$219 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 4/18. 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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Flight Deals

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

Sat, Apr 18 - Thu, Apr 23
Delta Logo
5:55 am - 11:12 pm
OAK
-
SJU
14h 17m
2 stops
Delta Logo
6:15 am - 11:54 pm
SJU
-
OAK
20h 39m
2 stops
$426Delta
Sat, Apr 18 - Sat, Apr 25
Delta Logo
5:55 am - 11:12 pm
OAK
-
SJU
14h 17m
2 stops
Delta Logo
6:15 am - 9:41 pm
SJU
-
OAK
18h 26m
2 stops
$461Delta
Fri, Apr 24 - Fri, May 1
Southwest Logo
11:55 pm - 1:20 pm
OAK
-
SJU
10h 25m
1 stop
Southwest Logo
6:50 am - 6:20 pm
SJU
-
OAK
14h 30m
2 stops
$494Southwest
Sat, Sep 12 - Tue, Sep 29
Delta Logo
5:05 pm - 11:48 am
OAK
-
SJU
15h 43m
2 stops
Delta Logo
7:30 am - 11:49 pm
SJU
-
OAK
19h 19m
2 stops
$496Delta
Sat, Apr 18 - Wed, Apr 22
Delta Logo
5:55 am - 11:12 pm
OAK
-
SJU
14h 17m
2 stops
Delta Logo
12:55 pm - 11:54 pm
SJU
-
OAK
13h 59m
2 stops
$508Delta
Sat, Apr 11 - Wed, Apr 15
Southwest Logo
7:35 pm - 9:05 am
OAK
-
SJU
10h 30m
2 stops
Southwest Logo
11:25 am - 9:55 pm
SJU
-
OAK
13h 30m
2 stops
$530Southwest
Fri, Apr 17 - Sat, Apr 25
Delta Logo
5:55 am - 11:12 pm
OAK
-
SJU
14h 17m
2 stops
Delta Logo
6:15 am - 9:41 pm
SJU
-
OAK
18h 26m
2 stops
$543Delta
Fri, May 1 - Tue, May 5
Southwest Logo
11:55 pm - 1:20 pm
OAK
-
SJU
10h 25m
1 stop
Southwest Logo
8:10 am - 6:50 pm
SJU
-
OAK
13h 40m
2 stops
$566Southwest
Fri, Apr 24 - Fri, May 1
Southwest Logo
5:55 am - 8:00 pm
OAK
-
SJU
11h 05m
2 stops
Southwest Logo
6:50 am - 6:20 pm
SJU
-
OAK
14h 30m
2 stops
$569Southwest
Sun, Apr 12 - Fri, Apr 17
Southwest Logo
7:35 pm - 9:10 am
OAK
-
SJU
10h 35m
2 stops
Southwest Logo
6:50 am - 6:20 pm
SJU
-
OAK
14h 30m
2 stops
$570Southwest
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 $382 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $925 and $666 respectively.

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Good to know

Low seasonOctober
Cheapest flight$219
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly and prices are also 11% lower on average.
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.

Reviews of the top airline 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 4333 reviews
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
8.0Comfort
Airline reviews

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

10.0 ExcellentMartie, Mar 2026
LGB - BNA
Read more Southwest reviews

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

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

The charges were ridiculous for an hour flight and the turbulence was very scary.

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

Great flight but super high price. Glad it was a business trip and not personal

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

Information on your arrival and departure airports

Oakland (OAK)