$343 Find Cheap Flights from Oakland 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 Oakland to Puerto Rico departing on 11/26. 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

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Cheap Flights from Oakland to Puerto Rico

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Aguadilla
Aguadilla3 stops$878
Aguadilla
Aguadilla3 stops$878

Book Cheap Oakland 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 Oakland 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 Oakland to Puerto Rico

Mon, Nov 10 - Sat, Nov 15
Southwest Logo
5:40 am - 10:20 pmOAK-SJU
12h 40m2 stops
Southwest Logo
8:20 am - 5:20 pmSJU-OAK
13h 00m2 stops
$429Southwest
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Tue, Oct 21 - Tue, Oct 28
Southwest Logo
5:20 am - 8:45 pmOAK-SJU
12h 25m2 stops
Southwest Logo
5:05 am - 5:05 pmSJU-OAK
15h 00m2 stops
$477Southwest
Find Deal
Thu, Jan 15 - Fri, Jan 23
Southwest Logo
9:10 am - 12:40 amOAK-SJU
11h 30m2 stops
Southwest Logo
12:10 pm - 9:25 pmSJU-OAK
13h 15m2 stops
$481Southwest
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Sun, Oct 26 - Sun, Nov 2
Southwest Logo
6:00 am - 12:15 amOAK-SJU
15h 15m2 stops
Southwest Logo
5:40 am - 2:35 pmSJU-OAK
12h 55m2 stops
$499Southwest
Find Deal
Thu, Feb 19 - Tue, Feb 24
Alaska Airlines Logo
6:35 pm - 4:55 amOAK-SJU
30h 20m2 stops
Alaska Airlines Logo
4:25 pm - 11:38 pmSJU-OAK
35h 13m2 stops
$804Alaska Airlines
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Sat, Feb 21 - Tue, Feb 24
Alaska Airlines Logo
6:45 pm - 2:43 pmOAK-SJU
15h 58m2 stops
Alaska Airlines Logo
8:04 am - 9:08 amSJU-OAK
29h 04m2 stops
$805Alaska Airlines
Find Deal
Thu, Feb 19 - Wed, Feb 25
Alaska Airlines Logo
6:35 pm - 4:55 amOAK-SJU
30h 20m2 stops
Alaska Airlines Logo
4:25 pm - 11:38 pmSJU-OAK
35h 13m2 stops
$813Alaska Airlines
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Fri, Nov 28 - Fri, Dec 5
Delta Logo
4:51 pm - 12:46 pmOAK-SJU
15h 55m2 stops
Delta Logo
3:32 pm - 12:08 amSJU-OAK
12h 36m2 stops
$1,033Delta
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Thu, Dec 4 - Mon, Dec 8
Delta Logo
4:54 pm - 2:14 pmOAK-SJU
17h 20m2 stops
Delta Logo
3:32 pm - 12:08 amSJU-OAK
12h 36m2 stops
$1,058Delta
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Wed, Nov 26 - Wed, Dec 3
Delta Logo
5:55 am - 11:13 pmOAK-SJU
13h 18m2 stops
Delta Logo
3:32 pm - 12:08 amSJU-OAK
12h 36m2 stops
$1,125Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Oakland to Puerto Rico flights

Get data-powered insights and trends into flights from Oakland 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 Oakland to Puerto Rico?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Oakland 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 Oakland to Puerto Rico is October, when tickets cost $298 (return) on average. On the other hand, the most expensive months are December and January, when the average cost of round-trip tickets is $873 and $702 respectively.

Good to know

Low seasonOctober
Cheapest flight$343
Best time to beat the crowds with an average 48% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Oakland to San Juan

FAQs - booking Puerto Rico flights

  • How does KAYAK find such low prices on flights from Oakland 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 Oakland to Puerto Rico.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Oakland 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 Oakland 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 Oakland 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 Oakland 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 Oakland to Puerto Rico up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Puerto Rico?

    The cheapest time of day to fly to Puerto Rico is generally in the evening, when round-trip flights cost $410 on average. Morning departures are around 22% more expensive than evening flights, on average. The most expensive time of day to fly to Puerto Rico is generally at night, which is peak travel time and where the average cost of a ticket is $535.

Reviews of the top airlines flying from Oakland to Puerto Rico

 
Need help choosing which airline to fly with from Oakland 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 4246 reviews
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

10.0 ExcellentRobert, Sep 2025SFO - LAS
Read more Southwest reviews

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

It was a perfect flight in all aspects! Both legs!

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Flight was cancelled without warning close to flight date. Stuck witha credit has to buy a new ticket from another airline in either to get to location. Email cancelling was lost in mail.

Spirit Airlines was ok but TRAVELHELPDESK, the 3rd party travel agent IS A JOKE! VERY RUDE CUSTOMER AGENTS ont he phone. NO HELP AT ALL. But the airlines was ok.

No frills - because you get what you pay for. The crew was amazing!! I had plenty of room to spread out because the flight was half full. Which made it easy to sleep.

The staff was very very rude in Las Vegas when boarding the flight. When presenting the boarding ticket. Las Vegas flight, it was hot and stuffy, it smelled really bad.

Dear All, I have harassment and accident with the flight attendant . This is my phone to talk 8168073567, please, leave phone message . Regards Emily,

Flight was on time but the amount of noise from several children and the kicking of my seat the entire flight was overwhelming.

Unbelievable check in horrible. Asked to print tickets at the gate after a delay

check in at security was a hassle being scanned. Spirit employees were helpful and professional.

Had a issue with catching flight due to airline, was unable to board flight

I liked how cheap it was but both my flights were delayed heavily

Everything you need to know for your flight from Oakland to Puerto Rico

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