BOS - VPS

$42 Find Cheap Flights from Boston to Valparaiso

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Valparaiso departing on 5/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Valparaiso

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Valparaiso, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Valparaiso, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$111
Overall average: $329
Allegiant Air
Fri 5/1Fri 5/8
BOS - VPS • Non-stop
Cheapest one-way
$42
Typical prices: $103-$208
Allegiant Air
Mon 5/11
BOS - VPS • Non-stop
Nonstop flights
Mon, Thu, Fri, Sat, Sun
You can fly direct with JetBlue and Allegiant Air. Average duration is 3h 17m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top airlines
Cheapest • from $111 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
+1
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 39% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 27% price drop
Most popular
Good to know
Good to know
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Good to know
Good to know
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Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Valparaiso!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Boston to Valparaiso (BOS-VPS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to Valparaiso that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Boston to Valparaiso

Fri, May 1 - Fri, May 8
Allegiant Air Logo
12:48 pm - 2:58 pm
BOS
-
VPS
3h 10mnonstop
Allegiant Air Logo
8:00 am - 11:58 am
VPS
-
BOS
2h 58mnonstop
$111Allegiant Air
Mon, Apr 13 - Sat, Apr 18
Allegiant Air Logo
12:48 pm - 2:58 pm
BOS
-
VPS
3h 10mnonstop
Allegiant Air Logo
7:30 am - 11:28 am
VPS
-
BOS
2h 58mnonstop
$126Allegiant Air
Mon, Apr 6 - Mon, Apr 13
Allegiant Air Logo
12:48 pm - 3:01 pm
BOS
-
VPS
3h 13mnonstop
Allegiant Air Logo
8:00 am - 11:58 am
VPS
-
BOS
2h 58mnonstop
$129Allegiant Air
Mon, Apr 6 - Mon, Apr 13
Allegiant Air Logo
12:48 pm - 3:01 pm
BOS
-
VPS
3h 13mnonstop
Allegiant Air Logo
8:00 am - 11:58 am
VPS
-
BOS
2h 58mnonstop
$138Allegiant Air
Fri, Apr 3 - Mon, Apr 6
Allegiant Air Logo
12:48 pm - 3:01 pm
BOS
-
VPS
3h 13mnonstop
Allegiant Air Logo
8:00 am - 11:58 am
VPS
-
BOS
2h 58mnonstop
$146Allegiant Air
Fri, May 8 - Mon, May 11
Allegiant Air Logo
12:48 pm - 2:58 pm
BOS
-
VPS
3h 10mnonstop
Allegiant Air Logo
8:00 am - 11:58 am
VPS
-
BOS
2h 58mnonstop
$148Allegiant Air
Fri, May 15 - Mon, May 18
Allegiant Air Logo
12:48 pm - 2:58 pm
BOS
-
VPS
3h 10mnonstop
Allegiant Air Logo
8:00 am - 11:58 am
VPS
-
BOS
2h 58mnonstop
$150Allegiant Air
Fri, Apr 3 - Mon, Apr 6
Allegiant Air Logo
12:48 pm - 3:01 pm
BOS
-
VPS
3h 13mnonstop
Allegiant Air Logo
8:00 am - 11:58 am
VPS
-
BOS
2h 58mnonstop
$157Allegiant Air
Sat, Jun 20 - Sat, Jun 27
Allegiant Air Logo
10:54 am - 1:02 pm
BOS
-
VPS
3h 08mnonstop
Allegiant Air Logo
6:00 am - 10:04 am
VPS
-
BOS
3h 04mnonstop
$166Allegiant Air
Mon, Apr 13 - Mon, Apr 20
Allegiant Air Logo
12:48 pm - 2:58 pm
BOS
-
VPS
3h 10mnonstop
Allegiant Air Logo
8:00 am - 11:58 am
VPS
-
BOS
2h 58mnonstop
$172Allegiant Air
Booking Insights

KAYAK's insights & trends for Boston to Valparaiso flights

Get data-powered insights and trends into flights from Boston to Valparaiso to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Boston to Valparaiso?

The average price of all round-trip flights from Boston to Valparaiso clicked on KAYAK for each day over the last 12 months.

For Boston to Valparaiso, Sunday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Valparaiso back to Boston, the best deals are generally found on Wednesday, with Thursday being the most expensive.

What is the cheapest month to fly from Boston to Valparaiso?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston to Valparaiso, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Boston to Valparaiso is January, where tickets cost $261 (return) on average. On the other hand, the most expensive months are November and October, where the average cost of round-trip tickets is $485 and $430 respectively.

Can I save money by flying with a layover from Boston to Valparaiso?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $285 on average.

How far in advance should I book a flight from Boston to Valparaiso?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Boston to Valparaiso, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Boston to Valparaiso, you should book around 3 weeks before departure, which saves you about 39% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$42
Best time to beat the crowds but there is an average 34% increase in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Boston to Valparaiso

When to book flights from Boston to Valparaiso

Are your dates flexible? Find out the best times to travel from Boston to Valparaiso based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Boston to Valparaiso

  • What is the cheapest flight from Boston to Valparaiso?

    In the last 3 days, the lowest price for a flight from Boston to Valparaiso was $42 for a one-way ticket and $111 for a round-trip.

  • Do I need a passport to fly between Boston and Valparaiso?

    No, a passport isn't needed to fly from Boston to Valparaiso. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Boston to Valparaiso?

    When flying out of Boston you will be using Boston Logan Intl. You will be landing at Valparaiso, also known as Valparaiso Destin-Ft Walton Beach.

  • Which airlines offer Wi-Fi service onboard planes from Boston to Valparaiso?

    JetBlue, and Delta offer inflight Wi-Fi service on the Boston to Valparaiso flight route.

  • Which aircraft models fly most regularly from Boston to Valparaiso?

    The Airbus A220-300 is the aircraft model that flies most regularly on the Boston to Valparaiso flight route.

  • Which airline alliances offer flights from Boston to Valparaiso?

    SkyTeam, and oneworld are the airline alliances operating flights between Boston and Valparaiso, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Boston to Valparaiso?

    You can catch a nonstop flight from Boston to Valparaiso on on Monday, Thursday, Friday, Saturday, and Sunday.

  • Which is the best airline for flights from Boston to Valparaiso, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Boston to Valparaiso are Southwest and Delta. With an average price for the route of $422 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $390 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from Boston to Valparaiso?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Boston to Valparaiso.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Boston to Valparaiso?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Valparaiso from Boston is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Boston to Valparaiso?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Valparaiso with an airline and back to Boston with another airline. Booking your flights between Boston and VPS can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Boston to Valparaiso?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Valparaiso from Boston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Boston to Valparaiso

  • Looking for a cheap flight? 25% of our users found flights on this route for $88 or less one-way and $200 or less round-trip.

Prefer to fly direct from Boston to Valparaiso?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Boston Logan Intl to Valparaiso Destin-Ft Walton Beach.
Find which airlines fly direct from Boston Logan Intl Airport to Valparaiso Destin-Ft Walton Beach Airport, which days they fly and book direct flights.

Direct departures

Boston Logan Intl to Valparaiso Destin-Ft Walton Beach

Monday

Allegiant Air,JetBlue

Allegiant Air,JetBlue

Thursday

JetBlue

JetBlue

Friday

Allegiant Air,JetBlue

Allegiant Air,JetBlue

Saturday

Allegiant Air,JetBlue

Allegiant Air,JetBlue

Sunday

JetBlue

JetBlue

See more direct flights

Direct returns

Valparaiso Destin-Ft Walton Beach to Boston Logan Intl

Monday

Allegiant Air,JetBlue

Allegiant Air,JetBlue

Thursday

JetBlue

JetBlue

Friday

Allegiant Air,JetBlue

Allegiant Air,JetBlue

Saturday

Allegiant Air,JetBlue

Allegiant Air,JetBlue

Sunday

JetBlue

JetBlue

See more direct flights

Reviews of the top 5 airlines serving from Boston to Valparaiso

 
See real verified KAYAK customer reviews for airlines flying from Boston to Valparaiso. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Boston to Valparaiso? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4318 reviews
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

The whole experience was excellent. As it most often is with Delta

Cabin was not pressurized properly. Several passengers had respiratory difficulties.

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

Good experience and the flight landed early. There was no food I had or entertainment.

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Excellent!!! Aeromexico is a great airline. What was not that good is the service provided by Kayak. It is never clear and not easy to manage.

Sorry I didn't realize I was writing a review for each leg. Please see my previous review - it applies to the entire flight, not just a single leg.

boarded at 5:30 pm, pushed away from gate at 6pm ... takeoff was not until ~6:45pm; disappointing

Superb. Staff great. Great flight. As with other airlines, seating too tight and restrictive.

There is not one likable thing about this airline. It’s starts with the deceptive pricing and continues through the whole flight. The worst staff I’ve ever experienced way over priced bags absolutely no food or drink (unacceptable and you should be embarrassed) the seats are cramped and uncomfortable there is no entertainment there is nothing about this trash airline that constitutes any amount of money. It’s worse than spirit and way more expensive it is disgraceful. Do not travel with Allegiant I repeat do not bother no matter what they say the price is it is never ever going to be the right choice I’m mind blown at how awful the entire experience was I’m embarrassed that I chose so poorly I cannot reiterate enough how beyond horrible this company and its staff are, not one person on this flight or at the airport is qualified to sweep up trash on a city sidewalk they should certainly never be given any job that requires a brain or manners or communication with human beings, what a disgrace to the human race. Your criminal chiselers and should be put out to pasture

Great flight. Friendly staff. Free snacks and drinks would be nice. I would love fewer taxes and fees added on.

My 90 year old father flew with me. He needed wheel chair assistance and is nearly deaf. The staff was amazing with him.

It was fine. Nobody was outstandingly friendly but no one was rude and everything was smooth . The captain thanked us for flying but no one greeted me as I walked on the plane or as I exited which is the least they could do lol

Clean, friendly, roomy. But check-in from the phone link was terrible. Repeated attempts wouldn’t save at the final step. Just kept spinning! It was very frustrating. Finally, I used the app (vs website link) to check-in which worked very smoothly on the first attempt.

Check in on the web portal was cumbersome! After several attempts I finally got the boarding pass.

Excellent flight and even arrived 23 min early. No entertainment , or wi fi on board, but I downloaded a couple of movies beforehand which kept me entertained. Really like flying Allegiant airlines.

WE were delayed about an hour and never any communications from the employees working the gate. We also were moved to a total of three gates.

I love how they show love to their customers and care about them too.

My check in was stressful. I somehow lost my seat from my original booking, the plane showed no availability/no seat when it was time to check-in. I called and was instructed to try to get a seat at the airport. I asked if it was a full flight and the travel agent said the site showed some seating but was not able to secure one for me. Why not? On my way to the airport the app finally revealed one available seat towards the back of the aircraft that I was able to book. It ended up being an overbooked flight, so glad I wasn't stuck.

Both flights were significantly delayed. The flight experience itself was great.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

Because of weather and mechanical issues our flight was 4 hours late. The only compensation offered to us was a meal voucher to be used only at Boston Airport and only on the day issued. But by the time it was offered to us all the restaurants were closed, so there was no way to use that offer.

It was good. I prefer JB over other airlines.I just wish we had headphones for the films, but other than that - good.

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

Check in was rough because the check in crew did not know how to manage my international visa documents. Required a long process and 4 people to finally be able to proceed to security. They told us incorrect information several times before acknowledging we did indeed have everything we needed from the start.

Never going to fly your airline again if it can be avoided.

Mechanical issue delayed us 2hrs and then once we landed sat on tarmac for 30mins because someone left a vehicle in front of the gaye

Plane from partner PSA was filthy. Plastic needs to be thoroughly cleaned. Really disgusting to look at and wonder about cleanliness of parts less visible.

Flight delay for mechanical. Inbound arrived on time. No one said why mechanical delay.

It was a train wreck but on an airplane. First off, flight was delayed then we board only to hear two announcements, First weather delays in Orlando and second backup battery warning on emergency lights. After sitting on the plane for almost 2 hours they have us deplane due to the maintenance issue. We were told they were getting another plane. In the mean time, I notice another American- Orlando flight and ask the gate agent if I can switch. He says he cant help me and I'd have to walk to A13 from A37. Really!? I get down there and get a seat only to get an announcement my original flight was RE-boarding. The Then inflight there's no communication and I notice on flightaware were circling over the Gulf of America. I call the flight attendant and of course she has no clue and apparently 5m later the pilot finally tells us about another delay. Why does American always have these service and delay issues? They are my LAST choice in flights now!

Flight boarded, departed and landed on time. Excellent service from flight attendant in FIRST

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

Worst experience ever. Flight could not land in Charlotte for what we were told was a ground stop. Had to be diverted to Raleigh to refuel. Strangely during ground stop, our connecting flight had no issue taking off on time causing us to miss our flight. We were told there were no other flights that day to our final destination and that two days out was the next one. The only flights to get us there were from Chicago the next morning. Completely opposite direction but it was a direct flight. So we get flown to Chicago and have to find a hotel in our own dime. The flight in the morning was also delayed. Thankfully only a short time. The non too of all this, our luggage did not arrive by the time we were there. Communication was terrible, through the entire trip. Complete incompetence. Will never fly American again.

We missed our flight and got stranded in Miami where we had to rent a hotel we could not afford. they would not work with us because they said it was weather related even though the gate attendant said it was not. I could go on but trying to get satisfaction has wore me down, which I believe is the intent. My only solution is to never fly AA again.

Everything you need to know for your flight from Boston to Valparaiso

Information on your arrival and departure airports