BOS - VPS

$61 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 8/16. 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

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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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

Sat, Aug 16 - Sun, Aug 17
 Logo
12:51 pm - 3:07 pmBOS-VPS
3h 16mnonstop
 Logo
6:00 am - 1:48 pmVPS-BOS
30h 48m3 stops
Thu, Aug 21 - Mon, Aug 25
 Logo
10:34 am - 5:02 pmBOS-VPS
7h 28m1 stop
 Logo
6:30 am - 11:12 pmVPS-BOS
15h 42m2 stops
Thu, Sep 25 - Mon, Sep 29
 Logo
6:49 pm - 10:52 pmBOS-VPS
29h 03m2 stops
 Logo
7:22 pm - 10:17 amVPS-BOS
13h 55m1 stop
Thu, Aug 21 - Mon, Aug 25
 Logo
10:34 am - 5:02 pmBOS-VPS
7h 28m1 stop
 Logo
6:30 am - 5:50 pmVPS-BOS
34h 20m3 stops
Wed, Aug 20 - Tue, Aug 26
Delta Logo
9:05 am - 12:41 pmBOS-VPS
4h 36m1 stop
Delta Logo
6:05 pm - 1:20 amVPS-BOS
6h 15m1 stop
$295Delta
Find Deal
Wed, Oct 8 - Tue, Oct 14
American Airlines Logo
1:01 pm - 8:07 pmBOS-VPS
8h 06m2 stops
American Airlines Logo
7:00 am - 2:58 pmVPS-BOS
6h 58m1 stop
$301American Airlines
Find Deal
Sat, Oct 11 - Wed, Oct 15
American Airlines Logo
8:29 am - 3:19 pmBOS-VPS
7h 50m1 stop
American Airlines Logo
7:00 am - 3:21 pmVPS-BOS
7h 21m2 stops
$302American Airlines
Find Deal
Tue, Oct 21 - Mon, Oct 27
Delta Logo
5:40 am - 9:59 amBOS-VPS
5h 19m1 stop
Delta Logo
7:10 pm - 1:13 amVPS-BOS
5h 03m1 stop
$310Delta
Find Deal
Tue, Sep 30 - Fri, Oct 3
Southwest Logo
5:40 am - 11:55 amBOS-VPS
7h 15m1 stop
Southwest Logo
12:00 pm - 9:00 pmVPS-BOS
8h 00m1 stop
$331Southwest
Find Deal
Tue, Sep 30 - Fri, Oct 3
Southwest Logo
5:20 am - 1:25 pmBOS-VPS
9h 05m2 stops
Southwest Logo
10:15 am - 9:00 pmVPS-BOS
9h 45m2 stops
$336Southwest
Find Deal
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, Tuesday 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 Saturday, with Friday 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 $354 (return) on average. On the other hand, the most expensive months are October and December, where the average cost of round-trip tickets is $541 and $494 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.

No, with an average price for the route of $325, prices are generally cheapest when you fly direct.

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 46% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$61
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 3% 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 $61 for a one-way ticket and $257 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?

    American Airlines, 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 A320-100/200 is the aircraft model that flies most regularly on the Boston to Valparaiso flight route.

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

    You can catch a nonstop flight from Boston to Valparaiso on on Saturday.

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

    The two airlines most popular with KAYAK users for flights from Boston to Valparaiso are Delta and Southwest. With an average price for the route of $406 and an overall rating of 8.0, Delta is the most popular choice. Southwest is also a great choice for the route, with an average price of $443 and an overall rating of 8.0.

  • 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.

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

Saturday

Allegiant Air

Allegiant Air

See more direct flights

Direct returns

Valparaiso Destin-Ft Walton Beach to Boston Logan Intl

Saturday

Allegiant Air

Allegiant Air

See more direct flights

Reviews of the top 4 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 4241 reviews
8.1Boarding
7.0Food
7.5Entertainment
8.0Comfort
8.6Crew
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

this crew didn't care much. bumping carts into seats more times than i care to remember

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

I want to single out flight attendant Mitch who was in the Premium Economy section. When my wife’s hearing aide dropped through the cushion under the seat he was able to locate it and return it to her. Food was a different matter. Dinner was fine. Breakfast was another matter. They had a yogurt dish that the ran out of and the alternative was not very good according to those we talked to.

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Great flight! Only complaint I had was that I didn’t get breakfast that morning because I don’t eat eggs for breakfast.. I ate an energy bar I bought in the airport which I had never done before. Otherwise, another great Delta flight!

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

Crew was friendly Love the entertainment in the seat head rest.

Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!

Flight delays numerous times. Everytime we would get close to boarding it would be delayed again. Strung along the entire time.

This flight never occurred because AA couldn’t get their act together.

Whenever a passenger purchase a ticket his advantage number should automatically to his information. It's not everyone remember the number. You request for your number and American airline agent say they will email it....and they never email anything and you loose your mileage just because you don't remember your number. It should automatically go your information and associate with your email account at all times

During service there was a garbage/beverage spill near our seats that never was cleaned up. On a relatively short flight when we’re fortunate enough to actually have in flight movies available, the flight attendants pitching the AADVANTAGE credit card shouldn’t talk for the last 10 minutes of the flight so that we miss the end of the movie.

I miss the screens they used to have for the long flights. I use a Kendal and it doesn’t work well with there WiFi. I tried my cell and the wifi was not good for it either this is the free wifi.

Waited on the runway for takeoff for 2.5 hours. Air traffic rerouted us. The plane didn't have enough fuel, so had to go back to the gate. Had to wait for a new pilot. Should have landed at 5:22. Didn't land until 9:10. Trash flight.

The boarding was pretty easy. However, the first class seats are not lay flat as other airlines (like JetBlue) has and therefore sleeping was a challenge.

It was nobody’s fault - but the plane came 4-hrs late and we were updated randomly in 20-30 mins increments which left us hostage to sit and wait expectantly. It was very long and got very late. Our plane didn’t land until nearly 1 am! Also the toilet wasn’t working. The hosts were nice enough but were clearly “about to pass out” as one told me. Lastly, there was no snack or even time for it. Just a bad experience overall.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

It was canceled. The flight wasn’t rescheduled, everyone had to figure out their own new arrangements. They said we would get refunded our original fare and receive an additional $150. We received links for $100 only and they expired before we could activate them.

The plane had originated in Las Vegas at 6:30 in the morning and flew to Moline where we boarded. The flight left around 12:30 PM and there were no boxed snacks available and many of the alcoholic beverages were unavailable. I would find it hard to believe that that many of the passengers coming from Las Vegas at 6:30 in the morning, drank and ate that much of the items. I can only come to the conclusion that someone failed to stock the plane for the round-trip. This is a huge revenue failure for the airline and disappointment for the passengers. The flight crew did not seem happy to be there and did not engage with passengers. Allegiant you can do better.

They did not let my husband on the plane with our service animal at the last minute. Do NOT fly this airline with a service animal!

Tight! Seats are not designed for those of us who wear extra-large clothes.

The non-stop flight from Grand Rapids was excellent. I neither expected or needed a budget flight and Allegiant made the trip easy and for an affordable price, Arriving at the Mesa Airport (AZA) is a delight compared to the international airport. For our return flight, we were able to arrive 75 minutes before the flight, return the rental car, check our bag and make it to the gate in plenty of time. That would never happen at most airports.

Easiest flights I’ve ever taken. Plane was comfortable without overly crowded seating.

Terrible. Still have not received the refund from them. They sent it to some account that I don't even know. Spoke with costumer service and they are unable to help.

I didn’t like it at all. I miss my second flight because of the delay on Allegiant Air now I m stuck in MCO.

Good, but a bit late on take off after loading. Don't like charging for carry ons!

First time flying with them and will definitely fly again in the future. Crew was so nice and friendly, fought was seamless. They are simple planes, no entertainment, but it’s fine for a short flight or if you have personal devices Rates are competitive, and they did so well with keeping the flight on time after a tropical storm, where other airlines had delays and cancellations.

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

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