$139 Find Cheap Flights from San Jose to Puerto Rico - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Jose to Puerto Rico departing on 8/17. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from San Jose to Puerto Rico

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Aguadilla
Aguadilla2 stops$653
Culebra
Culebra3 stops$1,900
Mayagüez
Mayagüez2 stops$1,895
Aguadilla
Aguadilla2 stops$653
Culebra
Culebra3 stops$1,900
Mayagüez
Mayagüez2 stops$1,895

Book Cheap San Jose to Puerto Rico Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Jose to Puerto Rico that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from San Jose to Puerto Rico

Mon, Aug 24 - Mon, Aug 31
American Airlines Logo
2:30 pm - 12:40 pm
SJC
-
SJU
19h 10m
2 stops
American Airlines Logo
10:33 am - 10:32 pm
SJU
-
SJC
14h 59m
2 stops
$379American Airlines
Sat, Dec 5 - Wed, Dec 9
Delta Logo
6:12 pm - 12:45 pm
SJC
-
SJU
14h 33m
2 stops
Delta Logo
7:00 am - 11:54 pm
SJU
-
SJC
20h 54m
2 stops
$386Delta
Sun, Sep 27 - Sun, Oct 4
Southwest Logo
10:30 pm - 2:30 pm
SJC
-
SJU
13h 00m
1 stop
Southwest Logo
5:00 am - 12:50 pm
SJU
-
SJC
10h 50m
1 stop
$391Southwest
Fri, Sep 18 - Mon, Sep 21
Southwest Logo
10:30 pm - 1:10 pm
SJC
-
SJU
11h 40m
1 stop
Southwest Logo
5:00 am - 1:35 pm
SJU
-
SJC
11h 35m
2 stops
$396Southwest
Fri, Aug 21 - Tue, Aug 25
Southwest Logo
8:00 pm - 10:50 am
SJC
-
SJU
11h 50m
2 stops
Southwest Logo
10:30 am - 8:15 pm
SJU
-
SJC
12h 45m
2 stops
$406Southwest
Fri, Sep 18 - Mon, Sep 21
Southwest Logo
6:30 am - 8:05 pm
SJC
-
SJU
10h 35m
2 stops
Southwest Logo
5:00 am - 1:35 pm
SJU
-
SJC
11h 35m
2 stops
$411Southwest
Fri, Aug 21 - Tue, Aug 25
Southwest Logo
7:35 pm - 9:25 am
SJC
-
SJU
10h 50m
2 stops
Southwest Logo
6:00 am - 6:20 pm
SJU
-
SJC
15h 20m
1 stop
$426Southwest
Wed, Dec 2 - Wed, Dec 9
Delta Logo
7:15 am - 11:20 pm
SJC
-
SJU
12h 05m
1 stop
Delta Logo
3:35 pm - 10:58 pm
SJU
-
SJC
11h 23m
1 stop
$427Delta
Mon, Aug 17 - Wed, Aug 19
United Airlines Logo
6:37 pm - 11:09 pm
SJC
-
BQN
25h 32m
2 stops
United Airlines Logo
12:15 am - 1:08 pm
BQN
-
SJC
15h 53m
2 stops
$653United Airlines
Mon, Aug 17 - Wed, Aug 19
United Airlines Logo
6:37 pm - 11:09 pm
SJC
-
BQN
25h 32m
2 stops
United Airlines Logo
12:15 am - 1:08 pm
BQN
-
SJC
15h 53m
2 stops
$723United Airlines
Booking Insights

KAYAK's insights & trends for San Jose to Puerto Rico flights

Get data-powered insights and trends into flights from San Jose to Puerto Rico to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from San Jose to Puerto Rico?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Jose to Puerto Rico, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from San Jose to Puerto Rico is September, when tickets cost $128 (return) on average. On the other hand, the most expensive months are June and March, when the average cost of round-trip tickets is $483 and $465 respectively.

Good to know

Low seasonSeptember
Cheapest flight$139
Best time to beat the crowds with an average 54% drop in price.
Most popular time to fly with an average 37% increase in price.
Flight from San Jose to San Juan

FAQs - booking Puerto Rico flights

  • How does KAYAK find such low prices on flights from San Jose to Puerto Rico?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from San Jose to Puerto Rico.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Jose to Puerto Rico?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from San Jose to Puerto Rico is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from San Jose to Puerto Rico?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from San Jose to Puerto Rico with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from San Jose to Puerto Rico?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from San Jose to Puerto Rico up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from San Jose to Puerto Rico

 
Need help choosing which airline to fly with from San Jose to Puerto Rico? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
Alaska AirlinesOverall score based on 12514 reviews
7.1Food
8.5Crew
7.0Entertainment
8.1Boarding
7.8Comfort
Airline reviews

It was a very short flight so there really wasn’t any entertainment my. The little pretzels were good though and the cabin crew was awesome.

10.0 ExcellentAnonymous, Jun 2026
LAX - EUG
Read more Alaska Airlines reviews

It was a very short flight so there really wasn’t any entertainment my. The little pretzels were good though and the cabin crew was awesome.

The first flight was fine, great crew, but the plane was delayed 45 minutes to go to Seattle because of they were missing a ramp. That would make sense if the plane was actually at the gate. Not if we’re still waiting for a plane. After we landed we waited 30-45 minutes on the tarmac just to get off the plane. Alaska made me miss my connecting flight, wasting my time, and my money. I should honestly be reimbursed, but hey, when does the airline ever actually take accountability? Never.

Over all it was great. My original flight was canceled but they quickly rebooked me. I was frustrated because I had to cancel my entire plans for the day but all considered, not bad. The crew tried to keep us calm while we sat in the plane for was felt was an hour or so but they could use a bit of a script. The seats were comfortable and I would give it another try.

Flight delayed Didn’t send second leg of trip itemerary First class was fair, but not great.

Short trip, was nice to have a drink on the short flight still.

Not able to get boarding pass for domestic connection flight when check in at international airport. I was told I need to get connection flight boarding pass after I entered US. It us very inconvenient.

Wish there were more complimentary drinks available - only had water and apple juice. Also - no snacks were provided during the flight, but we were offered some items as we exited the plane.

No negatives. Crew was great, flight was on time and there were no crazy passengers. 🤩

It might not have been their fault, but there was a two hour delay due to weather. Then we boarded and were about to leave when they said there were more problems at the destination, took us back to the gate where we had to fully deplane. But then five minutes later, they said everything was fine and to get back on the plane. This was the part that pissed everybody off.

The gate agents begged us to check our carryons. They BEGGED us, over and over, and said that the flight was completely, totally full, and said that if we don't check our bags, it will cause huge delays. They finally said that "group suchandsuch will be required to check bags!" So I checked mine. Well, the flight wasn't close to being full, and many of the overhead compartments were *empty*! Moreover, my bag was delayed at the carousel, and it wasn't on the carousel that was posted. COME ON, AIRLINE, you can look at the seating for the flight on your computer and decide whether it's really necessary to beg and beg and beg people to go through the hassle of checking their bags! This is annoying as hell and makes me not want to use your crummy airline ever again.

Was fine, delayed and feels like southwest is always late

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

Boarding was easy. The seats are small and fairly uncomfortable

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

N Everything was perfect from boarding to assistance to baggage in Tampa

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I took seat 15A in anticipation of window seat, there is no window.

Flight late, the waited for a long time for “personal” to arrive at gate to dock the plane in Rochester. So annoying. This flight was expected, why aren’t personel available for the jet bridge?

Luggage did not make it onto my plane. Business seats were economy with empty row seat. Just horrible experience. Why would the company allow for transfers that don’t give employees enough time to transfer luggages??

The gate experience at LAX was abysmal (same for the arrival experience two days prior). Despite the LAX -> SAT schedule of two flights daily, our departure gate was at a smaller hub that we had to be bussed to from Terminal 4. Fortunately, I arrived at LAX extra early and had time to spare, but if I had not known, I might have missed my flight. I looked at the LAX airport map in the AA app and there was no indication of the additional boarding process. Lastly the gate area we were bussed to was crowded with limited food and beverage options. On flight, the fight attendant was hospitable and attentive, the flight was smooth, and AA's free (and working) wifi for AA members were all on the positive side.

Our flight from JFK to Madrid was delayed. We had to go from one side of the Madrid airport (Terminal 4s to the far end of terminal 4 - Gate K98) to our gate in less than 30 minutes. Put passport control and security/baggage check and that’s very hard unless you’re Usain Bolt. I called Iberia Airlines and the telephone customer service told me that I was going to have to pay to re-book. Luckily the help desk in the airport (who was dealing with dozens of people from the same JFK-Madrid flight) did not charge us extra to reschedule to a flight 8 hours later. They also gave us a voucher for breakfast and lunch. Glad the actual person at the airport had some actual sense.

For an long range economy flight I feel more space and more meal options need to be offered for flights over 5 hours

Take-off delayed an hour because of a missing flight officer, so,arrived in Charlotte lates causing many passengers to miss connections. Otherwise a very good flight, safe and comfortable, with an excellent professional crew.

The flight from LA to Chicago was smooth and service was very good overall.

B-class on an old plane with antiquated amenities and poor service. Landed in Rome w/o bag that didn’t make the connection (plenty of time in London). Bag will come to hotel NOT the day it lands but the following night!! Still waiting for bag…BA had nothing to offer in support and couldn’t even tell me their comp, told to submit receipts and then I’ll learn what is or isn’t covered.

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

It's a long flight and that is always difficult. I was comfortable and well. The movies available were great and the crew was good.

Premium Economy Good crew, good service, excellent food. Seat back screen just not bright enough.

I like everything. Blythe at DCA is the absolute best!

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

They lost my luggage and refuse to help. Terrible airline. I've never experienced worse customer service in my life. Pretty much just told me too bad that I lost all my luggage, not caring that I am stuck in Europe for 2 weeks with absolutely nothing.

You should have had Wifi to make it much enjoyable.

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

The flight was delayed after already taxiing from the gate due to a malfunction. After 3 hours we were told the flight was canceled. The next flight available was Sunday. My daughter and I stayed overnight in the airport due to this issue. I was given a $12 meal voucher. Unacceptable

Whole experience was poor. Delayed 2 hours. Lied about the delays. Was all jet blues fault and tried to blame on air traffic control. Sent out other let trips and wouldn't allow people to switch aircraft.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

Nice plane, clean, wifi available and movies. All the flight attendants were courteous.

The gate attendant in Boston had a high raspy voice and spoke much too fast to be understood. Not pleasant.

Everything you need to know for your flight from San Jose to Puerto Rico

Information on your arrival and departure airports