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St. Maarten

$664+ Cheap flights from Oakland, CA (OAK) to St. Maarten

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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SXM
Jun 7 — Jun 141
Sun 6/7
Sun 6/14
1 adult, Economy
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Cheap flight deals from Oakland to St. Maarten

Cheapest flights from Oakland to St. Maarten
Explore the most affordable flight options available from Oakland to St. Maarten. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 8, 2026.

This Southwest deal was found by Cheapflights users on 5/6. 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 5/296:35 pm
OAK
-
SXM
2 stops14h 50m
Southwest
Fri 6/52:25 pm
SXM
-
OAK
2 stops22h 00m
Southwest
Deal found 5/6$664
This Southwest deal was found by Cheapflights users on 5/6. 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.
Sat 6/207:50 pm
OAK
-
SXM
2 stops16h 40m
Southwest
Sat 6/272:15 pm
SXM
-
OAK
2 stops22h 20m
Southwest
Deal found 5/6$902
This Delta deal was found by Cheapflights users on 5/4. 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 8/64:57 pm
OAK
-
SXM
2 stops17h 56m
Delta
Sun 8/93:18 pm
SXM
-
OAK
2 stops23h 34m
Delta
Deal found 5/4$1,441
This Delta deal was found by Cheapflights users on 5/4. 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 7/3012:30 pm
OAK
-
SXM
2 stops22h 25m
Delta
Sun 8/23:20 pm
SXM
-
OAK
2 stops23h 32m
Delta
Deal found 5/4$1,526

Find flight deals from Oakland to St. Maarten

Keep the following information in mind while searching for Oakland to St. Maarten flight deals. Data was last updated May 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$664
(Southwest)

Popular in

November

Cheapest in

September

Average price

$715
Provider with most accurate pricing for San Francisco-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Francisco-Simpson Bay Princess Juliana flights.
Search Deals
From Oakland to St. Maarten
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to St. Maarten 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 8, 2026.
Use the filters below to find and compare flights from Oakland to St. Maarten that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Fri 5/29

6:35 pm-12:25 pm

2 stops14h 50m

Simpson Bay Princess Juliana

Fri 6/5

2:25 pm-9:25 am

2 stops22h 00m

$664

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Sat 6/20

7:50 pm-3:30 pm

2 stops16h 40m

Simpson Bay Princess Juliana

Sat 6/27

2:15 pm-9:35 am

2 stops22h 20m

$902

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Thu 8/6

4:57 pm-1:53 pm

2 stops17h 56m

Simpson Bay Princess Juliana

Sun 8/9

3:18 pm-11:52 am

2 stops23h 34m

$1,441

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Thu 7/30

12:30 pm-1:55 pm

2 stops22h 25m

Simpson Bay Princess Juliana

Sun 8/2

3:20 pm-11:52 am

2 stops23h 32m

$1,526

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

Sorted by cheapest first

Best time to book a flight from Oakland to St. Maarten

Have a flexible travel schedule? Discover the best time to fly to St. Maarten 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 St. Maarten
No data available for this route at this time. Please check back soon.

Related info for your journey

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

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

  • How long is the flight from Oakland, California to St. Maarten?

    A quick flight from Oakland, California to St. Maarten can take about 14h 50m. Southwest provides one of the quickest options available for as low as $664. Oakland, California and St. Maarten are separated by a distance of 3788 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Oakland to St. Maarten that include hotel bookings?

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

  • How can I find direct flights from Oakland to St. Maarten?

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

  • Can I find deals for business class flights from Oakland to St. Maarten?

    Yes. Cheapflights offers flight deals from Oakland to St. Maarten by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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