$88+ Cheap flights from Orlando (ORL) to Massachusetts
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — BOS
Oct 22 — Oct 291
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
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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 September 22, 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 September 22, 2026.
This CheapOair deal was found by Cheapflights users on 9/21. 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 10/306:12 pm -
1 stop4h 14m
Mon 11/23:13 pm -
1 stop4h 30m
Deal found 9/21![Breeze Airways logo]()
$140
This Priceline deal was found by Cheapflights users on 9/21. 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 11/1211:30 am -
Nonstop2h 50m
Mon 11/161:04 pm -
1 stop4h 28m
Deal found 9/21![Multiple Airlines logo]()
$144
This Priceline deal was found by Cheapflights users on 9/21. 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 10/2911:30 am -
Nonstop2h 50m
Mon 11/23:13 pm -
1 stop4h 30m
Deal found 9/21![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 10/227:26 pm -
1 stop4h 10m
Mon 10/261:04 pm -
1 stop4h 28m
Deal found 9/18![Breeze Airways logo]()
$150
This Super.com deal was found by Cheapflights users on 9/21. 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 11/1211:30 am -
Nonstop2h 50m
Mon 11/163:15 pm -
Nonstop3h 08m
Deal found 9/21![Frontier logo]()
$151
This Priceline deal was found by Cheapflights users on 9/21. 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 10/297:26 pm -
1 stop4h 10m
Mon 11/23:13 pm -
1 stop4h 30m
Deal found 9/21![Breeze Airways logo]()
$154
This JetBlue deal was found by Cheapflights users on 9/17. 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.
Thu 10/156:59 pm -
1 stop4h 47m
Mon 10/196:25 am -
1 stop6h 49m
Deal found 9/17![JetBlue logo]()
$155
This Priceline deal was found by Cheapflights users on 9/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:12 pm -
1 stop4h 14m
Mon 11/23:15 pm -
Nonstop3h 08m
Deal found 9/18![Multiple Airlines logo]()
$156
This Priceline deal was found by Cheapflights users on 9/21. 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.
Fri 10/2311:30 am -
Nonstop2h 51m
Mon 10/261:04 pm -
1 stop4h 28m
Deal found 9/21![Multiple Airlines logo]()
$157
This Cheapflightsfares deal was found by Cheapflights users on 9/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/59:08 am -
Nonstop2h 53m
Mon 12/712:56 pm -
Nonstop3h 18m
Deal found 9/18![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 11/127:28 am -
1 stop8h 24m
Tue 11/172:47 pm -
1 stop21h 17m
Deal found 9/18![Multiple Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 12/57:01 am -
Nonstop3h 12m
Sun 12/611:35 am -
1 stop23h 09m
Deal found 9/21![Multiple Airlines logo]()
$204
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 September 22, 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 September 22, 2026.
This JetBlue deal was found by Cheapflights users on 9/19. 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.
Tue 10/207:55 pm -
Nonstop2h 51m
Tue 10/276:00 am -
1 stop7h 41m
Deal found 9/19![JetBlue logo]()
$217
This Delta deal was found by Cheapflights users on 9/18. 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 11/59:25 am -
1 stop5h 24m
Tue 11/107:00 pm -
1 stop5h 40m
Deal found 9/18![Delta logo]()
$229
This Southwest deal was found by Cheapflights users on 9/19. 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.
Tue 10/2010:05 am -
Nonstop2h 40m
Tue 10/275:00 pm -
Nonstop2h 55m
Deal found 9/19![Southwest logo]()
$243
This United Airlines deal was found by Cheapflights users on 9/21. 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 10/227:22 am -
1 stop5h 21m
Tue 10/276:00 am -
1 stop5h 57m
Deal found 9/21![United Airlines logo]()
$249
This KAYAK deal was found by Cheapflights users on 9/18. 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.
Mon 10/198:00 am -
1 stop7h 22m
Wed 10/217:05 pm -
1 stop5h 27m
Deal found 9/18![American Airlines logo]()
$373
This JetBlue deal was found by Cheapflights users on 9/18. 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.
Mon 11/28:56 am -
Nonstop2h 43m
Mon 11/97:30 am -
Nonstop3h 15m
Deal found 9/18![JetBlue logo]()
$243
This Southwest deal was found by Cheapflights users on 9/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:40 am -
1 stop5h 30m
Wed 11/43:05 pm -
1 stop6h 25m
Deal found 9/17![Southwest logo]()
$243
This Delta deal was found by Cheapflights users on 9/18. 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.
Sat 12/56:00 am -
1 stop5h 58m
Sat 12/54:10 pm -
1 stop8h 30m
Deal found 9/18![Delta logo]()
$259
This United Airlines deal was found by Cheapflights users on 9/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:21 pm -
1 stop4h 23m
Mon 11/27:35 pm -
1 stop5h 24m
Deal found 9/19![United Airlines logo]()
$285
This Delta deal was found by Cheapflights users on 9/16. 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.
Sun 10/186:07 pm -
1 stop5h 13m
Sat 10/247:25 pm -
Nonstop3h 20m
Deal found 9/16![Delta logo]()
$265
This Southwest deal was found by Cheapflights users on 9/16. 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 12/410:05 am -
1 stop4h 25m
Wed 12/911:20 am -
1 stop4h 40m
Deal found 9/16![Southwest logo]()
$266
This KAYAK deal was found by Cheapflights users on 9/18. 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.
Sat 10/318:00 am -
1 stop5h 11m
Sat 10/314:20 pm -
1 stop7h 39m
Deal found 9/18![Multiple Airlines logo]()
$588
This JetBlue deal was found by Cheapflights users on 9/18. 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.
Sat 10/315:30 pm -
Nonstop2h 50m
Sun 11/16:30 am -
1 stop5h 27m
Deal found 9/18![JetBlue logo]()
$291
This Delta deal was found by Cheapflights users on 9/16. 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.
Tue 11/33:51 pm -
1 stop7h 14m
Sun 11/86:00 am -
1 stop6h 44m
Deal found 9/16![Delta logo]()
$268
This Southwest deal was found by Cheapflights users on 9/19. 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 10/241:45 pm -
1 stop4h 35m
Mon 10/265:50 am -
2 stops7h 35m
Deal found 9/19![Southwest logo]()
$269
This Delta deal was found by Cheapflights users on 9/18. 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.
Mon 11/27:00 am -
Nonstop3h 10m
Mon 11/94:00 pm -
1 stop6h 55m
Deal found 9/18![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 9/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/303:40 pm -
2 stops8h 15m
Mon 11/22:30 pm -
2 stops10h 15m
Deal found 9/18![Southwest logo]()
$290
This JetBlue deal was found by Cheapflights users on 9/17. 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.
Thu 10/156:25 pm -
1 stop5h 34m
Mon 10/197:45 am -
Nonstop3h 04m
Deal found 9/17![JetBlue logo]()
$320
This United Airlines deal was found by Cheapflights users on 9/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:21 pm -
1 stop4h 38m
Mon 10/196:00 am -
2 stops7h 57m
Deal found 9/17![United Airlines logo]()
$353
This American Airlines deal was found by Cheapflights users on 9/21. 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 10/306:00 am -
2 stops10h 49m
Sun 11/15:36 pm -
1 stop5h 32m
Deal found 9/21![American Airlines logo]()
$414
This Southwest deal was found by Cheapflights users on 9/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1310:40 am -
2 stops11h 35m
Mon 11/164:00 pm -
2 stops7h 30m
Deal found 9/20![Southwest logo]()
$296
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/222:25 pm -
1 stop7h 45m
Mon 10/266:20 am -
1 stop7h 09m
Deal found 9/17![Delta logo]()
$299
This United Airlines deal was found by Cheapflights users on 9/21. 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 10/66:00 am -
2 stops8h 14m
Sun 10/117:35 pm -
1 stop5h 24m
Deal found 9/21![United Airlines logo]()
$376
This Southwest deal was found by Cheapflights users on 9/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/293:40 pm -
2 stops8h 15m
Mon 11/211:45 am -
2 stops6h 55m
Deal found 9/17![Southwest logo]()
$304
This JetBlue deal was found by Cheapflights users on 9/21. 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 10/26:45 pm -
1 stop5h 01m
Sun 10/43:40 pm -
Nonstop3h 02m
Deal found 9/21![JetBlue logo]()
$370
This Delta deal was found by Cheapflights users on 9/16. 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.
Fri 10/167:59 pm -
Nonstop3h 08m
Mon 10/198:35 pm -
Nonstop3h 15m
Deal found 9/16![Delta logo]()
$308
This JetBlue deal was found by Cheapflights users on 9/17. 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.
Fri 9/256:45 pm -
1 stop5h 01m
Mon 9/282:10 pm -
Nonstop3h 00m
Deal found 9/17![JetBlue logo]()
$370
This Delta deal was found by Cheapflights users on 9/16. 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.
Fri 10/97:59 pm -
Nonstop3h 08m
Mon 10/128:35 pm -
Nonstop3h 15m
Deal found 9/16![Delta logo]()
$308
This KAYAK deal was found by Cheapflights users on 9/18. 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.
Tue 10/278:00 am -
1 stop7h 09m
Sat 10/314:20 pm -
1 stop6h 39m
Deal found 9/18![Multiple Airlines logo]()
$593
This JetBlue deal was found by Cheapflights users on 9/19. 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.
Thu 10/86:25 pm -
1 stop5h 34m
Wed 10/147:45 am -
Nonstop3h 04m
Deal found 9/19![JetBlue logo]()
$372
Last-minute flights from Orlando to MassachusettsDiscover last-minute flight deals from Orlando to Massachusetts. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from Orlando to Massachusetts. Data last updated September 22, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 9/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:45 am -
Nonstop3h 17m
Fri 10/1611:47 am -
Nonstop3h 23m
Deal found 9/20![Frontier logo]()
$207
This JetBlue deal was found by Cheapflights users on 9/17. 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.
Thu 10/156:59 pm -
1 stop4h 47m
Mon 10/196:25 am -
1 stop6h 49m
Deal found 9/17![JetBlue logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 10/177:45 am -
Nonstop3h 17m
Sat 10/2410:19 am -
2 stops11h 11m
Deal found 9/21![Multiple Airlines logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 10/227:26 pm -
1 stop4h 10m
Mon 10/261:04 pm -
1 stop4h 28m
Deal found 9/18![Breeze Airways logo]()
$150
This Priceline deal was found by Cheapflights users on 9/21. 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.
Fri 10/2311:30 am -
Nonstop2h 51m
Mon 10/261:04 pm -
1 stop4h 28m
Deal found 9/21![Multiple Airlines logo]()
$157
This Priceline deal was found by Cheapflights users on 9/21. 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 10/2911:30 am -
Nonstop2h 50m
Mon 11/23:13 pm -
1 stop4h 30m
Deal found 9/21![Multiple Airlines logo]()
$148
This Priceline deal was found by Cheapflights users on 9/21. 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 10/297:26 pm -
1 stop4h 10m
Mon 11/23:13 pm -
1 stop4h 30m
Deal found 9/21![Breeze Airways logo]()
$154
This Super.com deal was found by Cheapflights users on 9/21. 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 10/2911:30 am -
Nonstop2h 50m
Mon 11/23:15 pm -
Nonstop3h 08m
Deal found 9/21![Frontier logo]()
$162
This CheapOair deal was found by Cheapflights users on 9/21. 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 10/306:12 pm -
1 stop4h 14m
Mon 11/23:13 pm -
1 stop4h 30m
Deal found 9/21![Breeze Airways logo]()
$140
This Priceline deal was found by Cheapflights users on 9/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:12 pm -
1 stop4h 14m
Mon 11/23:15 pm -
Nonstop3h 08m
Deal found 9/18![Multiple Airlines logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 9/21. 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 10/306:12 pm -
1 stop4h 14m
Wed 11/41:39 pm -
1 stop10h 03m
Deal found 9/21![Breeze Airways logo]()
$159
This CheapOair deal was found by Cheapflights users on 9/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:12 pm -
1 stop4h 14m
Sat 10/311:39 pm -
1 stop10h 03m
Deal found 9/20![Breeze Airways logo]()
$163
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 September 22, 2026.
Search for one-way flight options from Orlando to Massachusetts. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/20. 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.
Wed 10/2110:04 am -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Breeze Airways logo]()
$88
This CheapOair deal was found by Cheapflights users on 9/21. 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 10/310:04 am -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Breeze Airways logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 12/191:45 pm -
Nonstop2h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Thu 11/197:26 pm -
1 stop4h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Breeze Airways logo]()
$92
This Super.com deal was found by Cheapflights users on 9/18. 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.
Sat 10/32:29 pm -
Nonstop2h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$93
This JetBlue deal was found by Cheapflights users on 9/20. 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.
Fri 10/166:59 pm -
1 stop4h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![JetBlue logo]()
$94
This JetBlue deal was found by Cheapflights users on 9/19. 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.
Fri 10/26:45 pm -
1 stop5h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![JetBlue logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Tue 11/178:00 am -
1 stop9h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Breeze Airways logo]()
$96
This CheapOair deal was found by Cheapflights users on 9/21. 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 10/1010:04 am -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Breeze Airways logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Wed 11/1810:04 am -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Breeze Airways logo]()
$98
This JetBlue deal was found by Cheapflights users on 9/17. 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.
Wed 10/146:25 pm -
1 stop5h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![JetBlue logo]()
$100
This KAYAK deal was found by Cheapflights users on 9/18. 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.
Tue 10/277:00 am -
Nonstop3h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Delta logo]()
$113
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 September 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $140 (CheapOair) |
One-way from | $88 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $294 |
Good round-trip deal | $289 or less |
Good one-way deal | $193 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 September 22, 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
Fri 10/16
6:59 pm-11:46 pm
1 stop4h 47m
Hartford Bradley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$94
OrlandoAlbany
MCO Orlando - ALB Albany Intl
MCOALB
Orlando
Wed 10/21
4:35 pm-10:20 pm
1 stop5h 45m
Albany Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$122
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Sat 12/5
8:50 am-5:25 pm
2 stops8h 35m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$125
OrlandoHartford
MCO Orlando - BDL Hartford Bradley Intl
MCOBDL
Orlando
Mon 11/16
5:30 am-10:34 am
1 stop5h 04m
Hartford Bradley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$132
OrlandoHartford
MCO Orlando - BDL Hartford Bradley Intl
MCOBDL
Orlando
Tue 12/1
4:45 pm-12:15 am
1 stop7h 30m
Hartford Bradley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$132
OrlandoHartford
MCO Orlando - BDL Hartford Bradley Intl
MCOBDL
Orlando
Wed 12/16
9:16 am-7:17 pm
2 stops10h 01m
Hartford Bradley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$135
OrlandoHartford
MCO Orlando - BDL Hartford Bradley Intl
MCOBDL
Orlando
Mon 10/12
10:35 pm-8:15 am
1 stop9h 40m
Hartford Bradley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$137
Quickest round-trip
OrlandoHartford
MCO Orlando - BDL Hartford Bradley Intl
MCOBDL
Orlando
Tue 10/13
7:40 pm-10:25 pm
Nonstop2h 45m
Hartford Bradley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$139
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Thu 10/15
7:00 am-10:10 am
Nonstop3h 10m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$140
OrlandoAlbany
MCO Orlando - ALB Albany Intl
MCOALB
Orlando
Wed 2/17
6:00 am-11:39 am
1 stop5h 39m
Albany Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$146
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-MVY
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 September 22, 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 63% 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 September 22, 2026.
The most flights from ORL to USMA are scheduled on a Sunday (43 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (35 on average).
How much does it cost to fly round-trip from Orlando to Massachusetts?
Airfare is typical for this route at the moment.
Orlando to Massachusetts flights typically cost between $203 and $354 in December.The cheapest round-trip price found within the last 5 days was $204 on Multiple Airlines (Dec 5-Dec 6).
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 43 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 September 19, 2026.
Travelers seeking maximum savings on their Orlando to Massachusetts flight should consider departing on Friday at noon 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 September 22, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andJetBlue 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.
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
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
See prices for flight routes from nearby airports that may be better suited for you.
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 September 22, 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 September 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$54 | Average$217 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$127 | Average$305 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$133 | Average$309 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$209 | Average$370 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$266 | Average$410 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$330 | Average$474 | FlexibilityNo cancel fee | On-time69% |