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Calling all Canadians: YOW or YYZ flights to SJU?


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Can anyone with experience flying from Ottawa or Toronto to San Juan Puerto Rico help me? We're wondering what's the easiest way to fly to San Juan from our neck of the woods. Or would Ogdensburg, N.Y. be an option? It seems a bit early to book my dates for September 11-20, 2020 yet.


Thank you in advance,


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Easiest....well, that depends on your definition of "easiest".


Fewest number of flights?

Closest airport to home?

"Easiest" on the pockebook?


Try ITA Matrix to learn about your options.   matrix.itasoftware.com


And with Ogdensburg, you would be forced to fly only on United, and only through either Chicago or Dulles.

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I was looking at flights last year and there was direct one out of YYZ, but Air Canada kept changing the times and it kept getting worse. The options out of, and back to, YOW were also pretty terrible. Air Canada, westjet and United.


I finally booked American out of YUL, via Miami on the way there, and Philly on the way back.

I don't remember the prices but for my past few flights, YUL is significantly less expensive than YOW

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Hello YOWer, also live here.  I either will use here or YUL (if the savings are significant). YYZ is the last option because it is about 5 hours to YYZ and the savings won't be different when compared to YUL because of time. Usually from YOW I rarely  still start from the domestic side, always Transborder with a US airline (easier and usually cheaper if booked at the right time) despite the limited options, usually I fly Delta (DTW and LGA). American (PHL), but usually too long of a connect, and United (EWR, seasonal ORD). I haven't used Air Canada/Air Canada Express/WestJet since that is the last option because I will always end up through YYZ or YUL. 

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Also from Ottawa.... and of course you can’t get there from here 😥


Unless Toronto offers a great connection and/or price I would look at Montreal.

Try using a website like https://matrix.itasoftware.com to do some research.  It has a great feature where you can enter multiple departure airports to see all that is available. You cannot book using the site but it does show prices.


Good luck.

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In Ottawa, last 10 years flown out of Ottawa and always United.  Gave up on US departures due to price, parking and inconvenience.  Watch pricing and you should be able to do a return in economy under $500 Can.  Use itasoftware.com referred to earlier and google.ca/flights.  AC has had a N/S YUL-SJU, and United is discontinuing YOW-EWR as of March 1/20 as I recall. 

just Looked at google flights, with your dates $554 on Delta from YUL-SJU with decent times. YOW was higher with long layovers in Washington or Chicago.

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  • 3 weeks later...

OP: you state "easiest" rather than cheapest.
That being so, the key issue is changing plans.
To my knowledge, there are no direct or non-stop flights on the 2 paths you mention.
That being so, your best originating city to land at SJU is Miami.
So now you're looking at non-stop flights either from YOW or YYZ to Miami.

Or from YUL..
Whatever gets you a good connection to that all-important MIA - SJU flight.
On no account try to make it from home to your ship all on the day you set sail. Too many variables to go wrong (including lost baggage - which happened to me) on what would be a very tight time schedule.

Bon Voyage mon ami / mi amigo.

Edited by Canuker
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Looking on either the 10th or 11th of September (you weren't specific about what Sept 11 referred to), one of your easiest and cheapest options is to take the 6am flight from YYZ to JFK on Delta, connecting to a non-stop to SJU.  About 4 hours at JFK, so you have cushion if your flight from YYZ is delayed.  Arrive SJU about 4pm.


There's also a 6am flight on AA to MIA that would connnect to SJU, but with a shorter connect at MIA.  Price is competitive with DL on the 10th, not so on the 11th.


ITA Matrix is your friend.

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  • 1 month later...

Thank you for all the advice!!! We booked on Boxing day and  ended up getting a better price leaving from Montreal on Delta (YUL to JFK and JFK to SJU). Yay, only one flight change!  The layover is only 4 hours, so that works out. We'll have time to stretch our legs and rehydrate 😉 


Thanks again,




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