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San Juan

$248+ Cheap flights from Oakland, CA (OAK) to San Juan

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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Mar 18 — Mar 251
Wed 3/18
Wed 3/25
1 adult, Economy
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Cheap flight deals from Oakland to San Juan

Cheapest flights from Oakland to San Juan
Explore the most affordable flight options available from Oakland to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 16, 2026.

This Southwest deal was found by Cheapflights users on 2/13. 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 2/13$391
This Southwest deal was found by Cheapflights users on 2/12. 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 6/1710:25 am
OAK
-
SJU
2 stops10h 50m
Southwest
Wed 6/2411:15 am
SJU
-
OAK
2 stops12h 00m
Southwest
Deal found 2/12$416
This Southwest deal was found by Cheapflights users on 2/14. 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 4/127:35 pm
OAK
-
SJU
2 stops10h 35m
Southwest
Tue 4/218:10 am
SJU
-
OAK
2 stops13h 40m
Southwest
Deal found 2/14$419
This Southwest deal was found by Cheapflights users on 2/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/57:40 pm
OAK
-
SJU
2 stops11h 50m
Southwest
Thu 6/115:00 am
SJU
-
OAK
2 stops11h 30m
Southwest
Deal found 2/15$438
This Southwest deal was found by Cheapflights users on 2/13. 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 7/289:45 am
OAK
-
SJU
2 stops11h 30m
Southwest
Wed 8/55:15 am
SJU
-
OAK
2 stops11h 40m
Southwest
Deal found 2/13$456
This Southwest deal was found by Cheapflights users on 2/12. 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 5/137:35 pm
OAK
-
SJU
2 stops10h 35m
Southwest
Wed 5/208:10 am
SJU
-
OAK
2 stops13h 55m
Southwest
Deal found 2/12$463
This Southwest deal was found by Cheapflights users on 2/14. 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 4/117:35 pm
OAK
-
SJU
2 stops10h 30m
Southwest
Tue 4/218:10 am
SJU
-
OAK
2 stops13h 55m
Southwest
Deal found 2/14$484
This Southwest deal was found by Cheapflights users on 2/12. 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 7/27:50 am
OAK
-
SJU
2 stops13h 35m
Southwest
Wed 7/81:30 pm
SJU
-
OAK
2 stops12h 00m
Southwest
Deal found 2/12$491
This Southwest deal was found by Cheapflights users on 2/13. 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 2/13$500
This Southwest deal was found by Cheapflights users on 2/12. 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 3/237:35 pm
OAK
-
SJU
2 stops10h 45m
Southwest
Thu 3/261:05 pm
SJU
-
OAK
2 stops12h 15m
Southwest
Deal found 2/12$503
This Southwest deal was found by Cheapflights users on 2/14. 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 5/1511:55 pm
OAK
-
SJU
1 stop10h 25m
Southwest
Tue 5/2611:25 am
SJU
-
OAK
2 stops13h 30m
Southwest
Deal found 2/14$531
This Southwest deal was found by Cheapflights users on 2/14. 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 7/175:05 am
OAK
-
SJU
2 stops11h 20m
Southwest
Mon 7/208:15 pm
SJU
-
OAK
2 stops17h 10m
Southwest
Deal found 2/14$538

Find flight deals from Oakland to San Juan

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to San Juan (PR1). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 16, 2026.

Round-trip from

$391
(Southwest)

One-way from

$248
(Southwest)

Popular in

December

Cheapest in

October

Average price

$563
From Oakland to San Juan
Search Deals
One-way flight from Oakland to San Juan
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($120 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($32 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 San Juan 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 16, 2026.
Use the filters below to find and compare flights from Oakland to San Juan that are best for you.

Fly from

Oakland

Fly to

San Juan

Route

Depart

Return

Price

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Wed 6/17

10:25 am-12:15 am

2 stops10h 50m

San Juan Luis Munoz Marin Intl

Wed 6/24

6:30 am-1:50 pm

1 stop10h 20m

$416

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Wed 5/13

7:35 pm-9:10 am

2 stops10h 35m

San Juan Luis Munoz Marin Intl

Wed 5/20

8:10 am-7:05 pm

2 stops13h 55m

$463

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 8/3

7:50 am-12:25 am

2 stops13h 35m

San Juan Luis Munoz Marin Intl

Sat 8/15

5:05 am-1:40 pm

2 stops11h 35m

$463

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sat 4/11

7:35 pm-9:05 am

2 stops10h 30m

San Juan Luis Munoz Marin Intl

Tue 4/21

8:10 am-7:05 pm

2 stops13h 55m

$484

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 7/2

7:50 am-12:25 am

2 stops13h 35m

San Juan Luis Munoz Marin Intl

Wed 7/8

1:30 pm-10:30 pm

2 stops12h 00m

$491

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sun 3/1

10:35 am-1:35 am

2 stops11h 00m

San Juan Luis Munoz Marin Intl

Wed 3/4

10:20 am-7:50 pm

2 stops13h 30m

$500

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 3/23

7:35 pm-9:20 am

2 stops10h 45m

San Juan Luis Munoz Marin Intl

Thu 3/26

1:05 pm-10:20 pm

2 stops12h 15m

$503

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 5/15

11:55 pm-1:20 pm

1 stop10h 25m

San Juan Luis Munoz Marin Intl

Tue 5/26

11:25 am-9:55 pm

2 stops13h 30m

$531

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Fri 5/15

11:55 pm-1:20 pm

1 stop10h 25m

San Juan Luis Munoz Marin Intl

Fri 5/22

2:00 pm-10:30 pm

2 stops11h 30m

$531

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 3/2

6:30 am-12:40 am

2 stops14h 10m

San Juan Luis Munoz Marin Intl

Fri 3/6

6:30 am-2:20 pm

2 stops11h 50m

$540

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/13

Showing 1-10 of 19 results
1
2

Best time to book a flight from Oakland to San Juan

Have a flexible travel schedule? Discover the best time to fly to San Juan 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 San Juan

What is the cheapest month to book a flight from Oakland, California to San Juan?

Currently, January is the cheapest month in which you can book a flight from Oakland, California to San Juan (average of $162). Flying from Oakland, California to San Juan 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 San Juan

Get insights into the airlines that provide service to San Juan. 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 San Juan. Reviews last updated February 16, 2026.
Get a feel of what it's like to fly with Southwest from Oakland to San Juan by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,285 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

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
4,285 reviews
Southwest
8.0
Very good
4,285 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

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 San Juan. 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 San Juan?

    For a flight from Oakland to San Juan, you will be flying from Oakland. Oakland (OAK) is just 7.0 mi from the center of the city. Oakland is the only Oakland airport and it handles 0 outbound flights to San Juan per day. 1 airline has flights to San Juan from Oakland on a regular basis.

  • How long is the flight from Oakland, California to San Juan?

    Departing from Oakland, California to San Juan will take you 10h 50m. There are 3615 mi between Oakland, California and San Juan.

  • What is the cheapest airline to fly from Oakland, California to San Juan round-trip?

    Currently priced at $385, Southwest will fly you from Oakland, California to San Juan and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. Southwest is 32% cheaper than the average price of flights available within the next 90 days to this destination.

  • Can I find deals for flights from Oakland to San Juan that include hotel bookings?

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

  • How can I find direct flights from Oakland to San Juan?

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

  • Can I find deals for business class flights from Oakland to San Juan?

    Yes. Cheapflights offers flight deals from Oakland to San Juan 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 San Juan?

    Currently, January is the cheapest month in which you can book a flight from Oakland, California to San Juan (average of $162). Flying from Oakland, California to San Juan 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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Top airline flying from Oakland to San Juan

Discover the top airline that operate flights from Oakland to San Juan. 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 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$385Average$558FlexibilityNo cancel feeOn-time63%

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