$81+ Cheap flights from Indiana 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
IND — BOS
Jun 15 — Jun 221
Round-trip
1 adult, Economy
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Find cheap flights from Indiana to Massachusetts with Cheapflights
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Cheapest flights from Indiana to MassachusettsExplore the most affordable flight options available from Indiana to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 16, 2026.
Explore the most affordable flight options available from Indiana to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/96:00 am
MDW
- BOS
1 stop18h 27m
Frontier
Wed 6/106:00 am
BOS
- MDW
1 stop17h 11m
Frontier
Deal found 5/12![Frontier logo]()
$169
This SmartFares deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/13![JetBlue logo]()
$172
This SmartFares deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/301:56 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/12![JetBlue logo]()
$176
This SmartFares deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/810:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Mon 7/138:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 5/12![JetBlue logo]()
$179
This Southwest deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Mon 6/84:45 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 5/16![Southwest logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/13![JetBlue logo]()
$182
This American Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/93:15 pm
ORD
- BOS
Nonstop2h 35m
American Airlines
Wed 6/107:46 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 5/15![American Airlines logo]()
$186
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Sat 5/305:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 5/12![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/99:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 6/105:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/13![Southwest logo]()
$187
This SmartFares deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/41:55 pm
ORD
- BOS
Nonstop2h 38m
JetBlue
Tue 7/148:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 5/11![JetBlue logo]()
$188
This Priceline deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
Multiple Airlines
Wed 6/1012:01 pm
BOS
- ORD
1 stop8h 49m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$189
This Frontier deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/91:29 pm
ORD
- BOS
1 stop10h 58m
Frontier
Wed 6/1012:01 pm
BOS
- ORD
1 stop8h 49m
Frontier
Deal found 5/15![Frontier logo]()
$190
Best flights from Indiana to MassachusettsDiscover carefully curated flight deals from Indiana to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 16, 2026.
Discover carefully curated flight deals from Indiana to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 16, 2026.
This JetBlue deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Wed 6/106:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/15![JetBlue logo]()
$187
This United Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/107:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Tue 6/166:40 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 5/11![United Airlines logo]()
$192
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Thu 6/45:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/14![Southwest logo]()
$192
This KAYAK deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/157:26 pm
ORD
- BDL
Nonstop2h 20m
American Airlines
Wed 6/177:10 am
BDL
- ORD
Nonstop2h 50m
American Airlines
Deal found 5/15![American Airlines logo]()
$352
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:59 pm
MDW
- ALB
1 stop4h 07m
Delta
Mon 9/76:00 am
ALB
- MDW
1 stop3h 42m
Delta
Deal found 5/15![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Mon 6/16:40 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 5/15![United Airlines logo]()
$197
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/127:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 6/245:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/12![Southwest logo]()
$201
This JetBlue deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 7/228:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Tue 7/285:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Deal found 5/11![JetBlue logo]()
$205
This Sun Country Air deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/186:25 pm
ORD
- BDL
1 stop15h 42m
Sun Country Air
Mon 7/67:14 pm
BDL
- ORD
1 stop16h 40m
Sun Country Air
Deal found 5/13![Sun Country Air logo]()
$425
This United Airlines deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 8/89:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sat 8/158:27 pm
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 5/12![United Airlines logo]()
$197
This Southwest deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/127:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Sat 6/135:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/13![Southwest logo]()
$201
This United Airlines deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/169:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Wed 6/177:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 5/13![United Airlines logo]()
$197
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 7/207:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Thu 7/235:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/11![Southwest logo]()
$205
This United Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 7/189:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Mon 7/276:43 pm
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 5/11![United Airlines logo]()
$201
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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.
Sun 7/125:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Tue 7/143:45 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 5/11![Southwest logo]()
$207
This United Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/257:33 am
ORD
- BOS
Nonstop2h 32m
United Airlines
Tue 6/308:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 5/15![United Airlines logo]()
$201
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:10 pm
MDW
- BOS
2 stops6h 40m
Southwest
Sat 6/65:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/15![Southwest logo]()
$216
This United Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/197:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Tue 6/238:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 5/15![United Airlines logo]()
$201
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:10 pm
MDW
- BOS
2 stops8h 45m
Southwest
Mon 6/85:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/15![Southwest logo]()
$216
This KAYAK deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/88:54 pm
ORD
- ALB
Nonstop2h 18m
American Airlines
Fri 6/128:00 pm
ALB
- ORD
Nonstop2h 44m
American Airlines
Deal found 5/11![American Airlines logo]()
$353
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 7/183:45 pm
SDF
- BOS
Nonstop2h 37m
Delta
Wed 7/229:26 am
BOS
- SDF
Nonstop2h 43m
Delta
Deal found 5/11![Delta logo]()
$355
This United Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/316:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Tue 6/27:27 pm
BOS
- ORD
1 stop4h 59m
United Airlines
Deal found 5/15![United Airlines logo]()
$202
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 7/92:45 pm
MDW
- BOS
1 stop7h 40m
Southwest
Tue 7/145:25 am
BOS
- MDW
1 stop4h 15m
Southwest
Deal found 5/12![Southwest logo]()
$221
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:36 pm
MDW
- ALB
1 stop3h 42m
Delta
Tue 6/96:06 am
ALB
- MDW
1 stop4h 08m
Delta
Deal found 5/14![Delta logo]()
$357
This United Airlines deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Tue 6/167:27 pm
BOS
- ORD
1 stop4h 59m
United Airlines
Deal found 5/12![United Airlines logo]()
$202
This Sun Country Air deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/267:30 am
ORD
- BDL
1 stop25h 34m
Sun Country Air
Thu 7/3011:52 am
BDL
- ORD
1 stop6h 37m
Sun Country Air
Deal found 5/13![Sun Country Air logo]()
$435
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/168:14 am
CVG
- ALB
1 stop3h 31m
Delta
Tue 7/215:45 am
ALB
- CVG
1 stop7h 09m
Delta
Deal found 5/15![Delta logo]()
$362
This United Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:00 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Sun 10/48:10 pm
BOS
- ORD
Nonstop2h 54m
United Airlines
Deal found 5/15![United Airlines logo]()
$205
This American Airlines deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/45:10 am
ORD
- ALB
1 stop4h 42m
American Airlines
Mon 6/85:35 pm
ALB
- ORD
1 stop4h 55m
American Airlines
Deal found 5/11![American Airlines logo]()
$402
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/307:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 6/305:00 pm
BOS
- MDW
1 stop5h 35m
Southwest
Deal found 5/12![Southwest logo]()
$231
Last-minute flights from Indiana to MassachusettsDiscover last-minute flight deals from Indiana to Massachusetts. Data last updated May 16, 2026 and is based on user searches.
Discover last-minute flight deals from Indiana to Massachusetts. Data last updated May 16, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/13![JetBlue logo]()
$182
This SmartFares deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/13![JetBlue logo]()
$172
This SmartFares deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/301:56 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/12![JetBlue logo]()
$176
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Sat 5/305:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 5/11![Delta logo]()
$187
This Frontier deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/312:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Tue 6/96:00 am
BOS
- MDW
1 stop6h 12m
Frontier
Deal found 5/13![Frontier logo]()
$190
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/37:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Sat 6/65:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 5/13![Delta logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/96:00 am
MDW
- BOS
1 stop18h 27m
Frontier
Wed 6/106:00 am
BOS
- MDW
1 stop17h 11m
Frontier
Deal found 5/12![Frontier logo]()
$169
This American Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/93:15 pm
ORD
- BOS
Nonstop2h 35m
American Airlines
Wed 6/107:46 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 5/15![American Airlines logo]()
$186
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/99:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 6/105:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 5/12![Southwest logo]()
$187
This Priceline deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
Multiple Airlines
Wed 6/1012:01 pm
BOS
- ORD
1 stop8h 49m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$189
This Frontier deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/91:29 pm
ORD
- BOS
1 stop10h 58m
Frontier
Wed 6/1012:01 pm
BOS
- ORD
1 stop8h 49m
Frontier
Deal found 5/15![Frontier logo]()
$190
This Cheapflightsfares deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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.
Tue 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sun 6/148:00 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 5/13![JetBlue logo]()
$191
One-way flights from Indiana to MassachusettsSearch for one-way flight options from Indiana to Massachusetts. Find affordable one-way fares based on user searches. Data last updated May 16, 2026.
Search for one-way flight options from Indiana to Massachusetts. Find affordable one-way fares based on user searches. Data last updated May 16, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/912:24 pm
CVG
- BOS
1 stop13h 03m
Frontier
Deal found 5/14![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/812:46 pm
CVG
- BOS
1 stop19h 06m
Frontier
Deal found 5/13![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/96:55 am
ORD
- BOS
1 stop17h 32m
Frontier
Deal found 5/11![Frontier logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/96:00 am
MDW
- BOS
1 stop18h 27m
Frontier
Deal found 5/12![Frontier logo]()
$88
This Super.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/12![JetBlue logo]()
$91
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/97:25 pm
ORD
- BOS
Nonstop2h 37m
Delta
Deal found 5/12![Delta logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/59:23 pm
MDW
- BOS
1 stop11h 41m
Allegiant Air
Deal found 5/13![Allegiant Air logo]()
$93
This Delta deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 6/107:10 am
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 5/13![Delta logo]()
$94
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/26:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 5/12![Southwest logo]()
$94
This Super.com deal was found by Cheapflights users on 5/13. Clicking the “Pick Dates” 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 5/288:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/13![JetBlue logo]()
$97
This Cheapflightsfares deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/58:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/12![JetBlue logo]()
$98
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/17:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 5/12![Delta logo]()
$99
Find flight deals from Indiana to Massachusetts
Keep the following information in mind while searching for Indiana to Massachusetts flight deals. Data was last updated May 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $169 (Kiwi.com) |
One-way from | $81 (Kiwi.com) |
Popular in | March |
Cheapest in | June |
Average price | $447 |
Good round-trip deal | $413 or less |
Good one-way deal | $318 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Indiana 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 May 16, 2026.
Use the filters below to find and compare flights from Indiana to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 6/9
8:30 pm-11:59 pm
Nonstop2h 29m
Boston Logan Intl
Wed 6/10
6:00 am-7:59 am
Nonstop2h 59m
$187
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 6/10
7:45 pm-11:21 pm
Nonstop2h 36m
Boston Logan Intl
Tue 6/16
6:40 pm-8:40 pm
Nonstop3h 00m
$192
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 6/2
6:00 pm-9:20 pm
Nonstop2h 20m
Boston Logan Intl
Thu 6/4
5:25 am-7:00 am
Nonstop2h 35m
$192
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 6/1
6:05 am-9:29 am
Nonstop2h 24m
Boston Logan Intl
Mon 6/1
6:40 pm-8:40 pm
Nonstop3h 00m
$197
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 8/8
9:41 pm-1:14 am
Nonstop2h 33m
Boston Logan Intl
Sat 8/15
8:27 pm-10:26 pm
Nonstop2h 59m
$197
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 6/16
9:41 pm-1:14 am
Nonstop2h 33m
Boston Logan Intl
Wed 6/17
7:19 am-9:17 am
Nonstop2h 58m
$197
Quickest round-trip
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 6/12
7:35 pm-10:50 pm
Nonstop2h 15m
Boston Logan Intl
Wed 6/24
5:35 am-7:10 am
Nonstop2h 35m
$201
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 6/12
7:35 pm-10:50 pm
Nonstop2h 15m
Boston Logan Intl
Sat 6/13
5:20 am-6:55 am
Nonstop2h 35m
$201
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 7/18
9:41 pm-1:14 am
Nonstop2h 33m
Boston Logan Intl
Mon 7/27
6:43 pm-8:40 pm
Nonstop2h 57m
$201
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 6/25
7:33 am-11:05 am
Nonstop2h 32m
Boston Logan Intl
Tue 6/30
8:15 am-10:12 am
Nonstop2h 57m
$201
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Indiana to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Indiana with our price prediction graph.
MDW-BOS
ORD-BOS
CVG-BOS
CVG-ALB
ORD-BDL
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 Indiana to Massachusetts
USIN-USMA
MDW-BOS
ORD-BOS
CVG-BOS
CVG-ALB
How far ahead should I book a flight from Indiana to Massachusetts?
To ensure you get the cheapest price possible for a flight from Indiana to Massachusetts, you should look to book at least 26 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest month to book a flight from Indiana to Massachusetts?
Currently, August is the cheapest month in which you can book a flight from Indiana to Massachusetts (average of $70). Flying from Indiana to Massachusetts in January is currently the most expensive (average of $288). 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 IN to MA?
Find hourly flight availability from Indiana 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 May 16, 2026.
A simple way to save on the total cost of your ticket is to fly from Indiana to Massachusetts in the evening. If you’re flexible enough to do this you can expect to save up to 46% on your trip compared to booking a flight in the afternoon.
What is the cheapest day to fly from Indiana to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Indiana to Massachusetts. Price data was last updated on May 16, 2026.
Travelers seeking maximum savings on their Indiana to Massachusetts flight should consider departing on Friday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Indiana to Massachusetts
Explore weekly flight availability from Indiana 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 May 16, 2026.
The most flights from USIN to USMA are scheduled on a Thursday (17 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 on average).
How much does it cost to fly round-trip from Indiana 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 May 16, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Indiana to Massachusetts have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Indiana 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 Indiana 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 Indiana to Massachusetts by cabin class
Find flights from Indiana to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Indiana and Massachusetts flights
Browse other Indiana and Massachusetts flight options. Last updated on May 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Massachusetts
Find the right flight back to Indiana after your stay in Massachusetts
Indiana to Massachusetts flights
Consider these flights traveling from Indiana to Massachusetts.
Top 7 airlines flying from Indiana to Massachusetts
Discover the top 7 airlines that operate flights from Indiana 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 May 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$78 | Average$179 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$91 | Average$202 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$140 | Average$241 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$167 | Average$403 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$196 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$214 | Average$408 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$240 | Average$452 | FlexibilityNo cancel fee | On-time63% |