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Oakland

$168+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — OAK
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Round-trip from

$352
(Mytrip)

One-way from

$168
(Cheapflightsfares)

Popular in

June

Cheapest in

October

Average price

$471
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. 12% potential increase in price ($70 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/91:59 amSJU - OAK
3 stops35h 57mSpirit Airlines
Sat 6/145:30 amOAK - SJU
2 stops34h 49mSpirit Airlines
Deal found 4/30$352
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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.
Thu 7/173:23 pmSJU - OAK
2 stops44h 25mAlaska Airlines
Mon 8/48:00 amOAK - SJU
2 stops27h 33mAlaska Airlines
Deal found 4/30$1,050
This Delta deal was found by Cheapflights users on 4/30. 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.
Thu 7/101:06 pmPUJ - OAK
2 stops13h 49mDelta
Sun 7/134:58 pmOAK - PUJ
2 stops17h 29mDelta
Deal found 4/30$4,128
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2512:59 amSJU - OAK
2 stops20h 34mMultiple Airlines
Tue 7/228:00 amOAK - SJU
2 stops18h 06mMultiple Airlines
Deal found 4/30$4,448

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 May 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

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

Mon 6/9

1:59 am-10:56 am

3 stops35h 57m

Oakland

Sat 6/14

5:30 am-7:19 pm

2 stops34h 49m

$352

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

Thu 7/17

3:23 pm-8:48 am

2 stops44h 25m

Oakland

Mon 8/4

8:00 am-2:33 pm

2 stops27h 33m

$1,050

Punta CanaOakland

PUJ - OAK

PUJOAK

Punta Cana

Thu 7/10

1:06 pm-11:55 pm

2 stops13h 49m

Oakland

Sun 7/13

4:58 pm-1:27 pm

2 stops17h 29m

$4,128

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

Wed 6/25

12:59 am-6:33 pm

2 stops20h 34m

Oakland

Tue 7/22

8:00 am-5:06 am

2 stops18h 06m

$4,448

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

Fri 5/30

1:33 am-10:56 am

2 stops12h 23m

$168

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

Fri 5/9

1:55 pm-11:49 pm

2 stops12h 54m

$198

San JuanOakland

SJU - OAK

SJUOAK

San Juan Luis Munoz Marin Intl

Sat 8/2

4:20 pm-4:51 pm

1 stop27h 31m

$218

Santo DomingoOakland

SDQ - OAK

SDQOAK

Santo Domingo Las Americas

Mon 5/19

4:50 pm-10:25 pm

2 stops32h 35m

$258

Punta CanaOakland

PUJ - OAK

PUJOAK

Punta Cana

Mon 5/19

12:30 pm-10:25 pm

2 stops36h 55m

$306

Punta CanaOakland

PUJ - OAK

PUJOAK

Punta Cana

Mon 5/19

2:00 pm-10:25 pm

3 stops35h 25m

$332

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 14 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 May 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.

Rainfall in Oakland by month

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

In terms of precipitation, rainfall in Oakland, California ranges from 0.0 - 4.8 inches per month. January is typically the wettest month, when rainfall can reach 4.8 in. July is typically the driest time to visit Oakland, California when rainfall is around 0.0 in.

Temperature in Oakland by month

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

If weather is an important factor for your trip to Oakland, California, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 66.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 51.8 F).

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 May 1, 2025.
Alaska Airlines
8.0
Very good
9,972 reviews

Food

7.1

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

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
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Food

7.1

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

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
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Food

7.1

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Sun Country Air
6.9
Okay
346 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Food

7.1

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

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
7,963 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Food

7.1

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Crew

8.5

Overall

8.0

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 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 $168. Delta flights start at $198 while deals on Sun Country Air start at $218 one-way.

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

    Most travelers choose San Juan Luis Munoz Marin Intl - Oakland, Santo Domingo Las Americas - 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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