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Caribbean Islands

$145+ 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 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Apr 8 — Apr 151
Tue 4/8
Tue 4/15
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 April 3, 2025.

Round-trip from

$271
(Mytrip)

One-way from

$145
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$502
From Oakland to Caribbean Islands
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One-way flight from Oakland to Caribbean Islands
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Highest demand for flights based on searches. 7% potential increase in price ($41 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 April 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 April 3, 2025.

This Mytrip deal was found by Cheapflights users on 4/1. 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 5/56:29 pmOAK - SJU
2 stops26h 10mSpirit Airlines
Fri 5/912:36 pmSJU - OAK
2 stops12h 49mSpirit Airlines
Deal found 4/1$271
This CheapOair deal was found by Cheapflights users on 4/2. 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.
Fri 5/28:37 pmOAK - MBJ
2 stops12h 18mSpirit Airlines
Fri 5/912:07 pmMBJ - OAK
2 stops24h 49mSpirit Airlines
Deal found 4/2$374
This Delta deal was found by Cheapflights users on 4/1. 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 4/145:10 pmOAK - SJU
2 stops18h 09mDelta
Fri 4/187:15 amSJU - OAK
2 stops19h 28mDelta
Deal found 4/1$465
This Mytrip deal was found by Cheapflights users on 4/2. 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.
Fri 4/117:31 pmOAK - PUJ
2 stops13h 13mSpirit Airlines
Thu 4/173:48 pmPUJ - OAK
2 stops18h 01mSpirit Airlines
Deal found 4/2$471
This Southwest deal was found by Cheapflights users on 4/2. 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 9/78:35 pmOAK - SJU
2 stops10h 40mSouthwest
Sat 9/137:45 amSJU - OAK
2 stops13h 10mSouthwest
Deal found 4/2$508
This Mytrip deal was found by Cheapflights users on 4/3. 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.
Fri 5/165:45 amOAK - NAS
2 stops26h 15mMultiple Airlines
Tue 5/274:00 pmNAS - OAK
2 stops21h 56mMultiple Airlines
Deal found 4/3$590
This Mytrip deal was found by Cheapflights users on 4/2. 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 6/295:39 pmOAK - SJU
3 stops38h 45mMultiple Airlines
Sat 7/510:52 amSJU - OAK
2 stops15h 34mMultiple Airlines
Deal found 4/2$605
This Southwest deal was found by Cheapflights users on 4/2. 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 9/47:00 pmOAK - PUJ
2 stops16h 05mSouthwest
Mon 9/83:05 pmPUJ - OAK
2 stops19h 50mSouthwest
Deal found 4/2$642
This Southwest deal was found by Cheapflights users on 4/2. 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 7/108:25 pmOAK - NAS
2 stops13h 50mSouthwest
Fri 7/182:10 pmNAS - OAK
2 stops12h 55mSouthwest
Deal found 4/2$643
This Mytrip deal was found by Cheapflights users on 4/2. 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.
Sat 6/285:30 amOAK - STX
2 stops31h 17mSpirit Airlines
Sat 7/54:42 pmSTX - OAK
2 stops30h 37mSpirit Airlines
Deal found 4/2$653
This Delta deal was found by Cheapflights users on 4/3. 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 4/155:10 pmOAK - MBJ
2 stops15h 36mDelta
Thu 4/2412:11 pmMBJ - OAK
2 stops13h 32mDelta
Deal found 4/3$698
This Mytrip deal was found by Cheapflights users on 4/2. 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.
Sat 6/285:30 amOAK - MBJ
2 stops29h 15mMultiple Airlines
Sat 7/53:05 pmMBJ - OAK
2 stops31h 14mMultiple Airlines
Deal found 4/2$704

Cheapflights Fare Finder

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 April 3, 2025.
Use the filters below to find and compare flights from Oakland to Caribbean Islands that are best for you.

Fly from

Oakland

Fly to

Caribbean Islands

Route

Depart

Return

Price

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 5/5

6:29 pm-11:39 pm

2 stops26h 10m

San Juan Luis Munoz Marin Intl

Fri 5/9

12:36 pm-10:25 pm

2 stops12h 49m

$271

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Fri 5/2

8:37 pm-10:55 am

2 stops12h 18m

Montego Bay Sangster Intl

Fri 5/9

12:07 pm-10:56 am

2 stops24h 49m

$374

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 4/14

5:10 pm-2:19 pm

2 stops18h 09m

San Juan Luis Munoz Marin Intl

Fri 4/18

7:15 am-11:43 pm

2 stops19h 28m

$465

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Fri 4/11

7:31 pm-11:44 am

2 stops13h 13m

Punta Cana

Thu 4/17

3:48 pm-6:49 am

2 stops18h 01m

$471

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sun 9/7

8:35 pm-10:15 am

2 stops10h 40m

San Juan Luis Munoz Marin Intl

Sat 9/13

7:45 am-5:55 pm

2 stops13h 10m

$508

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Fri 5/16

5:45 am-11:00 am

2 stops26h 15m

Nassau Intl

Tue 5/27

4:00 pm-10:56 am

2 stops21h 56m

$590

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Sun 6/29

5:39 pm-11:24 am

3 stops38h 45m

San Juan Luis Munoz Marin Intl

Sat 7/5

10:52 am-11:26 pm

2 stops15h 34m

$605

OaklandChristiansted

OAK - STX

OAKSTX

Oakland

Sat 6/28

5:30 am-3:47 pm

2 stops31h 17m

Christiansted Henry Rohlsen

Sat 7/5

4:42 pm-8:19 pm

2 stops30h 37m

$653

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Tue 4/15

5:10 pm-10:46 am

2 stops15h 36m

Montego Bay Sangster Intl

Thu 4/24

12:11 pm-11:43 pm

2 stops13h 32m

$698

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Sat 6/28

5:30 am-12:45 pm

2 stops29h 15m

Montego Bay Sangster Intl

Sat 7/5

3:05 pm-8:19 pm

2 stops31h 14m

$704

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

Showing 1-10 of 28 results
1
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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.

Cheapflights Insights

Everything you need to know about your flight from Oakland to Caribbean Islands

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 December is currently the most expensive (average of $336). 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 April 3, 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 April 3, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest 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.
Alaska Airlines
8.0
Very good
9,827 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,827 reviews
Alaska Airlines
8.0
Very good
9,827 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,274 reviews
Alaska Airlines
8.0
Very good
9,827 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,897 reviews
Alaska Airlines
8.0
Very good
9,827 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Spirit Airlines
6.3
Okay
7,889 reviews
Alaska Airlines
8.0
Very good
9,827 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 ($145), Delta ($193), and Southwest ($243).

  • 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 - Montego Bay Sangster Intl or Oakland - Punta Cana.

  • 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 December is currently the most expensive (average of $336). 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 April 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$260Average$534FlexibilityNo cancel feeOn-time65%
DeltaCheapest$440Average$905FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$469Average$710FlexibilityNo cancel feeOn-time63%

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