$70+ 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 4/20. Fares are subject to change and may not be available on all flights or dates of travel.
IND — BOS
May 1 — May 81
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 April 1, 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 April 1, 2026.
This American Airlines deal was found by Cheapflights users on 3/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Tue 5/126:52 pm
BOS
- ORD
Nonstop3h 12m
American Airlines
Deal found 3/27![American Airlines logo]()
$135
This SmartFares deal was found by Cheapflights users on 3/31. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Sun 5/37:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
Deal found 3/31![JetBlue logo]()
$137
This Frontier deal was found by Cheapflights users on 3/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:08 pm
ORD
- BOS
1 stop6h 23m
Frontier
Mon 4/2712:31 pm
BOS
- ORD
1 stop11h 30m
Frontier
Deal found 3/27![Frontier logo]()
$140
This Travelocity deal was found by Cheapflights users on 3/31. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/84:52 pm
MDW
- BOS
1 stop15h 20m
Frontier
Mon 5/116:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Deal found 3/31![Frontier logo]()
$140
This Delta deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/127:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Tue 5/124:30 pm
BOS
- ORD
1 stop6h 57m
Delta
Deal found 3/27![Delta logo]()
$146
This Priceline deal was found by Cheapflights users on 3/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Wed 4/227:35 pm
BOS
- ORD
Nonstop3h 04m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$149
This CheapOair deal was found by Cheapflights users on 3/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/202:15 pm
MDW
- BOS
1 stop10h 16m
Frontier
Sat 5/211:16 am
BOS
- MDW
1 stop21h 25m
Frontier
Deal found 3/27![Frontier logo]()
$151
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/19:49 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Sun 5/37:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
Deal found 3/31![JetBlue logo]()
$152
This Expedia deal was found by Cheapflights users on 3/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/133:55 pm
ORD
- BOS
1 stop16h 17m
Multiple Airlines
Wed 5/206:47 pm
BOS
- ORD
Nonstop3h 06m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$154
This Southwest deal was found by Cheapflights users on 3/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sat 5/27:15 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 3/27![Southwest logo]()
$156
This Southwest deal was found by Cheapflights users on 3/31. 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.
Fri 5/89:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 5/117:10 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 3/31![Southwest logo]()
$157
This JetBlue deal was found by Cheapflights users on 3/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/27![JetBlue logo]()
$158
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 April 1, 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 April 1, 2026.
This JetBlue deal was found by Cheapflights users on 3/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/89:49 am
ORD
- BOS
Nonstop2h 29m
JetBlue
Tue 5/126:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 3/27![JetBlue logo]()
$157
This Delta deal was found by Cheapflights users on 3/29. 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.
Sat 4/117:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Mon 4/134:55 pm
BOS
- ORD
Nonstop3h 04m
Delta
Deal found 3/29![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 3/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:50 am
MDW
- BOS
1 stop5h 00m
Southwest
Sat 5/27:15 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 3/27![Southwest logo]()
$165
This United Airlines deal was found by Cheapflights users on 3/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/59:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sun 6/75:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 3/29![United Airlines logo]()
$199
This Southwest deal was found by Cheapflights users on 3/31. 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.
Thu 4/309:00 am
MDW
- BOS
1 stop6h 05m
Southwest
Sun 5/36:10 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 3/31![Southwest logo]()
$167
This Delta deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:30 am
ORD
- BOS
1 stop6h 47m
Delta
Sun 5/107:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 3/27![Delta logo]()
$169
This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Thu 4/168:53 pm
SBN
- BOS
1 stop12h 36m
Multiple Airlines
Sun 4/198:16 pm
BOS
- SBN
1 stop13h 43m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Wed 4/152:15 pm
MDW
- BDL
1 stop23h 34m
Frontier
Sun 4/198:42 pm
BDL
- MDW
2 stops26h 37m
Frontier
Deal found 3/31![Frontier logo]()
$366
This Delta deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/57:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Thu 6/117:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 3/27![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 3/30. 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.
Tue 5/192:40 pm
ORD
- BOS
1 stop6h 50m
Southwest
Tue 5/2611:40 am
BOS
- ORD
2 stops11h 15m
Southwest
Deal found 3/30![Southwest logo]()
$182
This United Airlines deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:40 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Mon 5/256:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 3/28![United Airlines logo]()
$205
This United Airlines deal was found by Cheapflights users on 3/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/284:45 pm
SBN
- BOS
1 stop5h 14m
United Airlines
Tue 5/512:30 pm
BOS
- SBN
1 stop5h 52m
United Airlines
Deal found 3/31![United Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 3/29. 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.
Fri 5/227:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Sun 5/247:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 3/29![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 3/29. 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.
Tue 4/282:40 pm
ORD
- BOS
1 stop6h 50m
Southwest
Tue 5/56:20 am
BOS
- ORD
2 stops10h 45m
Southwest
Deal found 3/29![Southwest logo]()
$222
This United Airlines deal was found by Cheapflights users on 3/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/116:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Thu 6/188:05 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 3/31![United Airlines logo]()
$237
This Southwest deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/117:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 4/148:10 am
BOS
- MDW
1 stop6h 20m
Southwest
Deal found 3/28![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:41 pm
ORD
- BOS
1 stop5h 13m
Delta
Sun 5/107:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 3/31![Delta logo]()
$236
This United Airlines deal was found by Cheapflights users on 3/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/116:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Wed 6/178:05 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 3/31![United Airlines logo]()
$237
This Southwest deal was found by Cheapflights users on 3/29. 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.
Sun 6/215:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Fri 6/265:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 3/29![Southwest logo]()
$231
This Southwest deal was found by Cheapflights users on 3/31. 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 6/36:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sat 6/65:00 pm
BOS
- MDW
1 stop7h 05m
Southwest
Deal found 3/31![Southwest logo]()
$241
This United Airlines deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:00 pm
ORD
- ALB
Nonstop2h 03m
United Airlines
Tue 5/199:20 am
ALB
- ORD
Nonstop2h 33m
United Airlines
Deal found 3/28![United Airlines logo]()
$289
This Southwest deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/117:45 am
MDW
- BOS
1 stop7h 05m
Southwest
Sun 4/126:10 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 3/28![Southwest logo]()
$241
This Southwest deal was found by Cheapflights users on 3/29. 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.
Tue 4/283:00 pm
MDW
- BOS
1 stop6h 30m
Southwest
Tue 5/52:25 pm
BOS
- MDW
2 stops6h 10m
Southwest
Deal found 3/29![Southwest logo]()
$242
This Delta deal was found by Cheapflights users on 3/30. 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.
Tue 4/287:14 am
ORD
- ALB
1 stop4h 57m
Delta
Thu 4/305:50 am
ALB
- ORD
1 stop6h 15m
Delta
Deal found 3/30![Delta logo]()
$324
This United Airlines deal was found by Cheapflights users on 3/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:15 am
SBN
- BOS
2 stops7h 14m
United Airlines
Sat 4/256:00 am
BOS
- SBN
2 stops8h 51m
United Airlines
Deal found 3/29![United Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 3/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:00 am
MDW
- BOS
1 stop6h 10m
Southwest
Sun 4/126:10 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 3/27![Southwest logo]()
$250
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/22:04 pm
SDF
- BOS
Nonstop2h 30m
Delta
Tue 5/510:39 am
BOS
- SDF
Nonstop2h 41m
Delta
Deal found 3/31![Delta logo]()
$335
This Southwest deal was found by Cheapflights users on 3/29. 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 4/227:50 am
MDW
- BOS
2 stops7h 05m
Southwest
Sun 4/265:30 am
BOS
- MDW
1 stop4h 15m
Southwest
Deal found 3/29![Southwest logo]()
$254
This United Airlines deal was found by Cheapflights users on 3/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/203:26 pm
SBN
- BOS
2 stops8h 33m
United Airlines
Fri 4/247:00 am
BOS
- SBN
1 stop7h 51m
United Airlines
Deal found 3/29![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/223:30 pm
CVG
- BOS
1 stop6h 58m
Delta
Sat 7/48:10 am
BOS
- CVG
Nonstop2h 29m
Delta
Deal found 3/26![Delta logo]()
$349
Last-minute flights from Indiana to MassachusettsDiscover last-minute flight deals from Indiana to Massachusetts. Data last updated April 1, 2026 and is based on user searches.
Discover last-minute flight deals from Indiana to Massachusetts. Data last updated April 1, 2026 and is based on user searches.
This JetBlue deal was found by Cheapflights users on 3/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/27![JetBlue logo]()
$158
This Priceline deal was found by Cheapflights users on 3/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/132:56 pm
MDW
- BOS
1 stop9h 30m
Frontier
Sat 5/210:25 am
BOS
- MDW
1 stop9h 12m
Frontier
Deal found 3/28![Frontier logo]()
$160
This Expedia deal was found by Cheapflights users on 3/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/191:12 pm
ORD
- BOS
1 stop21h 35m
Multiple Airlines
Thu 4/237:35 pm
BOS
- ORD
Nonstop3h 04m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$154
This CheapOair deal was found by Cheapflights users on 3/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/202:15 pm
MDW
- BOS
1 stop10h 16m
Frontier
Sat 5/211:16 am
BOS
- MDW
1 stop21h 25m
Frontier
Deal found 3/27![Frontier logo]()
$151
This Southwest deal was found by Cheapflights users on 3/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sat 5/27:15 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 3/27![Southwest logo]()
$156
This Frontier deal was found by Cheapflights users on 3/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:08 pm
ORD
- BOS
1 stop6h 23m
Frontier
Mon 4/2712:31 pm
BOS
- ORD
1 stop11h 30m
Frontier
Deal found 3/27![Frontier logo]()
$140
This Priceline deal was found by Cheapflights users on 3/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Wed 4/227:35 pm
BOS
- ORD
Nonstop3h 04m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$149
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/289:41 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Tue 5/57:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Deal found 3/31![JetBlue logo]()
$152
This Frontier deal was found by Cheapflights users on 3/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:15 pm
MDW
- BOS
1 stop10h 16m
Frontier
Tue 5/56:00 am
BOS
- MDW
1 stop6h 12m
Frontier
Deal found 3/29![Frontier logo]()
$140
This Frontier deal was found by Cheapflights users on 3/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:08 pm
ORD
- BOS
1 stop6h 23m
Frontier
Wed 5/1310:07 am
BOS
- ORD
1 stop14h 06m
Frontier
Deal found 3/31![Frontier logo]()
$160
This SmartFares deal was found by Cheapflights users on 3/31. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Sun 5/37:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
Deal found 3/31![JetBlue logo]()
$137
This Southwest deal was found by Cheapflights users on 3/31. 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.
Thu 4/307:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sun 5/36:10 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 3/31![Southwest logo]()
$157
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 April 1, 2026.
Search for one-way flight options from Indiana to Massachusetts. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
This Expedia deal was found by Cheapflights users on 3/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/204:28 pm
ORD
- BOS
1 stop8h 03m
Frontier
Deal found 3/28![Frontier logo]()
$70
This Expedia deal was found by Cheapflights users on 3/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/47:46 pm
CVG
- BOS
1 stop5h 45m
Frontier
Deal found 3/27![Frontier logo]()
$70
This Priceline deal was found by Cheapflights users on 3/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/305:50 am
ORD
- BDL
1 stop7h 59m
Frontier
Deal found 3/31![Frontier logo]()
$70
This Frontier deal was found by Cheapflights users on 3/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:00 am
MDW
- BDL
1 stop7h 49m
Frontier
Deal found 3/27![Frontier logo]()
$70
This Expedia deal was found by Cheapflights users on 3/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/191:12 pm
ORD
- BOS
1 stop21h 35m
Frontier
Deal found 3/29![Frontier logo]()
$76
This Frontier deal was found by Cheapflights users on 3/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:15 pm
MDW
- BOS
1 stop10h 16m
Frontier
Deal found 3/27![Frontier logo]()
$76
This Expedia deal was found by Cheapflights users on 3/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/199:30 pm
CVG
- BOS
1 stop11h 42m
Frontier
Deal found 3/31![Frontier logo]()
$76
This Expedia deal was found by Cheapflights users on 3/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:07 pm
IND
- BOS
1 stop11h 05m
Frontier
Deal found 3/31![Frontier logo]()
$76
This Priceline deal was found by Cheapflights users on 3/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:00 am
MDW
- BDL
1 stop9h 21m
Frontier
Deal found 3/31![Frontier logo]()
$76
This Jettzy deal was found by Cheapflights users on 3/27. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1612:16 pm
ORD
- BOS
1 stop22h 31m
Frontier
Deal found 3/27![Frontier logo]()
$77
This Jettzy deal was found by Cheapflights users on 3/29. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/189:14 am
MDW
- BOS
1 stop24h 02m
Frontier
Deal found 3/29![Frontier logo]()
$77
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Deal found 3/31![JetBlue logo]()
$78
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 April 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $137 (SmartFares) |
One-way from | $70 (Expedia) |
Popular in | November |
Cheapest in | June |
Average price | $390 |
Good round-trip deal | $405 or less |
Good one-way deal | $358 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 April 1, 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
Fri 5/8
9:49 am-1:18 pm
Nonstop2h 29m
Boston Logan Intl
Tue 5/12
6:47 pm-8:53 pm
Nonstop3h 06m
$157
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 4/11
7:00 am-10:25 am
Nonstop2h 25m
Boston Logan Intl
Mon 4/13
4:55 pm-6:59 pm
Nonstop3h 04m
$157
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Mon 4/20
7:50 am-1:50 pm
1 stop5h 00m
Boston Logan Intl
Sat 5/2
7:15 am-9:05 am
Nonstop2h 50m
$165
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Thu 4/30
9:00 am-4:05 pm
1 stop6h 05m
Boston Logan Intl
Sun 5/3
6:10 am-7:55 am
Nonstop2h 45m
$167
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 5/7
5:30 am-1:17 pm
1 stop6h 47m
Boston Logan Intl
Sun 5/10
7:35 am-9:27 am
Nonstop2h 52m
$169
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 6/5
7:16 pm-10:50 pm
Nonstop2h 34m
Boston Logan Intl
Thu 6/11
7:30 am-9:28 am
Nonstop2h 58m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 5/19
2:40 pm-10:30 pm
1 stop6h 50m
Boston Logan Intl
Tue 5/26
11:40 am-9:55 pm
2 stops11h 15m
$182
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 6/5
9:26 pm-12:59 am
Nonstop2h 33m
Boston Logan Intl
Sun 6/7
5:45 am-9:36 am
1 stop4h 51m
$199
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/23
7:40 pm-11:16 pm
Nonstop2h 36m
Boston Logan Intl
Mon 5/25
6:00 am-7:58 am
Nonstop2h 58m
$205
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 5/22
7:16 pm-10:50 pm
Nonstop2h 34m
Boston Logan Intl
Sun 5/24
7:35 am-9:27 am
Nonstop2h 52m
$217
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.
ORD-BOS
MDW-BOS
SBN-BOS
MDW-BDL
ORD-ALB
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
ORD-BOS
MDW-BOS
SBN-BOS
MDW-BDL
What is the cheapest month to book a flight from Indiana to Massachusetts?
Currently, May is the cheapest month in which you can book a flight from Indiana to Massachusetts (average of $85). Flying from Indiana to Massachusetts in January is currently the most expensive (average of $294). 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 April 1, 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 March 28, 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 April 1, 2026.
The most flights from USIN to USMA are scheduled on a Monday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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 April 1, 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.
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
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.
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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 April 1, 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 April 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$152 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$112 | Average$232 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$140 | Average$223 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$158 | Average$401 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$196 | Average$450 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$216 | Average$417 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$240 | Average$446 | FlexibilityNo cancel fee | On-time63% |