$100+ Cheap flights from Pensacola (PNS) to Massachusetts
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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — BOS
Jun 9 — Jun 161
Round-trip
1 adult, Economy
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Cheapest flights from Pensacola to MassachusettsExplore the most affordable flight options available from Pensacola to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 10, 2026.
Explore the most affordable flight options available from Pensacola to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 9/510:26 am
PNS
- BDL
1 stop7h 26m
Breeze Airways
Tue 9/87:15 am
BDL
- PNS
1 stop27h 35m
Breeze Airways
Deal found 5/6![Breeze Airways logo]()
$199
This Breeze Airways deal was found by Cheapflights users on 5/7. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/910:30 am
PNS
- BDL
1 stop6h 48m
Breeze Airways
Sat 9/126:00 am
BDL
- PNS
1 stop7h 45m
Breeze Airways
Deal found 5/7![Breeze Airways logo]()
$226
This Mytrip deal was found by Cheapflights users on 5/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/105:30 pm
PNS
- BOS
1 stop15h 39m
Frontier
Mon 7/1311:05 am
BOS
- PNS
1 stop28h 13m
Frontier
Deal found 5/6![Frontier logo]()
$259
This Gotogate deal was found by Cheapflights users on 5/7. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:15 pm
PNS
- BOS
1 stop17h 54m
Frontier
Sat 10/3111:05 am
BOS
- PNS
1 stop29h 13m
Frontier
Deal found 5/7![Frontier logo]()
$280
This Booking.com deal was found by Cheapflights users on 5/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/233:15 pm
PNS
- BOS
1 stop17h 54m
Frontier
Mon 7/2711:05 am
BOS
- PNS
1 stop6h 28m
Frontier
Deal found 5/8![Frontier logo]()
$282
This CheapOair deal was found by Cheapflights users on 5/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/175:30 pm
PNS
- BDL
1 stop24h 55m
Frontier
Mon 7/2012:24 pm
BDL
- PNS
1 stop26h 54m
Frontier
Deal found 5/5![Frontier logo]()
$300
This Gotogate deal was found by Cheapflights users on 5/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/13:15 pm
PNS
- BOS
1 stop17h 54m
Frontier
Tue 8/411:05 am
BOS
- PNS
1 stop28h 13m
Frontier
Deal found 5/6![Frontier logo]()
$300
This Booking.com deal was found by Cheapflights users on 5/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/93:15 pm
PNS
- BOS
1 stop17h 54m
Frontier
Mon 7/1311:05 am
BOS
- PNS
1 stop28h 13m
Frontier
Deal found 5/8![Frontier logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 8/277:38 pm
PNS
- BOS
1 stop13h 31m
Multiple Airlines
Sun 9/1311:05 am
BOS
- PNS
1 stop26h 40m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$308
This Kiwi.com deal was found by Cheapflights users on 5/7. 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.
Sun 8/167:38 pm
PNS
- BOS
1 stop13h 31m
Multiple Airlines
Wed 8/198:47 am
BOS
- PNS
2 stops30h 12m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 8/277:38 pm
PNS
- BOS
1 stop13h 31m
Multiple Airlines
Mon 9/1411:28 am
BOS
- PNS
2 stops26h 12m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 9/1910:30 am
PNS
- BOS
1 stop23h 02m
Multiple Airlines
Mon 10/129:15 am
BOS
- PNS
1 stop28h 25m
Multiple Airlines
Deal found 5/6![Multiple Airlines logo]()
$344
Best flights from Pensacola to MassachusettsDiscover carefully curated flight deals from Pensacola to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 10, 2026.
Discover carefully curated flight deals from Pensacola to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 10, 2026.
This Delta deal was found by Cheapflights users on 5/6. 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 6/1711:57 am
PNS
- BDL
1 stop5h 07m
Delta
Tue 6/236:15 pm
BDL
- PNS
1 stop6h 17m
Delta
Deal found 5/6![Delta logo]()
$371
This Southwest deal was found by Cheapflights users on 5/8. 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.
Tue 6/1612:05 pm
PNS
- BDL
2 stops9h 40m
Southwest
Wed 6/175:55 am
BDL
- PNS
2 stops8h 30m
Southwest
Deal found 5/8![Southwest logo]()
$381
This United Airlines deal was found by Cheapflights users on 5/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/179:00 am
PNS
- BDL
2 stops13h 59m
United Airlines
Tue 6/236:09 am
BDL
- PNS
1 stop7h 53m
United Airlines
Deal found 5/6![United Airlines logo]()
$395
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:24 pm
PNS
- ORH
2 stops20h 29m
American Airlines
Sat 6/135:18 pm
ORH
- PNS
1 stop18h 06m
American Airlines
Deal found 5/5![American Airlines logo]()
$408
This United Airlines deal was found by Cheapflights users on 5/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/302:09 pm
PNS
- BOS
1 stop8h 12m
United Airlines
Tue 7/75:45 am
BOS
- PNS
2 stops8h 22m
United Airlines
Deal found 5/9![United Airlines logo]()
$396
This Delta deal was found by Cheapflights users on 5/9. 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.
Fri 5/298:06 am
PNS
- BDL
1 stop7h 03m
Delta
Tue 6/22:07 pm
BDL
- PNS
1 stop5h 16m
Delta
Deal found 5/9![Delta logo]()
$399
This Southwest deal was found by Cheapflights users on 5/5. 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 7/77:50 am
PNS
- BOS
2 stops8h 55m
Southwest
Thu 7/301:10 pm
BOS
- PNS
2 stops8h 30m
Southwest
Deal found 5/5![Southwest logo]()
$409
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:35 pm
PNS
- ALB
1 stop7h 03m
Delta
Tue 9/2212:55 pm
ALB
- PNS
1 stop4h 38m
Delta
Deal found 5/5![Delta logo]()
$399
This Southwest deal was found by Cheapflights users on 5/8. 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.
Mon 6/11:15 pm
PNS
- ALB
2 stops8h 05m
Southwest
Tue 6/29:10 am
ALB
- PNS
2 stops10h 50m
Southwest
Deal found 5/8![Southwest logo]()
$415
This United Airlines deal was found by Cheapflights users on 5/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/232:04 pm
PNS
- BDL
1 stop6h 44m
United Airlines
Mon 6/298:47 am
BDL
- PNS
2 stops14h 14m
United Airlines
Deal found 5/9![United Airlines logo]()
$425
This American Airlines deal was found by Cheapflights users on 5/5. 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 6/45:22 am
PNS
- ALB
2 stops7h 57m
American Airlines
Thu 6/115:39 am
ALB
- PNS
1 stop5h 23m
American Airlines
Deal found 5/5![American Airlines logo]()
$495
This Delta deal was found by Cheapflights users on 5/9. 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.
Fri 10/26:15 pm
PNS
- BOS
1 stop5h 51m
Delta
Thu 10/85:45 am
BOS
- PNS
1 stop8h 06m
Delta
Deal found 5/9![Delta logo]()
$416
This United Airlines deal was found by Cheapflights users on 5/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/292:26 pm
PNS
- BOS
1 stop7h 54m
United Airlines
Sun 9/65:45 am
BOS
- PNS
2 stops8h 32m
United Airlines
Deal found 5/7![United Airlines logo]()
$426
This Southwest deal was found by Cheapflights users on 5/6. 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 9/211:10 pm
PNS
- BOS
2 stops8h 00m
Southwest
Sat 9/265:50 am
BOS
- PNS
2 stops11h 55m
Southwest
Deal found 5/6![Southwest logo]()
$432
This Southwest deal was found by Cheapflights users on 5/9. 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 6/206:30 pm
PNS
- BDL
2 stops12h 25m
Southwest
Wed 7/112:40 pm
BDL
- PNS
2 stops8h 15m
Southwest
Deal found 5/9![Southwest logo]()
$443
This United Airlines deal was found by Cheapflights users on 5/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/152:09 pm
PNS
- BDL
1 stop6h 24m
United Airlines
Tue 7/216:09 am
BDL
- PNS
1 stop7h 58m
United Airlines
Deal found 5/9![United Airlines logo]()
$456
This Delta deal was found by Cheapflights users on 5/7. 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.
Thu 5/214:35 pm
PNS
- ALB
1 stop6h 23m
Delta
Sun 5/241:00 pm
ALB
- PNS
1 stop5h 00m
Delta
Deal found 5/7![Delta logo]()
$467
This Southwest deal was found by Cheapflights users on 5/5. 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 9/187:45 am
PNS
- ALB
2 stops8h 40m
Southwest
Tue 9/2212:50 pm
ALB
- PNS
2 stops6h 35m
Southwest
Deal found 5/5![Southwest logo]()
$457
This United Airlines deal was found by Cheapflights users on 5/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/159:00 am
PNS
- BOS
2 stops13h 59m
United Airlines
Tue 7/213:54 pm
BOS
- PNS
1 stop7h 07m
United Airlines
Deal found 5/9![United Airlines logo]()
$466
This Southwest deal was found by Cheapflights users on 5/5. 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 6/310:10 am
PNS
- BOS
2 stops8h 30m
Southwest
Thu 6/45:35 am
BOS
- PNS
1 stop12h 05m
Southwest
Deal found 5/5![Southwest logo]()
$468
This Southwest deal was found by Cheapflights users on 5/7. 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 5/217:15 am
PNS
- BOS
1 stop6h 55m
Southwest
Sun 5/248:10 am
BOS
- PNS
2 stops9h 20m
Southwest
Deal found 5/7![Southwest logo]()
$472
This United Airlines deal was found by Cheapflights users on 5/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/242:04 pm
PNS
- BDL
1 stop6h 44m
United Airlines
Thu 5/288:20 am
BDL
- PNS
1 stop8h 46m
United Airlines
Deal found 5/9![United Airlines logo]()
$553
This Southwest deal was found by Cheapflights users on 5/8. 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.
Thu 7/236:20 pm
PNS
- BOS
1 stop4h 50m
Southwest
Sun 7/2610:05 pm
BOS
- PNS
2 stops14h 20m
Southwest
Deal found 5/8![Southwest logo]()
$478
This Delta deal was found by Cheapflights users on 5/9. 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.
Wed 5/207:05 am
PNS
- ORH
2 stops7h 28m
Delta
Mon 5/254:15 pm
ORH
- PNS
2 stops8h 15m
Delta
Deal found 5/9![Delta logo]()
$648
This United Airlines deal was found by Cheapflights users on 5/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:04 pm
PNS
- BDL
2 stops8h 55m
United Airlines
Fri 6/56:00 am
BDL
- PNS
2 stops8h 02m
United Airlines
Deal found 5/8![United Airlines logo]()
$567
This Southwest deal was found by Cheapflights users on 5/9. 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 6/2711:50 am
PNS
- BOS
2 stops11h 25m
Southwest
Sun 7/55:50 am
BOS
- PNS
1 stop12h 10m
Southwest
Deal found 5/9![Southwest logo]()
$483
This Southwest deal was found by Cheapflights users on 5/9. 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.
Mon 6/2211:05 am
PNS
- BOS
2 stops9h 35m
Southwest
Sun 6/2810:05 pm
BOS
- PNS
1 stop12h 55m
Southwest
Deal found 5/9![Southwest logo]()
$487
This Southwest deal was found by Cheapflights users on 5/5. 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 7/1711:55 am
PNS
- BDL
2 stops10h 00m
Southwest
Mon 7/205:50 am
BDL
- PNS
2 stops8h 40m
Southwest
Deal found 5/5![Southwest logo]()
$503
This Southwest deal was found by Cheapflights users on 5/6. 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 5/217:15 am
PNS
- ALB
1 stop6h 00m
Southwest
Mon 5/255:50 am
ALB
- PNS
2 stops10h 50m
Southwest
Deal found 5/6![Southwest logo]()
$512
This Southwest deal was found by Cheapflights users on 5/6. 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 5/2010:10 am
PNS
- ALB
2 stops7h 35m
Southwest
Sat 5/236:00 am
ALB
- PNS
2 stops9h 10m
Southwest
Deal found 5/6![Southwest logo]()
$517
Last-minute flights from Pensacola to MassachusettsDiscover last-minute flight deals from Pensacola to Massachusetts. Data last updated May 10, 2026 and is based on user searches.
Discover last-minute flight deals from Pensacola to Massachusetts. Data last updated May 10, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/9. 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.
Fri 5/294:35 pm
PNS
- BDL
1 stop6h 58m
Delta
Tue 6/307:00 am
BDL
- PNS
1 stop4h 52m
Delta
Deal found 5/9![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 5/9. 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 5/304:55 pm
PNS
- BDL
1 stop6h 38m
Delta
Tue 6/306:00 am
BDL
- PNS
1 stop5h 52m
Delta
Deal found 5/9![Delta logo]()
$388
This American Airlines deal was found by Cheapflights users on 5/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/14:41 pm
PNS
- ALB
1 stop4h 55m
American Airlines
Tue 6/25:38 am
ALB
- PNS
1 stop7h 42m
American Airlines
Deal found 5/8![American Airlines logo]()
$398
This American Airlines deal was found by Cheapflights users on 5/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1610:49 am
PNS
- BDL
1 stop4h 44m
American Airlines
Wed 6/172:46 pm
BDL
- PNS
1 stop7h 21m
American Airlines
Deal found 5/8![American Airlines logo]()
$379
This Southwest deal was found by Cheapflights users on 5/8. 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.
Tue 6/1612:05 pm
PNS
- BDL
2 stops9h 40m
Southwest
Wed 6/175:55 am
BDL
- PNS
2 stops8h 30m
Southwest
Deal found 5/8![Southwest logo]()
$381
This American Airlines deal was found by Cheapflights users on 5/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/164:41 pm
PNS
- BDL
2 stops6h 13m
American Airlines
Wed 6/245:23 pm
BDL
- PNS
1 stop4h 44m
American Airlines
Deal found 5/9![American Airlines logo]()
$394
This Delta deal was found by Cheapflights users on 5/6. 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 6/1711:57 am
PNS
- BDL
1 stop5h 07m
Delta
Tue 6/236:15 pm
BDL
- PNS
1 stop6h 17m
Delta
Deal found 5/6![Delta logo]()
$371
This Southwest deal was found by Cheapflights users on 5/7. 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 6/175:30 pm
PNS
- BOS
1 stop5h 00m
Southwest
Tue 6/235:25 am
BOS
- PNS
2 stops9h 00m
Southwest
Deal found 5/7![Southwest logo]()
$376
This American Airlines deal was found by Cheapflights users on 5/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/175:22 am
PNS
- BDL
2 stops7h 52m
American Airlines
Wed 6/245:23 pm
BDL
- PNS
1 stop4h 44m
American Airlines
Deal found 5/9![American Airlines logo]()
$385
This United Airlines deal was found by Cheapflights users on 5/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/179:00 am
PNS
- BDL
2 stops13h 59m
United Airlines
Tue 6/236:09 am
BDL
- PNS
1 stop7h 53m
United Airlines
Deal found 5/6![United Airlines logo]()
$395
This United Airlines deal was found by Cheapflights users on 5/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/242:04 pm
PNS
- BOS
1 stop6h 52m
United Airlines
Wed 7/16:00 am
BOS
- PNS
1 stop8h 07m
United Airlines
Deal found 5/9![United Airlines logo]()
$371
This United Airlines deal was found by Cheapflights users on 5/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/302:09 pm
PNS
- BOS
1 stop8h 12m
United Airlines
Tue 7/75:45 am
BOS
- PNS
2 stops8h 22m
United Airlines
Deal found 5/9![United Airlines logo]()
$396
One-way flights from Pensacola to MassachusettsSearch for one-way flight options from Pensacola to Massachusetts. Find affordable one-way fares based on user searches. Data last updated May 10, 2026.
Search for one-way flight options from Pensacola to Massachusetts. Find affordable one-way fares based on user searches. Data last updated May 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 9/510:26 am
PNS
- ALB
1 stop24h 14m
Breeze Airways
Deal found 5/7![Breeze Airways logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 5/7. 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.
Wed 9/29:26 am
PNS
- ALB
1 stop23h 59m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 5/6. 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 10/293:15 pm
PNS
- BOS
1 stop17h 01m
Frontier
Deal found 5/6![Frontier logo]()
$129
This Booking.com deal was found by Cheapflights users on 5/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/253:15 pm
PNS
- BOS
1 stop16h 05m
Frontier
Deal found 5/9![Frontier logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 10/305:30 pm
PNS
- BOS
1 stop15h 39m
Frontier
Deal found 5/5![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 8/314:10 pm
PNS
- BOS
2 stops41h 55m
Multiple Airlines
Deal found 5/7![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 10/318:58 am
PNS
- BOS
1 stop24h 18m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/112:46 pm
PNS
- ALB
1 stop27h 17m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$154
This Mytrip deal was found by Cheapflights users on 5/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/53:15 pm
PNS
- BOS
1 stop17h 54m
Frontier
Deal found 5/7![Frontier logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Sun 11/13:15 pm
PNS
- BOS
1 stop17h 01m
Frontier
Deal found 5/6![Frontier logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 5/8. 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.
Fri 10/308:58 am
PNS
- BOS
1 stop24h 11m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Tue 7/283:15 pm
PNS
- BOS
1 stop17h 54m
Frontier
Deal found 5/6![Frontier logo]()
$168
Find flight deals from Pensacola to Massachusetts
Keep the following information in mind while searching for Pensacola to Massachusetts flight deals. Data was last updated May 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $199 (Kiwi.com) |
One-way from | $100 (Kiwi.com) |
Popular in | March |
Cheapest in | May |
Average price | $348 |
Cheapflights Fare Finder
Customize your flight search to find flights from Pensacola to Massachusetts 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 May 10, 2026.
Use the filters below to find and compare flights from Pensacola to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PensacolaHartford
PNS - BDL
PNSBDL
Pensacola
Wed 6/17
11:57 am-6:04 pm
1 stop5h 07m
Hartford Bradley Intl
Tue 6/23
6:15 pm-11:32 pm
1 stop6h 17m
$371
PensacolaHartford
PNS - BDL
PNSBDL
Pensacola
Tue 6/16
12:05 pm-10:45 pm
2 stops9h 40m
Hartford Bradley Intl
Wed 6/17
5:55 am-1:25 pm
2 stops8h 30m
$381
PensacolaHartford
PNS - BDL
PNSBDL
Pensacola
Wed 6/17
9:00 am-11:59 pm
2 stops13h 59m
Hartford Bradley Intl
Tue 6/23
6:09 am-1:02 pm
1 stop7h 53m
$395
PensacolaBoston
PNS - BOS
PNSBOS
Pensacola
Tue 6/30
2:09 pm-11:21 pm
1 stop8h 12m
Boston Logan Intl
Tue 7/7
5:45 am-1:07 pm
2 stops8h 22m
$396
PensacolaHartford
PNS - BDL
PNSBDL
Pensacola
Fri 5/29
8:06 am-4:09 pm
1 stop7h 03m
Hartford Bradley Intl
Tue 6/2
2:07 pm-6:23 pm
1 stop5h 16m
$399
PensacolaAlbany
PNS - ALB
PNSALB
Pensacola
Fri 9/18
3:35 pm-11:38 pm
1 stop7h 03m
Albany Intl
Tue 9/22
12:55 pm-4:33 pm
1 stop4h 38m
$399
PensacolaWorcester
PNS - ORH
PNSORH
Pensacola
Sat 6/6
7:24 pm-4:53 pm
2 stops20h 29m
Worcester
Sat 6/13
5:18 pm-10:24 am
1 stop18h 06m
$408
PensacolaBoston
PNS - BOS
PNSBOS
Pensacola
Tue 7/7
7:50 am-5:45 pm
2 stops8h 55m
Boston Logan Intl
Thu 7/30
1:10 pm-8:40 pm
2 stops8h 30m
$409
PensacolaAlbany
PNS - ALB
PNSALB
Pensacola
Mon 6/1
1:15 pm-10:20 pm
2 stops8h 05m
Albany Intl
Tue 6/2
9:10 am-7:00 pm
2 stops10h 50m
$415
PensacolaBoston
PNS - BOS
PNSBOS
Pensacola
Fri 10/2
6:15 pm-1:06 am
1 stop5h 51m
Boston Logan Intl
Thu 10/8
5:45 am-12:51 pm
1 stop8h 06m
$416
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Pensacola to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Pensacola with our price prediction graph.
PNS-BDL
PNS-ORH
PNS-BOS
PNS-ALB
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 Pensacola to Massachusetts
PNS-USMA
PNS-BDL
PNS-ORH
PNS-BOS
PNS-ALB
How far ahead should I book a flight from Pensacola to Massachusetts?
The best time to book flights from Pensacola to Massachusetts is 35 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Pensacola to Massachusetts?
Currently, May is the cheapest month in which you can book a flight from Pensacola to Massachusetts (average of $87). Flying from Pensacola to Massachusetts in March is currently the most expensive (average of $366). 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.
How much does it cost to fly round-trip from Pensacola to Massachusetts?
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated May 10, 2026.
See what other customers who have flown with Southwest,Delta, andAmerican Airlines from Pensacola to Massachusetts have to say. 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.
Entertainment
7.5
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Pensacola to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Pensacola and Massachusetts flights
Browse other Pensacola and Massachusetts flight options. Last updated on May 10, 2026.
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Pensacola to Massachusetts flights
Consider these flights traveling from Pensacola to Massachusetts.
Top 4 airlines flying from Pensacola to Massachusetts
Discover the top 4 airlines that operate flights from Pensacola to Massachusetts. 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 May 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$206 | Average$239 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$266 | Average$455 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$281 | Average$440 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$296 | Average$404 | FlexibilityNo cancel fee | On-time71% |