2 stops19h 40m
Deal found 8/9C$ 685
Thu 8/108:45 a.m. -
2 stops37h 38m
Wed 14/1012:30 a.m. -
2 stops37h 07m
Deal found 10/9C$ 904
Sat 3/105:10 p.m. -
1 stop11h 20m
Tue 6/103:55 p.m. -
1 stop18h 50m
Deal found 8/9C$ 920
Tue 15/95:10 p.m. -
1 stop11h 20m
Tue 22/93:55 p.m. -
1 stop25h 30m
Deal found 8/9C$ 1,158

Find flight deals from Winnipeg to Port of Spain

Round-trip from

C$ 685

Popular in

March

Cheapest in

February

Average price

C$ 1,314
Air Canada
  • Air Canada
  • 3/10-5/10
  • 4 total stops
  • 53h 25m total
  • Winnipeg to Port of Spain
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Highest demand for flights based on searches. 2% potential increase in price (C$ 38 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease (C$ 105 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Winnipeg to Port of Spain that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegPort of Spain

YWG Winnipeg - POS Port of Spain Piarco Intl

YWGPOS

Winnipeg

Sat 3/10

1:30 p.m.-12:15 a.m.

2 stops33h 45m

Port of Spain Piarco Intl

Mon 5/10

1:20 a.m.-8:00 p.m.

2 stops19h 40m

C$ 685

WinnipegPort of Spain

YWG Winnipeg - POS Port of Spain Piarco Intl

YWGPOS

Winnipeg

Sun 10/1

7:00 a.m.-12:20 a.m.

2 stops39h 20m

Port of Spain Piarco Intl

Fri 19/2

1:30 a.m.-6:41 p.m.

2 stops19h 11m

C$ 904

WinnipegPort of Spain

YWG Winnipeg - POS Port of Spain Piarco Intl

YWGPOS

Winnipeg

Thu 8/10

8:45 a.m.-11:23 p.m.

2 stops37h 38m

Port of Spain Piarco Intl

Wed 14/10

12:30 a.m.-12:37 p.m.

2 stops37h 07m

C$ 904
Quickest round-trip

WinnipegPort of Spain

YWG Winnipeg - POS Port of Spain Piarco Intl

YWGPOS

Winnipeg

Sat 3/10

5:10 p.m.-5:30 a.m.

1 stop11h 20m

Port of Spain Piarco Intl

Tue 6/10

3:55 p.m.-9:45 a.m.

1 stop18h 50m

C$ 920

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/9

Sorted by cheapest first

Best time to book a flight from Winnipeg to Port of Spain

Have a flexible travel schedule? Discover the best time to fly to Port of Spain from Winnipeg with our price prediction graph.
Estimated round-trip price

Reviews of airlines servicing Port of Spain

Get a feel of what it's like to fly with Air Canada from Winnipeg to Port of Spain by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Canada
7.1
Good
11,608 reviews
Check prices

Crew

7.8

Comfort

7.1

Boarding

7.3

Entertainment

6.8

Food

6.3

Overall

7.1

Reviews

1 / 20
2.0
Mediocre

Sylvia,Aug 2026

YYZ - PHL

Our flight from Kelowna was 5 hours delayed. We missed our connection. We were able to get to a hotel by 3:00 a.m. but the breakfast cost us $40. The hotel was good. We were rescheduled for the flight the next night when it was canceled. There were no hotel vouchers available which didn't matter because there were no hotel rooms available. We decided to just drive which was not easy doing a one-way rental to the United States. Worst possible trip I've ever had
Air Canada
7.1
Good
11,608 reviews
Air Canada
7.1
Good
11,608 reviews
Check prices

Crew

7.8

Comfort

7.1

Boarding

7.3

Entertainment

6.8

Food

6.3

Overall

7.1

Reviews

1 / 20
2.0
Mediocre

Sylvia,Aug 2026

YYZ - PHL

Our flight from Kelowna was 5 hours delayed. We missed our connection. We were able to get to a hotel by 3:00 a.m. but the breakfast cost us $40. The hotel was good. We were rescheduled for the flight the next night when it was canceled. There were no hotel vouchers available which didn't matter because there were no hotel rooms available. We decided to just drive which was not easy doing a one-way rental to the United States. Worst possible trip I've ever had

Related info for your journey

  • How long is the flight from Winnipeg to Port of Spain?

    Departing from Winnipeg to Port of Spain will take you 33h 45m. Winnipeg and Port of Spain are separated by a distance of 5467 km. Both multi-stop and direct flights can be found to your destination and back.

  • What is the cheapest airline to fly from Winnipeg to Port of Spain round-trip?

    Currently priced at C$ 488, Air Canada will fly you from Winnipeg to Port of Spain and back. In addition to Air Canada, many other airlines offer competitively priced options for your trip. Users have found that Air Canada is 51% cheaper than the other options available to this destination.

  • Can I find deals for flights from Winnipeg to Port of Spain that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Port of Spain flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Port of Spain?

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

  • Can I find deals for business class flights from Winnipeg to Port of Spain?

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

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Complete your trip

Port of Spain car rentals
Port of Spain Piarco Intl Airport car rentals
Scarborough ANR Robinson Intl Airport car rentals
Crown Point car rentals

Top airline flying from Winnipeg to Port of Spain

AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 488AverageC$ 806FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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