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Valparaiso

$129+ 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — VPS
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Valparaiso Destin-Ft Walton Beach are usually found in January or May, booked 25 days in advance, depart on a Tuesday or Friday and return on a Monday

Cheap 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 August 14, 2025.

Round-trip from

$255
(Delta)

One-way from

$129
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$405

Good one-way deal

$168 or less
From Boston Logan Intl to Valparaiso Destin-Ft Walton Beach
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One-way flight from Boston Logan Intl to Valparaiso Destin-Ft Walton Beach
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Highest demand for flights based on searches. 8% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a one-way flight from Boston Logan Intl to Valparaiso Destin-Ft Walton Beach.
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Find 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 August 14, 2025.

This Delta deal was found by Cheapflights users on 8/13. 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 9/107:05 amBOS - VPS
1 stop6h 54mDelta
Tue 9/162:55 pmVPS - BOS
1 stop7h 07mDelta
Deal found 8/13$255
This American Airlines deal was found by Cheapflights users on 8/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/109:00 amBOS - VPS
2 stops9h 31mAmerican Airlines
Wed 9/178:10 amVPS - BOS
1 stop7h 07mAmerican Airlines
Deal found 8/14$261
This Delta deal was found by Cheapflights users on 8/13. 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 9/69:05 amBOS - VPS
1 stop6h 08mDelta
Wed 9/109:37 amVPS - BOS
1 stop7h 54mDelta
Deal found 8/13$274
This American Airlines deal was found by Cheapflights users on 8/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/216:00 amBOS - VPS
2 stops7h 54mAmerican Airlines
Mon 10/274:04 pmVPS - BOS
1 stop5h 56mAmerican Airlines
Deal found 8/14$280
This American Airlines deal was found by Cheapflights users on 8/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/205:16 pmBOS - VPS
2 stops6h 39mAmerican Airlines
Wed 9/248:10 amVPS - BOS
2 stops7h 55mAmerican Airlines
Deal found 8/14$286
This Delta deal was found by Cheapflights users on 8/13. 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 9/55:34 amBOS - VPS
1 stop7h 26mDelta
Tue 9/911:40 amVPS - BOS
1 stop5h 51mDelta
Deal found 8/13$290
This Delta deal was found by Cheapflights users on 8/13. 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 9/65:34 amBOS - VPS
1 stop7h 26mDelta
Thu 9/114:57 pmVPS - BOS
1 stop7h 21mDelta
Deal found 8/13$293
This American Airlines deal was found by Cheapflights users on 8/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/146:00 amBOS - VPS
2 stops6h 54mAmerican Airlines
Tue 9/168:10 amVPS - BOS
1 stop5h 55mAmerican Airlines
Deal found 8/14$296
This Delta deal was found by Cheapflights users on 8/13. 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 9/98:20 amBOS - VPS
1 stop5h 39mDelta
Wed 9/109:37 amVPS - BOS
2 stops11h 32mDelta
Deal found 8/13$298
This American Airlines deal was found by Cheapflights users on 8/13. 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 9/65:16 pmBOS - VPS
2 stops6h 39mAmerican Airlines
Sat 9/138:10 amVPS - BOS
1 stop7h 11mAmerican Airlines
Deal found 8/13$299
This American Airlines deal was found by Cheapflights users on 8/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/42:16 pmBOS - VPS
2 stops9h 17mAmerican Airlines
Mon 9/812:13 pmVPS - BOS
1 stop7h 12mAmerican Airlines
Deal found 8/14$300

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 August 14, 2025.
Use the filters below to find and compare flights from Boston to Valparaiso that are best for you.

Fly from

Boston

Fly to

Valparaiso

Route

Depart

Return

Price

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Tue 9/9

3:26 pm-9:54 pm

1 stop7h 28m

Valparaiso Destin-Ft Walton Beach

Tue 9/16

9:42 am-6:31 pm

1 stop7h 49m

$255

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Wed 9/10

5:43 pm-9:58 pm

1 stop5h 15m

Valparaiso Destin-Ft Walton Beach

Wed 9/17

6:01 pm-11:44 pm

1 stop4h 43m

$255

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Wed 9/10

7:05 am-12:59 pm

1 stop6h 54m

Valparaiso Destin-Ft Walton Beach

Wed 9/10

6:05 pm-1:24 am

1 stop6h 19m

$255

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Wed 9/10

7:05 am-12:59 pm

1 stop6h 54m

Valparaiso Destin-Ft Walton Beach

Tue 9/16

2:55 pm-11:02 pm

1 stop7h 07m

$255

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Wed 9/10

7:05 am-12:59 pm

1 stop6h 54m

Valparaiso Destin-Ft Walton Beach

Wed 9/17

6:05 pm-1:18 am

1 stop6h 13m

$255

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Tue 9/9

5:25 pm-9:54 pm

1 stop5h 29m

Valparaiso Destin-Ft Walton Beach

Wed 9/10

9:37 am-6:31 pm

1 stop7h 54m

$255

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Wed 9/3

8:30 am-12:59 pm

1 stop5h 29m

Valparaiso Destin-Ft Walton Beach

Tue 9/9

6:05 pm-1:21 am

1 stop6h 16m

$255

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Wed 9/3

7:00 am-12:59 pm

1 stop6h 59m

Valparaiso Destin-Ft Walton Beach

Wed 9/10

9:37 am-6:31 pm

1 stop7h 54m

$255

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Tue 12/9

5:48 am-12:10 pm

1 stop7h 22m

$129

BostonValparaiso

BOS - VPS

BOSVPS

Boston Logan Intl

Sun 8/31

5:35 am-10:35 am

1 stop6h 00m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 17 results
1
2

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?

Use this chart to determine the optimal time to book a round-trip flight from Boston to Valparaiso. Price data was last updated on August 8, 2025.

To ensure you get the cheapest price possible for a flight from Boston to Valparaiso, Florida, you should look to book at least 25 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, July is the cheapest month in which you can book a flight from Boston to Valparaiso, Florida (average of $291). Flying from Boston to Valparaiso, Florida in April is currently the most expensive (average of $386). 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 August 14, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 34% on flights from Boston to Valparaiso, Florida by exploring options for tickets in the morning.

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 August 14, 2025.
Read reviews from past customers who have flown Southwest, Delta, and American Airlines 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
4,244 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Allegiant Air
7.2
Good
701 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

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

    According to our current data, Allegiant Air ($84), Delta ($296), and American Airlines ($315) 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 flights from Boston to Valparaiso, Florida?

    On average you can expect to pay $187 for a flight from Boston to Valparaiso, Florida. The cheapest flight overall is $88 while the most popular route, (Boston Logan Intl - Valparaiso Destin-Ft Walton Beach) is currently priced at $255.

  • 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, July is the cheapest month in which you can book a flight from Boston to Valparaiso, Florida (average of $291). Flying from Boston to Valparaiso, Florida in April is currently the most expensive (average of $386). 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 4 airlines flying from Boston to Valparaiso

Discover the top 4 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$84Average$291FlexibilityNo cancel feeOn-time88%
DeltaCheapest$296Average$413FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$315Average$453FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$353Average$443FlexibilityNo cancel feeOn-time63%

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