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Jamaica

$593+ Cheap flights from Oakland, CA (OAK) to Jamaica

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/22. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MBJ
Apr 26 — May 31
Sun 4/26
Sun 5/3
1 adult, Economy
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Cheap 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 March 27, 2026.

This Southwest deal was found by Cheapflights users on 3/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/229:05 pm
OAK
-
MBJ
2 stops14h 15m
Southwest
Fri 6/261:50 pm
MBJ
-
OAK
1 stop12h 20m
Southwest
Deal found 3/26$593
This Southwest deal was found by Cheapflights users on 3/23. 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 5/89:30 pm
OAK
-
MBJ
2 stops11h 40m
Southwest
Fri 5/1512:35 pm
MBJ
-
OAK
2 stops13h 30m
Southwest
Deal found 3/23$617
This Southwest deal was found by Cheapflights users on 3/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/297:35 pm
OAK
-
MBJ
2 stops13h 40m
Southwest
Tue 5/512:15 pm
MBJ
-
OAK
2 stops12h 20m
Southwest
Deal found 3/26$641
This Southwest deal was found by Cheapflights users on 3/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/309:30 pm
OAK
-
MBJ
2 stops12h 05m
Southwest
Tue 5/512:15 pm
MBJ
-
OAK
2 stops12h 20m
Southwest
Deal found 3/26$665
This Southwest deal was found by Cheapflights users on 3/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/169:05 pm
OAK
-
MBJ
2 stops13h 45m
Southwest
Mon 7/2011:45 am
MBJ
-
OAK
2 stops14h 00m
Southwest
Deal found 3/26$689
This Southwest deal was found by Cheapflights users on 3/25. 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.
Wed 6/109:00 pm
OAK
-
MBJ
2 stops13h 50m
Southwest
Sun 6/142:30 pm
MBJ
-
OAK
1 stop11h 25m
Southwest
Deal found 3/25$698
This Southwest deal was found by Cheapflights users on 3/22. 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 4/248:55 pm
OAK
-
MBJ
2 stops12h 15m
Southwest
Sun 5/32:40 pm
MBJ
-
OAK
2 stops18h 25m
Southwest
Deal found 3/22$701
This Southwest deal was found by Cheapflights users on 3/25. 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.
Fri 6/267:40 pm
OAK
-
MBJ
2 stops12h 50m
Southwest
Fri 7/31:50 pm
MBJ
-
OAK
1 stop12h 20m
Southwest
Deal found 3/25$703
This Southwest deal was found by Cheapflights users on 3/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/297:35 pm
OAK
-
MBJ
2 stops13h 40m
Southwest
Mon 5/412:35 pm
MBJ
-
OAK
2 stops13h 30m
Southwest
Deal found 3/26$713
This Delta deal was found by Cheapflights users on 3/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:00 am
OAK
-
KIN
2 stops12h 00m
Delta
Sun 5/179:00 am
KIN
-
OAK
2 stops16h 57m
Delta
Deal found 3/26$1,243
This Delta deal was found by Cheapflights users on 3/27. 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 6/26:00 am
OAK
-
KIN
2 stops12h 00m
Delta
Thu 6/119:00 am
KIN
-
OAK
2 stops16h 54m
Delta
Deal found 3/27$2,858

Find flight deals from Oakland to Jamaica

Keep the following information in mind while searching for Oakland to Jamaica flight deals. Data was last updated March 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$593
(Southwest)

Popular in

December

Cheapest in

January

Average price

$639
Provider with most accurate pricing for San Francisco-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Francisco-Montego Bay Sangster Intl flights.
Search Deals
From Oakland to Jamaica
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($78 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 March 27, 2026.
Use the filters below to find and compare flights from Oakland to Jamaica that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Mon 6/22

9:05 pm-1:20 pm

2 stops14h 15m

Montego Bay Sangster Intl

Fri 6/26

1:50 pm-12:10 am

1 stop12h 20m

$593

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Fri 5/8

9:30 pm-11:10 am

2 stops11h 40m

Montego Bay Sangster Intl

Fri 5/15

12:35 pm-12:05 am

2 stops13h 30m

$617

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Wed 6/10

9:00 pm-12:50 pm

2 stops13h 50m

Montego Bay Sangster Intl

Sun 6/14

2:30 pm-12:25 am

2 stops11h 55m

$641

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Thu 5/7

11:55 pm-1:55 pm

2 stops12h 00m

Montego Bay Sangster Intl

Sun 5/10

2:40 pm-7:05 am

2 stops18h 25m

$641
Quickest round-trip

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Thu 4/30

9:30 pm-11:35 am

2 stops12h 05m

Montego Bay Sangster Intl

Tue 5/5

12:15 pm-10:35 pm

2 stops12h 20m

$665

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Thu 7/16

9:05 pm-12:50 pm

2 stops13h 45m

Montego Bay Sangster Intl

Mon 7/20

11:45 am-11:45 pm

2 stops14h 00m

$689

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Fri 4/24

8:55 pm-11:10 am

2 stops12h 15m

Montego Bay Sangster Intl

Sun 5/3

2:40 pm-7:05 am

2 stops18h 25m

$701

OaklandMontego Bay

OAK - MBJ

OAKMBJ

Oakland

Fri 6/26

7:40 pm-10:30 am

2 stops12h 50m

Montego Bay Sangster Intl

Fri 7/3

1:50 pm-12:10 am

1 stop12h 20m

$703

OaklandKingston

OAK - KIN

OAKKIN

Oakland

Sun 5/10

6:00 am-8:00 pm

2 stops12h 00m

Kingston Norman Manley

Sun 5/17

9:00 am-11:57 pm

2 stops16h 57m

$1,243

OaklandKingston

OAK - KIN

OAKKIN

Oakland

Tue 6/2

6:00 am-8:00 pm

2 stops12h 00m

Kingston Norman Manley

Thu 6/11

9:00 am-11:54 pm

2 stops16h 54m

$2,858

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 17 resultsSorted by cheapest first
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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, April is the cheapest month in which you can book a flight from Oakland, California to Jamaica (average of $253). Flying from Oakland, California to Jamaica in December is currently the most expensive (average of $528). 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.

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?

    Southwest and Delta can get you from Oakland, California to Jamaica in just under 12h. Your travel time can differ by up to 2h 15m. Airlines will cover a distance of 3054 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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, April is the cheapest month in which you can book a flight from Oakland, California to Jamaica (average of $253). Flying from Oakland, California to Jamaica in December is currently the most expensive (average of $528). 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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