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Oakland

$206+ Cheap flights from Caribbean to Oakland, CA (OAK)

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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — OAK
jul. 6 — jul. 131
dom. 7/6
dom. 7/13
1 adult, Economy
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Cheap flight deals from Caribbean to Oakland

Keep the following information in mind while searching for Caribbean to Oakland flight deals. Data was last updated julio 1, 2025.

Round-trip from

$502
(SmartFares)

One-way from

$206
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$551
From Caribbean to Oakland
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One-way flight from Caribbean to Oakland
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Highest demand for flights based on searches. 10% potential increase in price ($53 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Caribbean to Oakland

Cheapest flights from Caribbean to Oakland
Explore the most affordable flight options available from Caribbean to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 1, 2025.

This SmartFares deal was found by Cheapflights users on 7/1. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/3110:55 amSDQ - OAK
2 stops24h 33mSpirit Airlines
jue. 8/712:42 pmOAK - SDQ
2 stops24h 05mSpirit Airlines
Deal found 7/1$502
This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/122:25 pmSJU - OAK
2 stops12h 50mSouthwest
sáb. 10/256:30 amOAK - SJU
2 stops11h 40mSouthwest
Deal found 7/1$506
This Mytrip deal was found by Cheapflights users on 7/1. 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.
jue. 7/3110:55 amSDQ - OAK
2 stops24h 33mMultiple Airlines
jue. 8/72:38 pmOAK - SDQ
3 stops22h 51mMultiple Airlines
Deal found 7/1$520
This FlightHub deal was found by Cheapflights users on 7/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/169:44 amSJU - OAK
2 stops16h 49mSpirit Airlines
dom. 7/2012:42 pmOAK - SJU
2 stops20h 54mSpirit Airlines
Deal found 7/1$530
This Trip.com deal was found by Cheapflights users on 7/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/28:00 amSJU - OAK
2 stops18h 26mMultiple Airlines
vie. 7/410:31 amOAK - SJU
3 stops22h 57mMultiple Airlines
Deal found 7/1$867
This Delta deal was found by Cheapflights users on 6/30. 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.
jue. 7/36:15 amSJU - OAK
2 stops13h 01mDelta
lun. 7/74:55 pmOAK - SJU
2 stops17h 31mDelta
Deal found 6/30$896
This Alaska Airlines deal was found by Cheapflights users on 6/30. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/212:59 amSJU - OAK
2 stops26h 02mAlaska Airlines
lun. 7/77:58 pmOAK - SJU
2 stops24h 27mAlaska Airlines
Deal found 6/30$1,703

Cheapflights Fare Finder

Customize your flight search to find flights from Caribbean to Oakland 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 julio 1, 2025.
Use the filters below to find and compare flights from Caribbean to Oakland that are best for you.

Fly from

Caribbean

Fly to

Oakland

Route

Depart

Return

Price

Santo DomingoOakland

SDQ - OAK

SDQOAK

Santo Domingo Las Americas

jue. 7/31

10:55 am-8:28 am

2 stops24h 33m

Oakland

jue. 8/7

12:42 pm-3:47 pm

2 stops24h 05m

$502

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

dom. 10/12

2:25 pm-12:15 am

2 stops12h 50m

Oakland

sáb. 10/25

6:30 am-9:10 pm

2 stops11h 40m

$506

Santo DomingoOakland

SDQ - OAK

SDQOAK

Santo Domingo Las Americas

jue. 7/31

10:55 am-8:28 am

2 stops24h 33m

Oakland

jue. 8/7

2:38 pm-4:29 pm

3 stops22h 51m

$520

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

mié. 7/16

9:44 am-11:33 pm

2 stops16h 49m

Oakland

dom. 7/20

12:42 pm-12:36 pm

2 stops20h 54m

$530

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

mar. 8/12

4:43 pm-11:27 pm

3 stops33h 44m

$206

Punta CanaOakland

PUJ - OAK

PUJOAK

Punta Cana

dom. 9/21

11:45 am-7:03 am

2 stops22h 18m

$236

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

sáb. 7/19

1:05 pm-8:20 pm

1 stop10h 15m

$238

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

sáb. 8/16

4:20 pm-4:39 pm

1 stop27h 19m

$320

FreeportOakland

FPO - OAK

FPOOAK

Freeport Grand Bahama Intl

dom. 9/7

11:00 am-7:03 am

3 stops23h 03m

$351

Punta CanaOakland

PUJ - OAK

PUJOAK

Punta Cana

dom. 7/13

12:40 pm-12:27 pm

3 stops26h 47m

$363

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 13 results
1
2

Best time to book a flight from Caribbean to Oakland

Have a flexible travel schedule? Discover the best time to fly to Oakland from Caribbean 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 Caribbean to Oakland

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

Currently, April is the cheapest month in which you can book a flight from Caribbean to Oakland, California (average of $183). Flying from Caribbean to Oakland, California in November is currently the most expensive (average of $259). 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 CB to OAK?

Find hourly flight availability from Caribbean to Oakland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated julio 1, 2025.

When flying from Caribbean to Oakland, California, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Oakland

Get insights into the airlines that provide service to Oakland. 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 Oakland. Reviews last updated julio 1, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Sun Country Air from Caribbean to Oakland 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
4,273 reviews

Crew

8.6

Boarding

8.2

Food

7.0

Overall

8.0

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Southwest
8.0
Very good
4,273 reviews
Southwest
8.0
Very good
4,273 reviews

Crew

8.6

Boarding

8.2

Food

7.0

Overall

8.0

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Delta
8.0
Very good
7,973 reviews
Southwest
8.0
Very good
4,273 reviews

Crew

8.6

Boarding

8.2

Food

7.0

Overall

8.0

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Sun Country Air
6.9
Okay
340 reviews
Southwest
8.0
Very good
4,273 reviews

Crew

8.6

Boarding

8.2

Food

7.0

Overall

8.0

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Spirit Airlines
6.3
Okay
8,101 reviews
Southwest
8.0
Very good
4,273 reviews

Crew

8.6

Boarding

8.2

Food

7.0

Overall

8.0

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

Related info for your journey

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

    Most people fly into Oakland (OAK) if they book a flight to Oakland from Caribbean. Oakland is conveniently located just 7.0 mi from Oakland’s city center.

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

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $206. Southwest flights start at $238 while deals on Sun Country Air start at $320 one-way.

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

    Most travelers choose San Juan Luis Munoz Marin Intl - Oakland, Punta Cana - Oakland or Oranjestad Reina Beatrix - Oakland when deciding on the best route from Caribbean to Oakland, California.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean to Oakland 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 Caribbean to Oakland, California?

    Currently, April is the cheapest month in which you can book a flight from Caribbean to Oakland, California (average of $183). Flying from Caribbean to Oakland, California in November is currently the most expensive (average of $259). 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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See prices for flight routes from nearby airports that may be better suited for you.
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