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$159+ Cheap flights from Valparaiso, FL (VPS) to Massachusetts

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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — BOS
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Cheap flight deals from Valparaiso to Massachusetts

Keep the following information in mind while searching for Valparaiso to Massachusetts flight deals. Data was last updated October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$330
(Delta)

One-way from

$159
(Kiwi.com)

Popular in

February

Cheapest in

March

Average price

$381
Provider with most accurate pricing for Valparaiso Destin-Ft Walton Beach-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Valparaiso Destin-Ft Walton Beach-Boston Logan Intl flights.
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From Valparaiso Destin-Ft Walton Beach to Massachusetts
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One-way flight from Valparaiso Destin-Ft Walton Beach to Massachusetts
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Highest demand for flights based on searches. 31% potential increase in price ($201 potential increase over avg. RT price).
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Cheapest flight prices on average. 25% potential price decrease ($91 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Valparaiso to Massachusetts

Cheapest flights from Valparaiso to Massachusetts
Explore the most affordable flight options available from Valparaiso to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2025.

This Delta deal was found by Cheapflights users on 10/28. 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 12/132:14 pmVPS - BOS
1 stop6h 12mDelta
Tue 12/1612:10 pmBOS - VPS
1 stop5h 02mDelta
Deal found 10/28$330
This Delta deal was found by Cheapflights users on 10/29. 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.
Wed 12/242:43 pmVPS - BOS
1 stop5h 25mDelta
Tue 12/305:40 amBOS - VPS
1 stop6h 34mDelta
Deal found 10/29$332
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 12/137:35 amVPS - BOS
1 stop6h 04mAmerican Airlines
Tue 12/168:00 amBOS - VPS
2 stops8h 47mAmerican Airlines
Deal found 10/28$336
This Southwest deal was found by Cheapflights users on 10/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1311:00 amVPS - BOS
2 stops8h 50mSouthwest
Tue 12/1612:20 pmBOS - VPS
2 stops9h 50mSouthwest
Deal found 10/28$341
This Delta deal was found by Cheapflights users on 10/29. 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.
Mon 12/222:43 pmVPS - BOS
1 stop5h 25mDelta
Tue 12/305:40 amBOS - VPS
1 stop6h 34mDelta
Deal found 10/29$350
This Delta deal was found by Cheapflights users on 10/29. 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 12/207:24 pmVPS - BOS
1 stop4h 43mDelta
Tue 12/305:40 amBOS - VPS
1 stop6h 34mDelta
Deal found 10/29$390
This Southwest deal was found by Cheapflights users on 10/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:00 amVPS - BDL
1 stop9h 20mSouthwest
Thu 1/18:55 amBDL - VPS
2 stops13h 15mSouthwest
Deal found 10/29$401
This Delta deal was found by Cheapflights users on 10/29. 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.
Wed 12/246:00 amVPS - BOS
1 stop7h 47mDelta
Wed 12/247:15 pmBOS - VPS
1 stop14h 39mDelta
Deal found 10/29$407
This Southwest deal was found by Cheapflights users on 10/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/225:45 pmVPS - BOS
1 stop6h 15mSouthwest
Sat 11/295:05 amBOS - VPS
1 stop6h 50mSouthwest
Deal found 10/28$411
This Delta deal was found by Cheapflights users on 10/29. 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.
Mon 12/227:24 pmVPS - BOS
1 stop4h 43mDelta
Wed 12/247:15 pmBOS - VPS
1 stop14h 39mDelta
Deal found 10/29$425
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Wed 11/267:20 amVPS - BOS
1 stop7h 18mAmerican Airlines
Sat 11/295:25 amBOS - VPS
1 stop7h 49mAmerican Airlines
Deal found 10/28$430
This Delta deal was found by Cheapflights users on 10/29. 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.
Wed 12/246:00 amVPS - BOS
1 stop7h 47mDelta
Thu 12/255:40 amBOS - VPS
1 stop6h 34mDelta
Deal found 10/29$433

Cheapflights Fare Finder

 
Customize your flight search to find flights from Valparaiso to Massachusetts 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 29, 2025.
Use the filters below to find and compare flights from Valparaiso to Massachusetts that are best for you.

Fly from

Valparaiso

Fly to

Massachusetts

Route

Depart

Return

Price

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Sat 12/13

2:14 pm-9:26 pm

1 stop6h 12m

Boston Logan Intl

Tue 12/16

12:10 pm-4:12 pm

1 stop5h 02m

$330

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Wed 12/24

2:43 pm-9:08 pm

1 stop5h 25m

Boston Logan Intl

Tue 12/30

5:40 am-11:14 am

1 stop6h 34m

$332

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Sat 12/13

7:35 am-2:39 pm

1 stop6h 04m

Boston Logan Intl

Tue 12/16

8:00 am-3:47 pm

2 stops8h 47m

$336

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Sat 12/13

11:00 am-8:50 pm

2 stops8h 50m

Boston Logan Intl

Tue 12/16

12:20 pm-9:10 pm

2 stops9h 50m

$341

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Mon 12/22

2:43 pm-9:08 pm

1 stop5h 25m

Boston Logan Intl

Tue 12/30

5:40 am-11:14 am

1 stop6h 34m

$350

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Sat 12/20

7:24 pm-1:07 am

1 stop4h 43m

Boston Logan Intl

Tue 12/30

5:40 am-11:14 am

1 stop6h 34m

$390

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Fri 12/26

7:15 am-1:52 pm

1 stop5h 37m

Boston Logan Intl

Tue 12/30

5:40 am-11:14 am

1 stop6h 34m

$390

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Thu 12/25

9:40 am-11:14 pm

2 stops12h 34m

Boston Logan Intl

Tue 12/30

6:40 am-11:14 am

1 stop5h 34m

$395

ValparaisoHartford

VPS - BDL

VPSBDL

Valparaiso Destin-Ft Walton Beach

Tue 12/30

7:00 am-5:20 pm

1 stop9h 20m

Hartford Bradley Intl

Thu 1/1

8:55 am-9:10 pm

2 stops13h 15m

$401

ValparaisoAlbany

VPS - ALB

VPSALB

Valparaiso Destin-Ft Walton Beach

Tue 3/17

4:20 pm-11:36 pm

1 stop6h 16m

Albany Intl

Wed 3/18

6:00 am-11:16 am

1 stop6h 16m

$405

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 45 results
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Best time to book a flight from Valparaiso to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts 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.

Cheapflights Insights

Everything you need to know about your flight from Valparaiso to Massachusetts

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

Currently, March is the cheapest month in which you can book a flight from Valparaiso, Florida to Massachusetts (average of $82). Flying from Valparaiso, Florida to Massachusetts in August is currently the most expensive (average of $287). 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.

What is the cheapest time of day to fly from VPS to MA?

Find hourly flight availability from Valparaiso to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 29, 2025.

It’s optimal to fly from Valparaiso, Florida to Massachusetts in the afternoon. By choosing this option you can save up to 42% on the cost of your flight, compared to a flight in the evening.

How much does it cost to fly round-trip from Valparaiso, Florida to Massachusetts?

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated October 29, 2025.
Read reviews from past customers who have flown Southwest, Delta, and American Airlines from Valparaiso to Massachusetts. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,994 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,032 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Allegiant Air
7.2
Good
695 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Valparaiso to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Valparaiso to Massachusetts?

    Valparaiso Destin-Ft Walton Beach (VPS), located 3.1 mi from the city center, is the airport you fly out of when you book flights from Valparaiso to Massachusetts.

  • How long is the flight from Valparaiso, Florida to Massachusetts?

    For as low as $336, Delta can have you in Massachusetts from Valparaiso, Florida in 6h 04m. There are 1187 mi between Valparaiso, Florida and Massachusetts. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Valparaiso, Florida to Massachusetts one-way?

    The cheapest airline one-way is American Airlines, with whom users have recently found tickets for as low as $202. However, be on the lookout for offers from Delta and Southwest, as they are both options that can get you from Valparaiso, Florida to Massachusetts for a low price.

  • What are the most popular routes from Valparaiso, Florida to Massachusetts?

    When deciding which route to take from Valparaiso, Florida to Massachusetts consider Valparaiso Destin-Ft Walton Beach - Boston Logan Intl, Valparaiso Destin-Ft Walton Beach - Hartford Bradley Intl or Valparaiso Destin-Ft Walton Beach - Albany Intl as they are the most popular.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Valparaiso to Massachusetts 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 Massachusetts?

    Currently, March is the cheapest month in which you can book a flight from Valparaiso, Florida to Massachusetts (average of $82). Flying from Valparaiso, Florida to Massachusetts in August is currently the most expensive (average of $287). 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

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Alternative routes for Valparaiso to Massachusetts

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Top 4 airlines flying from Valparaiso to Massachusetts

Discover the top 4 airlines that operate flights from Valparaiso to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$204FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$283Average$395FlexibilityNo cancel feeOn-time71%
DeltaCheapest$289Average$395FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$330Average$410FlexibilityNo cancel feeOn-time63%

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