$223 Find Cheap Flights from San Jose to Puerto Rico - Compare and Save

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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 5 days
Sort by: Cheapest
San Juan
10h 30m2 stops
from $446per person
Aguadilla
13h 27m4 stops
from $647per person
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?

The cheapest month for flights from San Jose to Puerto Rico is January, when tickets cost $298 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $886 and $856 respectively.

Good to know

Low season

January

Cheapest flight

$223
Best time to beat the crowds with an average 49% drop in price.
Most popular time to fly with an average 46% 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.
8.0
SouthwestOverall score based on 4194 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

Southwest has been a nightmare. Delayed flights, missed connections, systems down. Never again am I flying southwest.

2.0 MediocrePhilip, Sep 2026
Read more Southwest reviews

Southwest has been a nightmare. Delayed flights, missed connections, systems down. Never again am I flying southwest.

had to check bag at gate when there was still overhead bin space. As usual the WIFI didn't really work.

The Southwest airline was ok. A big thank you to Kayak team (David), who worked with me on Sunday afternoon to rebook my travel from Burbank, CA, to CVG. My original flight on Sunday was delayed, so I had to cancel Sunday flight and rebook my travel to Monday. Could not have done it without help from David from Kayak team. Ante Soda GE Aerospace

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.

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

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Forget beverage, they didn't even have water for half the passangers?

Flight was not full! Had a whole row to myself.

Wifi didn’t work, no service, seats are hard as rocks

The problem was going through San Diego, a trip that's become a new development.

No complimentary snacks or food. Had to buy drinks and food.

in-flight wifi was not working well. also the cabin temperature was a bit hot.

I wasn’t able to check in prior to arriving at the airport, I was told by the agent I may not get a seat on the plane as others were waiting for seats, I sat there for 2 hours before being assigned a seat, very stressful. The plane was delayed. Overall not a great travel experience for a 44 minute flight.

Larger seats and more room would elevate the experience. Otherwise, it was good!

Check in went pretty well and you didn't lose my bag. After I got a drink from the drink cart they charged me for it, and at the crazy overpriced airport rates. Never had that happen before, is that an american thing? what madness.

I was delayed several times. Missed a very important event. The airline only provided a $12 voucher after being delayed 3 times.

One the nicest and great air crews I’ve experienced and I’ve flown a lot

Staff at Gate desk were helpful. My connecting flight from the first part of my trip Kona to Seattle was late. I had to run through SeaTac Seattle to catch my flight to San Jose. They made an exception to let me board. On my return trip San Jose to San Diego and San Diego to Honolulu the same thing happened. One flight arrived late and I had to run through the terminal to catch my connection. There are no Gluten-free & Vegan options meals and snacks to purchase.

Short flight was fine, but no entertainment and bathrooms broken.

Seats were old and very uncomfortable. Coach seating is way too tight

WiFi was a major problem and if it does not work on a 4 hour flight then that lowers the overall experience

I was impressed with how quickly the baggage transfers were made.

The Airline Attendant found us in flight and moved us to seats in the front of economy due to the short time we would have to make our connecting flight. We really appreciated it.

Carmen was an absolute delight on the flight staff! Everyone was lovely and made it a very pleasant flight.

Flight was delayed at airport with large backlog and WiFi was spotty

Flight was delayed from San Diego due to being overweight for weather conditions. We missed our connecting flight to our final destination due to the delay, as well as the connecting flight leaving before the scheduled departure time. We missed the connection within 10 - 15 minutes. We were booked on a later flight arriving 7 hours later. There were 7 passengers sharing the same originating and connecting flight.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Plane was turned around due to fog half way into the flight, Delta did not properly direct passengers to stay on same flight and instead failed to properly rebook on Alaska

Smooth flight, easy boarding process. Made up time in the air with initial delay due to weather pass through

Flight was over two hours late, but they notified us early in the morning. They ended up changing planes the food on board that was extremely mediocre and we were in premier class.

awesome team work seen since on board till off plane in my destination. thanks you so much.

Food was very bad Crew was not so welcoming. Chairs was so uncomfortable

Flight was on time, clean, etc. Despite connecting to your wi fi I was unable to use your app to watch entertainment.

The business class had to wait to board last. Unacceptable

The air hostess was excellent. I have taken so many flight domestic and international, this is the first time the air hostess was so caring. She was a delight

Return Premium Economy section to the smaller section with comfortable seats. Add internet, upgrade the meals, and upgrade/update the Movies and Music onboard.

I understand stuff happens, but plane failures are likely due to lack of maintenance. Additionally, air conditioning wasn't working, no snack/drink service, no WiFi. Fortunately, the crew was communicative and light-hearted. United grabbed another plane and we were able to get to our destination.

A good, solid, no frills experience. Departed and arrived on time, staff were pleasant and attentive. Loved the Bluetooth connectivity on the SJC to IAH leg. Being able to watch movies and listen to them with my noise cancelling headphones was lovely. Missed that on the IAH to LHR leg (so I put the wired buds on and my over ear Quiet Comforts over those).

Little communication with passengers after sitting over 1 hour for a maintenance issue Then we had to deplane- no crew communication Poor gate information after deplaned WiFi would not connect AT ALL

Had to pay for WiFi, delayed start, and sat on the runway forever.

British Airways canceled our original flight and rebooked us on Air Canada one day later. As a result, we lost one day of our Geneva trip and incurred financial losses for a prepaid hotel night and a day trip that we were unable to use.

On time and stellar premium class service. Not liking non LCD display in seat backs - miss the convenience of not using your own device.

It was my first time flying with Alaska Airlines and it was a pleasure!

Plane had mechanical issues. We had to de plane and board a different plane and were an hour late

More space for economy, and the bathroom size is only for people with size XS

Rough flight No beverage service due to turbulence Bottom Seat cushion was non existent

They are rarely on time! Very hard to plan your travels when flights or connections keep getting delayed.

Apart from the delay due to unforeseen circumstances. The leg from sjc to dfw was fine. It was the leg from dfw to orf that we encountered issues mainly due to the flight attendant crew not being friendly. We had two small children and we needed some assistance to warm up milk so the baby would sleep. The crew just didn’t get it and made things very difficult. One made a remark that the baby’s dirty diaper smell was a “gift” to the plane in a rude way. Normally I’d brush that off as a funny comment if the rest of the trip the attendants were helpful or understanding of the difficulty we faced. But that wasn’t the case. We were met with rudeness on the second leg. Whereas on the first leg the crew were so nice and helpful.

More options for your flight from San Jose to Puerto Rico

Complete your trip to Puerto Rico with a hotel stay or car rental