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Valparaiso

$33+ Cheap flights from Boston to Valparaiso, FL (BOS - 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 7/11. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — VPS
Jun 16 — Jun 231
Tue 6/16
Tue 6/23
1 adult, Economy
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1. Tell us where you want to go

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2. Select your favorite providers

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Cheapflights Tip: The best prices from Boston Logan Intl to Valparaiso Destin-Ft Walton Beach are usually found in June or May, booked 60 days in advance, depart on a Tuesday or Saturday and return on a Saturday

Cheap flight deals from Boston to Valparaiso

Cheapest flights from Boston to Valparaiso
Explore the most affordable flight options available from Boston to Valparaiso. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 17, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/14. 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.
Sat 5/3010:46 am
BOS
-
VPS
Nonstop3h 16m
Allegiant Air
Sat 6/66:00 am
VPS
-
BOS
Nonstop3h 04m
Allegiant Air
Deal found 5/14$66
This Kiwi.com deal was found by Cheapflights users on 5/15. 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.
Sat 6/610:54 am
BOS
-
VPS
Nonstop3h 08m
Allegiant Air
Sat 6/136:00 am
VPS
-
BOS
Nonstop3h 04m
Allegiant Air
Deal found 5/15$70
This Booking.com deal was found by Cheapflights users on 5/17. 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.
Sat 7/410:59 am
BOS
-
VPS
Nonstop3h 07m
Allegiant Air
Sat 7/116:00 am
VPS
-
BOS
Nonstop3h 09m
Allegiant Air
Deal found 5/17$92
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Sat 6/2710:54 am
BOS
-
VPS
Nonstop3h 08m
Allegiant Air
Sat 7/46:00 am
VPS
-
BOS
Nonstop3h 09m
Allegiant Air
Deal found 5/12$93
This FlightHub deal was found by Cheapflights users on 5/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/612:45 pm
BOS
-
VPS
Nonstop3h 19m
Multiple Airlines
Sat 6/136:00 am
VPS
-
BOS
Nonstop3h 04m
Multiple Airlines
Deal found 5/14$133
This FlightHub deal was found by Cheapflights users on 5/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/1512:45 pm
BOS
-
VPS
Nonstop3h 19m
Multiple Airlines
Sat 6/206:00 am
VPS
-
BOS
Nonstop3h 04m
Multiple Airlines
Deal found 5/15$147
This Cheapflightsfares deal was found by Cheapflights users on 5/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2010:54 am
BOS
-
VPS
Nonstop3h 08m
Allegiant Air
Sat 6/276:00 am
VPS
-
BOS
Nonstop3h 04m
Allegiant Air
Deal found 5/16$159

Find flight deals from Boston to Valparaiso

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) 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 May 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$66
(Kiwi.com)

One-way from

$33
(Kiwi.com)

Popular in

November

Cheapest in

June

Average price

$225

Good round-trip deal

$103 or less

Good one-way deal

$94 or less
Provider with most accurate pricing for Boston Logan Intl-Valparaiso Destin-Ft Walton Beach flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Valparaiso Destin-Ft Walton Beach flights.
Search Deals
From Boston Logan Intl to Valparaiso Destin-Ft Walton Beach
Search Deals
One-way flight from Boston Logan Intl to Valparaiso Destin-Ft Walton Beach
Search Deals
Highest demand for flights based on searches. 27% potential increase in price ($117 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Boston Logan Intl to Valparaiso Destin-Ft Walton Beach.
Search Deals
Price to beat on a one-way flight from Boston Logan Intl to Valparaiso Destin-Ft Walton Beach.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston 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 May 17, 2026.
Use the filters below to find and compare flights from Boston to Valparaiso that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Mon 6/1

12:42 pm-3:03 pm

Nonstop3h 21m

Valparaiso Destin-Ft Walton Beach

Fri 6/5

3:59 pm-7:55 pm

Nonstop2h 56m

$176

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Sat 10/3

7:00 pm-11:08 pm

1 stop5h 08m

Valparaiso Destin-Ft Walton Beach

Sat 10/10

5:05 pm-12:58 am

1 stop6h 53m

$246

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Mon 6/15

12:45 pm-3:04 pm

Nonstop3h 19m

Valparaiso Destin-Ft Walton Beach

Thu 6/18

9:59 am-5:22 pm

1 stop6h 23m

$274

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Mon 6/15

12:45 pm-3:04 pm

Nonstop3h 19m

Valparaiso Destin-Ft Walton Beach

Thu 7/2

9:59 am-5:22 pm

1 stop6h 23m

$279

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Sun 6/21

12:45 pm-3:04 pm

Nonstop3h 19m

Valparaiso Destin-Ft Walton Beach

Fri 6/26

9:59 am-5:22 pm

1 stop6h 23m

$294

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Fri 9/18

7:00 pm-11:08 pm

1 stop5h 08m

Valparaiso Destin-Ft Walton Beach

Tue 9/22

6:00 am-12:41 pm

1 stop5h 41m

$316

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Thu 10/15

5:45 am-11:13 am

1 stop6h 28m

Valparaiso Destin-Ft Walton Beach

Sun 10/18

7:05 pm-12:58 am

1 stop4h 53m

$337

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Thu 7/2

12:45 pm-3:04 pm

Nonstop3h 19m

Valparaiso Destin-Ft Walton Beach

Fri 7/3

3:59 pm-8:15 pm

Nonstop3h 16m

$356

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Fri 7/10

5:45 am-1:20 pm

1 stop8h 35m

Valparaiso Destin-Ft Walton Beach

Mon 7/13

12:30 pm-12:05 am

2 stops10h 35m

$361

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Wed 7/1

6:50 am-11:10 pm

1 stop17h 20m

Valparaiso Destin-Ft Walton Beach

Sat 7/4

5:07 pm-1:31 am

1 stop7h 24m

$364

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/13

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Boston 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 Boston to Valparaiso in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
Kiwi.comPrice 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 Boston-Valparaiso, Florida flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Valparaiso, Florida flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Boston-Valparaiso, Florida flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Boston-Valparaiso, Florida flights, Cheapflights users trust FlightHub the most. FlightHub 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 Boston-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 Boston to Valparaiso

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

How far ahead should I book a flight from Boston to Valparaiso, Florida?

To ensure you get the cheapest price possible for a flight from Boston to Valparaiso, Florida, you should look to book at least 59 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, June is the cheapest month in which you can book a flight from Boston to Valparaiso, Florida (average of $165). Flying from Boston to Valparaiso, Florida in November is currently the most expensive (average of $503). 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 BOS to VPS?

Find hourly flight availability from Boston to Valparaiso. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 17, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Boston to Valparaiso, Florida as you normally would.

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

Reviews of airlines servicing Valparaiso

Get insights into the airlines that provide service to Valparaiso. 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 Valparaiso. Reviews last updated May 17, 2026.
Read reviews from past customers who have flown Southwest,Delta, andAllegiant Air from Boston to Valparaiso. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,290 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,290 reviews
Southwest
8.0
Very good
4,290 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,449 reviews
Southwest
8.0
Very good
4,290 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Allegiant Air
7.3
Good
709 reviews
Southwest
8.0
Very good
4,290 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.2
Good
2,977 reviews
Southwest
8.0
Very good
4,290 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,654 reviews
Southwest
8.0
Very good
4,290 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

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

  • How popular is this Boston to Valparaiso, Florida flight route?

    Flights from Boston Logan Intl to Valparaiso Destin-Ft Walton Beach have been viewed 10 times in the past calendar month.

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

    Airlines like JetBlue and Delta fly from Boston to Valparaiso, Florida in about 3h 21m. The time it takes to get you to your destination can typically vary by up to 3h 23m. The distance from Boston to Valparaiso, Florida is about 1187 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    According to our current data, Allegiant Air ($62), JetBlue ($115), and Delta ($178) offers the cheapest pricing from Boston to Valparaiso, Florida. Allegiant Air is currently priced 80% below the average price you’ll pay for this route.

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

    The cheapest airline one-way is Allegiant Air, with whom users have recently found tickets for as low as $43. However, be on the lookout for offers from JetBlue and American Airlines, as they are both options that can get you from Boston to Valparaiso, Florida for a low price.

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

    On average you can expect to pay $186 for a flight from Boston to Valparaiso, Florida. The cheapest flight overall is $52 while the most popular route, (Boston Logan Intl - Valparaiso Destin-Ft Walton Beach) is currently priced at $64.

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

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

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

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

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

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

    Currently, June is the cheapest month in which you can book a flight from Boston to Valparaiso, Florida (average of $165). Flying from Boston to Valparaiso, Florida in November is currently the most expensive (average of $503). 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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Top 5 airlines flying from Boston to Valparaiso

Discover the top 5 airlines that operate flights from Boston 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 May 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$62Average$114FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$115Average$317FlexibilityNo cancel feeOn-time62%
DeltaCheapest$178Average$379FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$190Average$385FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$209Average$354FlexibilityNo cancel feeOn-time71%

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