$85+ 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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — BOS
May 29 — Jun 51
Round-trip
1 adult, Economy
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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 April 29, 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 April 29, 2026.
This Priceline deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Sat 5/94:09 pm
MCO
- BDL
Nonstop2h 49m
Multiple Airlines
Sat 5/237:32 pm
BDL
- MCO
1 stop4h 27m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$123
This Booking.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/238:25 pm
MCO
- BDL
1 stop16h 19m
Frontier
Sat 5/307:43 pm
BDL
- MCO
Nonstop3h 00m
Frontier
Deal found 4/25![Frontier logo]()
$125
This Mytrip deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:32 pm
MCO
- BDL
1 stop4h 17m
Breeze Airways
Wed 6/36:10 am
BDL
- MCO
Nonstop3h 00m
Breeze Airways
Deal found 4/26![Breeze Airways logo]()
$126
This Priceline deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/291:52 pm
MCO
- BDL
Nonstop2h 53m
Multiple Airlines
Wed 6/37:32 pm
BDL
- MCO
1 stop4h 27m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/94:09 pm
MCO
- BDL
Nonstop2h 49m
Multiple Airlines
Sat 5/167:32 pm
BDL
- MCO
1 stop4h 27m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/94:09 pm
MCO
- BDL
Nonstop2h 49m
Multiple Airlines
Mon 5/256:57 pm
BDL
- MCO
1 stop4h 30m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/94:09 pm
MCO
- BDL
Nonstop2h 49m
Multiple Airlines
Wed 5/137:32 pm
BDL
- MCO
1 stop4h 27m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/129:44 pm
MCO
- BOS
1 stop11h 00m
Multiple Airlines
Tue 5/1910:07 am
BOS
- MCO
Nonstop3h 23m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/94:09 pm
MCO
- BDL
Nonstop2h 49m
Multiple Airlines
Wed 5/276:10 am
BDL
- MCO
Nonstop3h 00m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/133:10 pm
MCO
- BOS
1 stop10h 14m
Frontier
Mon 5/1810:17 am
BOS
- MCO
Nonstop3h 23m
Frontier
Deal found 4/27![Frontier logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/94:09 pm
MCO
- BDL
Nonstop2h 49m
Multiple Airlines
Tue 5/267:15 am
BDL
- MCO
1 stop10h 56m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$133
This Booking.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/219:46 pm
MCO
- BDL
Nonstop2h 55m
Breeze Airways
Mon 7/276:57 pm
BDL
- MCO
1 stop4h 30m
Breeze Airways
Deal found 4/25![Breeze Airways logo]()
$134
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 April 29, 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 April 29, 2026.
This Breeze Airways deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 6/46:56 pm
MCO
- BDL
1 stop4h 15m
Breeze Airways
Tue 6/96:00 am
BDL
- MCO
Nonstop3h 00m
Breeze Airways
Deal found 4/26![Breeze Airways logo]()
$151
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/27:54 pm
MCO
- BOS
Nonstop3h 10m
Delta
Sat 6/67:00 am
BOS
- MCO
Nonstop3h 15m
Delta
Deal found 4/27![Delta logo]()
$197
This JetBlue deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 6/29:52 am
MCO
- BDL
Nonstop2h 48m
JetBlue
Tue 6/96:00 am
BDL
- MCO
Nonstop2h 53m
JetBlue
Deal found 4/24![JetBlue logo]()
$217
This Southwest deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/198:55 am
MCO
- ALB
Nonstop2h 45m
Southwest
Tue 5/264:55 pm
ALB
- MCO
Nonstop3h 00m
Southwest
Deal found 4/24![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/167:03 pm
MCO
- BDL
1 stop4h 41m
United Airlines
Wed 5/206:05 am
BDL
- MCO
2 stops10h 43m
United Airlines
Deal found 4/28![United Airlines logo]()
$232
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/225:00 am
MCO
- ORH
2 stops11h 53m
American Airlines
Sun 5/245:18 pm
ORH
- MCO
2 stops6h 55m
American Airlines
Deal found 4/28![American Airlines logo]()
$232
This JetBlue deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 6/47:45 pm
MCO
- BDL
Nonstop2h 55m
JetBlue
Mon 6/81:35 pm
BDL
- MCO
Nonstop2h 56m
JetBlue
Deal found 4/25![JetBlue logo]()
$227
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/1610:51 am
MCO
- ORH
1 stop6h 12m
Delta
Thu 7/95:40 pm
ORH
- MCO
1 stop5h 23m
Delta
Deal found 4/28![Delta logo]()
$232
This Breeze Airways deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 6/191:48 pm
MCO
- BDL
1 stop4h 29m
Breeze Airways
Wed 6/246:10 am
BDL
- MCO
Nonstop3h 00m
Breeze Airways
Deal found 4/24![Breeze Airways logo]()
$238
This JetBlue deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/2110:25 am
MCO
- ORH
Nonstop2h 51m
JetBlue
Tue 5/263:15 pm
ORH
- MCO
Nonstop3h 12m
JetBlue
Deal found 4/24![JetBlue logo]()
$228
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/1610:51 am
MCO
- ORH
1 stop6h 12m
Delta
Tue 7/145:40 pm
ORH
- MCO
1 stop5h 23m
Delta
Deal found 4/27![Delta logo]()
$232
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:30 am
MCO
- BDL
2 stops7h 36m
United Airlines
Fri 6/57:45 pm
BDL
- MCO
1 stop5h 16m
United Airlines
Deal found 4/26![United Airlines logo]()
$265
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/234:55 pm
MCO
- ALB
1 stop6h 00m
Southwest
Wed 5/2712:20 pm
ALB
- MCO
2 stops6h 35m
Southwest
Deal found 4/28![Southwest logo]()
$272
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/110:44 pm
MCO
- HYA
2 stops12h 18m
Multiple Airlines
Mon 6/810:29 am
HYA
- MCO
1 stop26h 00m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$547
This JetBlue deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 7/2310:46 am
MCO
- ORH
Nonstop2h 53m
JetBlue
Tue 7/282:35 pm
ORH
- MCO
Nonstop3h 05m
JetBlue
Deal found 4/25![JetBlue logo]()
$228
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/3010:51 am
MCO
- ORH
1 stop6h 12m
Delta
Tue 7/75:40 pm
ORH
- MCO
1 stop5h 23m
Delta
Deal found 4/28![Delta logo]()
$232
This JetBlue deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/2110:25 am
MCO
- ORH
Nonstop2h 51m
JetBlue
Mon 5/252:16 pm
ORH
- MCO
Nonstop2h 54m
JetBlue
Deal found 4/24![JetBlue logo]()
$228
This Breeze Airways deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/169:46 pm
MCO
- BDL
Nonstop2h 55m
Breeze Airways
Fri 6/196:57 pm
BDL
- MCO
1 stop4h 30m
Breeze Airways
Deal found 4/28![Breeze Airways logo]()
$276
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/267:15 am
MCO
- ALB
1 stop8h 25m
Southwest
Tue 6/26:40 am
ALB
- MCO
Nonstop2h 55m
Southwest
Deal found 4/28![Southwest logo]()
$282
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:11 am
MCO
- ACK
1 stop7h 55m
American Airlines
Sat 9/53:36 pm
ACK
- MCO
1 stop7h 17m
American Airlines
Deal found 4/26![American Airlines logo]()
$312
This United Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/85:10 pm
MCO
- BOS
1 stop5h 04m
United Airlines
Mon 5/117:27 pm
BOS
- MCO
1 stop5h 32m
United Airlines
Deal found 4/24![United Airlines logo]()
$307
This JetBlue deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 6/37:45 pm
MCO
- BDL
Nonstop2h 55m
JetBlue
Sun 6/76:00 am
BDL
- MCO
Nonstop2h 53m
JetBlue
Deal found 4/26![JetBlue logo]()
$237
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/2910:15 am
MCO
- BDL
2 stops5h 55m
Southwest
Mon 6/112:35 pm
BDL
- MCO
2 stops6h 40m
Southwest
Deal found 4/28![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 6/1510:51 am
MCO
- ORH
1 stop6h 12m
Delta
Wed 6/175:43 pm
ORH
- MCO
1 stop5h 12m
Delta
Deal found 4/26![Delta logo]()
$263
This American Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/246:15 am
MCO
- HYA
2 stops11h 22m
American Airlines
Fri 7/32:08 pm
HYA
- MCO
2 stops7h 52m
American Airlines
Deal found 4/25![American Airlines logo]()
$327
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:40 am
MCO
- BOS
1 stop5h 32m
United Airlines
Thu 6/46:00 am
BOS
- MCO
2 stops8h 43m
United Airlines
Deal found 4/26![United Airlines logo]()
$312
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/128:40 am
MCO
- BDL
1 stop6h 00m
Southwest
Thu 5/2111:40 am
BDL
- MCO
1 stop12h 30m
Southwest
Deal found 4/28![Southwest logo]()
$287
This JetBlue deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/2710:25 am
MCO
- ORH
Nonstop2h 51m
JetBlue
Fri 5/292:16 pm
ORH
- MCO
Nonstop2h 58m
JetBlue
Deal found 4/28![JetBlue logo]()
$246
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:15 pm
MCO
- ALB
1 stop5h 43m
Delta
Sun 5/246:00 pm
ALB
- MCO
1 stop6h 12m
Delta
Deal found 4/26![Delta logo]()
$283
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/1210:20 am
MCO
- ALB
2 stops7h 40m
Southwest
Fri 5/1511:40 am
ALB
- MCO
2 stops7h 10m
Southwest
Deal found 4/28![Southwest logo]()
$288
Last-minute flights from Orlando to MassachusettsDiscover last-minute flight deals from Orlando to Massachusetts. Data last updated April 29, 2026 and is based on user searches.
Discover last-minute flight deals from Orlando to Massachusetts. Data last updated April 29, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Sat 5/94:09 pm
MCO
- BDL
Nonstop2h 49m
Multiple Airlines
Sat 5/237:32 pm
BDL
- MCO
1 stop4h 27m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/94:09 pm
MCO
- BDL
Nonstop2h 49m
Multiple Airlines
Sat 5/167:32 pm
BDL
- MCO
1 stop4h 27m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/94:09 pm
MCO
- BDL
Nonstop2h 49m
Multiple Airlines
Mon 5/256:57 pm
BDL
- MCO
1 stop4h 30m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/94:09 pm
MCO
- BDL
Nonstop2h 49m
Multiple Airlines
Wed 5/137:32 pm
BDL
- MCO
1 stop4h 27m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/94:09 pm
MCO
- BDL
Nonstop2h 49m
Multiple Airlines
Wed 5/276:10 am
BDL
- MCO
Nonstop3h 00m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/94:09 pm
MCO
- BDL
Nonstop2h 49m
Multiple Airlines
Tue 5/267:15 am
BDL
- MCO
1 stop10h 56m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/129:44 pm
MCO
- BOS
1 stop11h 00m
Multiple Airlines
Tue 5/1910:07 am
BOS
- MCO
Nonstop3h 23m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$130
This Frontier deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/123:10 pm
MCO
- BOS
1 stop10h 14m
Frontier
Tue 5/1910:07 am
BOS
- MCO
Nonstop3h 23m
Frontier
Deal found 4/24![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/133:10 pm
MCO
- BOS
1 stop10h 14m
Frontier
Mon 5/1810:17 am
BOS
- MCO
Nonstop3h 23m
Frontier
Deal found 4/27![Frontier logo]()
$131
This Booking.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/238:25 pm
MCO
- BDL
1 stop16h 19m
Frontier
Sat 5/307:43 pm
BDL
- MCO
Nonstop3h 00m
Frontier
Deal found 4/25![Frontier logo]()
$125
This Mytrip deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:32 pm
MCO
- BDL
1 stop4h 17m
Breeze Airways
Wed 6/36:10 am
BDL
- MCO
Nonstop3h 00m
Breeze Airways
Deal found 4/26![Breeze Airways logo]()
$126
This Priceline deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/291:52 pm
MCO
- BDL
Nonstop2h 53m
Multiple Airlines
Wed 6/37:32 pm
BDL
- MCO
1 stop4h 27m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$127
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 April 29, 2026.
Search for one-way flight options from Orlando to Massachusetts. Find affordable one-way fares based on user searches. Data last updated April 29, 2026.
This Mytrip deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:12 pm
MCO
- BDL
1 stop4h 15m
Breeze Airways
Deal found 4/24![Breeze Airways logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:36 pm
MCO
- BOS
Nonstop3h 06m
Spirit Airlines
Deal found 4/28![Spirit Airlines logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/191:12 pm
MCO
- BDL
1 stop4h 15m
Breeze Airways
Deal found 4/24![Breeze Airways logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:33 pm
MCO
- BOS
Nonstop3h 08m
Spirit Airlines
Deal found 4/27![Spirit Airlines logo]()
$89
This Trip.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Sun 5/1711:20 pm
MCO
- BDL
1 stop29h 50m
Frontier
Deal found 4/25![Frontier logo]()
$90
This Frontier deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:20 am
MCO
- BOS
Nonstop3h 12m
Frontier
Deal found 4/26![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/237:27 pm
MCO
- BDL
1 stop4h 32m
Breeze Airways
Deal found 4/28![Breeze Airways logo]()
$92
This Mytrip deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/121:48 pm
MCO
- BDL
1 stop4h 29m
Breeze Airways
Deal found 4/28![Breeze Airways logo]()
$93
This Super.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Sun 5/176:00 am
MCO
- BOS
Nonstop3h 12m
Frontier
Deal found 4/28![Frontier logo]()
$93
This Booking.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/309:56 pm
MCO
- BDL
Nonstop2h 55m
Breeze Airways
Deal found 4/25![Breeze Airways logo]()
$94
This Booking.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/279:56 pm
MCO
- BDL
Nonstop2h 55m
Breeze Airways
Deal found 4/28![Breeze Airways logo]()
$95
This Cheapflightsfares deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/156:41 pm
MCO
- BOS
1 stop5h 13m
Spirit Airlines
Deal found 4/25![Spirit Airlines logo]()
$96
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 April 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $123 (Priceline) |
One-way from | $85 (Mytrip) |
Popular in | April |
Cheapest in | January |
Average price | $254 |
Good round-trip deal | $243 or less |
Good one-way deal | $96 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 2,558,603 searches. Data last updated April 29, 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 - BDL
MCOBDL
Orlando
Thu 6/4
6:56 pm-11:11 pm
1 stop4h 15m
Hartford Bradley Intl
Tue 6/9
6:00 am-9:00 am
Nonstop3h 00m
$151
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Tue 6/2
7:54 pm-11:04 pm
Nonstop3h 10m
Boston Logan Intl
Sat 6/6
7:00 am-10:15 am
Nonstop3h 15m
$197
Quickest round-trip
OrlandoHartford
MCO - BDL
MCOBDL
Orlando
Tue 6/2
9:52 am-12:40 pm
Nonstop2h 48m
Hartford Bradley Intl
Tue 6/9
6:00 am-8:53 am
Nonstop2h 53m
$217
OrlandoAlbany
MCO - ALB
MCOALB
Orlando
Tue 5/19
8:55 am-11:40 am
Nonstop2h 45m
Albany Intl
Tue 5/26
4:55 pm-7:55 pm
Nonstop3h 00m
$227
OrlandoHartford
MCO - BDL
MCOBDL
Orlando
Thu 6/4
7:45 pm-10:40 pm
Nonstop2h 55m
Hartford Bradley Intl
Mon 6/8
1:35 pm-4:31 pm
Nonstop2h 56m
$227
OrlandoWorcester
MCO - ORH
MCOORH
Orlando
Thu 5/21
10:25 am-1:16 pm
Nonstop2h 51m
Worcester
Tue 5/26
3:15 pm-6:27 pm
Nonstop3h 12m
$228
OrlandoWorcester
MCO - ORH
MCOORH
Orlando
Thu 7/23
10:46 am-1:39 pm
Nonstop2h 53m
Worcester
Tue 7/28
2:35 pm-5:40 pm
Nonstop3h 05m
$228
OrlandoWorcester
MCO - ORH
MCOORH
Orlando
Thu 5/21
10:25 am-1:16 pm
Nonstop2h 51m
Worcester
Mon 5/25
2:16 pm-5:10 pm
Nonstop2h 54m
$228
OrlandoHartford
MCO - BDL
MCOBDL
Orlando
Sat 5/16
7:03 pm-11:44 pm
1 stop4h 41m
Hartford Bradley Intl
Wed 5/20
6:05 am-4:48 pm
2 stops10h 43m
$232
OrlandoWorcester
MCO - ORH
MCOORH
Orlando
Fri 5/22
5:00 am-4:53 pm
2 stops11h 53m
Worcester
Sun 5/24
5:18 pm-12:13 am
2 stops6h 55m
$232
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-BOS
MCO-ORH
MCO-ALB
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-BOS
MCO-ORH
MCO-ALB
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 52 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Orlando to Massachusetts?
Currently, February is the cheapest month in which you can book a flight from Orlando to Massachusetts (average of $27). Flying from Orlando to Massachusetts in August is currently the most expensive (average of $590). 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 April 29, 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 74% versus a flight in the afternoon.
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 April 25, 2026.
Travelers seeking maximum savings on their Orlando to Massachusetts flight should consider departing on Saturday 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.
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 April 29, 2026.
The most flights from ORL to USMA are scheduled on a Tuesday (55 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (17 on average).
How much does it cost to fly round-trip from Orlando to Massachusetts?
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated April 29, 2026.
Peruse reviews from past customers who have flown with Delta,JetBlue, 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.
Comfort
7.9
Food
7.2
Overall
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Comfort
7.9
Food
7.2
Overall
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Comfort
7.9
Food
7.2
Overall
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Comfort
7.9
Food
7.2
Overall
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Comfort
7.9
Food
7.2
Overall
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Comfort
7.9
Food
7.2
Overall
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 April 29, 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 2,558,603 searches. Data last updated April 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$37 | Average$131 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$69 | Average$160 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$106 | Average$323 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$114 | Average$267 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$198 | Average$336 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$198 | Average$292 | FlexibilityNo cancel fee | On-time71% |