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$59+ Cheap flights from Valparaiso, FL to Boston (VPS - BOS)

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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — BOS
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap flight deals from Valparaiso to Boston

Cheapest flights from Valparaiso to Boston
Explore the most affordable flight options available from Valparaiso to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.

This American Airlines deal was found by Cheapflights users on 1/20. 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 2/310:47 am
VPS
-
BOS
1 stop5h 18m
American Airlines
Tue 2/175:30 pm
BOS
-
VPS
1 stop5h 45m
American Airlines
Deal found 1/20$193
This American Airlines deal was found by Cheapflights users on 1/20. 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 2/35:00 pm
VPS
-
BOS
1 stop5h 51m
American Airlines
Sat 2/712:07 pm
BOS
-
VPS
2 stops9h 53m
American Airlines
Deal found 1/20$198
This Delta deal was found by Cheapflights users on 1/20. 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.
Fri 7/317:05 pm
VPS
-
BOS
1 stop5h 01m
Delta
Sat 8/154:20 pm
BOS
-
VPS
1 stop5h 23m
Delta
Deal found 1/20$216
This American Airlines deal was found by Cheapflights users on 1/20. 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 3/54:40 pm
VPS
-
BOS
1 stop5h 00m
American Airlines
Sat 3/76:00 am
BOS
-
VPS
1 stop5h 07m
American Airlines
Deal found 1/20$219
This Delta deal was found by Cheapflights users on 1/20. 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.
Thu 2/512:05 pm
VPS
-
BOS
1 stop5h 49m
Delta
Sat 2/76:55 am
BOS
-
VPS
1 stop7h 05m
Delta
Deal found 1/20$231
This Delta deal was found by Cheapflights users on 1/20. 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 8/175:05 pm
VPS
-
BOS
1 stop7h 01m
Delta
Thu 8/205:40 am
BOS
-
VPS
1 stop6h 54m
Delta
Deal found 1/20$237
This Delta deal was found by Cheapflights users on 1/21. 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.
Fri 4/37:24 pm
VPS
-
BOS
1 stop4h 49m
Delta
Mon 4/66:50 pm
BOS
-
VPS
1 stop5h 25m
Delta
Deal found 1/21$256
This American Airlines deal was found by Cheapflights users on 1/20. 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 2/36:00 am
VPS
-
BOS
1 stop7h 49m
American Airlines
Fri 2/66:00 am
BOS
-
VPS
1 stop5h 17m
American Airlines
Deal found 1/20$262

Find flight deals from Valparaiso to Boston

Discover tips and strategies to find the most affordable flight options for your journey from Valparaiso (VPS) to Boston (BOS). 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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$193
(American Airlines)

One-way from

$59
(Kiwi.com)

Popular in

February

Cheapest in

March

Average price

$348

Good one-way deal

$219 or less
Provider with most accurate pricing for Valparaiso Destin-Ft Walton Beach-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Valparaiso Destin-Ft Walton Beach-Boston Logan Intl flights.
Search Deals
From Valparaiso Destin-Ft Walton Beach to Boston Logan Intl
Search Deals
One-way flight from Valparaiso Destin-Ft Walton Beach to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($66 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 14% potential price decrease ($49 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a one-way flight from Valparaiso Destin-Ft Walton Beach to Boston Logan Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Valparaiso to Boston 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 21, 2026.
Use the filters below to find and compare flights from Valparaiso to Boston that are best for you.

Fly from

Valparaiso

Fly to

Boston

Route

Depart

Return

Price

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Tue 2/3

5:00 pm-11:51 pm

1 stop5h 51m

Boston Logan Intl

Sat 2/7

12:07 pm-9:00 pm

2 stops9h 53m

$198

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Tue 2/3

11:00 am-8:11 pm

2 stops8h 11m

Boston Logan Intl

Tue 2/17

6:25 pm-11:59 pm

1 stop6h 34m

$198

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Fri 3/27

7:05 am-1:39 pm

1 stop5h 34m

Boston Logan Intl

Tue 3/31

2:00 pm-8:52 pm

1 stop7h 52m

$216

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Thu 2/5

12:05 pm-6:54 pm

1 stop5h 49m

Boston Logan Intl

Sat 2/7

6:55 am-1:00 pm

1 stop7h 05m

$231

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Fri 4/3

7:24 pm-1:13 am

1 stop4h 49m

Boston Logan Intl

Mon 4/6

6:50 pm-11:15 pm

1 stop5h 25m

$256

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Tue 2/3

6:00 am-2:49 pm

1 stop7h 49m

Boston Logan Intl

Fri 2/6

6:00 am-10:17 am

1 stop5h 17m

$262

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Thu 3/5

7:42 am-3:17 pm

2 stops6h 35m

Boston Logan Intl

Sat 3/7

5:30 pm-10:24 pm

1 stop5h 54m

$265

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Thu 3/26

9:59 am-5:08 pm

1 stop6h 09m

Boston Logan Intl

Mon 3/30

12:38 pm-2:59 pm

Nonstop3h 21m

$289

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Fri 3/6

3:55 pm-7:51 pm

Nonstop2h 56m

$67

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Thu 3/5

3:55 pm-7:51 pm

Nonstop2h 56m

$67

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 15 results
1
2

Compare providers for flights from Valparaiso to Boston

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 Valparaiso to Boston in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

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

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

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

Currently, March is the cheapest month in which you can book a flight from Valparaiso, Florida to Boston (average of $82). Flying from Valparaiso, Florida to Boston in December is currently the most expensive (average of $266). 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 Boston

Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated January 21, 2026.
Peruse reviews from past customers who have flown with Delta, American Airlines, and Allegiant Air from Valparaiso to Boston to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,086 reviews

Crew

8.5

Food

7.2

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
7.9
Good
8,086 reviews
Delta
7.9
Good
8,086 reviews

Crew

8.5

Food

7.2

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.2
Good
11,172 reviews
Delta
7.9
Good
8,086 reviews

Crew

8.5

Food

7.2

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Allegiant Air
7.2
Good
705 reviews
Delta
7.9
Good
8,086 reviews

Crew

8.5

Food

7.2

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from Valparaiso to Boston. 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 Boston?

    American Airlines and Delta can get you from Valparaiso, Florida to Boston in just under 5h 34m. Your travel time can differ by up to 17m. Valparaiso, Florida and Boston are separated by a distance of 1187 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Valparaiso, Florida to Boston round-trip?

    Cheapflights users have booked flights from Valparaiso, Florida to Boston round-trip from $82. Other airlines that can offer you cheap pricing are Delta, from $229, and American Airlines, from $251. Users have found that Allegiant Air is 78% cheaper than the other options available to this destination.

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

    For one-way options, check prices for Allegiant Air. According to our data, you can fly for as low as $39. Users have also found prices from $107 and $147 on American Airlines and Delta, respectively.

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

    Looking at all options, your cheapest flight can be booked for $78. While the most popular route (Valparaiso Destin-Ft Walton Beach - Boston Logan Intl) can be booked for $216 on average, our data indicates $224 when flying from Valparaiso, Florida to Boston.

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

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

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

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

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

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

    Currently, March is the cheapest month in which you can book a flight from Valparaiso, Florida to Boston (average of $82). Flying from Valparaiso, Florida to Boston in December is currently the most expensive (average of $266). 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 Boston?

Book flights to Boston if you plan to visit one of these locations
Cambridge
Medford
Hampton Beach
Watertown
Seekonk
Brockton
Warwick
Seabrook
Cranston
Lincoln
Smithfield
Peabody
Quincy
York Beach
Londonderry
Swansea
Old Orchard Beach
Waltham
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Top 3 airlines flying from Valparaiso to Boston

Discover the top 3 airlines that operate flights from Valparaiso to Boston. 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 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$165FlexibilityNo cancel feeOn-time88%
DeltaCheapest$229Average$414FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$251Average$383FlexibilityNo cancel feeOn-time71%

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