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Puerto Rico

$250+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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 December 18, 2025.

This Southwest deal was found by Cheapflights users on 12/17. 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 12/2010:20 amOAK - SJU
2 stops10h 25mSouthwest
Thu 12/255:45 amSJU - OAK
2 stops12h 20mSouthwest
Deal found 12/17$733
This Southwest deal was found by Cheapflights users on 12/16. 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 12/275:50 amOAK - SJU
2 stops12h 40mSouthwest
Thu 1/15:45 amSJU - OAK
2 stops12h 20mSouthwest
Deal found 12/16$1,005
This Southwest deal was found by Cheapflights users on 12/16. 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 12/2311:00 amOAK - SJU
2 stops10h 40mSouthwest
Mon 12/2911:35 amSJU - OAK
2 stops14h 15mSouthwest
Deal found 12/16$1,045
This Southwest deal was found by Cheapflights users on 12/17. 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 12/287:25 pmOAK - SJU
2 stops11h 20mSouthwest
Sat 1/35:35 amSJU - OAK
2 stops13h 20mSouthwest
Deal found 12/17$1,106
This Delta deal was found by Cheapflights users on 12/15. 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.
Wed 12/315:53 amOAK - SJU
2 stops13h 27mDelta
Tue 1/137:30 amSJU - OAK
2 stops19h 23mDelta
Deal found 12/15$1,169
This Southwest deal was found by Cheapflights users on 12/17. 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 12/275:50 amOAK - SJU
2 stops12h 40mSouthwest
Sat 1/35:35 amSJU - OAK
2 stops13h 20mSouthwest
Deal found 12/17$1,170
This Southwest deal was found by Cheapflights users on 12/16. 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 12/258:20 amOAK - SJU
2 stops12h 05mSouthwest
Sat 1/37:05 amSJU - OAK
2 stops11h 50mSouthwest
Deal found 12/16$1,171
This Delta deal was found by Cheapflights users on 12/15. 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.
Wed 12/315:53 amOAK - SJU
2 stops13h 27mDelta
Mon 1/126:15 amSJU - OAK
2 stops13h 59mDelta
Deal found 12/15$1,194
This Delta deal was found by Cheapflights users on 12/15. 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.
Tue 12/305:53 amOAK - SJU
2 stops11h 16mDelta
Tue 1/137:30 amSJU - OAK
2 stops12h 44mDelta
Deal found 12/15$1,206
This Delta deal was found by Cheapflights users on 12/15. 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.
Wed 12/315:53 amOAK - SJU
2 stops11h 16mDelta
Fri 1/166:15 amSJU - OAK
2 stops20h 38mDelta
Deal found 12/15$1,222
This Delta deal was found by Cheapflights users on 12/15. 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.
Tue 12/305:53 amOAK - SJU
2 stops11h 16mDelta
Mon 1/126:15 amSJU - OAK
2 stops20h 38mDelta
Deal found 12/15$1,231
This Delta deal was found by Cheapflights users on 12/15. 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.
Tue 12/305:53 amOAK - SJU
2 stops11h 16mDelta
Fri 1/166:15 amSJU - OAK
2 stops20h 38mDelta
Deal found 12/15$1,259

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 December 18, 2025.

Round-trip from

$405
(Southwest)

One-way from

$250
(Southwest)

Popular in

December

Cheapest in

May

Average price

$595
From Oakland to Puerto Rico
Search Deals
One-way flight from Oakland to Puerto Rico
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 18, 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

Sat 1/17

8:35 am-12:10 am

2 stops11h 35m

San Juan Luis Munoz Marin Intl

Thu 1/22

5:40 am-2:55 pm

2 stops13h 15m

$489

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 4/30

11:55 pm-2:55 pm

2 stops12h 00m

San Juan Luis Munoz Marin Intl

Mon 5/4

2:00 pm-10:30 pm

2 stops11h 30m

$527

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 1/1

8:25 am-12:25 am

2 stops12h 00m

San Juan Luis Munoz Marin Intl

Wed 1/14

5:40 am-2:55 pm

2 stops13h 15m

$575

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 1/22

8:10 am-12:35 am

2 stops12h 25m

San Juan Luis Munoz Marin Intl

Mon 1/26

12:10 pm-9:25 pm

2 stops13h 15m

$603

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 2/13

7:50 pm-10:00 am

2 stops10h 10m

San Juan Luis Munoz Marin Intl

Sat 2/21

4:20 pm-11:50 pm

1 stop11h 30m

$721

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 2/14

6:25 pm-10:30 am

2 stops12h 05m

San Juan Luis Munoz Marin Intl

Sat 2/21

1:45 pm-9:35 pm

2 stops11h 50m

$744

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 1/17

8:10 am-3:00 pm

2 stops26h 50m

San Juan Luis Munoz Marin Intl

Thu 1/29

6:00 am-4:23 pm

2 stops38h 23m

$801

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 1/16

5:17 pm-3:00 pm

2 stops41h 43m

San Juan Luis Munoz Marin Intl

Fri 1/30

7:07 am-10:28 am

2 stops31h 21m

$841

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 1/17

8:10 am-3:00 pm

2 stops26h 50m

San Juan Luis Munoz Marin Intl

Wed 2/4

6:00 am-4:23 pm

2 stops38h 23m

$841

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sun 1/18

8:03 pm-9:39 pm

2 stops21h 36m

San Juan Luis Munoz Marin Intl

Fri 1/30

7:07 am-10:28 am

2 stops31h 21m

$852

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 23 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 $315). 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 December 18, 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 December 18, 2025.
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
7.9
Good
4,250 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

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.
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

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 11h 35m. Southwest provides one of the quickest options available for as low as $489. 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, 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 $315). 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 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$385Average$555FlexibilityNo cancel feeOn-time63%

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