HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$817+ 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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SXM
Jul 23 — Jul 301
Wed 7/23
Wed 7/30
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 July 18, 2025.

Round-trip from

$817
(Delta)

Popular in

December

Cheapest in

September

Average price

$902
From Oakland to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($189 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($59 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

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 July 18, 2025.

This Delta deal was found by Cheapflights users on 7/17. 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.
Sat 9/2712:37 pmOAK - SXM
2 stops22h 13mDelta
Fri 10/33:20 pmSXM - OAK
2 stops23h 36mDelta
Deal found 7/17$817

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 July 18, 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

Sat 9/27

12:37 pm-1:50 pm

2 stops22h 13m

Simpson Bay Princess Juliana

Fri 10/3

3:20 pm-11:56 am

2 stops23h 36m

$817

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/17

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 $655). 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.

Reviews of airlines servicing Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Simpson Bay. Reviews last updated July 18, 2025.
Read through reviews of airlines operating flights from Oakland to Simpson Bay, such as Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,958 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,958 reviews
Delta
8.0
Very good
7,958 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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 March is currently the most expensive (average of $655). 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

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.