$83+ 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 6/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — BOS
Jul 2 — Jul 91
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 June 2, 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 June 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 6/99:46 pm
MCO
- BDL
Nonstop2h 55m
Breeze Airways
Wed 6/107:32 pm
BDL
- MCO
1 stop4h 27m
Breeze Airways
Deal found 5/29![Breeze Airways logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 5/28. 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.
Tue 6/99:46 pm
MCO
- BDL
Nonstop2h 55m
Multiple Airlines
Wed 6/1012:39 pm
BDL
- MCO
Nonstop3h 01m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 5/28. 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 6/69:56 pm
MCO
- BDL
Nonstop2h 55m
Breeze Airways
Wed 6/106:10 am
BDL
- MCO
Nonstop3h 00m
Breeze Airways
Deal found 5/28![Breeze Airways logo]()
$153
This Priceline deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
Tue 7/149:46 pm
MCO
- BDL
Nonstop2h 55m
Breeze Airways
Fri 8/281:30 pm
BDL
- MCO
1 stop4h 22m
Breeze Airways
Deal found 6/1![Breeze Airways logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 5/28. 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.
Wed 6/109:56 pm
MCO
- BDL
Nonstop2h 55m
Breeze Airways
Sat 6/137:32 pm
BDL
- MCO
1 stop4h 27m
Breeze Airways
Deal found 5/28![Breeze Airways logo]()
$157
This Expedia deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Wed 7/810:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 5/30![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 6/99:46 pm
MCO
- BDL
Nonstop2h 55m
Breeze Airways
Mon 7/201:30 pm
BDL
- MCO
1 stop4h 22m
Breeze Airways
Deal found 6/1![Breeze Airways logo]()
$159
This deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
Wed 7/86:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Tue 7/1410:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 6/1![Frontier logo]()
$159
This Breeze Airways deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:50 pm
MCO
- BDL
1 stop6h 17m
Breeze Airways
Mon 9/282:38 pm
BDL
- MCO
1 stop8h 20m
Breeze Airways
Deal found 6/1![Breeze Airways logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 8/2611:40 am
MCO
- BDL
Nonstop2h 55m
Breeze Airways
Wed 9/28:00 am
BDL
- MCO
Nonstop3h 00m
Breeze Airways
Deal found 5/30![Breeze Airways logo]()
$162
This Super.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
Wed 6/109:00 am
MCO
- BDL
Nonstop2h 54m
Frontier
Mon 7/2012:27 pm
BDL
- MCO
Nonstop3h 03m
Frontier
Deal found 6/1![Frontier logo]()
$167
This Southwest deal was found by Cheapflights users on 5/28. 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 8/186:20 am
MCO
- BOS
1 stop6h 20m
Southwest
Wed 8/198:30 am
BOS
- MCO
1 stop8h 05m
Southwest
Deal found 5/28![Southwest logo]()
$177
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 June 2, 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 June 2, 2026.
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 8/198:30 am
MCO
- BOS
1 stop6h 10m
Southwest
Wed 8/262:30 pm
BOS
- MCO
1 stop7h 55m
Southwest
Deal found 5/29![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 5/28. 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.
Wed 9/97:00 am
MCO
- BOS
Nonstop3h 08m
Delta
Wed 9/168:20 pm
BOS
- MCO
Nonstop3h 15m
Delta
Deal found 5/28![Delta logo]()
$197
This Breeze Airways deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 7/316:32 pm
MCO
- BDL
1 stop4h 17m
Breeze Airways
Mon 8/107:11 pm
BDL
- MCO
1 stop4h 30m
Breeze Airways
Deal found 5/29![Breeze Airways logo]()
$206
This American Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/205:00 am
MCO
- ORH
2 stops11h 53m
American Airlines
Tue 6/305:18 pm
ORH
- MCO
2 stops18h 13m
American Airlines
Deal found 6/1![American Airlines logo]()
$267
This Flysmarter deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/910:47 am
MCO
- ORH
Nonstop2h 54m
JetBlue
Mon 7/132:37 pm
ORH
- MCO
Nonstop3h 07m
JetBlue
Deal found 6/1![JetBlue logo]()
$281
This United Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 9/247:18 pm
MCO
- BDL
1 stop4h 41m
United Airlines
Sun 9/276:00 am
BDL
- MCO
2 stops7h 57m
United Airlines
Deal found 6/1![United Airlines logo]()
$322
This Southwest deal was found by Cheapflights users on 5/28. 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 8/1811:20 am
MCO
- BOS
1 stop7h 15m
Southwest
Wed 8/1910:50 am
BOS
- MCO
2 stops7h 10m
Southwest
Deal found 5/28![Southwest logo]()
$182
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/164:00 pm
MCO
- BOS
1 stop7h 17m
Delta
Tue 9/228:20 pm
BOS
- MCO
Nonstop3h 15m
Delta
Deal found 5/29![Delta logo]()
$207
This Breeze Airways deal was found by Cheapflights users on 5/27. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/126:32 pm
MCO
- BDL
1 stop4h 17m
Breeze Airways
Tue 6/167:15 am
BDL
- MCO
1 stop10h 56m
Breeze Airways
Deal found 5/27![Breeze Airways logo]()
$231
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 9/1910:56 am
MCO
- BOS
1 stop5h 32m
Delta
Tue 9/223:10 pm
BOS
- MCO
1 stop5h 25m
Delta
Deal found 5/30![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 9/36:50 pm
MCO
- ALB
Nonstop2h 50m
Southwest
Wed 9/99:05 am
ALB
- MCO
Nonstop2h 55m
Southwest
Deal found 5/29![Southwest logo]()
$251
This Breeze Airways deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 8/118:00 am
MCO
- BDL
1 stop9h 10m
Breeze Airways
Sat 8/298:00 am
BDL
- MCO
Nonstop3h 00m
Breeze Airways
Deal found 6/1![Breeze Airways logo]()
$256
This American Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/256:30 am
MCO
- ORH
1 stop10h 23m
American Airlines
Sun 6/285:18 pm
ORH
- MCO
1 stop16h 21m
American Airlines
Deal found 5/30![American Airlines logo]()
$288
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 8/187:00 am
MCO
- BOS
Nonstop3h 10m
Delta
Sun 8/238:20 pm
BOS
- MCO
Nonstop3h 14m
Delta
Deal found 5/29![Delta logo]()
$257
This JetBlue deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 6/1611:10 am
MCO
- ORH
Nonstop2h 54m
JetBlue
Sat 6/2012:39 pm
ORH
- MCO
Nonstop3h 02m
JetBlue
Deal found 6/1![JetBlue logo]()
$313
This Southwest deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/123:30 pm
MCO
- ALB
2 stops8h 15m
Southwest
Fri 6/199:55 am
ALB
- MCO
Nonstop2h 50m
Southwest
Deal found 5/30![Southwest logo]()
$272
This American Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2710:30 am
MCO
- ORH
1 stop6h 28m
American Airlines
Wed 9/25:23 pm
ORH
- MCO
1 stop21h 40m
American Airlines
Deal found 6/1![American Airlines logo]()
$304
This KAYAK deal was found by Cheapflights users on 5/28. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/77:45 am
MCO
- EWB
2 stops8h 50m
Multiple Airlines
Thu 7/1611:13 am
EWB
- MCO
2 stops10h 04m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$672
This Delta deal was found by Cheapflights users on 5/28. 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.
Fri 9/187:05 am
MCO
- BOS
Nonstop3h 10m
Delta
Tue 9/223:34 pm
BOS
- MCO
Nonstop3h 20m
Delta
Deal found 5/28![Delta logo]()
$257
This JetBlue deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 9/47:45 am
MCO
- BOS
Nonstop3h 03m
JetBlue
Tue 9/84:10 pm
BOS
- MCO
1 stop5h 07m
JetBlue
Deal found 5/30![JetBlue logo]()
$320
This United Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 8/127:40 am
MCO
- ALB
1 stop7h 25m
United Airlines
Tue 8/186:00 am
ALB
- MCO
2 stops12h 02m
United Airlines
Deal found 6/1![United Airlines logo]()
$368
This Southwest deal was found by Cheapflights users on 5/28. 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 6/126:30 am
MCO
- ALB
Nonstop2h 45m
Southwest
Mon 6/155:55 pm
ALB
- MCO
1 stop6h 50m
Southwest
Deal found 5/28![Southwest logo]()
$277
This JetBlue deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/266:30 pm
MCO
- BDL
1 stop5h 29m
JetBlue
Sun 6/284:40 pm
BDL
- MCO
Nonstop3h 06m
JetBlue
Deal found 5/30![JetBlue logo]()
$337
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 6/264:45 pm
MCO
- ALB
1 stop7h 14m
Delta
Mon 6/296:29 pm
ALB
- MCO
1 stop5h 44m
Delta
Deal found 6/1![Delta logo]()
$293
This Southwest deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 9/305:30 pm
MCO
- BDL
Nonstop2h 40m
Southwest
Thu 10/17:10 pm
BDL
- MCO
Nonstop3h 00m
Southwest
Deal found 5/31![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 5/28. 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.
Mon 8/36:15 am
MCO
- ORH
2 stops10h 45m
Delta
Fri 8/75:40 pm
ORH
- MCO
1 stop5h 23m
Delta
Deal found 5/28![Delta logo]()
$298
This JetBlue deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 8/228:44 am
MCO
- ACK
1 stop8h 12m
JetBlue
Wed 8/2611:15 am
ACK
- MCO
1 stop6h 11m
JetBlue
Deal found 5/29![JetBlue logo]()
$365
This American Airlines deal was found by Cheapflights users on 5/28. 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.
Sun 7/127:28 am
MCO
- ACK
1 stop7h 40m
American Airlines
Fri 7/175:10 pm
ACK
- MCO
1 stop15h 45m
American Airlines
Deal found 5/28![American Airlines logo]()
$404
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 7/151:45 pm
MCO
- BOS
1 stop9h 00m
Southwest
Fri 7/313:55 pm
BOS
- MCO
2 stops8h 25m
Southwest
Deal found 5/29![Southwest logo]()
$314
This JetBlue deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 8/188:44 am
MCO
- ACK
1 stop8h 12m
JetBlue
Thu 8/206:02 pm
ACK
- MCO
1 stop5h 26m
JetBlue
Deal found 5/31![JetBlue logo]()
$366
Last-minute flights from Orlando to MassachusettsDiscover last-minute flight deals from Orlando to Massachusetts. Data last updated June 2, 2026 and is based on user searches.
Discover last-minute flight deals from Orlando to Massachusetts. Data last updated June 2, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/28. 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 6/69:56 pm
MCO
- BDL
Nonstop2h 55m
Breeze Airways
Wed 6/106:10 am
BDL
- MCO
Nonstop3h 00m
Breeze Airways
Deal found 5/28![Breeze Airways logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 6/99:46 pm
MCO
- BDL
Nonstop2h 55m
Breeze Airways
Wed 6/107:32 pm
BDL
- MCO
1 stop4h 27m
Breeze Airways
Deal found 5/29![Breeze Airways logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 5/28. 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.
Tue 6/99:46 pm
MCO
- BDL
Nonstop2h 55m
Multiple Airlines
Wed 6/1012:39 pm
BDL
- MCO
Nonstop3h 01m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 6/99:46 pm
MCO
- BDL
Nonstop2h 55m
Breeze Airways
Mon 7/201:30 pm
BDL
- MCO
1 stop4h 22m
Breeze Airways
Deal found 6/1![Breeze Airways logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 6/99:46 pm
MCO
- BDL
Nonstop2h 55m
Breeze Airways
Wed 7/226:10 am
BDL
- MCO
Nonstop3h 00m
Breeze Airways
Deal found 5/31![Breeze Airways logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 5/28. 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.
Wed 6/109:56 pm
MCO
- BDL
Nonstop2h 55m
Breeze Airways
Sat 6/137:32 pm
BDL
- MCO
1 stop4h 27m
Breeze Airways
Deal found 5/28![Breeze Airways logo]()
$157
This Super.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
Wed 6/109:00 am
MCO
- BDL
Nonstop2h 54m
Frontier
Mon 7/2012:27 pm
BDL
- MCO
Nonstop3h 03m
Frontier
Deal found 6/1![Frontier logo]()
$167
This Expedia deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Wed 7/810:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 5/30![Frontier logo]()
$158
This Super.com deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Fri 7/1010:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 5/30![Frontier logo]()
$182
This deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
Wed 7/86:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Tue 7/1410:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 6/1![Frontier logo]()
$159
This Priceline deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
Tue 7/149:46 pm
MCO
- BDL
Nonstop2h 55m
Breeze Airways
Fri 8/281:30 pm
BDL
- MCO
1 stop4h 22m
Breeze Airways
Deal found 6/1![Breeze Airways logo]()
$154
This Frontier deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/206:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Wed 7/2210:04 am
BOS
- MCO
Nonstop3h 36m
Frontier
Deal found 6/2![Frontier logo]()
$178
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 June 2, 2026.
Search for one-way flight options from Orlando to Massachusetts. Find affordable one-way fares based on user searches. Data last updated June 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 6/249:56 pm
MCO
- BDL
Nonstop2h 55m
Breeze Airways
Deal found 6/1![Breeze Airways logo]()
$83
This Frontier deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
Wed 7/158:48 am
MCO
- BDL
Nonstop2h 44m
Frontier
Deal found 5/30![Frontier logo]()
$84
This CheapOair deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
Mon 8/172:02 pm
MCO
- BDL
1 stop4h 29m
Breeze Airways
Deal found 6/1![Breeze Airways logo]()
$85
This Breeze Airways deal was found by Cheapflights users on 5/28. 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.
Fri 6/196:32 pm
MCO
- BDL
1 stop4h 17m
Breeze Airways
Deal found 5/28![Breeze Airways logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 6/209:56 pm
MCO
- BDL
Nonstop2h 55m
Breeze Airways
Deal found 5/29![Breeze Airways logo]()
$88
This American Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:13 pm
MCO
- BDL
1 stop6h 34m
American Airlines
Deal found 5/30![American Airlines logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 8/251:12 pm
MCO
- BDL
1 stop4h 15m
Breeze Airways
Deal found 5/30![Breeze Airways logo]()
$93
This CheapOair deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 6/139:56 pm
MCO
- BDL
Nonstop2h 55m
Breeze Airways
Deal found 6/1![Breeze Airways logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 6/226:32 pm
MCO
- BDL
1 stop4h 17m
Breeze Airways
Deal found 6/1![Breeze Airways logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 7/291:14 pm
MCO
- BDL
1 stop5h 38m
Breeze Airways
Deal found 5/30![Breeze Airways logo]()
$96
This Frontier deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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.
Thu 8/136:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/1![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 7/246:00 am
MCO
- BOS
Nonstop3h 09m
Frontier
Deal found 6/1![Frontier logo]()
$101
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 June 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $154 (Priceline) |
One-way from | $83 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $267 |
Good round-trip deal | $247 or less |
Good one-way deal | $168 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 June 2, 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 - BOS
MCOBOS
Orlando
Wed 8/19
8:30 am-2:40 pm
1 stop6h 10m
Boston Logan Intl
Wed 8/26
2:30 pm-10:25 pm
1 stop7h 55m
$177
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Tue 8/18
11:20 am-6:35 pm
1 stop7h 15m
Boston Logan Intl
Wed 8/19
10:50 am-6:00 pm
2 stops7h 10m
$182
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Wed 9/9
7:00 am-10:08 am
Nonstop3h 08m
Boston Logan Intl
Wed 9/16
8:20 pm-11:35 pm
Nonstop3h 15m
$197
OrlandoHartford
MCO - BDL
MCOBDL
Orlando
Fri 7/31
6:32 pm-10:49 pm
1 stop4h 17m
Hartford Bradley Intl
Mon 8/10
7:11 pm-11:41 pm
1 stop4h 30m
$206
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Wed 9/16
4:00 pm-11:17 pm
1 stop7h 17m
Boston Logan Intl
Tue 9/22
8:20 pm-11:35 pm
Nonstop3h 15m
$207
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Sat 9/19
10:56 am-4:28 pm
1 stop5h 32m
Boston Logan Intl
Tue 9/22
3:10 pm-8:35 pm
1 stop5h 25m
$217
OrlandoHartford
MCO - BDL
MCOBDL
Orlando
Fri 6/12
6:32 pm-10:49 pm
1 stop4h 17m
Hartford Bradley Intl
Tue 6/16
7:15 am-6:11 pm
1 stop10h 56m
$231
OrlandoAlbany
MCO - ALB
MCOALB
Orlando
Thu 9/3
6:50 pm-9:40 pm
Nonstop2h 50m
Albany Intl
Wed 9/9
9:05 am-12:00 pm
Nonstop2h 55m
$251
OrlandoHartford
MCO - BDL
MCOBDL
Orlando
Tue 8/11
8:00 am-5:10 pm
1 stop9h 10m
Hartford Bradley Intl
Sat 8/29
8:00 am-11:00 am
Nonstop3h 00m
$256
OrlandoBoston
MCO - BOS
MCOBOS
Orlando
Tue 8/18
7:00 am-10:10 am
Nonstop3h 10m
Boston Logan Intl
Sun 8/23
8:20 pm-11:34 pm
Nonstop3h 14m
$257
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
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 $589). 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 June 2, 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 70% 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 June 2, 2026.
The most flights from ORL to USMA are scheduled on a Monday (50 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (20 on average).
How much does it cost to fly round-trip from Orlando to Massachusetts?
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 30 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 May 30, 2026.
Travelers seeking maximum savings on their Orlando to Massachusetts flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated June 2, 2026.
Peruse reviews from past customers who have flown with Delta,American Airlines, 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.
Overall
7.9
Crew
8.5
Comfort
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Overall
7.9
Crew
8.5
Comfort
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Overall
7.9
Crew
8.5
Comfort
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Overall
7.9
Crew
8.5
Comfort
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Spirit Airlines
Overall
7.9
Crew
8.5
Comfort
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Reviews
1 / 20
6.0
Goodpilar,May 2025
RSW - ATL
Overall
7.9
Crew
8.5
Comfort
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
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 June 2, 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 5 airlines flying from Orlando to Massachusetts
Discover the top 5 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 June 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$39 | Average$146 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$109 | Average$270 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$114 | Average$276 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$293 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$207 | Average$297 | FlexibilityNo cancel fee | On-time71% |