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Valparaiso

$359+ Cheap flights from New Windsor to Valparaiso, FL (SWF - VPS)

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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — VPS
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Find flight deals from Stewart to Valparaiso

Cheapest flights from Stewart to Valparaiso
Explore the most affordable flight options available from Stewart to Valparaiso. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 28, 2025.

This Mytrip deal was found by Cheapflights users on 10/25. 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 12/227:10 pmSWF - VPS
2 stops26h 09mAllegiant Air
Fri 12/269:00 amVPS - SWF
2 stops24h 00mAllegiant Air
Deal found 10/25$767
This Mytrip deal was found by Cheapflights users on 10/26. 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.
Wed 11/267:25 pmSWF - VPS
2 stops22h 56mAllegiant Air
Sun 11/3012:16 pmVPS - SWF
2 stops19h 50mAllegiant Air
Deal found 10/26$1,004
This Mytrip deal was found by Cheapflights users on 10/26. 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.
Wed 11/267:25 pmSWF - VPS
2 stops22h 56mAllegiant Air
Sat 11/2912:12 pmVPS - SWF
2 stops20h 10mAllegiant Air
Deal found 10/26$1,060

Cheap flight deals from Stewart to Valparaiso

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Valparaiso (VPS). 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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$482
(Mytrip)

One-way from

$359
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$315
Provider with most accurate pricing for New Windsor Stewart-Valparaiso Destin-Ft Walton Beach flight deals.
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Provider most trusted by Cheapflights users for New Windsor Stewart-Valparaiso Destin-Ft Walton Beach flights.
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From New Windsor Stewart to Valparaiso Destin-Ft Walton Beach
Search Deals
One-way flight from New Windsor Stewart to Valparaiso Destin-Ft Walton Beach
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($80 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Valparaiso 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 October 28, 2025.
Use the filters below to find and compare flights from New Windsor to Valparaiso that are best for you.

Fly from

Stewart

Fly to

Valparaiso

Route

Depart

Return

Price

New WindsorValparaiso

SWF - VPS

SWFVPS

New Windsor Stewart

Mon 12/22

7:10 pm-8:19 pm

2 stops26h 09m

Valparaiso Destin-Ft Walton Beach

Fri 12/26

9:00 am-10:00 am

2 stops24h 00m

$767

New WindsorValparaiso

SWF - VPS

SWFVPS

New Windsor Stewart

Wed 11/26

7:25 pm-5:21 pm

2 stops22h 56m

Valparaiso Destin-Ft Walton Beach

Sun 11/30

12:16 pm-9:06 am

2 stops19h 50m

$1,004

New WindsorValparaiso

SWF - VPS

SWFVPS

New Windsor Stewart

Wed 11/26

7:25 pm-5:21 pm

2 stops22h 56m

Valparaiso Destin-Ft Walton Beach

Sat 11/29

12:12 pm-9:22 am

2 stops20h 10m

$1,060

New WindsorValparaiso

SWF - VPS

SWFVPS

New Windsor Stewart

Thu 11/6

6:14 pm-7:04 pm

2 stops25h 50m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Compare providers for flights from Stewart to Valparaiso

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Stewart to Valparaiso in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on New Windsor-Valparaiso, Florida flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on New Windsor-Valparaiso, Florida flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from New Windsor-Valparaiso, Florida flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-Valparaiso, Florida flights, Cheapflights users trust eDreams the most. eDreams 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 New Windsor-Valparaiso, Florida 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 Stewart to Valparaiso

Have a flexible travel schedule? Discover the best time to fly to Valparaiso from Stewart 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 New Windsor to Valparaiso

What is the cheapest month to book a flight from New Windsor to Valparaiso, Florida?

Currently, March is the cheapest month in which you can book a flight from New Windsor to Valparaiso, Florida (average of $89). Flying from New Windsor to Valparaiso, Florida in November is currently the most expensive (average of $197). 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 Stewart to Valparaiso. 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 New Windsor to Valparaiso, Florida?

    Airlines like Allegiant Air fly from New Windsor to Valparaiso, Florida in about 26h 09m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 1028 mi.

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

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

  • How can I find direct flights from Stewart to Valparaiso?

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

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

    Yes. Cheapflights offers flight deals from Stewart to Valparaiso 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 New Windsor to Valparaiso, Florida?

    Currently, March is the cheapest month in which you can book a flight from New Windsor to Valparaiso, Florida (average of $89). Flying from New Windsor to Valparaiso, Florida in November is currently the most expensive (average of $197). 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 Valparaiso?

Book flights to Valparaiso if you plan to visit one of these locations
Crestview
Andalusia
Niceville

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