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Jamaica

$535+ Cheap flights from Oakland, CA (OAK) to Jamaica

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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MBJ
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
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Cheap flight deals from Oakland to Jamaica

Keep the following information in mind while searching for Oakland to Jamaica flight deals. Data was last updated October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$583
(Delta)

One-way from

$535
(Delta)

Popular in

December

Cheapest in

March

Average price

$755
Provider with most accurate pricing for San Francisco-Montego Bay Sangster Intl flight deals.
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Provider most trusted by Cheapflights users for San Francisco-Montego Bay Sangster Intl flights.
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From Oakland to Jamaica
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One-way flight from Oakland to Jamaica
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Highest demand for flights based on searches. 6% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Oakland to Jamaica

Cheapest flights from Oakland to Jamaica
Explore the most affordable flight options available from Oakland to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 16, 2025.

This Southwest deal was found by Cheapflights users on 10/15. 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 12/128:55 pmOAK - MBJ
2 stops14h 40mSouthwest
Thu 12/181:50 pmMBJ - OAK
2 stops12h 30mSouthwest
Deal found 10/15$794
This Delta deal was found by Cheapflights users on 10/13. 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.
Wed 12/245:53 amOAK - MBJ
2 stops26h 12mDelta
Mon 12/294:15 pmMBJ - OAK
2 stops22h 39mDelta
Deal found 10/13$1,148
This Delta deal was found by Cheapflights users on 10/13. 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 12/2512:34 pmOAK - MBJ
2 stops19h 31mDelta
Mon 12/294:15 pmMBJ - OAK
2 stops22h 39mDelta
Deal found 10/13$1,260
This Delta deal was found by Cheapflights users on 10/13. 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 12/234:50 pmOAK - MBJ
2 stops24h 51mDelta
Mon 12/294:15 pmMBJ - OAK
2 stops22h 39mDelta
Deal found 10/13$1,310
This Delta deal was found by Cheapflights users on 10/13. 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.
Fri 12/265:53 amOAK - MBJ
2 stops26h 23mDelta
Mon 12/294:15 pmMBJ - OAK
2 stops22h 39mDelta
Deal found 10/13$1,360
This Delta deal was found by Cheapflights users on 10/14. 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.
Wed 12/245:53 amOAK - MBJ
2 stops28h 05mDelta
Tue 12/301:57 pmMBJ - OAK
2 stops24h 57mDelta
Deal found 10/14$1,366
This Delta deal was found by Cheapflights users on 10/16. 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.
Sun 11/165:55 amOAK - KIN
2 stops11h 05mDelta
Sat 11/229:00 amKIN - OAK
2 stops15h 39mDelta
Deal found 10/16$1,377
This Delta deal was found by Cheapflights users on 10/13. 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.
Sat 12/275:53 amOAK - MBJ
2 stops28h 34mDelta
Mon 12/294:15 pmMBJ - OAK
2 stops22h 39mDelta
Deal found 10/13$1,410
This Delta deal was found by Cheapflights users on 10/13. 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.
Wed 12/245:53 amOAK - MBJ
2 stops28h 05mDelta
Thu 1/18:00 amMBJ - OAK
2 stops30h 54mDelta
Deal found 10/13$1,517
This Delta deal was found by Cheapflights users on 10/14. 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.
Wed 12/245:53 amOAK - MBJ
2 stops28h 05mDelta
Wed 12/312:12 pmMBJ - OAK
2 stops24h 42mDelta
Deal found 10/14$1,531
This Delta deal was found by Cheapflights users on 10/15. 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.
Wed 12/2412:34 pmOAK - KIN
2 stops28h 22mDelta
Mon 12/299:00 amKIN - OAK
2 stops17h 58mDelta
Deal found 10/15$1,560
This Delta deal was found by Cheapflights users on 10/14. 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 12/2512:34 pmOAK - MBJ
2 stops19h 31mDelta
Tue 12/301:57 pmMBJ - OAK
2 stops24h 57mDelta
Deal found 10/14$1,575

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to Jamaica 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 October 16, 2025.
Use the filters below to find and compare flights from Oakland to Jamaica that are best for you.

Fly from

Oakland

Fly to

Jamaica

Route

Depart

Return

Price

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Tue 3/31

5:55 am-10:10 am

2 stops26h 15m

Montego Bay Sangster Intl

Wed 4/8

8:00 am-11:53 pm

2 stops17h 53m

$662

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Wed 2/18

5:05 pm-2:00 pm

2 stops17h 55m

Montego Bay Sangster Intl

Wed 2/25

4:40 pm-12:30 pm

2 stops22h 50m

$662

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Fri 4/3

5:55 am-11:55 am

2 stops28h 00m

Montego Bay Sangster Intl

Wed 4/8

8:00 am-11:53 pm

2 stops17h 53m

$662

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Fri 2/20

5:55 am-11:20 am

2 stops26h 25m

Montego Bay Sangster Intl

Tue 2/24

8:00 am-11:53 pm

2 stops18h 53m

$663

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Sun 4/5

5:55 am-1:40 pm

2 stops29h 45m

Montego Bay Sangster Intl

Thu 4/9

3:05 pm-4:34 pm

2 stops27h 29m

$700

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Fri 2/20

1:15 pm-11:20 am

2 stops19h 05m

Montego Bay Sangster Intl

Thu 2/26

8:00 am-11:53 pm

2 stops18h 53m

$700

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Mon 4/6

5:55 am-11:45 am

2 stops27h 50m

Montego Bay Sangster Intl

Thu 4/9

3:05 pm-4:34 pm

2 stops27h 29m

$700

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Fri 2/20

1:15 pm-11:20 am

2 stops19h 05m

Montego Bay Sangster Intl

Mon 2/23

8:00 am-11:53 pm

2 stops42h 53m

$731

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Tue 3/3

5:05 pm-11:10 am

2 stops15h 05m

Montego Bay Sangster Intl

Thu 3/5

2:05 pm-11:53 pm

2 stops36h 48m

$731

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Mon 2/16

5:55 am-12:45 pm

2 stops27h 50m

Montego Bay Sangster Intl

Wed 2/25

4:40 pm-12:30 pm

2 stops22h 50m

$742

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 21 results
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Best time to book a flight from Oakland to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica 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 Jamaica

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

Currently, September is the cheapest month in which you can book a flight from Oakland, California to Jamaica (average of $276). Flying from Oakland, California to Jamaica in December is currently the most expensive (average of $505). 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 JM?

Find hourly flight availability from Oakland to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 16, 2025.

It’s typically best to fly out from Oakland, California to Jamaica in the afternoon. Doing so could potentially save you 12% on the flight price compared to flying in the morning, which is usually more expensive.

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. 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 Jamaica. Reviews last updated October 16, 2025.
Read reviews from past customers who have flown Southwest from Oakland to Jamaica. 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
8.0
Very good
4,241 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Oakland to Jamaica. 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 Jamaica?

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

  • How long is the flight from Oakland, California to Jamaica?

    Delta can get you from Oakland, California to Jamaica in just under 26h 15m. Your travel time can differ by up to . Airlines will cover a distance of 2971 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Oakland to Jamaica 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 Jamaica?

    Currently, September is the cheapest month in which you can book a flight from Oakland, California to Jamaica (average of $276). Flying from Oakland, California to Jamaica in December is currently the most expensive (average of $505). 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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Top airline flying from Oakland to Jamaica

Discover the top airline that operate flights from Oakland to Jamaica. 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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$641Average$793FlexibilityNo cancel feeOn-time63%

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