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Simpson Bay

$221+ 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 7/11. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SXM
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$485
(FlightHub)

One-way from

$221
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$829
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. 18% potential increase in price ($182 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($57 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This FlightHub deal was found by Cheapflights users on 6/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/119:23 amOAK - SXM
2 stops25h 37mSpirit Airlines
Fri 7/183:05 pmSXM - OAK
2 stops20h 23mSpirit Airlines
Deal found 6/12$485
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Thu 6/2610:31 amOAK - SXM
3 stops24h 29mMultiple Airlines
Sun 7/68:35 pmSXM - OAK
3 stops27h 05mMultiple Airlines
Deal found 6/11$648

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 June 12, 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

Fri 7/11

9:23 am-2:00 pm

2 stops25h 37m

Simpson Bay Princess Juliana

Fri 7/18

3:05 pm-8:28 am

2 stops20h 23m

$485

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Thu 6/26

10:31 am-2:00 pm

3 stops24h 29m

Simpson Bay Princess Juliana

Sun 7/6

8:35 pm-8:40 pm

3 stops27h 05m

$648

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Fri 7/11

9:23 am-2:00 pm

2 stops25h 37m

$221

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 $657). 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 June 12, 2025.
Spirit Airlines
6.3
Okay
8,052 reviews

Food

5.1

Boarding

6.6

Crew

7.1

Entertainment

5.0

Comfort

5.9

Overall

6.3

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

DTW - LAS

About the same as any other airline. Check in boarding was okay. Seats were tight & uncomfortable. Brand new luggage was damaged & can no longer be used. Waited for 45 minutes to get our luggage when we returned back home
Spirit Airlines
6.3
Okay
8,052 reviews
Spirit Airlines
6.3
Okay
8,052 reviews

Food

5.1

Boarding

6.6

Crew

7.1

Entertainment

5.0

Comfort

5.9

Overall

6.3

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

DTW - LAS

About the same as any other airline. Check in boarding was okay. Seats were tight & uncomfortable. Brand new luggage was damaged & can no longer be used. Waited for 45 minutes to get our luggage when we returned back home

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 $657). 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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