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Caribbean Islands

$155+ 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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Cheap flight deals from Oakland to Caribbean Islands

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to Caribbean Islands (zzEPX). 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 December 18, 2024.

Round-trip from

$219
(CheapOair)

One-way from

$155
(CheapOair)
From Oakland to Caribbean Islands
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One-way flight from Oakland to Caribbean Islands
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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 December 18, 2024.

This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/176:00 amOAK - SJU
2 stops14h 59mDelta
Tue 12/247:30 amSJU - OAK
2 stops19h 43mDelta
Deal found 12/16$547
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/252:04 pmOAK - SJU
3 stops32h 09mSpirit Airlines
Sat 12/2811:42 amSJU - OAK
3 stops26h 47mSpirit Airlines
Deal found 12/17$664
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/285:30 amOAK - STT
2 stops25h 09mSpirit Airlines
Tue 1/711:44 amSTT - OAK
2 stops15h 08mSpirit Airlines
Deal found 12/16$711
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/305:30 amOAK - PUJ
2 stops30h 25mSpirit Airlines
Fri 1/34:38 pmPUJ - OAK
2 stops31h 52mSpirit Airlines
Deal found 12/17$883
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/234:52 pmOAK - KIN
3 stops37h 17mSpirit Airlines
Mon 12/3010:14 amKIN - OAK
3 stops26h 29mSpirit Airlines
Deal found 12/16$956
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/306:36 pmOAK - PUJ
3 stops25h 09mMultiple Airlines
Fri 1/34:50 pmPUJ - OAK
3 stops31h 40mMultiple Airlines
Deal found 12/17$998
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.
Mon 12/3011:50 amOAK - PUJ
2 stops21h 55mSouthwest
Sat 1/44:55 pmPUJ - OAK
2 stops17h 50mSouthwest
Deal found 12/17$1,008
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/229:25 pmOAK - SJU
3 stops32h 22mMultiple Airlines
Wed 12/259:46 amSJU - OAK
3 stops30h 52mMultiple Airlines
Deal found 12/17$1,019
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.
Wed 12/259:55 amOAK - SJU
2 stops10h 50mSouthwest
Sat 12/283:45 pmSJU - OAK
1 stop12h 50mSouthwest
Deal found 12/17$1,034
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/226:36 pmOAK - FPO
2 stops14h 49mMultiple Airlines
Sun 12/2910:45 amFPO - OAK
3 stops25h 44mMultiple Airlines
Deal found 12/17$1,040
This CheapOair deal was found by Cheapflights users on 12/18. 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 12/266:36 pmOAK - MBJ
2 stops16h 09mSpirit Airlines
Wed 1/12:38 pmMBJ - OAK
2 stops54h 03mSpirit Airlines
Deal found 12/18$1,052
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/243:55 pmOAK - KIN
3 stops37h 58mMultiple Airlines
Thu 1/210:14 amKIN - OAK
3 stops27h 15mMultiple Airlines
Deal found 12/17$1,052

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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 1/14

7:02 pm-7:45 pm

2 stops20h 43m

San Juan Luis Munoz Marin Intl

Sat 1/18

7:00 am-11:36 pm

2 stops20h 36m

$229

OaklandSaint Thomas Island

OAK - STT

OAKSTT

Oakland

Fri 2/7

5:45 am-10:46 am

2 stops25h 01m

Saint Thomas Island Cyril E King

Mon 2/10

11:51 am-11:36 pm

2 stops15h 45m

$302

OaklandSanto Domingo

OAK - SDQ

OAKSDQ

Oakland

Thu 1/23

6:19 pm-12:55 pm

2 stops14h 36m

Santo Domingo Las Americas

Wed 1/29

1:55 pm-6:47 am

2 stops20h 52m

$400

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Wed 2/26

8:15 am-12:40 am

2 stops12h 25m

San Juan Luis Munoz Marin Intl

Sat 3/8

7:55 am-8:15 pm

2 stops16h 20m

$419

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Thu 1/23

6:19 pm-12:10 pm

2 stops14h 51m

Montego Bay Sangster Intl

Sun 1/26

1:16 pm-6:47 am

2 stops20h 31m

$429

OaklandKingston

OAK - KIN

OAKKIN

Oakland

Mon 1/6

5:30 am-9:09 am

2 stops24h 39m

Kingston Norman Manley

Fri 1/10

2:38 pm-11:36 pm

2 stops11h 58m

$451

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Fri 1/10

5:45 am-3:45 pm

3 stops30h 00m

Punta Cana

Fri 1/17

4:50 pm-11:46 am

3 stops22h 56m

$467

OaklandSan Juan

OAK - SJU

OAKSJU

Oakland

Tue 2/25

6:35 am-8:19 pm

3 stops33h 44m

San Juan Luis Munoz Marin Intl

Sun 3/2

2:55 pm-11:45 am

2 stops24h 50m

$532

OaklandSanto Domingo

OAK - SDQ

OAKSDQ

Oakland

Fri 2/7

1:27 pm-12:55 pm

3 stops19h 28m

Santo Domingo Las Americas

Sat 2/15

9:00 am-11:45 am

2 stops30h 45m

$555

OaklandPunta Cana

OAK - PUJ

OAKPUJ

Oakland

Wed 2/5

11:37 am-3:30 pm

2 stops23h 53m

Punta Cana

Mon 2/10

4:50 pm-7:25 pm

3 stops30h 35m

$579

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 32 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.

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 $334). 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 December 18, 2024.

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 December 18, 2024.
Read reviews from past customers who have flown Spirit Airlines, Southwest and Alaska Airlines 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
4,848 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

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
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

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
9,554 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

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
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

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
8,119 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

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 ($155), Southwest ($242), and Delta ($352).

  • 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 - Saint Thomas Island Cyril E King or Oakland - Freeport Grand Bahama 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 $334). 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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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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$262Average$470FlexibilityNo cancel feeOn-time65%
DeltaCheapest$334Average$773FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$389Average$741FlexibilityNo cancel feeOn-time63%
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