Flight cost to San Juan

I ussually always use Southwest to book flights due to their cost and their passenger of size policy. However, for our San Juan cruise, I have to go to another airline since due to an inner ear issues, we can not afford to have several legs to the trip.

In any case, I am trying to have a feel on how a trip Chicago/San Juan for airfaire would be. I have seen price varying wildly, what should I consider being a "good deal" or a regular pricing? I need to book early because of the limitation of booking a full row, I just want to make sure I'm not paying crazy prices for booking early.

Thank you for your help!

I don't travel to Chicago in some time but if you can find something below 300.00 it's a great deal. 350.00 it's most likely. The last time I travel to ORD was 3 years ago and I pay 278.00 round trip.

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We are flying from Chicago in a couple weeks and a direct flight was $500pp. Cheapest we found

About a month ago I found a direct flight to San Juan from Atlanta on Delta, round trip for $411. I had to keep watch often, and grabbed it when I saw it come around again. The flight is in April/May. I also adjusted my days going and coming, going on Friday and returning on Monday. They wanted $100 more per person for flying out on Sunday. That pays for the hotel. I am satisfied with this price. Keep checking and be prepared to grab something fast if you see what you want.

Thank you all for the feedback!

I booked today for 373 a person (need 3 tickets, 2 people (long story), direct flight with aa, which seems a good price. And I got exactly the flight I wanted.. Going in on Friday, leaving on Saturday. Will cost me an additional $100 for luggage, but hey, it is what it is.

Thanks again!

Airfares are high this year for Xmas cruise.

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Thank you all for the feedback!

 

I booked today for 373 a person (need 3 tickets, 2 people (long story), direct flight with aa, which seems a good price. And I got exactly the flight I wanted.. Going in on Friday, leaving on Saturday. Will cost me an additional $100 for luggage, but hey, it is what it is.

 

Thanks again!

That's a real good price! Last March ORD to SJU non-stop was running around 700 with one stops in the 500's. We were able to grab a non-stop one day when the price dropped to 510. Next day it was back up. This year we got them for around 500 again. We are stopping in CLT on the way down, but that was by choice.

When are you traveling?

That's a real good price! Last March ORD to SJU non-stop was running around 700 with one stops in the 500's. We were able to grab a non-stop one day when the price dropped to 510. Next day it was back up. This year we got them for around 500 again. We are stopping in CLT on the way down, but that was by choice.

 

When are you traveling?

book the same AA flights on 12&20 Jan 2018 as soon as they opened for $744 (all taxes included) for 2 seats. there are ups and down but around $800 for 2 seats non-stop ORD to SJU been pretty common for the last year or so. First class seats are about double or more on same flights.

Almost $1,000 for economy on dec 22-30. Highest year for airfare in 16 cruises at Xmas. Tentative if I will go this year.

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jan 12 - jan 20th. Glad I book when I did.. now the same flight is 507 per person!!!

We need flights for those exact dates, too, but we're coming in from Calgary - our best option AA flights (only one stop, in Dallas) are coming in at just shy of $1,200 CDN ($900ish US) per person! Our San Juan flights in January 2016 were under $900/person.

I wasn't expecting the flights to be this pricey. United has some cheaper options, but all of them have a red-eye and we were trying to avoid that.

Good luck. I just got notice the flights went up again. Even AA agents aren't sure what's driving it.

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just seen where Frontier airlines is going to be doing a Philli to san Juan with a intro fare of 59 dollars

Wow that's great. I looked for business out of LGA to San Juan thru Charlotte was $500 less than Memphis thru Charlotte. I just don't get it

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565$ delta comfort from Bangor Maine

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I guess I should go ahead and buy my tickets. Our cruise is July 1, the tickets have stayed around 578.00. 1157$ For 2 people just sounds so expensive.

We aren't flying out of the same airports, however we found a decent rate on American Airlines to SJU a while back.....their Business class wasn't that much more than economy so we went that route. We usually use miles on long hauls, but this one wasn't worth that hassle of waiting for seats to open up on decent connecting times. Not sure if they still have attractive fares but with summer travel hitting, my guess is that the prices are only going to go up.....

just seen where Frontier airlines is going to be doing a Philli to san Juan with a intro fare of 59 dollars

I still wouldn't fly Frontier.

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We need flights for those exact dates, too, but we're coming in from Calgary - our best option AA flights (only one stop, in Dallas) are coming in at just shy of $1,200 CDN ($900ish US) per person! Our San Juan flights in January 2016 were under $900/person.

 

I wasn't expecting the flights to be this pricey. United has some cheaper options, but all of them have a red-eye and we were trying to avoid that.

Flights for us Canucks are pricey. I decided to book for our New Year cruise the day the tickets were released. Managed to get one with a 4 hour layover on the way down and direct back, both to and from Toronto - Delta down, Air Canada back. I managed to book for $711 Canadian (just over $500 US). Currently going for $1300 Canadian ($925 US). Prices went up about 2 or 3 days after the airlines released them and have stayed constant for the past 4 months. I was not willing to risk waiting for lower prices since it is over the holiday period and I required 6 tickets (which may be hard to come by at a good price if we waited).

Lesson to all who pre-plan trips far in advance, try to book the first day or two that flights are released, and you will likely get a good price. After that, it is a crap shoot and if you are traveling at peak times, you will likely only see prices go up and up.

We bought mid-week Detroit to San Juan return for January 12 - 23 on Spirit Airlines where the Spirit web site says $133 each way... but really!!!!! You can't cruise without luggage which is $60 there and back. Security fees, US - International Departure Tax and Passenger Facility Fees seem to be the bulk of the cost. Total for two pax $652

Gambling that the Spirit pilots work-to-rule problems will be settled by January.

I think it depends on the time of year that you are flying. I've been watching airfare for the February time frame and it's running around $800/person. Southwest hasn't released their airfare past the end of December yet, so hopefully they will be a little cheaper when then do release the next round.

I've been watching too, traveling in March 2018. JetBlue hasn't posted their flights yet either. Once both JetBlue & Southwest are in the mix, prices should go down. As of today, flights in September are under $400 per person, but if you want to pick the best time, it's about $450ish. Good Luck!

Just booked last week, 2 tickets round trip, St. Louis to San Juan for $618.00 total on Southwest. This is for March 2018. This is less than what I paid 7 years ago. Had to leave on a Thursday and return on a Monday for best prices. Flight down has one stop in FLL and flight back stops in Tampa. These prices are economy and may be gone by now.

Finally booked our SJU flights for January 2018! To get a decent price and overall shortest travel time, we had to go with the red-eye to get to SJU - ended up booking United, YYC-SJU with a stop in Houston both directions. Paid $837 CDN/each, round trip. Interesting, though... booking YYC-SJU round-trip was going to be $900 person, but when I broke out the first flight into two "legs" (YYC-IAH and then IAH-SJU), it was cheaper! Flying Jan 11, 2018-Jan 20, 2018.

We're in Minneapolis. Quick flight from Chicago. Sun Country has cheap direct flights to San Juan. Only flies Fri. - Mon. Doing a transition cruise in Feb. and coming back from PR for $212