$101+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — BOS
Nov 18 — Nov 251
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 October 19, 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 October 19, 2026.
This Delta deal was found by Cheapflights users on 10/19. 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.
Fri 12/115:04 pm -
1 stop5h 54m
Wed 12/167:35 pm -
Nonstop3h 20m
Deal found 10/19![Delta logo]()
$209
This deal was found by Cheapflights users on 10/16. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:45 am -
Nonstop3h 17m
Thu 10/2211:47 am -
Nonstop3h 23m
Deal found 10/16![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 12/412:53 pm -
2 stops44h 48m
Mon 12/711:08 am -
Nonstop3h 44m
Deal found 10/19![Multiple Airlines logo]()
$212
This FlightHub deal was found by Cheapflights users on 10/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:01 am -
Nonstop3h 10m
Sun 12/1311:08 am -
Nonstop3h 44m
Deal found 10/16![Frontier logo]()
$213
This Southwest deal was found by Cheapflights users on 10/16. 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 12/310:05 am -
1 stop4h 25m
Sat 12/53:05 pm -
1 stop5h 25m
Deal found 10/16![Southwest logo]()
$214
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:55 pm -
Nonstop3h 04m
Tue 11/1710:15 am -
Nonstop3h 21m
Deal found 10/16![JetBlue logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 10/16. 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.
Sat 12/510:52 am -
2 stops22h 49m
Mon 12/711:08 am -
Nonstop3h 44m
Deal found 10/16![Multiple Airlines logo]()
$218
This Delta deal was found by Cheapflights users on 10/19. 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.
Sat 12/53:45 pm -
1 stop5h 21m
Sun 12/67:04 pm -
1 stop5h 36m
Deal found 10/19![Delta logo]()
$219
This Southwest deal was found by Cheapflights users on 10/16. 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 12/310:05 am -
1 stop4h 25m
Tue 1/55:10 am -
2 stops9h 40m
Deal found 10/16![Southwest logo]()
$220
This Cheapflightsfares deal was found by Cheapflights users on 10/14. 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.
Wed 11/257:05 am -
1 stop25h 25m
Sat 12/511:08 am -
Nonstop3h 44m
Deal found 10/14![Frontier logo]()
$221
This Cheapflightsfares deal was found by Cheapflights users on 10/15. 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.
Mon 11/237:01 am -
Nonstop3h 10m
Sat 12/511:08 am -
Nonstop3h 44m
Deal found 10/15![Frontier logo]()
$222
This CheapOair deal was found by Cheapflights users on 10/15. 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.
Thu 12/37:01 am -
Nonstop3h 10m
Thu 12/1011:34 am -
1 stop11h 53m
Deal found 10/15![Frontier logo]()
$223
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 October 19, 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 October 19, 2026.
This Delta deal was found by Cheapflights users on 10/18. 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.
Fri 1/156:00 am -
1 stop7h 21m
Wed 1/209:55 am -
1 stop6h 06m
Deal found 10/18![Delta logo]()
$219
This Southwest deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/49:25 am -
1 stop7h 25m
Wed 11/113:30 pm -
1 stop7h 00m
Deal found 10/15![Southwest logo]()
$229
This JetBlue deal was found by Cheapflights users on 10/16. 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 11/207:50 am -
Nonstop2h 50m
Sun 11/224:30 pm -
1 stop5h 49m
Deal found 10/16![JetBlue logo]()
$324
This United Airlines deal was found by Cheapflights users on 10/17. 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.
Sat 12/59:00 am -
1 stop5h 32m
Mon 12/77:33 pm -
1 stop5h 25m
Deal found 10/17![United Airlines logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 12/209:46 pm -
1 stop10h 52m
Thu 12/3111:31 am -
1 stop9h 25m
Deal found 10/14![Allegiant Air logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 10/317:13 pm -
1 stop15h 29m
Sat 11/711:27 am -
2 stops46h 53m
Deal found 10/14![Multiple Airlines logo]()
$358
This Delta deal was found by Cheapflights users on 10/16. 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.
Sat 11/1410:10 am -
1 stop6h 02m
Mon 11/168:00 am -
1 stop7h 22m
Deal found 10/16![Delta logo]()
$239
This Southwest deal was found by Cheapflights users on 10/18. 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.
Thu 12/310:05 am -
1 stop4h 25m
Sat 12/511:35 am -
2 stops10h 35m
Deal found 10/18![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 10/18. 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.
Wed 11/1812:05 pm -
2 stops7h 00m
Mon 11/234:20 pm -
1 stop8h 00m
Deal found 10/18![Southwest logo]()
$260
This Delta deal was found by Cheapflights users on 10/14. 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 11/123:43 pm -
Nonstop3h 01m
Mon 11/1611:20 am -
Nonstop3h 17m
Deal found 10/14![Delta logo]()
$269
This JetBlue deal was found by Cheapflights users on 10/18. 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.
Thu 11/197:50 am -
Nonstop2h 50m
Fri 11/274:30 pm -
1 stop5h 49m
Deal found 10/18![JetBlue logo]()
$330
This Southwest deal was found by Cheapflights users on 10/14. 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 12/47:05 am -
1 stop6h 35m
Mon 12/711:20 am -
1 stop4h 40m
Deal found 10/14![Southwest logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 10/17. 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 10/298:43 pm -
1 stop12h 28m
Sat 10/319:02 am -
1 stop9h 21m
Deal found 10/17![Allegiant Air logo]()
$342
This Southwest deal was found by Cheapflights users on 10/18. 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 12/188:35 am -
1 stop5h 45m
Mon 12/215:35 am -
1 stop6h 45m
Deal found 10/18![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 10/15. 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 1/79:45 am -
1 stop6h 33m
Thu 1/145:30 am -
1 stop7h 20m
Deal found 10/15![Delta logo]()
$329
This JetBlue deal was found by Cheapflights users on 10/16. 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.
Wed 11/257:50 am -
Nonstop2h 50m
Mon 11/304:30 pm -
1 stop5h 49m
Deal found 10/16![JetBlue logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 10/16. 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.
Wed 11/1111:27 am -
1 stop22h 02m
Sat 11/149:09 am -
1 stop9h 23m
Deal found 10/16![Allegiant Air logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 10/16. 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.
Wed 11/111:31 pm -
2 stops22h 13m
Sat 11/149:09 am -
1 stop9h 23m
Deal found 10/16![Multiple Airlines logo]()
$423
This Kiwi.com deal was found by Cheapflights users on 10/14. 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 12/209:46 pm -
1 stop10h 52m
Wed 12/3010:28 am -
1 stop10h 15m
Deal found 10/14![Allegiant Air logo]()
$377
This KAYAK deal was found by Cheapflights users on 10/16. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:50 am -
Nonstop2h 50m
Sun 11/294:30 pm -
1 stop5h 49m
Deal found 10/16![JetBlue logo]()
$387
This Southwest deal was found by Cheapflights users on 10/14. 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 11/124:25 pm -
2 stops7h 20m
Mon 11/1611:20 am -
2 stops8h 40m
Deal found 10/14![Southwest logo]()
$338
This JetBlue deal was found by Cheapflights users on 10/18. 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 11/1410:00 am -
1 stop5h 50m
Fri 11/274:30 pm -
1 stop5h 49m
Deal found 10/18![JetBlue logo]()
$387
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 11/28:07 pm -
1 stop14h 35m
Sat 11/79:09 am -
1 stop9h 23m
Deal found 10/15![Allegiant Air logo]()
$390
This Delta deal was found by Cheapflights users on 10/18. 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.
Wed 11/187:45 am -
2 stops7h 34m
Mon 11/234:00 pm -
1 stop6h 55m
Deal found 10/18![Delta logo]()
$396
This Southwest deal was found by Cheapflights users on 10/14. 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 12/212:30 pm -
2 stops6h 50m
Thu 1/78:50 am -
1 stop7h 05m
Deal found 10/14![Southwest logo]()
$340
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 11/138:58 pm -
1 stop11h 21m
Sun 11/1510:39 am -
1 stop8h 57m
Deal found 10/16![Allegiant Air logo]()
$391
This JetBlue deal was found by Cheapflights users on 10/15. 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 11/259:00 am -
1 stop6h 20m
Sun 11/294:30 pm -
1 stop5h 49m
Deal found 10/15![JetBlue logo]()
$396
This Delta deal was found by Cheapflights users on 10/16. 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 1/134:45 pm -
1 stop21h 52m
Mon 1/183:18 pm -
1 stop18h 40m
Deal found 10/16![Delta logo]()
$402
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 10/317:13 pm -
1 stop15h 29m
Sat 11/79:09 am -
1 stop9h 23m
Deal found 10/19![Allegiant Air logo]()
$398
This JetBlue deal was found by Cheapflights users on 10/18. 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 12/59:53 am -
Nonstop2h 47m
Mon 12/71:30 pm -
Nonstop3h 16m
Deal found 10/18![JetBlue logo]()
$415
Last-minute flights from Orlando to MassachusettsDiscover last-minute flight deals from Orlando to Massachusetts. Data last updated October 19, 2026 and is based on user searches.
Discover last-minute flight deals from Orlando to Massachusetts. Data last updated October 19, 2026 and is based on user searches.
This deal was found by Cheapflights users on 10/16. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:45 am -
Nonstop3h 17m
Thu 10/2211:47 am -
Nonstop3h 23m
Deal found 10/16![Frontier logo]()
$211
This Delta deal was found by Cheapflights users on 10/14. 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 10/307:59 pm -
Nonstop3h 08m
Tue 11/1711:20 am -
Nonstop3h 17m
Deal found 10/14![Delta logo]()
$219
This JetBlue deal was found by Cheapflights users on 10/14. 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 11/412:50 pm -
Nonstop3h 30m
Sat 11/74:09 pm -
1 stop7h 29m
Deal found 10/14![JetBlue logo]()
$223
This Southwest deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/49:25 am -
1 stop7h 25m
Wed 11/113:30 pm -
1 stop7h 00m
Deal found 10/15![Southwest logo]()
$229
This Delta deal was found by Cheapflights users on 10/17. 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.
Sat 11/77:59 pm -
Nonstop3h 08m
Tue 11/108:00 am -
1 stop5h 40m
Deal found 10/17![Delta logo]()
$209
This JetBlue deal was found by Cheapflights users on 10/14. 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 11/103:05 pm -
1 stop6h 42m
Tue 11/176:00 am -
Nonstop3h 21m
Deal found 10/14![JetBlue logo]()
$234
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:55 pm -
Nonstop3h 04m
Tue 11/1710:15 am -
Nonstop3h 21m
Deal found 10/16![JetBlue logo]()
$217
This Cheapflightsfares deal was found by Cheapflights users on 10/15. 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.
Mon 11/237:01 am -
Nonstop3h 10m
Sat 12/511:08 am -
Nonstop3h 44m
Deal found 10/15![Frontier logo]()
$222
This FlightHub deal was found by Cheapflights users on 10/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:01 am -
Nonstop3h 10m
Sun 12/1311:08 am -
Nonstop3h 44m
Deal found 10/16![Frontier logo]()
$213
This Cheapflightsfares deal was found by Cheapflights users on 10/14. 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.
Wed 11/257:05 am -
1 stop25h 25m
Sat 12/511:08 am -
Nonstop3h 44m
Deal found 10/14![Frontier logo]()
$221
This deal was found by Cheapflights users on 10/17. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/267:01 am -
Nonstop3h 10m
Sun 11/2911:06 am -
Nonstop3h 29m
Deal found 10/17![Frontier logo]()
$233
This Cheapflightsfares deal was found by Cheapflights users on 10/14. 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.
Thu 11/267:01 am -
Nonstop3h 10m
Sun 12/611:08 am -
Nonstop3h 44m
Deal found 10/14![Frontier logo]()
$236
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 October 19, 2026.
Search for one-way flight options from Orlando to Massachusetts. Find affordable one-way fares based on user searches. Data last updated October 19, 2026.
This Super.com deal was found by Cheapflights users on 10/18. 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.
Mon 12/147:01 am -
Nonstop3h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$101
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/116:01 am -
Nonstop3h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$102
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/86:01 am -
Nonstop3h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$103
This Priceline deal was found by Cheapflights users on 10/14. 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 12/47:01 am -
Nonstop3h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$104
This United Airlines deal was found by Cheapflights users on 10/18. 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 11/189:22 am -
1 stop8h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![United Airlines logo]()
$105
This Trip.com deal was found by Cheapflights users on 10/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/156:24 am -
Nonstop3h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 10/18. 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.
Wed 12/29:15 am -
2 stops24h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$108
This Southwest deal was found by Cheapflights users on 10/16. 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.
Tue 1/57:30 am -
1 stop9h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Southwest logo]()
$110
This Trip.com deal was found by Cheapflights users on 10/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/296:24 am -
Nonstop3h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$111
This Super.com deal was found by Cheapflights users on 10/15. 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 11/219:47 pm -
1 stop10h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Frontier logo]()
$113
This WAYA deal was found by Cheapflights users on 10/16. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:58 pm -
1 stop11h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Allegiant Air logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 10/17. 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.
Sun 2/217:57 pm -
1 stop13h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Allegiant Air logo]()
$125
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 October 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $209 (Delta) |
One-way from | $101 (Super.com) |
Popular in | June |
Cheapest in | January |
Average price | $291 |
Good round-trip deal | $274 or less |
Good one-way deal | $204 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 October 19, 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
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Tue 1/5
7:30 am-4:50 pm
1 stop9h 20m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$110
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Wed 12/9
2:35 pm-7:00 pm
1 stop4h 25m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$115
OrlandoBoston
SFB Orlando Sanford Intl - BOS Boston Logan Intl
SFBBOS
Orlando Sanford Intl
Fri 11/13
8:58 pm-8:19 am
1 stop11h 21m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$123
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Sat 1/23
8:30 am-5:35 pm
2 stops9h 05m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$125
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Wed 11/11
7:05 am-1:40 pm
1 stop6h 35m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$128
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Sun 1/10
9:00 am-2:30 pm
1 stop5h 30m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$140
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Sun 1/10
10:10 am-4:05 pm
2 stops5h 55m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$145
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Fri 11/27
7:00 am-1:31 pm
1 stop6h 31m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$167
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Wed 11/11
6:00 am-8:58 am
Nonstop2h 58m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$169
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Mon 11/16
9:22 am-5:24 pm
1 stop8h 02m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$169
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-BOS
MCO-ORH
SFB-BOS
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-BOS
MCO-ORH
SFB-BOS
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 $134). Flying from Orlando to Massachusetts in June is currently the most expensive (average of $325). 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 October 19, 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 59% 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 October 19, 2026.
The most flights from ORL to USMA are scheduled on a Sunday (57 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (42 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 $237 and $374 in December.The cheapest round-trip price found within the last 5 days was $209 on Delta (Dec 11-Dec 16).
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 October 17, 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 at noon 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 October 19, 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.
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
7.9
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
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 October 19, 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 October 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$55 | Average$226 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$127 | Average$305 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$137 | Average$312 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$209 | Average$372 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$258 | Average$413 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$307 | Average$450 | FlexibilityNo cancel fee | On-time69% |