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Caribbean Islands

$165+ 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Jul 1 — Jul 81
Tue 7/1
Tue 7/8
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 June 26, 2025.

Round-trip from

$323
(FlightHub)

One-way from

$165
(CheapOair)

Popular in

December

Cheapest in

September

Average price

$572
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. 10% potential increase in price ($58 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($25 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 26, 2025.

This FlightHub deal was found by Cheapflights users on 6/26. 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.
Fri 9/57:30 amOAK - STT
2 stops22h 15mSpirit Airlines
Thu 9/119:40 amSTT - OAK
2 stops16h 59mSpirit Airlines
Deal found 6/26$323
This FlightHub deal was found by Cheapflights users on 6/26. 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.
Tue 7/299:23 amOAK - SJU
2 stops23h 09mSpirit Airlines
Fri 8/11:37 amSJU - OAK
2 stops24h 56mSpirit Airlines
Deal found 6/26$343
This Southwest deal was found by Cheapflights users on 6/25. 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 8/185:35 amOAK - SJU
2 stops12h 10mSouthwest
Thu 8/285:50 amSJU - OAK
2 stops17h 25mSouthwest
Deal found 6/25$369
This Mytrip deal was found by Cheapflights users on 6/25. 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 8/188:13 amOAK - SJU
2 stops13h 31mMultiple Airlines
Wed 8/271:59 amSJU - OAK
3 stops17h 54mMultiple Airlines
Deal found 6/25$419
This CheapOair deal was found by Cheapflights users on 6/25. 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.
Thu 8/712:42 pmOAK - PUJ
2 stops22h 48mSpirit Airlines
Wed 8/1311:06 amPUJ - OAK
2 stops23h 12mSpirit Airlines
Deal found 6/25$442
This FlightHub deal was found by Cheapflights users on 6/24. 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.
Fri 7/119:23 amOAK - MBJ
2 stops23h 42mSpirit Airlines
Thu 7/1710:48 amMBJ - OAK
2 stops23h 40mSpirit Airlines
Deal found 6/24$461
This Mytrip deal was found by Cheapflights users on 6/26. 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 7/102:38 pmOAK - PUJ
3 stops26h 16mMultiple Airlines
Wed 7/163:25 pmPUJ - OAK
3 stops24h 02mMultiple Airlines
Deal found 6/26$485
This Mytrip deal was found by Cheapflights users on 6/25. 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.
Wed 7/239:23 amOAK - MBJ
2 stops22h 30mMultiple Airlines
Wed 7/303:05 pmMBJ - OAK
2 stops22h 42mMultiple Airlines
Deal found 6/25$495
This CheapOair deal was found by Cheapflights users on 6/24. 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.
Thu 8/712:42 pmOAK - SDQ
2 stops24h 05mSpirit Airlines
Wed 8/131:01 pmSDQ - OAK
2 stops21h 17mSpirit Airlines
Deal found 6/24$523
This Southwest deal was found by Cheapflights users on 6/24. 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 9/56:55 pmOAK - NAS
2 stops15h 35mSouthwest
Fri 9/122:15 pmNAS - OAK
2 stops12h 05mSouthwest
Deal found 6/24$543
This Mytrip deal was found by Cheapflights users on 6/24. 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 9/57:30 amOAK - NAS
2 stops24h 00mMultiple Airlines
Fri 9/124:00 pmNAS - OAK
3 stops23h 13mMultiple Airlines
Deal found 6/24$580
This Mytrip deal was found by Cheapflights users on 6/24. 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 7/129:23 amOAK - AUA
2 stops26h 17mSpirit Airlines
Sun 7/203:45 pmAUA - OAK
2 stops19h 43mSpirit Airlines
Deal found 6/24$581

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 June 26, 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

OaklandSaint Thomas Island

OAK - STT

OAKSTT

Oakland

Fri 9/5

7:30 am-8:45 am

2 stops22h 15m

Saint Thomas Island Cyril E King

Thu 9/11

9:40 am-11:39 pm

2 stops16h 59m

$323

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 7/29

9:23 am-11:32 am

2 stops23h 09m

San Juan Luis Munoz Marin Intl

Fri 8/1

1:37 am-11:33 pm

2 stops24h 56m

$343

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 8/18

5:35 am-8:45 pm

2 stops12h 10m

San Juan Luis Munoz Marin Intl

Thu 8/28

5:50 am-8:15 pm

2 stops17h 25m

$369

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Mon 8/18

8:13 am-12:44 am

2 stops13h 31m

San Juan Luis Munoz Marin Intl

Wed 8/27

1:59 am-4:53 pm

3 stops17h 54m

$419

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Thu 8/7

12:42 pm-2:30 pm

2 stops22h 48m

Punta Cana

Wed 8/13

11:06 am-7:18 am

2 stops23h 12m

$442

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Fri 7/11

9:23 am-11:05 am

2 stops23h 42m

Montego Bay Sangster Intl

Thu 7/17

10:48 am-8:28 am

2 stops23h 40m

$461

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Thu 7/10

2:38 pm-7:54 pm

3 stops26h 16m

Punta Cana

Wed 7/16

3:25 pm-12:27 pm

3 stops24h 02m

$485

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Wed 7/23

9:23 am-9:53 am

2 stops22h 30m

Montego Bay Sangster Intl

Wed 7/30

3:05 pm-11:47 am

2 stops22h 42m

$495

OaklandSanto Domingo

OAK - SDQ

OAKSDQ

Oakland

Thu 8/7

12:42 pm-3:47 pm

2 stops24h 05m

Santo Domingo Las Americas

Wed 8/13

1:01 pm-7:18 am

2 stops21h 17m

$523

OaklandNassau

OAK - NAS

OAKNAS

Oakland

Fri 9/5

6:55 pm-1:30 pm

2 stops15h 35m

Nassau Intl

Fri 9/12

2:15 pm-11:20 pm

2 stops12h 05m

$543

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/25

Showing 1-10 of 38 results
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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 June is currently the most expensive (average of $339). 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 June 26, 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.

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 June 26, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Delta from Oakland to Caribbean Islands by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,276 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,964 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Spirit Airlines
6.3
Okay
8,089 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Entertainment

7.1

Comfort

7.8

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 ($165), Delta ($407), and Alaska Airlines ($702).

  • 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 June is currently the most expensive (average of $339). 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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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 June 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$260Average$391FlexibilityNo cancel feeOn-time65%
DeltaCheapest$380Average$730FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$430Average$684FlexibilityNo cancel feeOn-time63%

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