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Simpson Bay

$553+ Cheap flights from Valparaiso, FL (VPS) 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — SXM
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Valparaiso to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Valparaiso (VPS) 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 September 11, 2025.

Round-trip from

$553
(Mytrip)
From Valparaiso Destin-Ft Walton Beach to Simpson Bay Princess Juliana
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Find flight deals from Valparaiso to Simpson Bay

Cheapest flights from Valparaiso to Simpson Bay
Explore the most affordable flight options available from Valparaiso to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Mytrip deal was found by Cheapflights users on 9/11. 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.
Sun 9/286:30 amVPS - SXM
2 stops12h 00mMultiple Airlines
Sat 10/43:05 pmSXM - VPS
2 stops22h 45mMultiple Airlines
Deal found 9/11$553
This American Airlines deal was found by Cheapflights users on 9/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/286:27 pmVPS - SXM
2 stops17h 52mAmerican Airlines
Sat 10/42:40 pmSXM - VPS
1 stop9h 15mAmerican Airlines
Deal found 9/11$713
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/286:00 amVPS - SXM
1 stop6h 50mDelta
Sat 10/43:20 pmSXM - VPS
1 stop7h 29mDelta
Deal found 9/11$753
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/276:00 amVPS - SXM
1 stop6h 50mDelta
Sat 10/43:20 pmSXM - VPS
1 stop7h 29mDelta
Deal found 9/11$959

Cheapflights Fare Finder

 
Customize your flight search to find flights from Valparaiso 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 September 11, 2025.
Use the filters below to find and compare flights from Valparaiso to Simpson Bay that are best for you.

Fly from

Valparaiso

Fly to

Simpson Bay

Route

Depart

Return

Price

ValparaisoSimpson Bay

VPS - SXM

VPSSXM

Valparaiso Destin-Ft Walton Beach

Sun 9/28

6:30 am-7:30 pm

2 stops12h 00m

Simpson Bay Princess Juliana

Sat 10/4

3:05 pm-12:50 pm

2 stops22h 45m

$553

ValparaisoSimpson Bay

VPS - SXM

VPSSXM

Valparaiso Destin-Ft Walton Beach

Sun 9/28

6:27 pm-1:19 pm

2 stops17h 52m

Simpson Bay Princess Juliana

Sat 10/4

2:40 pm-10:55 pm

1 stop9h 15m

$713

ValparaisoSimpson Bay

VPS - SXM

VPSSXM

Valparaiso Destin-Ft Walton Beach

Sun 9/28

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Sat 10/4

3:20 pm-9:49 pm

1 stop7h 29m

$753

ValparaisoSimpson Bay

VPS - SXM

VPSSXM

Valparaiso Destin-Ft Walton Beach

Sat 9/27

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Sat 10/4

3:20 pm-9:49 pm

1 stop7h 29m

$959

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Best time to book a flight from Valparaiso to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Valparaiso 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.

Related info for your journey

Find useful and relevant information for your journey from Valparaiso 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 Valparaiso, Florida to Simpson Bay?

    A quick flight from Valparaiso, Florida to Simpson Bay can take about 6h 50m. American Airlines provides one of the quickest options available for as low as $753. There are 1702 mi between Valparaiso, Florida and Simpson Bay. This flight may include one or multiple stops.

  • Can I find deals for flights from Valparaiso to Simpson Bay that include hotel bookings?

    Yes. In addition to deals on Valparaiso to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Valparaiso to Simpson Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Valparaiso to Simpson Bay.

  • Can I find deals for business class flights from Valparaiso to Simpson Bay?

    Yes. Cheapflights offers flight deals from Valparaiso 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 Valparaiso, Florida to Simpson Bay?

    Currently, September is the cheapest month in which you can book a flight from Valparaiso, Florida to Simpson Bay (average of $459). Flying from Valparaiso, Florida to Simpson Bay in March is currently the most expensive (average of $652). 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?

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Philipsburg

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