Puerto Rico

$213+ Cheap flights from Oakland, CA (OAK) to Puerto Rico

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
May 2 — May 91
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Oakland to Puerto Rico with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Oakland to Puerto Rico

Cheapest flights from Oakland to Puerto Rico
Explore the most affordable flight options available from Oakland to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 2, 2026.

This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/37:40 pm
OAK
-
SJU
2 stops12h 20m
Southwest
Fri 8/75:00 am
SJU
-
OAK
2 stops11h 45m
Southwest
Deal found 3/29$460
This Delta deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:05 pm
OAK
-
SJU
2 stops15h 56m
Delta
Wed 5/132:35 pm
SJU
-
OAK
2 stops12h 22m
Delta
Deal found 3/28$461
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/139:30 pm
OAK
-
SJU
2 stops10h 05m
Southwest
Fri 4/245:05 am
SJU
-
OAK
2 stops13h 05m
Southwest
Deal found 3/30$495
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/104:49 pm
OAK
-
SJU
2 stops15h 58m
Delta
Sat 4/186:15 am
SJU
-
OAK
2 stops13h 11m
Delta
Deal found 4/1$496
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/275:10 am
OAK
-
SJU
2 stops13h 05m
Southwest
Thu 8/65:00 am
SJU
-
OAK
2 stops13h 00m
Southwest
Deal found 3/31$530
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/104:49 pm
OAK
-
SJU
2 stops15h 01m
Delta
Wed 4/152:03 pm
SJU
-
OAK
2 stops12h 51m
Delta
Deal found 4/1$543
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/197:45 pm
OAK
-
SJU
2 stops12h 00m
Southwest
Wed 7/296:30 am
SJU
-
OAK
2 stops12h 10m
Southwest
Deal found 3/31$566
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:05 am
OAK
-
SJU
2 stops15h 00m
Southwest
Sun 5/247:25 am
SJU
-
OAK
2 stops14h 45m
Southwest
Deal found 3/31$571
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/268:20 am
OAK
-
SJU
1 stop12h 35m
Southwest
Fri 7/315:00 am
SJU
-
OAK
2 stops13h 10m
Southwest
Deal found 3/31$605
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/269:20 pm
OAK
-
SJU
2 stops10h 15m
Southwest
Tue 6/211:25 am
SJU
-
OAK
2 stops13h 30m
Southwest
Deal found 3/29$621
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:05 am
OAK
-
SJU
2 stops10h 55m
Southwest
Wed 4/2211:25 am
SJU
-
OAK
2 stops13h 40m
Southwest
Deal found 3/30$641

Find flight deals from Oakland to Puerto Rico

Keep the following information in mind while searching for Oakland to Puerto Rico flight deals. Data was last updated April 2, 2026.

Round-trip from

$460
(Southwest)

One-way from

$213
(Delta)

Popular in

December

Cheapest in

May

Average price

$486
From Oakland to Puerto Rico
One-way flight from Oakland to Puerto Rico
Highest demand for flights based on searches. 7% potential increase in price ($37 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Average for round-trip flights in April 2026

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to Puerto Rico that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 2, 2026.
Use the filters below to find and compare flights from Oakland to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 4/13

9:30 pm-10:35 am

2 stops10h 05m

San Juan Luis Munoz Marin Intl

Fri 4/24

5:05 am-3:10 pm

2 stops13h 05m

$495

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 4/11

5:55 am-11:15 pm

2 stops14h 20m

San Juan Luis Munoz Marin Intl

Sat 4/18

6:15 am-4:26 pm

2 stops13h 11m

$496

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 7/27

9:00 am-12:05 am

2 stops12h 05m

San Juan Luis Munoz Marin Intl

Mon 8/3

7:00 am-4:45 pm

2 stops12h 45m

$530

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 4/14

5:55 am-11:12 pm

2 stops14h 17m

San Juan Luis Munoz Marin Intl

Sat 4/18

6:15 am-4:26 pm

2 stops13h 11m

$543

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 4/11

5:55 am-11:15 pm

2 stops14h 20m

San Juan Luis Munoz Marin Intl

Wed 4/15

2:03 pm-11:54 pm

2 stops12h 51m

$543

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sun 7/19

8:20 am-11:55 pm

1 stop12h 35m

San Juan Luis Munoz Marin Intl

Wed 7/29

6:30 am-4:00 pm

2 stops12h 30m

$566

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 5/8

5:05 pm-12:01 pm

2 stops15h 56m

San Juan Luis Munoz Marin Intl

Wed 5/13

2:35 pm-11:57 pm

2 stops12h 22m

$672

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 4/13

5:04 pm-11:45 am

2 stops15h 41m

San Juan Luis Munoz Marin Intl

Sat 4/18

6:15 am-4:26 pm

2 stops13h 11m

$707

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sun 5/31

6:05 am-12:05 am

2 stops15h 00m

San Juan Luis Munoz Marin Intl

Sun 6/7

5:45 am-6:35 pm

1 stop15h 50m

$751

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 7/31

5:10 am-12:15 am

2 stops16h 05m

San Juan Luis Munoz Marin Intl

Sun 8/9

1:50 pm-11:30 pm

2 stops12h 40m

$751

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/29

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

Best time to book a flight from Oakland to Puerto Rico

Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Oakland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Oakland, California to Puerto Rico?

Currently, January is the cheapest month in which you can book a flight from Oakland, California to Puerto Rico (average of $162). Flying from Oakland, California to Puerto Rico in March is currently the most expensive (average of $338). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Puerto Rico

Get insights into the airlines that provide service to Puerto Rico. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Puerto Rico. Reviews last updated April 2, 2026.
See what other customers who have flown with Southwest from Oakland to Puerto Rico have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

Related info for your journey

Find useful and relevant information for your journey from Oakland to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • What airport do you fly from for flights from Oakland to Puerto Rico?

    Most people fly from Oakland (OAK) if they book a flight from Oakland to Puerto Rico. Oakland is conveniently located just 7.0 mi from Oakland’s city center.

  • How long is the flight from Oakland, California to Puerto Rico?

    A quick flight from Oakland, California to Puerto Rico can take about 10h 05m. Southwest provides one of the quickest options available for as low as $495. Airlines will cover a distance of 3615 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from Oakland, California to Puerto Rico?

  • Can I find deals for flights from Oakland to Puerto Rico that include hotel bookings?

    Yes. In addition to deals on Oakland to Puerto Rico flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oakland to Puerto Rico?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oakland to Puerto Rico.

  • Can I find deals for business class flights from Oakland to Puerto Rico?

    Yes. Cheapflights offers flight deals from Oakland to Puerto Rico by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Oakland, California to Puerto Rico?

    Currently, January is the cheapest month in which you can book a flight from Oakland, California to Puerto Rico (average of $162). Flying from Oakland, California to Puerto Rico in March is currently the most expensive (average of $338). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top airline flying from Oakland to Puerto Rico

Discover the top airline that operate flights from Oakland to Puerto Rico. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$410Average$605FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.