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Valparaiso

$60+ Cheap flights from Massachusetts to Valparaiso, FL (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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — VPS
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Massachusetts to Valparaiso

Cheapest flights from Massachusetts to Valparaiso
Explore the most affordable flight options available from Massachusetts to Valparaiso. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/2512:46 pm
BOS
-
VPS
Nonstop3h 16m
Allegiant Air
Sat 5/306:00 am
VPS
-
BOS
Nonstop2h 56m
Allegiant Air
Deal found 1/28$148
This Booking.com deal was found by Cheapflights users on 1/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/812:48 pm
BOS
-
VPS
Nonstop3h 10m
Allegiant Air
Mon 5/118:00 am
VPS
-
BOS
Nonstop2h 58m
Allegiant Air
Deal found 1/26$167
This American Airlines deal was found by Cheapflights users on 1/28. 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 3/48:35 am
BOS
-
VPS
1 stop8h 17m
American Airlines
Tue 3/107:59 am
VPS
-
BOS
1 stop5h 58m
American Airlines
Deal found 1/28$175
This American Airlines deal was found by Cheapflights users on 1/28. 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.
Fri 2/205:30 pm
BOS
-
VPS
1 stop5h 54m
American Airlines
Tue 2/244:38 pm
VPS
-
BOS
1 stop4h 37m
American Airlines
Deal found 1/28$195
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Tue 5/53:17 pm
BOS
-
VPS
1 stop7h 22m
American Airlines
Wed 5/274:53 pm
VPS
-
BOS
1 stop6h 41m
American Airlines
Deal found 1/27$215
This Delta deal was found by Cheapflights users on 1/28. 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.
Tue 2/241:37 pm
BOS
-
VPS
1 stop5h 42m
Delta
Wed 2/255:11 pm
VPS
-
BOS
1 stop4h 32m
Delta
Deal found 1/28$216
This Delta deal was found by Cheapflights users on 1/28. 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.
Mon 2/236:45 pm
BOS
-
VPS
1 stop5h 18m
Delta
Tue 3/36:00 am
VPS
-
BOS
1 stop7h 15m
Delta
Deal found 1/28$226
This Delta deal was found by Cheapflights users on 1/27. 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.
Tue 2/245:50 pm
ALB
-
VPS
1 stop6h 13m
Delta
Tue 3/36:00 am
VPS
-
ALB
1 stop4h 55m
Delta
Deal found 1/27$336
This Delta deal was found by Cheapflights users on 1/28. 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 2/2811:55 am
BDL
-
VPS
1 stop5h 08m
Delta
Sat 3/76:00 am
VPS
-
BDL
1 stop6h 41m
Delta
Deal found 1/28$347
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Thu 3/125:24 pm
BDL
-
VPS
1 stop6h 00m
American Airlines
Mon 3/164:40 pm
VPS
-
BDL
1 stop6h 48m
American Airlines
Deal found 1/27$357
This Delta deal was found by Cheapflights users on 1/28. 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 4/185:54 pm
BDL
-
VPS
1 stop6h 25m
Delta
Thu 4/237:15 am
VPS
-
BDL
1 stop5h 01m
Delta
Deal found 1/28$358
This Delta deal was found by Cheapflights users on 1/27. 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 4/46:04 pm
ALB
-
VPS
1 stop6h 14m
Delta
Wed 4/86:00 am
VPS
-
ALB
1 stop5h 07m
Delta
Deal found 1/27$358

Find flight deals from Massachusetts to Valparaiso

Keep the following information in mind while searching for Massachusetts to Valparaiso flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$148
(Kiwi.com)

One-way from

$60
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$287

Good round-trip deal

$195 or less

Good one-way deal

$139 or less
Provider with most accurate pricing for Boston Logan Intl-Valparaiso Destin-Ft Walton Beach flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Valparaiso Destin-Ft Walton Beach flights.
Search Deals
From Massachusetts to Valparaiso Destin-Ft Walton Beach
Search Deals
One-way flight from Massachusetts to Valparaiso Destin-Ft Walton Beach
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($61 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Massachusetts to Valparaiso Destin-Ft Walton Beach.
Search Deals
Price to beat on a one-way flight from Massachusetts to Valparaiso Destin-Ft Walton Beach.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts 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 January 29, 2026.
Use the filters below to find and compare flights from Massachusetts to Valparaiso that are best for you.

Fly from

Massachusetts

Fly to

Valparaiso

Route

Depart

Return

Price

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Tue 4/14

2:15 pm-8:28 pm

1 stop7h 13m

Valparaiso Destin-Ft Walton Beach

Tue 4/21

4:59 pm-1:15 am

1 stop7h 16m

$216

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Mon 2/23

5:25 pm-11:03 pm

1 stop6h 38m

Valparaiso Destin-Ft Walton Beach

Mon 3/2

7:16 pm-1:09 am

1 stop4h 53m

$216

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Tue 3/3

10:10 am-4:03 pm

1 stop6h 53m

Valparaiso Destin-Ft Walton Beach

Fri 3/13

7:24 pm-1:13 am

1 stop4h 49m

$256

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Sun 4/19

7:50 am-2:13 pm

1 stop7h 23m

Valparaiso Destin-Ft Walton Beach

Fri 5/15

7:05 pm-1:03 am

1 stop4h 58m

$256

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Fri 4/24

4:00 pm-8:28 pm

1 stop5h 28m

Valparaiso Destin-Ft Walton Beach

Fri 5/1

7:15 am-1:45 pm

1 stop5h 30m

$256

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Sun 4/19

7:50 am-2:13 pm

1 stop7h 23m

Valparaiso Destin-Ft Walton Beach

Wed 4/22

7:15 am-2:45 pm

1 stop6h 30m

$256

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Sun 4/19

7:50 am-2:13 pm

1 stop7h 23m

Valparaiso Destin-Ft Walton Beach

Tue 5/12

7:45 am-3:09 pm

1 stop6h 24m

$256

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Wed 3/4

6:45 pm-11:03 pm

1 stop5h 18m

Valparaiso Destin-Ft Walton Beach

Sat 3/7

5:12 pm-11:48 pm

1 stop5h 36m

$256

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Sun 4/19

7:50 am-2:13 pm

1 stop7h 23m

Valparaiso Destin-Ft Walton Beach

Tue 4/21

7:15 am-2:45 pm

1 stop6h 30m

$266

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Sat 4/11

12:40 pm-3:00 pm

Nonstop3h 20m

Valparaiso Destin-Ft Walton Beach

Sat 4/18

8:00 am-11:54 am

Nonstop2h 54m

$271

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 46 results
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Best time to book a flight from Massachusetts to Valparaiso

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

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

Currently, June is the cheapest month in which you can book a flight from Massachusetts to Valparaiso, Florida (average of $84). Flying from Massachusetts to Valparaiso, Florida in November is currently the most expensive (average of $252). 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.

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

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Valparaiso. 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 into for flights to Valparaiso from Massachusetts?

    Valparaiso Destin-Ft Walton Beach (VPS) is the airport you will fly into if you book a flight from Massachusetts to Valparaiso. It is only a 3.1 mi journey from Destin-Ft Walton Beach (VPS) to Valparaiso’s city center.

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

    A quick flight from Massachusetts to Valparaiso, Florida can take about 5h 15m. Delta provides one of the quickest options available for as low as $363. Massachusetts and Valparaiso, Florida are separated by a distance of 1102 mi. This flight may include one or multiple stops.

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

    $43 is the cheapest one-way deal found within the past few days, from Allegiant Air. You may also be able to find cheap deals on American Airlines and Delta, with prices starting from $108 and $134, respectively.

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

    While some choose either Hartford Bradley Intl - Valparaiso Destin-Ft Walton Beach or Albany Intl - Valparaiso Destin-Ft Walton Beach, Boston Logan Intl - Valparaiso Destin-Ft Walton Beach is the most popular route from Massachusetts to Valparaiso, Florida.

  • What are the cheapest flights from Massachusetts to Valparaiso, Florida?

    Looking at all options, your cheapest flight can be booked for $128. While the most popular route (Boston Logan Intl - Valparaiso Destin-Ft Walton Beach) can be booked for $148 on average, our data indicates $263 when flying from Massachusetts to Valparaiso, Florida.

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

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

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

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

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

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

    Currently, June is the cheapest month in which you can book a flight from Massachusetts to Valparaiso, Florida (average of $84). Flying from Massachusetts to Valparaiso, Florida in November is currently the most expensive (average of $252). 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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Alternative routes for Massachusetts to Valparaiso

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Massachusetts to Valparaiso

Discover the top 5 airlines that operate flights from Massachusetts to Valparaiso. 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$84Average$289FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$118Average$270FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$190Average$423FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$215Average$386FlexibilityNo cancel feeOn-time71%
DeltaCheapest$217Average$392FlexibilityNo cancel feeOn-timeN/A

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