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Caribbean Islands

$138+ Cheap flights from Oakland, CA (OAK) to Caribbean Islands

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 5/21. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap flight deals from Oakland to Caribbean Islands

Keep the following information in mind while searching for Oakland to Caribbean Islands flight deals. Data was last updated February 20, 2025.

Round-trip from

$239
(CheapOair)

One-way from

$138
(CheapOair)

Popular in

December

Cheapest in

September

Average price

$468
From Oakland to Caribbean Islands
Search Deals
One-way flight from Oakland to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Find flight deals from Oakland to Caribbean Islands

Cheapest flights from Oakland to Caribbean Islands
Explore the most affordable flight options available from Oakland to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This CheapOair deal was found by Cheapflights users on 2/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/105:52 pmOAK - SJU
2 stops22h 06mSpirit Airlines
Mon 3/178:03 pmSJU - OAK
2 stops23h 54mSpirit Airlines
Deal found 2/19$239
This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/316:55 pmOAK - STT
2 stops15h 05mSpirit Airlines
Sat 4/512:43 pmSTT - OAK
2 stops20h 53mSpirit Airlines
Deal found 2/20$263
This CheapOair deal was found by Cheapflights users on 2/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2512:11 pmOAK - PUJ
2 stops21h 06mSpirit Airlines
Mon 3/312:29 pmPUJ - OAK
2 stops23h 47mSpirit Airlines
Deal found 2/19$333
This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/77:30 amOAK - MBJ
2 stops26h 11mSpirit Airlines
Mon 5/1212:11 pmMBJ - OAK
2 stops13h 28mSpirit Airlines
Deal found 2/19$382
This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/306:29 pmOAK - KIN
2 stops16h 02mSpirit Airlines
Wed 5/712:21 pmKIN - OAK
2 stops13h 18mSpirit Airlines
Deal found 2/20$393
This Southwest deal was found by Cheapflights users on 2/19. 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 9/1210:00 amOAK - SJU
2 stops10h 50mSouthwest
Mon 9/155:50 amSJU - OAK
2 stops15h 30mSouthwest
Deal found 2/19$471
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2711:28 amOAK - SJU
2 stops22h 30mMultiple Airlines
Fri 3/712:59 amSJU - OAK
2 stops33h 17mMultiple Airlines
Deal found 2/19$477
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/66:55 pmOAK - MBJ
2 stops14h 07mMultiple Airlines
Sat 4/123:05 pmMBJ - OAK
2 stops17h 44mMultiple Airlines
Deal found 2/20$493
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/277:31 amOAK - NAS
3 stops23h 59mMultiple Airlines
Mon 3/3112:00 pmNAS - OAK
2 stops26h 16mMultiple Airlines
Deal found 2/20$516
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/147:46 amOAK - SDQ
3 stops34h 59mMultiple Airlines
Sat 4/193:41 pmSDQ - OAK
2 stops18h 08mMultiple Airlines
Deal found 2/19$560
This Delta deal was found by Cheapflights users on 2/19. 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 2/266:00 amOAK - SJU
2 stops13h 59mDelta
Mon 3/32:00 pmSJU - OAK
2 stops13h 56mDelta
Deal found 2/19$693
This Delta deal was found by Cheapflights users on 2/20. 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.
Sun 8/310:45 pmOAK - MBJ
1 stop12h 12mDelta
Wed 8/61:15 pmMBJ - OAK
1 stop10h 17mDelta
Deal found 2/20$791

Find flights from Oakland to Caribbean Islands within your budget

Customize your flight search to find flights from Oakland to Caribbean Islands 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 20, 2025.

Fly from

Oakland

Fly to

Caribbean Islands

Route

Depart

Return

Price

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 3/10

5:52 pm-6:58 pm

2 stops22h 06m

San Juan Luis Munoz Marin Intl

Mon 3/17

8:03 pm-4:57 pm

2 stops23h 54m

$239

OaklandSaint Thomas Island

OAK - STT

OAKSTT

Oakland

Mon 3/31

6:55 pm-1:00 pm

2 stops15h 05m

Saint Thomas Island Cyril E King

Sat 4/5

12:43 pm-6:36 am

2 stops20h 53m

$263

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Tue 3/25

12:11 pm-12:17 pm

2 stops21h 06m

Punta Cana

Mon 3/31

2:29 pm-11:16 am

2 stops23h 47m

$333

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Wed 5/7

7:30 am-11:41 am

2 stops26h 11m

Montego Bay Sangster Intl

Mon 5/12

12:11 pm-11:39 pm

2 stops13h 28m

$382

OaklandKingston

OAK - KIN

OAKKIN

Oakland

Wed 4/30

6:29 pm-12:31 pm

2 stops16h 02m

Kingston Norman Manley

Wed 5/7

12:21 pm-11:39 pm

2 stops13h 18m

$393

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 2/27

11:28 am-1:58 pm

2 stops22h 30m

San Juan Luis Munoz Marin Intl

Fri 3/7

12:59 am-6:16 am

2 stops33h 17m

$477

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Sun 4/6

6:55 pm-11:02 am

2 stops14h 07m

Montego Bay Sangster Intl

Sat 4/12

3:05 pm-6:49 am

2 stops17h 44m

$493

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Thu 3/27

7:31 am-10:30 am

3 stops23h 59m

Nassau Intl

Mon 3/31

12:00 pm-11:16 am

2 stops26h 16m

$516

OaklandSanto Domingo

OAK - SDQ

OAKSDQ

Oakland

Mon 4/14

7:46 am-9:45 pm

3 stops34h 59m

Santo Domingo Las Americas

Sat 4/19

3:41 pm-6:49 am

2 stops18h 08m

$560

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Thu 2/27

6:10 am-9:40 pm

2 stops11h 30m

San Juan Luis Munoz Marin Intl

Sat 3/8

4:10 pm-10:50 pm

1 stop10h 40m

$609

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 30 results
1
2
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Best time to book a flight from Oakland to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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.

Travel insights for flights from Oakland to Caribbean Islands

Get recent, data-driven insights about flights from Oakland to Caribbean Islands including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Oakland, California to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Oakland, California to Caribbean Islands (average of $254). Flying from Oakland, California to Caribbean Islands in March is currently the most expensive (average of $363). 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 EPX?

Find hourly flight availability from Oakland to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 20, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oakland, California to Caribbean Islands as you normally would.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Caribbean Islands. Reviews last updated February 20, 2025.
Read reviews from past customers who have flown Southwest, Alaska Airlines and Delta from Oakland to Caribbean Islands. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

10.0
Excellent

Arlene,May 2024

SAN - OAK

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

10.0
Excellent

Arlene,May 2024

SAN - OAK

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

10.0
Excellent

Arlene,May 2024

SAN - OAK

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

10.0
Excellent

Arlene,May 2024

SAN - OAK

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Spirit Airlines
6.3
Okay
8,013 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

10.0
Excellent

Arlene,May 2024

SAN - OAK

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Related info for your journey

Find useful and relevant information for your journey from Oakland to Caribbean Islands. 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 Caribbean Islands?

    Oakland (OAK), located 7.0 mi from the city center, is the airport you fly out of when you book flights from Oakland to Caribbean Islands.

  • What are the cheapest airlines to fly from Oakland, California to Caribbean Islands one-way?

    The cheapest airlines for a one-way flight from Oakland, California to Caribbean Islands are Spirit Airlines ($138), Delta ($758), and Alaska Airlines ($1,135).

  • What are the most popular routes from Oakland, California to Caribbean Islands?

    The most popular route from Oakland, California to Caribbean Islands is Oakland - San Juan Luis Munoz Marin Intl. You may also consider Oakland - Punta Cana or Oakland - Montego Bay Sangster Intl.

  • Can I find deals for flights from Oakland to Caribbean Islands that include hotel bookings?

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

  • How can I find direct flights from Oakland to Caribbean Islands?

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

  • Can I find deals for business class flights from Oakland to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Oakland to Caribbean Islands 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 Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from Oakland, California to Caribbean Islands (average of $254). Flying from Oakland, California to Caribbean Islands in March is currently the most expensive (average of $363). 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.

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Alternative routes for Oakland to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Oakland to Caribbean Islands

Discover the top 3 airlines that operate flights from Oakland to Caribbean Islands. 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 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$262Average$459FlexibilityNo cancel feeOn-time65%
DeltaCheapest$275Average$885FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$469Average$711FlexibilityNo cancel feeOn-time63%
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