Puerto Rico
in $580s-$590s RT
Welcome to San Juan—where the streets are cobblestone, the buildings are pastel, and your willpower to resist ordering a piña colada (which was invented right there!) before noon dissolves on arrival. This is the kind of place where you go for the sunshine, and somehow end up salsa-dancing with a stranger, eating mofongo the size of your face, and briefly considering a career change to beach-bar owner.
And while you’re there, do yourself a favour: take a dip in a bioluminescent bay. It’s like Mother Nature handed you your own personal glow stick... except it's not just a stick, it's actually a whole entire gulf :-)
Taking off ✈️
Tip Published: Dec 11, 2025
To
- San Juan (SJU) - $584 (up to $599)
From
- Calgary (YYC)
How to Book
This is a Takeoff-only Flight for Jack's Flight Club Takeoff members only. For step by step instructions on how to book it you'll need to login or upgrade to Takeoff membership.