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Simpson Bay

$324+ Cheap flights from Oakland, CA (OAK) to Simpson Bay (SXM)

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 3/28. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SXM
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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Cheap flight deals from Oakland to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$735
(Southwest)

One-way from

$324
(Kiwi.com)

Popular in

July

Cheapest in

October

Average price

$688
Provider with most accurate pricing for Oakland-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Oakland-Simpson Bay Princess Juliana flights.
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From Oakland to Simpson Bay Princess Juliana
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One-way flight from Oakland to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 11% potential increase in price ($95 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Oakland to Simpson Bay

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

This Southwest deal was found by Cheapflights users on 1/8. 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 4/249:30 pmOAK - SXM
2 stops13h 10mSouthwest
Sat 5/21:20 pmSXM - OAK
2 stops20h 15mSouthwest
Deal found 1/8$735
This Delta deal was found by Cheapflights users on 1/7. 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 2/55:00 pmOAK - SXM
2 stops15h 30mDelta
Wed 2/181:38 pmSXM - OAK
2 stops14h 13mDelta
Deal found 1/7$1,213
This Delta deal was found by Cheapflights users on 1/7. 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 2/65:00 pmOAK - SXM
2 stops15h 30mDelta
Wed 2/181:38 pmSXM - OAK
2 stops14h 13mDelta
Deal found 1/7$1,243
This Delta deal was found by Cheapflights users on 1/7. 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.
Mon 5/111:15 pmOAK - SXM
2 stops21h 44mDelta
Tue 5/193:20 pmSXM - OAK
2 stops24h 04mDelta
Deal found 1/7$1,354
This Delta deal was found by Cheapflights users on 1/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2012:40 pmOAK - SXM
2 stops21h 35mDelta
Fri 2/271:38 pmSXM - OAK
2 stops14h 13mDelta
Deal found 1/6$1,473
This Delta deal was found by Cheapflights users on 1/7. 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 2/2112:40 pmOAK - SXM
2 stops20h 45mDelta
Sat 2/284:15 pmSXM - OAK
2 stops23h 40mDelta
Deal found 1/7$1,640
This Delta deal was found by Cheapflights users on 1/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1312:33 pmOAK - SXM
2 stops22h 36mDelta
Fri 4/171:50 pmSXM - OAK
2 stops12h 59mDelta
Deal found 1/6$2,566

Cheapflights Fare Finder

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

Fly from

Oakland

Fly to

Simpson Bay

Route

Depart

Return

Price

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Fri 4/24

9:30 pm-1:40 pm

2 stops13h 10m

Simpson Bay Princess Juliana

Sat 5/2

1:20 pm-6:35 am

2 stops20h 15m

$735

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Thu 2/5

5:00 pm-12:30 pm

2 stops15h 30m

Simpson Bay Princess Juliana

Wed 2/18

1:38 pm-11:51 pm

2 stops14h 13m

$1,213

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Fri 2/6

5:00 pm-12:30 pm

2 stops15h 30m

Simpson Bay Princess Juliana

Wed 2/18

1:38 pm-11:51 pm

2 stops14h 13m

$1,243

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Mon 5/11

1:15 pm-1:59 pm

2 stops21h 44m

Simpson Bay Princess Juliana

Tue 5/19

3:20 pm-12:24 pm

2 stops24h 04m

$1,354

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Sat 2/21

12:40 pm-1:25 pm

2 stops20h 45m

Simpson Bay Princess Juliana

Sat 2/28

4:15 pm-11:55 am

2 stops23h 40m

$1,640

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Mon 4/13

12:33 pm-2:09 pm

2 stops22h 36m

Simpson Bay Princess Juliana

Fri 4/17

1:50 pm-11:49 pm

2 stops12h 59m

$2,566

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Sat 3/28

6:40 pm-1:08 pm

3 stops39h 28m

$324

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Mon 6/8

5:55 am-2:00 pm

2 stops29h 05m

$478

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Sat 6/6

5:55 am-2:00 pm

2 stops29h 05m

$563

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Tue 6/9

5:55 am-2:00 pm

2 stops29h 05m

$603

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 14 results
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  • Most accurate provider: When it comes to deals on Oakland, California-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Oakland, California-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Oakland, California-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Oakland, California-Simpson Bay flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Oakland, California-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Oakland to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay 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.

Related info for your journey

Find useful and relevant information for your journey from Oakland to Simpson Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    Southwest and Delta can get you from Oakland, California to Simpson Bay in just under 13h 10m. Your travel time can differ by up to 2h 20m. The distance between Oakland, California and Simpson Bay is about 3788 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 Simpson Bay that include hotel bookings?

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

  • How can I find direct flights from Oakland to Simpson Bay?

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

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

    Yes. Cheapflights offers flight deals from Oakland to Simpson Bay 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

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

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