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Puerto Rico

$208+ 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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find 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 October 30, 2025.

This Southwest deal was found by Cheapflights users on 10/27. 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.
Wed 12/108:20 amOAK - SJU
2 stops12h 15mSouthwest
Thu 1/15:45 amSJU - OAK
2 stops12h 20mSouthwest
Deal found 10/27$635
This Southwest deal was found by Cheapflights users on 10/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/227:25 pmOAK - SJU
2 stops11h 20mSouthwest
Tue 12/303:25 pmSJU - OAK
2 stops13h 00mSouthwest
Deal found 10/28$958
This Southwest deal was found by Cheapflights users on 10/29. 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.
Sun 11/236:00 amOAK - SJU
2 stops12h 20mSouthwest
Sat 11/292:35 pmSJU - OAK
2 stops13h 05mSouthwest
Deal found 10/29$1,080
This Southwest deal was found by Cheapflights users on 10/29. 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.
Sat 12/207:45 pmOAK - SJU
2 stops11h 00mSouthwest
Sat 12/273:50 pmSJU - OAK
2 stops19h 10mSouthwest
Deal found 10/29$1,088
This Southwest deal was found by Cheapflights users on 10/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/227:25 pmOAK - SJU
2 stops11h 20mSouthwest
Sun 12/286:35 amSJU - OAK
2 stops16h 00mSouthwest
Deal found 10/28$1,105
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/178:03 pmOAK - SJU
2 stops15h 03mAlaska Airlines
Wed 11/197:15 amSJU - OAK
2 stops20h 44mAlaska Airlines
Deal found 10/28$1,129
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/45:55 amOAK - SJU
2 stops13h 25mDelta
Mon 12/87:00 amSJU - OAK
2 stops13h 04mDelta
Deal found 10/30$1,139
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/52:31 pmOAK - SJU
2 stops20h 13mAlaska Airlines
Wed 12/107:00 amSJU - OAK
2 stops20h 59mAlaska Airlines
Deal found 10/29$1,242
This Delta deal was found by Cheapflights users on 10/28. 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.
Mon 11/245:55 amOAK - SJU
2 stops13h 18mDelta
Thu 11/277:00 amSJU - OAK
2 stops15h 13mDelta
Deal found 10/28$1,266
This Southwest deal was found by Cheapflights users on 10/29. 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 12/237:25 pmOAK - SJU
2 stops11h 00mSouthwest
Fri 1/27:30 amSJU - OAK
2 stops14h 05mSouthwest
Deal found 10/29$1,275
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/135:55 amOAK - SJU
2 stops13h 18mDelta
Sat 11/227:00 amSJU - OAK
2 stops18h 39mDelta
Deal found 10/29$1,311

Cheap 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 October 30, 2025.

Round-trip from

$355
(Southwest)

One-way from

$208
(Southwest)

Popular in

December

Cheapest in

May

Average price

$443
From Oakland to Puerto Rico
Search Deals
One-way flight from Oakland to Puerto Rico
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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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 October 30, 2025.
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

Tue 1/27

7:25 pm-11:20 am

2 stops11h 55m

San Juan Luis Munoz Marin Intl

Mon 2/2

12:10 pm-9:25 pm

2 stops13h 15m

$355

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Wed 1/28

9:40 am-12:35 am

2 stops10h 55m

San Juan Luis Munoz Marin Intl

Mon 2/2

12:10 pm-9:25 pm

2 stops13h 15m

$355

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Wed 1/14

5:55 am-11:59 pm

2 stops14h 04m

San Juan Luis Munoz Marin Intl

Fri 1/23

6:15 am-4:14 pm

2 stops13h 59m

$927

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Wed 1/14

5:55 am-11:59 pm

2 stops14h 04m

San Juan Luis Munoz Marin Intl

Thu 1/22

3:20 pm-11:53 pm

2 stops12h 33m

$927

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Wed 1/14

5:55 am-11:59 pm

2 stops14h 04m

San Juan Luis Munoz Marin Intl

Mon 1/26

2:15 pm-11:53 pm

2 stops13h 38m

$1,000

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 1/10

8:10 am-10:26 pm

2 stops34h 16m

San Juan Luis Munoz Marin Intl

Thu 1/22

4:28 pm-8:40 pm

2 stops32h 12m

$1,051

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 1/10

8:10 am-10:26 pm

2 stops34h 16m

San Juan Luis Munoz Marin Intl

Fri 1/23

6:00 am-10:28 am

2 stops32h 28m

$1,051

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sun 11/23

6:00 am-10:20 pm

2 stops12h 20m

San Juan Luis Munoz Marin Intl

Sat 11/29

2:35 pm-11:40 pm

2 stops13h 05m

$1,080

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 12/20

7:45 pm-10:45 am

2 stops11h 00m

San Juan Luis Munoz Marin Intl

Sat 12/27

3:50 pm-7:00 am

2 stops19h 10m

$1,088

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 12/22

7:25 pm-10:45 am

2 stops11h 20m

San Juan Luis Munoz Marin Intl

Sun 12/28

6:35 am-6:35 pm

2 stops16h 00m

$1,105

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 21 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, December is the cheapest month in which you can book a flight from Oakland, California to Puerto Rico (average of $169). Flying from Oakland, California to Puerto Rico in October is currently the most expensive (average of $329). 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.

What is the cheapest time of day to fly from OAK to PR?

Find hourly flight availability from Oakland to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

One of the essential ways to save on airfare from Oakland, California to Puerto Rico is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 34% on airfare.

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 October 30, 2025.
See what other customers who have flown with Southwest and Spirit Airlines 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
4,242 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,115 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 11h 55m. Southwest provides one of the quickest options available for as low as $355. 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?

    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, December is the cheapest month in which you can book a flight from Oakland, California to Puerto Rico (average of $169). Flying from Oakland, California to Puerto Rico in October is currently the most expensive (average of $329). 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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Top 2 airlines flying from Oakland to Puerto Rico

Discover the top 2 airlines 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$278Average$534FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$389Average$560FlexibilityNo cancel feeOn-time63%

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