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Simpson Bay

$572+ Cheap flights from Oakland, CA (OAK) to Simpson Bay (SXM)

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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SXM
Apr 27 — May 41
Sun 4/27
Sun 5/4
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 April 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
2 stars

Round-trip from

$572
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$684
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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Highest demand for flights based on searches. 15% potential increase in price ($151 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($50 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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 April 22, 2025.

This Mytrip deal was found by Cheapflights users on 4/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/57:46 amOAK - SXM
2 stops26h 29mMultiple Airlines
Fri 5/93:05 pmSXM - OAK
2 stops22h 51mMultiple Airlines
Deal found 4/21$572

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 April 22, 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

Mon 5/5

7:46 am-1:15 pm

2 stops26h 29m

Simpson Bay Princess Juliana

Fri 5/9

3:05 pm-10:56 am

2 stops22h 51m

$572

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

  • 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, September is the cheapest month in which you can book a flight from Oakland, California to Simpson Bay (average of $459). Flying from Oakland, California to Simpson Bay in July is currently the most expensive (average of $675). 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.

  • 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, September is the cheapest month in which you can book a flight from Oakland, California to Simpson Bay (average of $459). Flying from Oakland, California to Simpson Bay in July is currently the most expensive (average of $675). 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.

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