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Puerto Rico

$243+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
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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 February 12, 2026.

This Southwest deal was found by Cheapflights users on 2/11. 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 5/107:35 pm
OAK
-
SJU
2 stops10h 35m
Southwest
Wed 5/138:10 am
SJU
-
OAK
2 stops13h 55m
Southwest
Deal found 2/11$366
This Southwest deal was found by Cheapflights users on 2/8. 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 7/67:50 am
OAK
-
SJU
2 stops13h 35m
Southwest
Tue 7/76:30 am
SJU
-
OAK
1 stop10h 20m
Southwest
Deal found 2/8$376
This Southwest deal was found by Cheapflights users on 2/9. 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 5/199:05 pm
OAK
-
SJU
2 stops10h 30m
Southwest
Tue 5/268:10 am
SJU
-
OAK
2 stops13h 55m
Southwest
Deal found 2/9$381
This Southwest deal was found by Cheapflights users on 2/11. 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 9/147:55 pm
OAK
-
SJU
2 stops12h 05m
Southwest
Wed 9/306:00 am
SJU
-
OAK
2 stops17h 00m
Southwest
Deal found 2/11$391
This Southwest deal was found by Cheapflights users on 2/9. 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.
Sat 5/27:35 pm
OAK
-
SJU
2 stops10h 30m
Southwest
Wed 5/68:10 am
SJU
-
OAK
2 stops13h 55m
Southwest
Deal found 2/9$421
This Southwest deal was found by Cheapflights users on 2/10. 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 4/149:05 pm
OAK
-
SJU
2 stops10h 30m
Southwest
Fri 4/245:05 am
SJU
-
OAK
2 stops13h 00m
Southwest
Deal found 2/10$431
This Southwest deal was found by Cheapflights users on 2/11. 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 4/149:05 pm
OAK
-
SJU
2 stops10h 30m
Southwest
Mon 4/272:00 pm
SJU
-
OAK
2 stops12h 55m
Southwest
Deal found 2/11$438
This Southwest deal was found by Cheapflights users on 2/9. 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.
Fri 8/146:15 am
OAK
-
SJU
2 stops10h 50m
Southwest
Tue 8/186:00 am
SJU
-
OAK
2 stops17h 00m
Southwest
Deal found 2/9$446
This Southwest deal was found by Cheapflights users on 2/9. 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.
Sat 2/286:25 pm
OAK
-
SJU
2 stops11h 30m
Southwest
Wed 3/410:20 am
SJU
-
OAK
2 stops13h 30m
Southwest
Deal found 2/9$465

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 February 12, 2026.

Round-trip from

$366
(Southwest)

One-way from

$243
(Southwest)

Popular in

December

Cheapest in

May

Average price

$488
From Oakland to Puerto Rico
Search Deals
One-way flight from Oakland to Puerto Rico
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 12, 2026.
Use the filters below to find and compare flights from Oakland to Puerto Rico that are best for you.

Fly from

Oakland

Fly to

Puerto Rico

Route

Depart

Return

Price

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 5/9

7:35 pm-9:05 am

2 stops10h 30m

San Juan Luis Munoz Marin Intl

Wed 5/13

8:10 am-7:05 pm

2 stops13h 55m

$421

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 4/14

9:05 pm-10:35 am

2 stops10h 30m

San Juan Luis Munoz Marin Intl

Fri 4/24

5:05 am-3:05 pm

2 stops13h 00m

$431

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 2/28

6:25 pm-9:55 am

2 stops11h 30m

San Juan Luis Munoz Marin Intl

Wed 3/4

10:20 am-7:50 pm

2 stops13h 30m

$465

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 5/4

9:30 pm-10:35 am

2 stops10h 05m

San Juan Luis Munoz Marin Intl

Sat 5/9

11:15 am-8:35 pm

2 stops12h 20m

$466

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 3/3

7:25 pm-11:20 am

2 stops11h 55m

San Juan Luis Munoz Marin Intl

Sat 3/7

3:35 pm-12:20 am

1 stop12h 45m

$481

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 2/24

6:15 am-8:55 pm

2 stops10h 40m

San Juan Luis Munoz Marin Intl

Sat 2/28

2:10 pm-11:15 pm

2 stops13h 05m

$490

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 4/6

8:30 pm-10:35 am

2 stops11h 05m

San Juan Luis Munoz Marin Intl

Fri 4/10

6:50 am-6:20 pm

2 stops14h 30m

$491

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 3/9

7:35 pm-9:20 am

2 stops10h 45m

San Juan Luis Munoz Marin Intl

Wed 3/11

10:10 am-10:00 pm

2 stops14h 50m

$491

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 5/8

11:55 pm-1:20 pm

1 stop10h 25m

San Juan Luis Munoz Marin Intl

Fri 5/15

5:05 am-3:05 pm

2 stops13h 00m

$496

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 5/1

11:55 pm-1:20 pm

1 stop10h 25m

San Juan Luis Munoz Marin Intl

Tue 5/5

11:25 am-10:05 pm

2 stops13h 40m

$516

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/9

Showing 1-10 of 22 results
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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 February is currently the most expensive (average of $349). 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 February 12, 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.
Southwest
8.0
Very good
4,280 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

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.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

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 30m. Southwest provides one of the quickest options available for as low as $421. Airlines will cover a distance of 3615 mi.

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

    Most travelers choose Oakland - San Juan Luis Munoz Marin Intl, Oakland - Aguadilla Borinquen or Oakland - Culebra when deciding on the best route 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 February is currently the most expensive (average of $349). 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

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Alternative routes for Oakland to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
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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 February 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$385Average$558FlexibilityNo cancel feeOn-time63%

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