United Airlines is showing a few flights in May 2018 from Calgary to Port of Spain, Trinidad and Tobago for $458 CAD RT including taxes.
The flights have 1 stop in Houston each way, for 2.5 – 3.5 hours.
Well priced, fast flights from Calgary to Trinidad and Tobago are very rare.
Below, I've posted some info about flying between Trinidad (POS) and Tobago (TAB) for $65 CAD RT including taxes.
Availability for travel
How to find and book these flights
1. Go to Momondo
2. Search for a flight from Calgary (YYC) to Port of Spain, Trinidad and Tobago (POS)
– Try the following dates:
May 4, 5 to May 17, 18
May 6, 8, 10 to May 17, 18
May 11, 12 to May 17, 18
screenshot from Momondo
Flying between Trinidad (POS) and Tobago (TAB)
The country of Trinidad and Tobago is comprised of 2 islands. Trinidad's landscape is more mangrove and rain forest, while Tobago is probably more what you're picturing when you think of a beautiful Caribbean island (palm trees, white sand, etc).
It costs around $48 USD ($65 CAD) RT including taxes to fly between Port of Spain (POS) on Trinidad, and Tobago (TAB), using Caribbean Airlines.
There are flights departing nearly every hour, and it takes about 25 minutes. The first piece of checked luggage is included free.
You can find these flights at Caribbean-Airlines.com.
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