$186 Find Cheap Flights from San Jose to Puerto Rico

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 8/22. 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$768
Mayagüez
Mayagüez2 stops$1,895
Aguadilla
Aguadilla2 stops$768
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

Sun, Aug 23 - Sat, Aug 29
Delta Logo
6:30 am - 10:29 pm
SJC
-
SJU
12h 59m
1 stop
Delta Logo
6:48 am - 7:25 pm
SJU
-
SJC
15h 37m
2 stops
$386Delta
Sun, Aug 30 - Sat, Sep 5
American Airlines Logo
7:12 pm - 2:51 pm
SJC
-
SJU
16h 39m
2 stops
American Airlines Logo
7:05 am - 6:30 pm
SJU
-
SJC
14h 25m
2 stops
$440American Airlines
Wed, Aug 12 - Sun, Aug 16
Southwest Logo
8:00 am - 10:00 pm
SJC
-
SJU
11h 00m
2 stops
Southwest Logo
5:30 am - 1:15 pm
SJU
-
SJC
10h 45m
1 stop
$455Southwest
Sun, Aug 23 - Sat, Aug 29
Delta Logo
6:30 am - 10:29 pm
SJC
-
SJU
12h 59m
1 stop
Delta Logo
12:56 pm - 9:58 pm
SJU
-
SJC
12h 02m
1 stop
$466Delta
Fri, Jul 3 - Wed, Jul 15
Delta Logo
5:01 pm - 1:04 pm
SJC
-
SJU
17h 03m
2 stops
Delta Logo
2:42 pm - 10:49 pm
SJU
-
SJC
11h 07m
1 stop
$491Delta
Wed, Aug 12 - Sun, Aug 16
Southwest Logo
10:30 pm - 2:30 pm
SJC
-
SJU
13h 00m
1 stop
Southwest Logo
5:30 am - 1:15 pm
SJU
-
SJC
10h 45m
1 stop
$494Southwest
Wed, Aug 12 - Sun, Aug 16
Southwest Logo
8:00 am - 10:00 pm
SJC
-
SJU
11h 00m
2 stops
Southwest Logo
1:50 pm - 11:20 pm
SJU
-
SJC
12h 30m
2 stops
$524Southwest
Mon, Jun 1 - Fri, Jun 5
United Airlines Logo
6:37 pm - 12:34 pm
SJC
-
SJU
14h 57m
2 stops
United Airlines Logo
1:00 am - 1:24 pm
SJU
-
SJC
15h 24m
2 stops
$542United Airlines
Sat, May 30 - Tue, Jun 2
United Airlines Logo
2:45 pm - 5:29 am
SJC
-
SJU
11h 44m
2 stops
United Airlines Logo
2:05 am - 12:03 pm
SJU
-
SJC
12h 58m
1 stop
$544United Airlines
Fri, Jul 3 - Wed, Jul 15
Delta Logo
8:19 pm - 3:11 pm
SJC
-
SJU
15h 52m
2 stops
Delta Logo
2:21 pm - 11:39 pm
SJU
-
SJC
12h 18m
2 stops
$549Delta
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 March and October, when the average cost of round-trip tickets is $465 and $388 respectively.

How far in advance should I book a flight from San Jose to Puerto Rico?

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from San Jose to Puerto Rico, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$186
Best time to beat the crowds with an average 43% drop in price.
Most popular time to fly with an average 63% 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 12331 reviews
8.1Boarding
7.0Entertainment
8.5Crew
7.1Food
7.8Comfort
Airline reviews

I had to cancel my trip due to medical reasons. I have been unable to cancel online through either Kayak or Alaska Airlines.. I am trying to get my insured trip reimbursed by XCover. They are requiring a notice of cancellation or not using to get my refund. Please help me get that information. I have been unable to get this information from either Kayak or Alaska Airlines.

2.0 MediocreDave, May 2026
PSP - SEA
Read more Alaska Airlines reviews

I had to cancel my trip due to medical reasons. I have been unable to cancel online through either Kayak or Alaska Airlines.. I am trying to get my insured trip reimbursed by XCover. They are requiring a notice of cancellation or not using to get my refund. Please help me get that information. I have been unable to get this information from either Kayak or Alaska Airlines.

Alaska is by far the best airline to fly with 😍

They were flexible and able to get me home a day earlier due to a family members illness. Flight was on time and great friendly crew.

Affirmed my disability by allowing me to board when most accessible. Very parable, helpful and friendly staff. Smooth flight overall! I always fly Alaska when possible! Thank you!

Agent could not provide me a boarding pass for the second leg of my flights - yet with a partner airline. Not understood.

I had to change my flight last minute due to a medical emergency. Their agent was compassionate and extremely helpful. This airlines really cares about making travel, for fun, work, or an emergency a customer-focused experience. Thank you!

More efficient with checking lines and boarding/checking bags when needed.

They were really helpful with every question and my kids had never been on a plane and the staff made them feel comfortable

Overall, it was a good flight. My only quip- they made us check our carry on bags when there was plenty of overhead space left. My wife and I thought maybe the aircraft was really full, but that wasn’t the case. There were a number of open seats, and even more overhead compartments with no luggage. A minor annoyance, sure, but when we intentionally didn’t check luggage to make it easier, it was disappointing to have to do it anyways.

The flight would have been very good , if not dor the constantly screaming baby in the row behind me. Is there a way to isolate people traveling with infants? This is not the first time this has happened to me.

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.

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

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?

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

The crew was very attentive through out the flight. Seats were comfortable, nice flight bag with pillow and blanket. Food was okay, since it was a overnight flight seemed to go by fast.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

Boarding gate at LAX was too crowded—two gates next to one another

On time departure and early arrival. Flight attendant very nice.

The business class layout of chairs was weired. You are sitting directly across stranger.,

The SFO Lounge crew were amazing. The bartender Faris was great. Thanks!

Friendly crew is the only nice thing. Seats uncomfortable. Food and snacks horrible. Movies were the same as the first 10 hour flight two weeks before

Was not able to do a online check-in because the American Airlines system doesn't store our visa or other passport information, allowing us to have a trouble-free check-in. We were forced to have to check-in at the counter which Changes are upgrade status given that we were not able to check in much earlier.

Good flight, seated and had a water within 5 minutes. Crew was hospitable.

We left at 1030 am pacific from LA and supposed to land at 7 pm Eastern in NY. They made a detour, stopped in Philadelphia and didn’t land till 1130 PM Eastern!!! Worst flight experience with no pilot communication with no explanation as to what was going on. Everyone was very frustrated to say the least.

Direct tv did not work on flight Short flight so no good service offered Arrived early to destination and had to wait for gate to open. Deplaned LATER than if we arrived on time!! Poor planning Jet blue has had something go wrong on every flight I’ve taken with them in last five years. Terribly run airline

Given us a free miles or free flight for waiting for 9 hours I didn’t get home till 5am in the morning and I was supposed to be home at 9:30 touch down.

Excellent price. Everything on time. two bad parts. Kayak said I couldn't sign in for the flight online, but I got an email at the same time from Jet Blue and they let me sign in online. Second bad part was that, although I had provided my known traveler number, neither of my boarding passes, for this flight and the previous one, had TSA pre-check showing.

Jet blue was great But the Jayak system Wasa pure nightmare and wasted so much of my time and energy by not giving me a way to access jet blue to check in the flight back I didn’t even get the number confirmation code 24 hours before. Because I didn’t receive the email with the confirmation code I could NoT CHECk IN. I spoke to a kayak third party and they informed me I could not carry a carry on, on the flight which caused me so much extra stress it was just too much. You can be sure I will not be using it recommending your site. Again.

There was a screen but no earphones that could use the older input so I could listen to anything.

My experience with JetBlue was fine BUT I am very upset with Kayak! JetBlue had delayed our scheduled departure by an hour and you NEVER notified me of the change. I did not hear directly from JetBlue because the trip was booked through Kayak, a mistake I will not repeat. Your reminder of the our trip last week still had the WRONG departure time. Our return trip has also changed, and again no notice from you.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

Boarding was quick and efficient. The flight crew were friendly. There were limited food options available on the flight. The pocket guide said there would be salad and sandwich sections available on flights over 3.5 hours. The only food available were snack boxes. And those were limited as well. My flight was over 5 hours. The entertainment system worked well. I had both extra legroom seats and regular coach seats. The seats were not very comfortable. The entertainment controls in the armrest made it difficult to rest my arm without changing the channel on my neighbors TV. Overall, my experience was mediocre.

Purchased through 3rd party vendor which made everything difficult. Unable to check in online. Unable to get flight updates easily, tsa precheck information didn’t carry through, longer time to check in in person. Entertainment looked good but had to purchase conventional headphones to view.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

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

Information on your arrival and departure airports