$93+ 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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — VPS
Sep 12 — Sep 191
Round-trip
1 adult, Economy
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Find cheap flights from Boston to Valparaiso with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Boston Logan Intl to Valparaiso Destin-Ft Walton Beach are usually found in July or June, booked 60 days in advance, depart on a Saturday or Tuesday and return on a Friday
Cheap flight deals from Boston to Valparaiso
Cheapest
Best
Last-minute
One-way
Cheapest flights from Boston to ValparaisoExplore 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 13, 2026.
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 13, 2026.
This Delta deal was found by Cheapflights users on 8/10. 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 10/272:59 pm -
1 stop4h 43m
Mon 11/95:00 pm -
1 stop7h 15m
Deal found 8/10![Delta logo]()
$215
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:15 pm -
1 stop6h 28m
Mon 10/56:11 am -
1 stop6h 12m
Deal found 8/12![American Airlines logo]()
$228
This Delta deal was found by Cheapflights users on 8/10. 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 10/302:59 pm -
1 stop4h 43m
Tue 11/1012:08 pm -
1 stop5h 52m
Deal found 8/10![Delta logo]()
$234
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:25 am -
1 stop5h 10m
Mon 8/3112:40 pm -
1 stop8h 50m
Deal found 8/12![Southwest logo]()
$236
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:00 pm -
1 stop6h 52m
Sun 9/66:00 am -
1 stop9h 10m
Deal found 8/12![American Airlines logo]()
$239
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:50 am -
1 stop8h 25m
Mon 9/2112:40 pm -
1 stop8h 55m
Deal found 8/10![Southwest logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 8/1510:59 am -
Nonstop3h 16m
Thu 8/2010:57 am -
2 stops23h 50m
Deal found 8/8![Multiple Airlines logo]()
$241
This American Airlines deal was found by Cheapflights users on 8/11. 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 9/175:22 pm -
1 stop7h 21m
Sun 9/205:40 am -
1 stop7h 09m
Deal found 8/11![American Airlines logo]()
$245
This American Airlines deal was found by Cheapflights users on 8/11. 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 8/203:21 pm -
1 stop9h 31m
Mon 8/3112:41 pm -
1 stop5h 33m
Deal found 8/11![American Airlines logo]()
$247
This Delta deal was found by Cheapflights users on 8/10. 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 10/302:59 pm -
1 stop4h 43m
Fri 11/62:46 pm -
1 stop5h 22m
Deal found 8/10![Delta logo]()
$253
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:00 am -
1 stop5h 48m
Sat 9/122:48 pm -
1 stop6h 45m
Deal found 8/12![Delta logo]()
$256
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/269:05 am -
1 stop7h 57m
Tue 10/276:00 am -
1 stop6h 49m
Deal found 8/12![Delta logo]()
$260
Best flights from Boston to ValparaisoDiscover carefully curated flight deals from Boston to Valparaiso that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 13, 2026.
Discover carefully curated flight deals from Boston to Valparaiso that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 13, 2026.
This JetBlue deal was found by Cheapflights users on 8/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:44 pm -
Nonstop3h 20m
Mon 8/313:59 pm -
Nonstop3h 47m
Deal found 8/10![JetBlue logo]()
$287
This Delta deal was found by Cheapflights users on 8/9. 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.
Sun 9/67:55 am -
1 stop7h 05m
Sun 9/137:13 pm -
1 stop5h 04m
Deal found 8/9![Delta logo]()
$290
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1511:50 am -
2 stops10h 10m
Tue 10/202:15 pm -
1 stop7h 25m
Deal found 8/12![Southwest logo]()
$300
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:21 pm -
1 stop6h 27m
Sun 10/116:11 am -
1 stop6h 12m
Deal found 8/12![American Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 8/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:10 am -
1 stop5h 35m
Tue 11/1711:10 am -
2 stops9h 40m
Deal found 8/9![Southwest logo]()
$311
This Delta deal was found by Cheapflights users on 8/9. 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 9/57:00 am -
1 stop5h 48m
Sat 9/129:21 am -
1 stop4h 36m
Deal found 8/9![Delta logo]()
$326
This Southwest deal was found by Cheapflights users on 8/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:30 am -
2 stops10h 25m
Tue 11/37:00 am -
2 stops11h 00m
Deal found 8/9![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:10 am -
1 stop7h 10m
Tue 9/2212:05 pm -
2 stops9h 15m
Deal found 8/10![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 8/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:05 am -
2 stops9h 45m
Tue 11/37:00 am -
2 stops11h 00m
Deal found 8/8![Southwest logo]()
$363
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:50 am -
1 stop8h 25m
Mon 9/2112:40 pm -
2 stops8h 35m
Deal found 8/11![Southwest logo]()
$372
Last-minute flights from Boston to ValparaisoDiscover last-minute flight deals from Boston to Valparaiso. Data last updated August 13, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Valparaiso. Data last updated August 13, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:25 am -
1 stop5h 10m
Mon 8/3112:40 pm -
1 stop8h 50m
Deal found 8/12![Southwest logo]()
$236
This American Airlines deal was found by Cheapflights users on 8/11. 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 8/203:21 pm -
1 stop9h 31m
Mon 8/3112:41 pm -
1 stop5h 33m
Deal found 8/11![American Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:15 pm -
2 stops7h 45m
Mon 8/3112:40 pm -
1 stop8h 50m
Deal found 8/12![Southwest logo]()
$241
This American Airlines deal was found by Cheapflights users on 8/10. 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 8/287:26 am -
1 stop5h 25m
Fri 9/412:41 pm -
1 stop6h 25m
Deal found 8/10![American Airlines logo]()
$264
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:20 pm -
1 stop7h 59m
Sat 9/55:06 pm -
1 stop6h 32m
Deal found 8/12![Delta logo]()
$215
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:00 pm -
1 stop6h 52m
Sun 9/66:00 am -
1 stop9h 10m
Deal found 8/12![American Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:00 am -
1 stop5h 48m
Sat 9/122:48 pm -
1 stop6h 45m
Deal found 8/12![Delta logo]()
$256
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 9/94:25 pm -
1 stop7h 57m
Sun 9/137:13 pm -
1 stop5h 04m
Deal found 8/13![Delta logo]()
$260
This Southwest deal was found by Cheapflights users on 8/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/111:10 pm -
1 stop5h 35m
Mon 9/1412:40 pm -
1 stop8h 55m
Deal found 8/11![Southwest logo]()
$234
This American Airlines deal was found by Cheapflights users on 8/11. 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 9/175:22 pm -
1 stop7h 21m
Sun 9/205:40 am -
1 stop7h 09m
Deal found 8/11![American Airlines logo]()
$245
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:50 am -
1 stop8h 25m
Mon 9/2112:40 pm -
1 stop8h 55m
Deal found 8/10![Southwest logo]()
$240
One-way flights from Boston to ValparaisoSearch for one-way flight options from Boston to Valparaiso. Find affordable one-way fares based on user searches. Data last updated August 13, 2026.
Search for one-way flight options from Boston to Valparaiso. Find affordable one-way fares based on user searches. Data last updated August 13, 2026.
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/45:10 am -
1 stop6h 10m
Deal found 8/12![Southwest logo]()
$93
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/95:10 am -
1 stop5h 35m
Deal found 8/10![Southwest logo]()
$102
This American Airlines deal was found by Cheapflights users on 8/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:27 am -
1 stop7h 24m
Deal found 8/12![American Airlines logo]()
$103
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:50 am -
2 stops11h 45m
Deal found 8/12![Southwest logo]()
$108
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:00 pm -
1 stop5h 20m
Deal found 8/12![Delta logo]()
$109
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/95:40 am -
2 stops14h 15m
Deal found 8/10![Southwest logo]()
$113
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/910:05 am -
2 stops12h 00m
Deal found 8/10![Southwest logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Thu 11/1211:24 am -
1 stop26h 57m
Deal found 8/11![Allegiant Air logo]()
$124
This Delta deal was found by Cheapflights users on 8/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/132:55 pm -
1 stop7h 01m
Deal found 8/12![Delta logo]()
$128
This JetBlue deal was found by Cheapflights users on 8/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/612:44 pm -
Nonstop3h 20m
Deal found 8/10![JetBlue logo]()
$129
This American Airlines deal was found by Cheapflights users on 8/10. 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 8/263:38 pm -
1 stop5h 25m
Deal found 8/10![American Airlines logo]()
$139
This Southwest deal was found by Cheapflights users on 8/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:15 pm -
2 stops7h 45m
Deal found 8/12![Southwest logo]()
$144
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 August 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $203 (American Airlines) |
One-way from | $93 (Southwest) |
Popular in | November |
Cheapest in | July |
Average price | $272 |
Good round-trip deal | $243 or less |
Good one-way deal | $133 or less |
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 13, 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
Cheapest round-trip
Quickest round-trip
BostonValparaiso
BOS Boston Logan Intl - VPS Valparaiso Destin-Ft Walton Beach
BOSVPS
Boston Logan Intl
Fri 8/28
12:44 pm-3:04 pm
Nonstop3h 20m
Valparaiso Destin-Ft Walton Beach
Mon 8/31
3:59 pm-8:46 pm
Nonstop3h 47m
$287
BostonValparaiso
BOS Boston Logan Intl - VPS Valparaiso Destin-Ft Walton Beach
BOSVPS
Boston Logan Intl
Sun 9/6
7:55 am-2:00 pm
1 stop7h 05m
Valparaiso Destin-Ft Walton Beach
Sun 9/13
7:13 pm-1:17 am
1 stop5h 04m
$290
BostonValparaiso
BOS Boston Logan Intl - VPS Valparaiso Destin-Ft Walton Beach
BOSVPS
Boston Logan Intl
Thu 10/15
11:50 am-9:00 pm
2 stops10h 10m
Valparaiso Destin-Ft Walton Beach
Tue 10/20
2:15 pm-10:40 pm
1 stop7h 25m
$300
BostonValparaiso
BOS Boston Logan Intl - VPS Valparaiso Destin-Ft Walton Beach
BOSVPS
Boston Logan Intl
Fri 11/13
5:10 am-9:45 am
1 stop5h 35m
Valparaiso Destin-Ft Walton Beach
Tue 11/17
11:10 am-9:50 pm
2 stops9h 40m
$311
BostonValparaiso
BOS Boston Logan Intl - VPS Valparaiso Destin-Ft Walton Beach
BOSVPS
Boston Logan Intl
Sat 9/5
7:00 am-11:48 am
1 stop5h 48m
Valparaiso Destin-Ft Walton Beach
Sat 9/12
9:21 am-2:57 pm
1 stop4h 36m
$326
BostonValparaiso
BOS Boston Logan Intl - VPS Valparaiso Destin-Ft Walton Beach
BOSVPS
Boston Logan Intl
Thu 10/8
6:21 pm-11:48 pm
1 stop6h 27m
Valparaiso Destin-Ft Walton Beach
Sun 10/11
6:11 am-1:23 pm
1 stop6h 12m
$335
BostonValparaiso
BOS Boston Logan Intl - VPS Valparaiso Destin-Ft Walton Beach
BOSVPS
Boston Logan Intl
Sat 10/31
5:30 am-2:55 pm
2 stops10h 25m
Valparaiso Destin-Ft Walton Beach
Tue 11/3
7:00 am-7:00 pm
2 stops11h 00m
$337
BostonValparaiso
BOS Boston Logan Intl - VPS Valparaiso Destin-Ft Walton Beach
BOSVPS
Boston Logan Intl
Sat 9/19
8:10 am-2:20 pm
1 stop7h 10m
Valparaiso Destin-Ft Walton Beach
Tue 9/22
12:05 pm-10:20 pm
2 stops9h 15m
$341
BostonValparaiso
BOS Boston Logan Intl - VPS Valparaiso Destin-Ft Walton Beach
BOSVPS
Boston Logan Intl
Fri 10/30
7:05 am-3:50 pm
2 stops9h 45m
Valparaiso Destin-Ft Walton Beach
Tue 11/3
7:00 am-7:00 pm
2 stops11h 00m
$363
BostonValparaiso
BOS Boston Logan Intl - VPS Valparaiso Destin-Ft Walton Beach
BOSVPS
Boston Logan Intl
Fri 9/18
5:50 am-1:15 pm
1 stop8h 25m
Valparaiso Destin-Ft Walton Beach
Mon 9/21
12:40 pm-10:15 pm
2 stops8h 35m
$372
Showing 1-10 of 20 resultsSorted by cheapest first
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 August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- 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.
BOS-VPS
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
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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, July is the cheapest month in which you can book a flight from Boston to Valparaiso, Florida (average of $114). Flying from Boston to Valparaiso, Florida in November is currently the most expensive (average of $485). 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 13, 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.
What’s the top layover airport for flights from Boston to Valparaiso, Florida?
Share of 1-stop round-trip flights from Boston to Valparaiso, Florida chosen by Cheapflights users in the past 12 months, using the same layover each way.
Washington, D.C. (DCA) – chosen by Cheapflights users on 50% of 1-stop itineraries from Boston to Valparaiso, Florida on Cheapflights.
What’s the cheapest layover airport for flights from Boston to Valparaiso, Florida?
Average round-trip fare for 1-stop flights from Boston to Valparaiso, Florida, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Charlotte (CLT) is the most affordable 1-stop option, with an average round-trip price of $239.
What’s the fastest layover option from Boston to Valparaiso, Florida?
Shortest average travel time for 1-stop one-way flights from Boston to Valparaiso, Florida, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Atlanta (ATL) have the shortest average one-way travel time for 1-stop routes: 4h 35m.
Which airport typically offers the quickest layover for flights from Boston to Valparaiso, Florida?
Average layover duration for 1-stop one-way flights from Boston to Valparaiso, Florida, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Washington, D.C. (DCA) offer the fastest connection on this route, with an average layover time of 0h 40m.
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 13, 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.
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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.
Traveling to a place near Valparaiso?
Book flights to Valparaiso if you plan to visit one of these locationsAndalusia
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Boston and Valparaiso flights
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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 August 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$61 | Average$93 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$125 | Average$277 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$175 | Average$313 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$178 | Average$363 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$205 | Average$377 | FlexibilityNo cancel fee | On-time63% |