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$145+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — BOS
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap 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 September 16, 2025.

Round-trip from

$325
(Kiwi.com)

One-way from

$145
(Kiwi.com)

Popular in

February

Cheapest in

March

Average price

$339
From Valparaiso Destin-Ft Walton Beach to Boston Logan Intl
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One-way flight from Valparaiso Destin-Ft Walton Beach to Boston Logan Intl
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Highest demand for flights based on searches. 12% potential increase in price ($58 potential increase over avg. RT price).
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Cheapest flight prices on average. 12% potential price decrease ($44 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/222:45 pmVPS - BOS
2 stops22h 03mMultiple Airlines
Sat 9/2711:07 amBOS - VPS
1 stop24h 24mMultiple Airlines
Deal found 9/16$305
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/227:22 pmVPS - BOS
1 stop13h 21mAllegiant Air
Sat 9/2711:07 amBOS - VPS
1 stop24h 24mAllegiant Air
Deal found 9/16$313
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Mon 9/297:22 pmVPS - BOS
1 stop13h 55mMultiple Airlines
Fri 10/36:49 pmBOS - VPS
2 stops29h 41mMultiple Airlines
Deal found 9/14$325
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/75:00 pmVPS - BOS
1 stop7h 13mDelta
Mon 11/106:25 pmBOS - VPS
1 stop5h 39mDelta
Deal found 9/15$335
This American Airlines deal was found by Cheapflights users on 9/14. 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 11/2510:51 amVPS - BOS
1 stop7h 12mAmerican Airlines
Fri 11/285:25 amBOS - VPS
1 stop7h 49mAmerican Airlines
Deal found 9/14$340
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Fri 10/241:44 pmVPS - BOS
1 stop5h 11mAmerican Airlines
Mon 10/276:00 amBOS - VPS
2 stops6h 44mAmerican Airlines
Deal found 9/14$341
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1612:34 pmVPS - BOS
1 stop7h 21mAmerican Airlines
Sun 10/196:00 amBOS - VPS
1 stop5h 20mAmerican Airlines
Deal found 9/15$365
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 9/267:24 pmVPS - BOS
1 stop13h 53mMultiple Airlines
Sun 9/289:38 amBOS - VPS
2 stops29h 17mMultiple Airlines
Deal found 9/15$376
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/38:10 amVPS - BOS
1 stop7h 11mAmerican Airlines
Wed 10/86:00 amBOS - VPS
1 stop5h 20mAmerican Airlines
Deal found 9/15$383

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 September 16, 2025.
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

Mon 9/29

7:22 pm-10:17 am

1 stop13h 55m

Boston Logan Intl

Fri 10/3

6:49 pm-11:30 pm

2 stops29h 41m

$325

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Thu 1/1

7:39 am-3:24 pm

1 stop6h 45m

Boston Logan Intl

Mon 1/5

5:53 am-12:23 pm

1 stop7h 30m

$327

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Fri 11/7

5:00 pm-1:13 am

1 stop7h 13m

Boston Logan Intl

Mon 11/10

6:25 pm-11:04 pm

1 stop5h 39m

$335

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Tue 11/25

12:59 pm-8:22 pm

2 stops6h 23m

Boston Logan Intl

Fri 11/28

6:59 am-3:48 pm

2 stops9h 49m

$351

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Thu 10/16

12:34 pm-8:55 pm

1 stop7h 21m

Boston Logan Intl

Sun 10/19

6:00 am-10:20 am

1 stop5h 20m

$365

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Fri 11/7

12:59 pm-8:22 pm

2 stops6h 23m

Boston Logan Intl

Mon 11/10

5:16 am-12:01 pm

2 stops7h 45m

$376

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Thu 10/9

7:07 am-3:24 pm

2 stops7h 17m

Boston Logan Intl

Tue 10/14

6:00 am-10:20 am

1 stop5h 20m

$376

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Fri 10/3

8:10 am-4:21 pm

1 stop7h 11m

Boston Logan Intl

Wed 10/8

6:00 am-10:20 am

1 stop5h 20m

$383

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Mon 9/29

7:22 pm-10:17 am

1 stop13h 55m

$145

ValparaisoBoston

VPS - BOS

VPSBOS

Valparaiso Destin-Ft Walton Beach

Fri 10/3

3:46 pm-1:48 pm

2 stops21h 02m

$174

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 17 results
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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, January is the cheapest month in which you can book a flight from Valparaiso, Florida to Boston (average of $218). Flying from Valparaiso, Florida to Boston in July is currently the most expensive (average of $311). 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 BOS?

Find hourly flight availability from Valparaiso to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

It’s typically best to fly out from Valparaiso, Florida to Boston in the morning. Doing so could potentially save you 77% on the flight price compared to flying in the evening, which is usually more expensive.

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

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 September 16, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and American Airlines 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.
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

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
8.0
Very good
7,957 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

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
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

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
699 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

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 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 6h 45m. Your travel time can differ by up to 28m. 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 American Airlines, from $283, and Delta, from $289. Users have found that Allegiant Air is 79% cheaper than the other options available to this destination.

  • 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, January is the cheapest month in which you can book a flight from Valparaiso, Florida to Boston (average of $218). Flying from Valparaiso, Florida to Boston in July is currently the most expensive (average of $311). 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
Seabrook
Seekonk
Lincoln
Lowell
Smithfield
Cranston
Chestnut Hill
Chelsea
Warwick
Peabody
Quincy
York Beach
Swansea
Old Orchard Beach
Brockton
Waltham

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Alternative routes for Valparaiso to Boston

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Valparaiso to Boston

Discover the top 4 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$82Average$204FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$283Average$396FlexibilityNo cancel feeOn-time71%
DeltaCheapest$289Average$395FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$324Average$410FlexibilityNo cancel feeOn-time63%

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