HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$1,533+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SXM
nov. 1 — nov. 81
sáb. 11/1
sáb. 11/8
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Oakland to Simpson Bay with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 octubre 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$1,533
(Delta)

Popular in

October

Cheapest in

April

Average price

$999
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
Highest demand for flights based on searches. 8% potential increase in price ($69 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Find flight deals from Oakland to Simpson Bay

Best flights from Oakland to Simpson Bay
Discover carefully curated flight deals from Oakland to Simpson Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated octubre 2, 2025.

This Delta deal was found by Cheapflights users on 9/30. 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. 3/35:05 pmOAK - SXM
2 stops17h 51mDelta
vie. 3/64:26 pmSXM - OAK
2 stops24h 04mDelta
Deal found 9/30$1,533

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 octubre 2, 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

5:05 pm-2:56 pm

2 stops17h 51m

Simpson Bay Princess Juliana

vie. 3/6

4:26 pm-12:30 pm

2 stops24h 04m

$1,533

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/30

  • 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 March is currently the most expensive (average of $648). 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 17h 51m. 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, 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 March is currently the most expensive (average of $648). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.