$86+ 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 9/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — BOS
Oct 7 — Oct 141
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Orlando to Massachusetts
Cheapest
Best
Last-minute
One-way
Cheapest flights from Orlando to MassachusettsExplore the most affordable flight options available from Orlando to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 7, 2026.
Explore the most affordable flight options available from Orlando to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 7, 2026.
This Priceline deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 12/121:45 pm -
Nonstop2h 51m
Mon 12/145:31 pm -
Nonstop3h 18m
Deal found 9/3![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:12 pm -
1 stop4h 14m
Mon 10/121:04 pm -
1 stop4h 28m
Deal found 9/2![Breeze Airways logo]()
$134
This Priceline deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/211:30 am -
Nonstop2h 48m
Mon 10/53:16 pm -
Nonstop3h 01m
Deal found 9/3![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/263:50 pm -
1 stop7h 52m
Tue 9/297:05 am -
1 stop11h 32m
Deal found 9/5![Breeze Airways logo]()
$139
This CheapOair deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:12 pm -
1 stop4h 14m
Mon 10/51:04 pm -
1 stop4h 28m
Deal found 9/6![Breeze Airways logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:12 pm -
1 stop4h 14m
Mon 10/121:04 pm -
1 stop4h 28m
Deal found 9/5![Breeze Airways logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/1511:30 am -
Nonstop2h 51m
Mon 10/191:04 pm -
1 stop4h 28m
Deal found 9/4![Multiple Airlines logo]()
$144
This Mytrip deal was found by Cheapflights users on 9/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:12 pm -
1 stop4h 14m
Mon 10/123:16 pm -
Nonstop3h 03m
Deal found 9/2![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:24 pm -
1 stop19h 27m
Mon 11/29:04 pm -
1 stop26h 23m
Deal found 9/2![Multiple Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/278:00 am -
1 stop6h 07m
Fri 10/308:04 pm -
1 stop16h 39m
Deal found 9/2![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/208:00 am -
1 stop6h 07m
Tue 10/272:47 pm -
1 stop21h 17m
Deal found 9/3![Multiple Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/207:25 am -
1 stop6h 42m
Mon 11/29:04 pm -
1 stop26h 23m
Deal found 9/4![Multiple Airlines logo]()
$201
Best flights from Orlando to MassachusettsDiscover carefully curated flight deals from Orlando to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 7, 2026.
Discover carefully curated flight deals from Orlando to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 7, 2026.
This Breeze Airways deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:12 pm -
1 stop4h 14m
Mon 10/263:13 pm -
1 stop4h 30m
Deal found 9/5![Breeze Airways logo]()
$168
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/1712:11 pm -
1 stop7h 11m
Wed 10/215:05 pm -
1 stop6h 12m
Deal found 9/5![Delta logo]()
$219
This Southwest deal was found by Cheapflights users on 9/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:15 am -
Nonstop2h 40m
Tue 10/136:00 am -
Nonstop2h 55m
Deal found 9/2![Southwest logo]()
$243
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/34:05 pm -
2 stops7h 39m
Sat 10/107:35 pm -
1 stop5h 24m
Deal found 9/4![United Airlines logo]()
$250
This JetBlue deal was found by Cheapflights users on 9/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:30 am -
Nonstop2h 46m
Tue 10/610:05 am -
Nonstop2h 59m
Deal found 9/2![JetBlue logo]()
$290
This American Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/1012:21 pm -
1 stop4h 46m
Tue 11/175:36 pm -
1 stop16h 08m
Deal found 9/6![American Airlines logo]()
$374
This Breeze Airways deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:12 pm -
1 stop4h 14m
Mon 9/213:13 pm -
1 stop4h 30m
Deal found 9/6![Breeze Airways logo]()
$228
This Southwest deal was found by Cheapflights users on 9/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/305:30 pm -
Nonstop2h 45m
Wed 10/76:00 am -
Nonstop2h 55m
Deal found 9/2![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/83:40 pm -
Nonstop3h 09m
Wed 10/146:00 am -
1 stop6h 44m
Deal found 9/3![Delta logo]()
$255
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/67:00 am -
Nonstop3h 10m
Tue 11/105:40 pm -
Nonstop3h 23m
Deal found 9/6![Delta logo]()
$255
This United Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:21 pm -
1 stop4h 38m
Wed 10/217:38 am -
2 stops10h 50m
Deal found 9/3![United Airlines logo]()
$294
This Southwest deal was found by Cheapflights users on 9/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:15 am -
2 stops9h 40m
Sat 10/32:30 pm -
1 stop7h 40m
Deal found 9/2![Southwest logo]()
$270
This Breeze Airways deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/84:10 pm -
1 stop5h 57m
Sun 10/116:30 am -
1 stop9h 56m
Deal found 9/5![Breeze Airways logo]()
$275
This JetBlue deal was found by Cheapflights users on 9/1. 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.
Thu 11/55:30 pm -
Nonstop2h 50m
Mon 11/97:30 am -
Nonstop3h 17m
Deal found 9/1![JetBlue logo]()
$307
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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.
Mon 10/57:21 pm -
1 stop4h 23m
Mon 10/196:03 am -
2 stops7h 54m
Deal found 9/5![United Airlines logo]()
$301
This Delta deal was found by Cheapflights users on 9/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:07 pm -
1 stop5h 13m
Tue 10/276:00 am -
1 stop6h 44m
Deal found 9/2![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/63:40 pm -
2 stops8h 05m
Mon 11/912:45 pm -
1 stop4h 55m
Deal found 9/3![Southwest logo]()
$277
This JetBlue deal was found by Cheapflights users on 9/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/19:00 am -
Nonstop2h 51m
Mon 10/512:41 pm -
Nonstop3h 04m
Deal found 9/2![JetBlue logo]()
$329
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 12/39:00 am -
1 stop4h 59m
Tue 12/86:00 am -
2 stops8h 57m
Deal found 9/4![United Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/203:55 pm -
1 stop5h 34m
Sun 10/256:00 am -
1 stop6h 44m
Deal found 9/5![Delta logo]()
$285
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 11/78:00 am -
1 stop4h 45m
Wed 11/1112:50 pm -
2 stops7h 10m
Deal found 9/3![Southwest logo]()
$289
This American Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:00 am -
2 stops10h 49m
Sun 9/275:16 pm -
2 stops17h 38m
Deal found 9/6![American Airlines logo]()
$403
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/105:42 pm -
1 stop5h 26m
Sat 10/178:35 am -
1 stop6h 21m
Deal found 9/4![Delta logo]()
$285
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/217:17 pm -
1 stop4h 42m
Tue 12/16:00 am -
2 stops9h 12m
Deal found 9/6![United Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:45 am -
1 stop11h 05m
Tue 9/224:20 pm -
2 stops39h 49m
Deal found 9/3![Multiple Airlines logo]()
$881
This JetBlue deal was found by Cheapflights users on 9/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/255:49 pm -
1 stop5h 25m
Sat 9/261:12 pm -
Nonstop2h 58m
Deal found 9/2![JetBlue logo]()
$371
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:30 pm -
Nonstop2h 50m
Sat 10/245:10 pm -
Nonstop3h 00m
Deal found 9/3![Southwest logo]()
$318
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 11/128:00 am -
1 stop7h 19m
Sun 11/154:03 pm -
1 stop6h 52m
Deal found 9/3![Delta logo]()
$302
This United Airlines deal was found by Cheapflights users on 9/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:54 am -
1 stop6h 10m
Sun 9/276:03 am -
2 stops7h 54m
Deal found 9/2![United Airlines logo]()
$342
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 9/2911:55 am -
1 stop5h 10m
Wed 9/308:30 am -
1 stop5h 45m
Deal found 9/4![Southwest logo]()
$331
Last-minute flights from Orlando to MassachusettsDiscover last-minute flight deals from Orlando to Massachusetts. Data last updated September 7, 2026 and is based on user searches.
Discover last-minute flight deals from Orlando to Massachusetts. Data last updated September 7, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 9/2411:30 am -
Nonstop2h 48m
Fri 10/23:16 pm -
Nonstop3h 01m
Deal found 9/3![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:12 pm -
1 stop4h 14m
Mon 9/281:04 pm -
1 stop4h 28m
Deal found 9/3![Breeze Airways logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/263:50 pm -
1 stop7h 52m
Tue 9/297:05 am -
1 stop11h 32m
Deal found 9/5![Breeze Airways logo]()
$139
This Priceline deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/211:30 am -
Nonstop2h 48m
Mon 10/53:16 pm -
Nonstop3h 01m
Deal found 9/3![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:12 pm -
1 stop4h 14m
Mon 10/121:04 pm -
1 stop4h 28m
Deal found 9/5![Breeze Airways logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:12 pm -
1 stop4h 14m
Mon 10/121:04 pm -
1 stop4h 28m
Deal found 9/2![Breeze Airways logo]()
$134
This Mytrip deal was found by Cheapflights users on 9/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:12 pm -
1 stop4h 14m
Mon 10/123:16 pm -
Nonstop3h 03m
Deal found 9/2![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/1511:30 am -
Nonstop2h 51m
Mon 10/191:04 pm -
1 stop4h 28m
Deal found 9/4![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/208:00 am -
1 stop6h 07m
Tue 10/272:47 pm -
1 stop21h 17m
Deal found 9/3![Multiple Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/207:25 am -
1 stop6h 42m
Mon 11/29:04 pm -
1 stop26h 23m
Deal found 9/4![Multiple Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/278:00 am -
1 stop6h 07m
Fri 10/308:04 pm -
1 stop16h 39m
Deal found 9/2![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:24 pm -
1 stop19h 27m
Mon 11/29:04 pm -
1 stop26h 23m
Deal found 9/2![Multiple Airlines logo]()
$185
One-way flights from Orlando to MassachusettsSearch for one-way flight options from Orlando to Massachusetts. Find affordable one-way fares based on user searches. Data last updated September 7, 2026.
Search for one-way flight options from Orlando to Massachusetts. Find affordable one-way fares based on user searches. Data last updated September 7, 2026.
This Super.com deal was found by Cheapflights users on 9/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2411:30 am -
Nonstop2h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$86
This Frontier deal was found by Cheapflights users on 9/2. 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 11/211:30 am -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Frontier logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 11/410:04 am -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Breeze Airways logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:12 pm -
1 stop4h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Breeze Airways logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:26 pm -
1 stop4h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![Breeze Airways logo]()
$90
This JetBlue deal was found by Cheapflights users on 9/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:00 pm -
1 stop6h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![JetBlue logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/1010:04 am -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Breeze Airways logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 9/307:10 am -
1 stop16h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Breeze Airways logo]()
$94
This Super.com deal was found by Cheapflights users on 9/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:00 pm -
1 stop5h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![JetBlue logo]()
$95
This Breeze Airways deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:12 pm -
1 stop4h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Breeze Airways logo]()
$96
This Breeze Airways deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 9/103:50 pm -
1 stop6h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Breeze Airways logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:04 am -
Nonstop2h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Breeze Airways logo]()
$98
Find flight deals from Orlando to Massachusetts
Keep the following information in mind while searching for Orlando to Massachusetts flight deals. Data was last updated September 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $134 (Kiwi.com) |
One-way from | $86 (Super.com) |
Popular in | June |
Cheapest in | January |
Average price | $270 |
Good round-trip deal | $281 or less |
Good one-way deal | $189 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Orlando to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 7, 2026.
Use the filters below to find and compare flights from Orlando to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OrlandoHartford
MCO Orlando - BDL Hartford Bradley Intl
MCOBDL
Orlando
Sat 9/19
3:50 pm-11:42 pm
1 stop7h 52m
Hartford Bradley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$100
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Sat 10/10
6:20 pm-11:59 pm
1 stop5h 39m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$110
OrlandoAlbany
MCO Orlando - ALB Albany Intl
MCOALB
Orlando
Tue 12/1
4:35 pm-11:44 pm
2 stops7h 09m
Albany Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$118
OrlandoHartford
MCO Orlando - BDL Hartford Bradley Intl
MCOBDL
Orlando
Sat 9/12
3:50 pm-11:42 pm
1 stop7h 52m
Hartford Bradley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$121
OrlandoHartford
MCO Orlando - BDL Hartford Bradley Intl
MCOBDL
Orlando
Mon 10/5
8:15 pm-11:00 pm
Nonstop2h 45m
Hartford Bradley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$122
OrlandoAlbany
MCO Orlando - ALB Albany Intl
MCOALB
Orlando
Mon 11/2
9:55 am-12:40 pm
Nonstop2h 45m
Albany Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$126
OrlandoHartford
MCO Orlando - BDL Hartford Bradley Intl
MCOBDL
Orlando
Tue 11/10
5:30 am-10:34 am
1 stop5h 04m
Hartford Bradley Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$132
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Tue 11/3
9:22 am-5:24 pm
1 stop8h 02m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$140
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Sat 11/14
9:22 am-5:24 pm
1 stop8h 02m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$140
OrlandoBoston
MCO Orlando - BOS Boston Logan Intl
MCOBOS
Orlando
Sat 10/3
7:15 am-4:21 pm
1 stop9h 06m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$145
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Orlando to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Orlando with our price prediction graph.
MCO-BDL
MCO-ALB
MCO-BOS
MCO-ORH
MCO-HYA
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Orlando to Massachusetts
ORL-USMA
MCO-BDL
MCO-ALB
MCO-BOS
MCO-ORH
What is the cheapest month to book a flight from Orlando to Massachusetts?
Currently, January is the cheapest month in which you can book a flight from Orlando to Massachusetts (average of $132). Flying from Orlando to Massachusetts in June is currently the most expensive (average of $323). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from ORL to MA?
Find hourly flight availability from Orlando to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 7, 2026.
When flying from Orlando to Massachusetts, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 63% versus a flight in the afternoon.
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 $208 and $362 in September.The cheapest round-trip price found within the last 5 days was $204 on Frontier (Sep 21-Oct 3).
How far ahead should I book a flight from Orlando to Massachusetts?
The price you pay for your flight from Orlando to Massachusetts may vary depending on when you book. For the best chance of a lower fare, look to book 43 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Orlando to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Orlando to Massachusetts. Price data was last updated on September 5, 2026.
Travelers seeking maximum savings on their Orlando to Massachusetts flight should consider departing on Tuesday 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 September 7, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andAmerican Airlines from Orlando to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Orlando to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Orlando to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Orlando to Massachusetts by cabin class
Find flights from Orlando to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Orlando and Massachusetts flights
Browse other Orlando and Massachusetts flight options. Last updated on September 7, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Orlando to Massachusetts flights
Consider these flights traveling from Orlando to Massachusetts.
Top 6 airlines flying from Orlando to Massachusetts
Discover the top 6 airlines that operate flights from Orlando to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$48 | Average$207 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$126 | Average$305 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$127 | Average$303 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$197 | Average$392 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$209 | Average$369 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$353 | Average$474 | FlexibilityNo cancel fee | On-time69% |