$78+ Cheap flights from Orlando (ORL) 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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — BOS
Sep 20 — Sep 271
Round-trip
1 adult, Economy
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Find cheap flights from Orlando to Massachusetts 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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Cheapest flights from Orlando to MassachusettsExplore the most affordable flight options available from Orlando to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
Explore the most affordable flight options available from Orlando to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/2610:04 am -
Nonstop2h 50m
Mon 9/283:13 pm -
1 stop4h 30m
Deal found 8/18![Breeze Airways logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/2610:04 am -
Nonstop2h 50m
Mon 10/51:04 pm -
1 stop4h 28m
Deal found 8/19![Breeze Airways logo]()
$136
This Breeze Airways deal was found by Cheapflights users on 8/17. 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.
Fri 9/186:12 pm -
1 stop4h 14m
Mon 9/213:13 pm -
1 stop4h 30m
Deal found 8/17![Breeze Airways logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 9/122:29 pm -
Nonstop2h 49m
Tue 9/157:05 am -
1 stop11h 32m
Deal found 8/17![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/103:50 pm -
1 stop6h 17m
Tue 9/157:05 am -
1 stop11h 32m
Deal found 8/19![Breeze Airways logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 10/96:12 pm -
1 stop4h 14m
Wed 10/146:00 am -
Nonstop3h 24m
Deal found 8/19![Breeze Airways logo]()
$140
This Priceline deal was found by Cheapflights users on 8/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1711:30 am -
Nonstop2h 48m
Mon 9/213:13 pm -
1 stop4h 30m
Deal found 8/20![Multiple Airlines logo]()
$141
This Priceline deal was found by Cheapflights users on 8/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:30 am -
Nonstop2h 48m
Mon 9/143:13 pm -
1 stop4h 30m
Deal found 8/20![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:12 pm -
1 stop4h 14m
Tue 9/157:05 am -
1 stop11h 32m
Deal found 8/18![Breeze Airways logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:12 pm -
1 stop4h 14m
Fri 9/183:13 pm -
1 stop4h 30m
Deal found 8/20![Breeze Airways logo]()
$145
This CheapOair deal was found by Cheapflights users on 8/17. 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.
Sat 9/1210:04 am -
Nonstop2h 50m
Mon 9/143:13 pm -
1 stop4h 30m
Deal found 8/17![Breeze Airways logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/243:38 pm -
1 stop18h 51m
Mon 9/288:18 pm -
1 stop20h 10m
Deal found 8/18![Multiple Airlines logo]()
$169
Best flights from Orlando to MassachusettsDiscover carefully curated flight deals from Orlando to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
Discover carefully curated flight deals from Orlando to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
This Breeze Airways deal was found by Cheapflights users on 8/17. 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.
Tue 9/158:00 am -
1 stop9h 08m
Tue 9/227:05 am -
1 stop11h 32m
Deal found 8/17![Breeze Airways logo]()
$170
This Delta deal was found by Cheapflights users on 8/19. 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 9/237:05 am -
Nonstop3h 10m
Wed 9/307:00 am -
1 stop7h 43m
Deal found 8/19![Delta logo]()
$219
This United Airlines deal was found by Cheapflights users on 8/18. 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 9/236:00 am -
1 stop6h 47m
Wed 9/3010:51 am -
1 stop5h 13m
Deal found 8/18![United Airlines logo]()
$229
This JetBlue deal was found by Cheapflights users on 8/17. 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.
Mon 9/146:00 pm -
1 stop5h 14m
Mon 9/212:10 pm -
Nonstop3h 00m
Deal found 8/17![JetBlue logo]()
$273
This American Airlines deal was found by Cheapflights users on 8/20. 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 10/37:05 am -
1 stop9h 44m
Mon 10/55:16 pm -
1 stop18h 05m
Deal found 8/20![American Airlines logo]()
$302
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:45 pm -
Nonstop2h 50m
Mon 11/94:50 pm -
Nonstop3h 05m
Deal found 8/16![Southwest logo]()
$302
This Breeze Airways deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/410:04 am -
Nonstop2h 50m
Mon 11/93:13 pm -
1 stop4h 30m
Deal found 8/16![Breeze Airways logo]()
$174
This Breeze Airways deal was found by Cheapflights users on 8/19. 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.
Fri 10/26:12 pm -
1 stop4h 14m
Sun 10/42:05 pm -
1 stop4h 41m
Deal found 8/19![Breeze Airways logo]()
$187
This Delta deal was found by Cheapflights users on 8/18. 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 10/224:02 pm -
1 stop7h 25m
Sun 10/256:55 am -
1 stop7h 52m
Deal found 8/18![Delta logo]()
$227
This Breeze Airways deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:27 pm -
1 stop4h 32m
Sun 9/61:54 pm -
1 stop4h 22m
Deal found 8/16![Breeze Airways logo]()
$191
This Delta deal was found by Cheapflights users on 8/18. 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 9/174:08 pm -
1 stop7h 14m
Mon 9/216:23 pm -
1 stop5h 59m
Deal found 8/18![Delta logo]()
$227
This Delta deal was found by Cheapflights users on 8/19. 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 10/74:02 pm -
1 stop7h 25m
Tue 10/135:50 am -
1 stop5h 15m
Deal found 8/19![Delta logo]()
$227
This JetBlue deal was found by Cheapflights users on 8/20. 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.
Thu 11/56:45 pm -
1 stop5h 12m
Mon 11/97:10 am -
Nonstop3h 03m
Deal found 8/20![JetBlue logo]()
$280
This Breeze Airways deal was found by Cheapflights users on 8/19. 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.
Thu 10/84:05 pm -
1 stop6h 02m
Sun 10/112:05 pm -
1 stop4h 41m
Deal found 8/19![Breeze Airways logo]()
$226
This Delta deal was found by Cheapflights users on 8/20. 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 10/166:07 pm -
1 stop4h 54m
Mon 10/195:50 am -
1 stop5h 15m
Deal found 8/20![Delta logo]()
$227
This American Airlines deal was found by Cheapflights users on 8/20. 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 10/710:40 am -
1 stop6h 09m
Wed 10/145:16 pm -
2 stops17h 19m
Deal found 8/20![American Airlines logo]()
$312
This Southwest deal was found by Cheapflights users on 8/19. 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 10/109:25 am -
1 stop4h 55m
Sat 10/1712:55 pm -
2 stops6h 40m
Deal found 8/19![Southwest logo]()
$312
This JetBlue deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:59 am -
Nonstop2h 49m
Sun 9/131:40 pm -
Nonstop3h 01m
Deal found 8/16![JetBlue logo]()
$284
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/97:21 pm -
1 stop4h 38m
Fri 10/166:00 am -
2 stops7h 57m
Deal found 8/16![United Airlines logo]()
$316
This KAYAK deal was found by Cheapflights users on 8/18. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:00 am -
2 stops28h 50m
Tue 10/67:00 am -
2 stops16h 35m
Deal found 8/18![Multiple Airlines logo]()
$648
This JetBlue deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/139:00 am -
Nonstop2h 50m
Mon 11/164:45 pm -
1 stop5h 24m
Deal found 8/16![JetBlue logo]()
$287
This American Airlines deal was found by Cheapflights users on 8/20. 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 9/176:00 am -
2 stops10h 49m
Thu 9/245:16 pm -
2 stops14h 44m
Deal found 8/20![American Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/82:30 pm -
2 stops6h 30m
Tue 10/135:55 am -
2 stops7h 50m
Deal found 8/16![Southwest logo]()
$332
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:16 pm -
1 stop5h 11m
Sun 11/812:20 pm -
1 stop6h 20m
Deal found 8/16![Delta logo]()
$253
This JetBlue deal was found by Cheapflights users on 8/20. 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.
Thu 11/57:00 am -
Nonstop2h 58m
Mon 11/95:00 pm -
Nonstop3h 25m
Deal found 8/20![JetBlue logo]()
$291
This JetBlue deal was found by Cheapflights users on 8/19. 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.
Wed 9/94:35 pm -
Nonstop2h 49m
Sun 9/132:10 pm -
Nonstop3h 00m
Deal found 8/19![JetBlue logo]()
$295
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:40 pm -
1 stop6h 37m
Wed 9/166:05 am -
1 stop6h 40m
Deal found 8/16![Delta logo]()
$270
This Breeze Airways deal was found by Cheapflights users on 8/20. 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.
Thu 9/37:20 am -
1 stop4h 10m
Thu 9/172:05 pm -
1 stop4h 41m
Deal found 8/20![Breeze Airways logo]()
$301
This JetBlue deal was found by Cheapflights users on 8/18. 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.
Wed 9/305:49 pm -
1 stop5h 25m
Tue 10/610:05 am -
Nonstop2h 59m
Deal found 8/18![JetBlue logo]()
$310
This Delta deal was found by Cheapflights users on 8/20. 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 12/223:10 pm -
1 stop7h 03m
Thu 12/317:00 am -
Nonstop3h 27m
Deal found 8/20![Delta logo]()
$301
Last-minute flights from Orlando to MassachusettsDiscover last-minute flight deals from Orlando to Massachusetts. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Orlando to Massachusetts. Data last updated August 21, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/103:50 pm -
1 stop6h 17m
Tue 9/157:05 am -
1 stop11h 32m
Deal found 8/19![Breeze Airways logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/103:50 pm -
1 stop6h 17m
Sat 9/126:13 pm -
Nonstop3h 00m
Deal found 8/19![Multiple Airlines logo]()
$140
This Priceline deal was found by Cheapflights users on 8/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:30 am -
Nonstop2h 48m
Mon 9/143:13 pm -
1 stop4h 30m
Deal found 8/20![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:12 pm -
1 stop4h 14m
Tue 9/157:05 am -
1 stop11h 32m
Deal found 8/18![Breeze Airways logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:12 pm -
1 stop4h 14m
Fri 9/183:13 pm -
1 stop4h 30m
Deal found 8/20![Breeze Airways logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 9/122:29 pm -
Nonstop2h 49m
Tue 9/157:05 am -
1 stop11h 32m
Deal found 8/17![Multiple Airlines logo]()
$138
This CheapOair deal was found by Cheapflights users on 8/17. 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.
Sat 9/1210:04 am -
Nonstop2h 50m
Mon 9/143:13 pm -
1 stop4h 30m
Deal found 8/17![Breeze Airways logo]()
$146
This Priceline deal was found by Cheapflights users on 8/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1711:30 am -
Nonstop2h 48m
Mon 9/213:13 pm -
1 stop4h 30m
Deal found 8/20![Multiple Airlines logo]()
$141
This Breeze Airways deal was found by Cheapflights users on 8/17. 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.
Fri 9/186:12 pm -
1 stop4h 14m
Mon 9/213:13 pm -
1 stop4h 30m
Deal found 8/17![Breeze Airways logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/243:38 pm -
1 stop18h 51m
Mon 9/288:18 pm -
1 stop20h 10m
Deal found 8/18![Multiple Airlines logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/2610:04 am -
Nonstop2h 50m
Mon 9/283:13 pm -
1 stop4h 30m
Deal found 8/18![Breeze Airways logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/2610:04 am -
Nonstop2h 50m
Mon 10/51:04 pm -
1 stop4h 28m
Deal found 8/19![Breeze Airways logo]()
$136
One-way flights from Orlando to MassachusettsSearch for one-way flight options from Orlando to Massachusetts. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
Search for one-way flight options from Orlando to Massachusetts. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/1910:04 am -
Nonstop2h 50m
Deal found 8/18![Breeze Airways logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/56:12 pm -
1 stop4h 14m
Deal found 8/17![Breeze Airways logo]()
$79
This CheapOair deal was found by Cheapflights users on 8/18. 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.
Sat 9/192:29 pm -
Nonstop2h 49m
Deal found 8/18![Frontier logo]()
$80
This Super.com deal was found by Cheapflights users on 8/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:35 am -
1 stop13h 55m
Deal found 8/17![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:18 am -
1 stop4h 15m
Deal found 8/20![Breeze Airways logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:12 pm -
1 stop4h 14m
Deal found 8/16![Breeze Airways logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/26:12 pm -
1 stop4h 14m
Deal found 8/17![Breeze Airways logo]()
$84
This Super.com deal was found by Cheapflights users on 8/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1811:30 am -
Nonstop2h 48m
Deal found 8/18![Frontier logo]()
$85
This Super.com deal was found by Cheapflights users on 8/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1511:00 pm -
1 stop21h 30m
Deal found 8/18![Frontier logo]()
$86
This Super.com deal was found by Cheapflights users on 8/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:10 pm -
1 stop24h 20m
Deal found 8/17![Frontier logo]()
$87
This Breeze Airways deal was found by Cheapflights users on 8/17. 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.
Sat 9/121:11 pm -
1 stop10h 31m
Deal found 8/17![Breeze Airways logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/178:00 am -
1 stop6h 07m
Deal found 8/16![Breeze Airways logo]()
$100
Find flight deals from Orlando to Massachusetts
Keep the following information in mind while searching for Orlando to Massachusetts flight deals. Data was last updated August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $135 (Kiwi.com) |
One-way from | $78 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $268 |
Good round-trip deal | $250 or less |
Good one-way deal | $159 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Orlando 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 7,457,451 searches. Data last updated August 21, 2026.
Use the filters below to find and compare flights from Orlando to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OrlandoHartford
MCO Orlando - BDL Hartford Bradley Intl
MCOBDL
Orlando
Tue 9/15
8:00 am-5:08 pm
1 stop9h 08m
Hartford Bradley Intl
Tue 9/22
7:05 am-6:37 pm
1 stop11h 32m
$170
OrlandoHartford
MCO Orlando - BDL Hartford Bradley Intl
MCOBDL
Orlando
Wed 11/4
10:04 am-12:54 pm
Nonstop2h 50m
Hartford Bradley Intl
Mon 11/9
3:13 pm-7:43 pm
1 stop4h 30m
$174
OrlandoHartford
MCO Orlando - BDL Hartford Bradley Intl
MCOBDL
Orlando
Fri 10/2
6:12 pm-10:26 pm
1 stop4h 14m
Hartford Bradley Intl
Sun 10/4
2:05 pm-6:46 pm
1 stop4h 41m
$187
OrlandoHartford
MCO Orlando - BDL Hartford Bradley Intl
MCOBDL
Orlando
Sat 9/5
7:27 pm-11:59 pm
1 stop4h 32m
Hartford Bradley Intl
Sun 9/6
1:54 pm-6:16 pm
1 stop4h 22m
$191
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Wed 9/23
7:05 am-10:15 am
Nonstop3h 10m
Boston Logan Intl
Wed 9/30
7:00 am-2:43 pm
1 stop7h 43m
$219
OrlandoHartford
MCO Orlando - BDL Hartford Bradley Intl
MCOBDL
Orlando
Thu 10/8
4:05 pm-10:07 pm
1 stop6h 02m
Hartford Bradley Intl
Sun 10/11
2:05 pm-6:46 pm
1 stop4h 41m
$226
OrlandoAlbany
MCO Orlando - ALB Albany Intl
MCOALB
Orlando
Thu 10/22
4:02 pm-11:27 pm
1 stop7h 25m
Albany Intl
Sun 10/25
6:55 am-2:47 pm
1 stop7h 52m
$227
OrlandoAlbany
MCO Orlando - ALB Albany Intl
MCOALB
Orlando
Thu 9/17
4:08 pm-11:22 pm
1 stop7h 14m
Albany Intl
Mon 9/21
6:23 pm-12:22 am
1 stop5h 59m
$227
OrlandoAlbany
MCO Orlando - ALB Albany Intl
MCOALB
Orlando
Wed 10/7
4:02 pm-11:27 pm
1 stop7h 25m
Albany Intl
Tue 10/13
5:50 am-11:05 am
1 stop5h 15m
$227
OrlandoAlbany
MCO Orlando - ALB Albany Intl
MCOALB
Orlando
Fri 10/16
6:07 pm-11:01 pm
1 stop4h 54m
Albany Intl
Mon 10/19
5:50 am-11:05 am
1 stop5h 15m
$227
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Orlando to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Orlando with our price prediction graph.
MCO-BDL
MCO-ALB
MCO-BOS
MCO-ORH
MCO-EWB
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 Orlando to Massachusetts
ORL-USMA
MCO-BDL
MCO-ALB
MCO-BOS
MCO-ORH
What is the cheapest month to book a flight from Orlando to Massachusetts?
Currently, January is the cheapest month in which you can book a flight from Orlando to Massachusetts (average of $132). Flying from Orlando to Massachusetts in June is currently the most expensive (average of $323). 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 ORL to MA?
Find hourly flight availability from Orlando to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 21, 2026.
When flying from Orlando to Massachusetts, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 65% versus a flight in the afternoon.
Weekly flight availability from Orlando to Massachusetts
Explore weekly flight availability from Orlando to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 21, 2026.
The most flights from ORL to USMA are scheduled on a Thursday (50 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (18 on average).
How much does it cost to fly round-trip from Orlando to Massachusetts?
Airfare is below average for this route at the moment.
Orlando to Massachusetts flights typically cost between $200 and $334 in September.The cheapest round-trip price found within the last 5 days was $191 on Frontier (Sep 10-Sep 12).
How far ahead should I book a flight from Orlando to Massachusetts?
The price you pay for your flight from Orlando to Massachusetts may vary depending on when you book. For the best chance of a lower fare, look to book 53 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Orlando to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Orlando to Massachusetts. Price data was last updated on August 15, 2026.
Travelers seeking maximum savings on their Orlando to Massachusetts flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 August 21, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andAmerican Airlines from Orlando to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Orlando 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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Alternative routes for Orlando to Massachusetts
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Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Orlando to Massachusetts by cabin class
Find flights from Orlando to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Orlando and Massachusetts flights
Browse other Orlando and Massachusetts flight options. Last updated on August 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Orlando to Massachusetts flights
Consider these flights traveling from Orlando to Massachusetts.
Top 6 airlines flying from Orlando to Massachusetts
Discover the top 6 airlines that operate flights from Orlando 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 7,457,451 searches. Data last updated August 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$47 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$117 | Average$299 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$125 | Average$297 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$197 | Average$391 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$207 | Average$355 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$336 | Average$474 | FlexibilityNo cancel fee | On-time69% |