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Simpson Bay

$600+ 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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SXM
dic. 20 — dic. 271
sáb. 12/20
sáb. 12/27
1 adult, Economy
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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 noviembre 20, 2025.

This Delta deal was found by Cheapflights users on 11/19. 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.
lun. 11/245:55 amOAK - SXM
2 stops29h 00mDelta
jue. 11/274:20 pmSXM - OAK
2 stops23h 28mDelta
Deal found 11/19$1,390
This Delta deal was found by Cheapflights users on 11/17. 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.
vie. 12/265:53 amOAK - SXM
2 stops28h 24mDelta
jue. 1/14:15 pmSXM - OAK
2 stops27h 49mDelta
Deal found 11/17$1,486
This Delta deal was found by Cheapflights users on 11/17. 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.
vie. 12/265:53 amOAK - SXM
2 stops28h 24mDelta
lun. 1/54:20 pmSXM - OAK
2 stops23h 37mDelta
Deal found 11/17$1,536
This Delta deal was found by Cheapflights users on 11/19. 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.
lun. 11/244:51 pmOAK - SXM
2 stops18h 04mDelta
vie. 11/284:20 pmSXM - OAK
2 stops23h 28mDelta
Deal found 11/19$1,630
This Delta deal was found by Cheapflights users on 11/19. 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.
lun. 11/244:51 pmOAK - SXM
2 stops18h 04mDelta
sáb. 11/294:30 pmSXM - OAK
2 stops23h 18mDelta
Deal found 11/19$1,755
This Delta deal was found by Cheapflights users on 11/17. 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.
mié. 12/245:53 amOAK - SXM
2 stops28h 57mDelta
jue. 1/14:15 pmSXM - OAK
2 stops23h 39mDelta
Deal found 11/17$1,788
This Delta deal was found by Cheapflights users on 11/17. 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.
mié. 12/2412:34 pmOAK - SXM
2 stops22h 16mDelta
lun. 1/54:20 pmSXM - OAK
2 stops27h 54mDelta
Deal found 11/17$1,838
This Delta deal was found by Cheapflights users on 11/17. 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.
mar. 12/234:50 pmOAK - SXM
2 stops42h 00mDelta
jue. 1/14:15 pmSXM - OAK
2 stops23h 39mDelta
Deal found 11/17$2,038
This Delta deal was found by Cheapflights users on 11/17. 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.
mar. 12/234:50 pmOAK - SXM
2 stops42h 00mDelta
lun. 1/54:20 pmSXM - OAK
2 stops27h 54mDelta
Deal found 11/17$2,088
This Delta deal was found by Cheapflights users on 11/17. 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.
sáb. 12/274:50 pmOAK - SXM
2 stops42h 00mDelta
jue. 1/14:15 pmSXM - OAK
2 stops23h 39mDelta
Deal found 11/17$2,142
This Delta deal was found by Cheapflights users on 11/17. 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.
sáb. 12/274:50 pmOAK - SXM
2 stops42h 00mDelta
lun. 1/54:20 pmSXM - OAK
2 stops23h 37mDelta
Deal found 11/17$2,192

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 noviembre 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$1,281
(Delta)

One-way from

$600
(Delta)

Popular in

July

Cheapest in

October

Average price

$872
Provider with most accurate pricing for Oakland-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Oakland-Simpson Bay Princess Juliana flights.
Search Deals
From Oakland to Simpson Bay Princess Juliana
Search Deals
One-way flight from Oakland to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($72 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 noviembre 20, 2025.
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

mar. 3/3

5:55 am-2:56 pm

2 stops29h 01m

Simpson Bay Princess Juliana

vie. 3/6

4:26 pm-11:57 am

2 stops23h 31m

$856

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

dom. 2/8

12:38 pm-2:55 pm

2 stops22h 17m

Simpson Bay Princess Juliana

jue. 2/12

4:26 pm-4:14 pm

2 stops27h 48m

$1,281

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

vie. 12/26

5:53 am-2:17 pm

2 stops28h 24m

Simpson Bay Princess Juliana

jue. 1/1

4:15 pm-4:04 pm

2 stops27h 49m

$1,486

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

vie. 12/26

5:53 am-2:17 pm

2 stops28h 24m

Simpson Bay Princess Juliana

lun. 1/5

4:20 pm-11:57 am

2 stops23h 37m

$1,536

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

mié. 12/24

5:53 am-2:50 pm

2 stops28h 57m

Simpson Bay Princess Juliana

jue. 1/1

4:15 pm-11:54 am

2 stops23h 39m

$1,788

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

mié. 12/24

12:34 pm-2:50 pm

2 stops22h 16m

Simpson Bay Princess Juliana

lun. 1/5

4:20 pm-4:14 pm

2 stops27h 54m

$1,838

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

mar. 12/23

4:50 pm-2:50 pm

2 stops42h 00m

Simpson Bay Princess Juliana

jue. 1/1

4:15 pm-11:54 am

2 stops23h 39m

$2,038

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

mar. 12/23

4:50 pm-2:50 pm

2 stops42h 00m

Simpson Bay Princess Juliana

lun. 1/5

4:20 pm-4:14 pm

2 stops27h 54m

$2,088

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

sáb. 12/27

4:50 pm-2:50 pm

2 stops42h 00m

Simpson Bay Princess Juliana

lun. 1/5

4:20 pm-11:57 am

2 stops23h 37m

$2,192

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

sáb. 12/13

4:50 pm-2:28 pm

2 stops17h 38m

$600

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

Showing 1-10 of 11 results
1
2
  • 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.

Cheapflights Insights

Everything you need to know about your flight from Oakland to Simpson Bay

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

Currently, May is the cheapest month in which you can book a flight from Oakland, California to Simpson Bay (average of $283). Flying from Oakland, California to Simpson Bay in September is currently the most expensive (average of $640). 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 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?

    Delta can get you from Oakland, California to Simpson Bay in just under 29h 01m. Your travel time can differ by up to . The distance between Oakland, California and Simpson Bay is about 3788 mi.

  • 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.

  • What is the cheapest month to book a flight from Oakland, California to Simpson Bay?

    Currently, May is the cheapest month in which you can book a flight from Oakland, California to Simpson Bay (average of $283). Flying from Oakland, California to Simpson Bay in September is currently the most expensive (average of $640). 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

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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