$62+ Cheap flights from Massachusetts to Indiana
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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — IND
Aug 3 — Aug 101
Round-trip
1 adult, Economy
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Cheapest flights from Massachusetts to IndianaExplore the most affordable flight options available from Massachusetts to Indiana. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 4, 2026.
Explore the most affordable flight options available from Massachusetts to Indiana. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 8/287:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Mon 8/3110:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Deal found 7/3![Breeze Airways logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/217:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Mon 8/2410:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Deal found 6/30![Breeze Airways logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/77:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Mon 8/1010:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Deal found 7/1![Breeze Airways logo]()
$147
This Breeze Airways deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/247:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Mon 7/2710:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Deal found 7/1![Breeze Airways logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Mon 11/96:02 am
BDL
- SDF
1 stop3h 43m
Breeze Airways
Fri 11/1310:25 am
SDF
- BDL
1 stop3h 28m
Breeze Airways
Deal found 7/2![Breeze Airways logo]()
$149
This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 7/265:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 7/1![Southwest logo]()
$170
This American Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:01 pm
BOS
- ORD
Nonstop3h 01m
American Airlines
Wed 7/226:00 am
ORD
- BOS
Nonstop2h 34m
American Airlines
Deal found 7/1![American Airlines logo]()
$170
This Southwest deal was found by Cheapflights users on 6/30. 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.
Wed 8/197:30 am
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 8/194:40 pm
MDW
- BOS
1 stop4h 35m
Southwest
Deal found 6/30![Southwest logo]()
$172
This United Airlines deal was found by Cheapflights users on 7/3. 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 7/258:20 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Tue 7/286:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 7/3![United Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Wed 8/192:56 pm
SDF
- BDL
1 stop3h 56m
Breeze Airways
Deal found 6/29![Breeze Airways logo]()
$172
This Southwest deal was found by Cheapflights users on 7/2. 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 8/257:15 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 9/96:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/2![Southwest logo]()
$173
This United Airlines deal was found by Cheapflights users on 7/3. 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 7/258:20 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Sat 9/193:35 pm
ORD
- BOS
Nonstop2h 44m
United Airlines
Deal found 7/3![United Airlines logo]()
$173
Best flights from Massachusetts to IndianaDiscover carefully curated flight deals from Massachusetts to Indiana that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 4, 2026.
Discover carefully curated flight deals from Massachusetts to Indiana that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 4, 2026.
This Southwest deal was found by Cheapflights users on 7/2. 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.
Thu 7/305:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Fri 7/317:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/2![Southwest logo]()
$170
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/225:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Sat 7/257:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 7/1![United Airlines logo]()
$172
This JetBlue deal was found by Cheapflights users on 7/2. 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.
Tue 9/15:20 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Sat 9/55:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Deal found 7/2![JetBlue logo]()
$175
This Breeze Airways deal was found by Cheapflights users on 6/30. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/107:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Wed 8/122:56 pm
SDF
- BDL
1 stop3h 56m
Breeze Airways
Deal found 6/30![Breeze Airways logo]()
$198
This Delta deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/82:32 pm
ALB
- ORD
1 stop7h 23m
Delta
Mon 8/105:30 am
ORD
- ALB
1 stop5h 07m
Delta
Deal found 6/30![Delta logo]()
$304
This United Airlines deal was found by Cheapflights users on 7/3. 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.
Wed 8/125:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Sat 8/1512:52 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 7/3![United Airlines logo]()
$172
This JetBlue deal was found by Cheapflights users on 7/2. 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 8/215:21 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Mon 8/246:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Deal found 7/2![JetBlue logo]()
$183
This American Airlines deal was found by Cheapflights users on 7/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:29 pm
ALB
- ORD
1 stop6h 01m
American Airlines
Sun 8/29:08 pm
ORD
- ALB
Nonstop2h 14m
American Airlines
Deal found 7/3![American Airlines logo]()
$369
This Southwest deal was found by Cheapflights users on 6/29. 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.
Mon 7/205:45 am
BOS
- ORD
2 stops10h 15m
Southwest
Wed 7/222:40 pm
ORD
- BOS
2 stops7h 40m
Southwest
Deal found 6/29![Southwest logo]()
$187
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Sun 8/309:40 pm
ORD
- BOS
Nonstop2h 31m
United Airlines
Deal found 7/1![United Airlines logo]()
$180
This Southwest deal was found by Cheapflights users on 6/29. 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.
Mon 7/205:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 7/228:10 am
MDW
- BOS
1 stop4h 35m
Southwest
Deal found 6/29![Southwest logo]()
$188
This JetBlue deal was found by Cheapflights users on 7/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:21 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Thu 8/278:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/3![JetBlue logo]()
$190
This Sun Country Air deal was found by Cheapflights users on 6/30. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2311:32 am
BDL
- ORD
1 stop7h 47m
Sun Country Air
Sun 7/267:30 am
ORD
- BDL
1 stop25h 49m
Sun Country Air
Deal found 6/30![Sun Country Air logo]()
$455
This JetBlue deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/44:55 pm
BOS
- ORD
1 stop6h 03m
JetBlue
Tue 9/86:00 am
ORD
- BOS
1 stop7h 41m
JetBlue
Deal found 6/29![JetBlue logo]()
$193
This United Airlines deal was found by Cheapflights users on 7/2. 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.
Thu 7/237:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sun 7/269:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 7/2![United Airlines logo]()
$196
This Southwest deal was found by Cheapflights users on 7/2. 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.
Fri 7/175:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 7/207:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/2![Southwest logo]()
$209
This JetBlue deal was found by Cheapflights users on 7/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/318:41 am
BOS
- ORD
1 stop8h 36m
JetBlue
Sat 9/121:00 pm
ORD
- BOS
1 stop6h 49m
JetBlue
Deal found 7/3![JetBlue logo]()
$202
This Southwest deal was found by Cheapflights users on 6/30. 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.
Thu 8/272:15 pm
BOS
- MDW
1 stop5h 00m
Southwest
Sun 8/306:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 6/30![Southwest logo]()
$211
This JetBlue deal was found by Cheapflights users on 7/2. 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 10/235:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Mon 10/261:00 pm
ORD
- BOS
1 stop5h 51m
JetBlue
Deal found 7/2![JetBlue logo]()
$208
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:45 am
ALB
- ORD
2 stops9h 24m
Delta
Mon 8/175:20 pm
ORD
- ALB
1 stop4h 45m
Delta
Deal found 7/1![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 6/29. 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.
Fri 8/216:40 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Tue 8/252:00 pm
MDW
- BOS
2 stops7h 10m
Southwest
Deal found 6/29![Southwest logo]()
$225
This Delta deal was found by Cheapflights users on 6/29. 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 9/189:36 am
ALB
- ORD
1 stop4h 23m
Delta
Tue 9/223:40 pm
ORD
- ALB
1 stop7h 15m
Delta
Deal found 6/29![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 7/2. 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 8/35:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Thu 8/63:20 pm
MDW
- BOS
1 stop6h 00m
Southwest
Deal found 7/2![Southwest logo]()
$225
This Delta deal was found by Cheapflights users on 7/3. 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 10/15:50 am
ALB
- ORD
2 stops11h 40m
Delta
Sat 10/311:17 am
ORD
- ALB
2 stops8h 50m
Delta
Deal found 7/3![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 7/3. 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.
Wed 7/292:30 pm
BOS
- MDW
1 stop7h 40m
Southwest
Sat 8/15:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/3![Southwest logo]()
$226
This United Airlines deal was found by Cheapflights users on 6/29. 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.
Tue 10/133:11 pm
BDL
- SDF
2 stops8h 38m
United Airlines
Thu 10/156:00 am
SDF
- BDL
1 stop3h 37m
United Airlines
Deal found 6/29![United Airlines logo]()
$303
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/297:00 am
BDL
- SDF
1 stop4h 51m
Delta
Thu 7/305:28 pm
SDF
- BDL
1 stop5h 46m
Delta
Deal found 7/1![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/238:00 pm
BOS
- MDW
1 stop5h 10m
Southwest
Sun 7/265:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 6/29![Southwest logo]()
$236
This United Airlines deal was found by Cheapflights users on 6/29. 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.
Tue 10/66:03 am
ALB
- ORD
1 stop6h 45m
United Airlines
Fri 10/97:30 am
ORD
- ALB
Nonstop2h 09m
United Airlines
Deal found 6/29![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 6/30. 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.
Thu 10/226:00 am
ALB
- MDW
1 stop4h 18m
Delta
Sun 10/251:28 pm
MDW
- ALB
2 stops9h 28m
Delta
Deal found 6/30![Delta logo]()
$349
Last-minute flights from Massachusetts to IndianaDiscover last-minute flight deals from Massachusetts to Indiana. Data last updated July 4, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Indiana. Data last updated July 4, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/185:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 7/277:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/1![Southwest logo]()
$178
This Southwest deal was found by Cheapflights users on 6/30. 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.
Wed 7/225:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Thu 7/307:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/30![Southwest logo]()
$179
This Breeze Airways deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/247:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Mon 7/2710:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Deal found 7/1![Breeze Airways logo]()
$148
This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 7/265:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 7/1![Southwest logo]()
$170
This Southwest deal was found by Cheapflights users on 7/3. 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 7/255:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 7/277:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/3![Southwest logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/77:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Mon 8/1010:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Deal found 7/1![Breeze Airways logo]()
$147
This Southwest deal was found by Cheapflights users on 7/2. 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 8/115:50 pm
BOS
- MDW
1 stop5h 30m
Southwest
Wed 8/198:45 am
MDW
- BOS
Nonstop2h 30m
Southwest
Deal found 7/2![Southwest logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Wed 8/192:56 pm
SDF
- BDL
1 stop3h 56m
Breeze Airways
Deal found 6/29![Breeze Airways logo]()
$172
This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:30 am
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 8/194:40 pm
MDW
- BOS
1 stop4h 35m
Southwest
Deal found 7/1![Southwest logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/217:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Mon 8/2410:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Deal found 6/30![Breeze Airways logo]()
$103
This Southwest deal was found by Cheapflights users on 7/2. 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 8/257:15 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 9/96:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/2![Southwest logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 8/287:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Mon 8/3110:35 am
SDF
- BDL
Nonstop2h 10m
Breeze Airways
Deal found 7/3![Breeze Airways logo]()
$98
One-way flights from Massachusetts to IndianaSearch for one-way flight options from Massachusetts to Indiana. Find affordable one-way fares based on user searches. Data last updated July 4, 2026.
Search for one-way flight options from Massachusetts to Indiana. Find affordable one-way fares based on user searches. Data last updated July 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 10/19:04 am
BOS
- IND
Nonstop2h 30m
Allegiant Air
Deal found 7/2![Allegiant Air logo]()
$62
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Deal found 7/1![Breeze Airways logo]()
$63
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/177:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Deal found 6/29![Breeze Airways logo]()
$69
This Breeze Airways deal was found by Cheapflights users on 6/30. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/77:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Deal found 6/30![Breeze Airways logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 7/4. 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.
Mon 7/277:35 am
BDL
- SDF
Nonstop2h 20m
Breeze Airways
Deal found 7/4![Breeze Airways logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 7/4. 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.
Sun 10/49:04 am
BOS
- IND
Nonstop2h 30m
Allegiant Air
Deal found 7/4![Allegiant Air logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 8/78:02 pm
ALB
- ORD
1 stop17h 13m
Multiple Airlines
Deal found 7/3![Multiple Airlines logo]()
$91
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 pm
BOS
- ORD
1 stop5h 15m
United Airlines
Deal found 7/1![United Airlines logo]()
$98
This Southwest deal was found by Cheapflights users on 7/3. 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 9/227:15 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/3![Southwest logo]()
$99
This Super.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/105:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/1![JetBlue logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 6/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/34:00 pm
BOS
- ORD
1 stop7h 06m
JetBlue
Deal found 6/29![JetBlue logo]()
$100
This JetBlue deal was found by Cheapflights users on 7/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:55 am
BOS
- ORD
1 stop5h 52m
JetBlue
Deal found 7/3![JetBlue logo]()
$101
Find flight deals from Massachusetts to Indiana
Keep the following information in mind while searching for Massachusetts to Indiana flight deals. Data was last updated July 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $98 (Kiwi.com) |
One-way from | $62 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $429 |
Good round-trip deal | $317 or less |
Good one-way deal | $149 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Massachusetts to Indiana 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 July 4, 2026.
Use the filters below to find and compare flights from Massachusetts to Indiana that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 7/30
5:25 am-7:00 am
Nonstop2h 35m
Chicago Midway
Fri 7/31
7:35 pm-10:55 pm
Nonstop2h 20m
$170
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 7/22
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
Sat 7/25
7:45 pm-11:21 pm
Nonstop2h 36m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 8/12
5:45 am-9:38 am
1 stop4h 53m
Chicago O'Hare Intl
Sat 8/15
12:52 pm-4:27 pm
Nonstop2h 35m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 9/1
5:20 pm-7:26 pm
Nonstop3h 06m
Chicago O'Hare Intl
Sat 9/5
5:27 pm-11:59 pm
1 stop5h 32m
$175
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 8/27
5:45 am-9:38 am
1 stop4h 53m
Chicago O'Hare Intl
Sun 8/30
9:40 pm-1:11 am
Nonstop2h 31m
$180
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 8/21
5:21 pm-7:27 pm
Nonstop3h 06m
Chicago O'Hare Intl
Mon 8/24
6:00 am-2:43 pm
1 stop7h 43m
$183
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 7/20
5:45 am-3:00 pm
2 stops10h 15m
Chicago O'Hare Intl
Wed 7/22
2:40 pm-11:20 pm
2 stops7h 40m
$187
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Mon 7/20
5:25 am-7:00 am
Nonstop2h 35m
Chicago Midway
Wed 7/22
8:10 am-1:45 pm
1 stop4h 35m
$188
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 8/24
5:21 pm-7:27 pm
Nonstop3h 06m
Chicago O'Hare Intl
Thu 8/27
8:20 pm-11:51 pm
Nonstop2h 31m
$190
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 9/4
4:55 pm-9:58 pm
1 stop6h 03m
Chicago O'Hare Intl
Tue 9/8
6:00 am-2:41 pm
1 stop7h 41m
$193
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Massachusetts to Indiana
Have a flexible travel schedule? Discover the best time to fly to Indiana from Massachusetts with our price prediction graph.
BDL-SDF
BOS-ORD
BOS-MDW
BDL-ORD
BOS-IND
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 Massachusetts to Indiana
USMA-USIN
BDL-SDF
BOS-ORD
BOS-MDW
BDL-ORD
What is the cheapest month to book a flight from Massachusetts to Indiana?
Currently, August is the cheapest month in which you can book a flight from Massachusetts to Indiana (average of $81). Flying from Massachusetts to Indiana in May is currently the most expensive (average of $219). 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 MA to IN?
Find hourly flight availability from Massachusetts to Indiana. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 4, 2026.
It’s optimal to fly from Massachusetts to Indiana in the morning. By choosing this option you can save up to 53% on the cost of your flight, compared to a flight in the afternoon.
Weekly flight availability from Massachusetts to Indiana
Explore weekly flight availability from Massachusetts to Indiana. 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 July 4, 2026.
The most flights from USMA to USIN are scheduled on a Monday (15 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).
How much does it cost to fly round-trip from Massachusetts to Indiana?
How far ahead should I book a flight from Massachusetts to Indiana?
The best time to book flights from Massachusetts to Indiana is 77 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Massachusetts to Indiana?
Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Indiana. Price data was last updated on June 27, 2026.
Travelers seeking maximum savings on their Massachusetts to Indiana flight should consider departing on Monday 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 Indiana
Get insights into the airlines that provide service to Indiana. 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 Indiana. Reviews last updated July 4, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Massachusetts to Indiana to help guide your decision. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Massachusetts to Indiana. 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 Massachusetts to Indiana
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Indiana by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Massachusetts to Indiana by cabin class
Find flights from Massachusetts to Indiana, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Massachusetts and Indiana flights
Browse other Massachusetts and Indiana flight options. Last updated on July 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Indiana
Find the right flight back to Massachusetts after your stay in Indiana
Massachusetts to Indiana flights
Consider these flights traveling from Massachusetts to Indiana.
Top 6 airlines flying from Massachusetts to Indiana
Discover the top 6 airlines that operate flights from Massachusetts to Indiana. 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 July 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$223 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$186 | Average$430 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$197 | Average$442 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$218 | Average$397 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$296 | Average$396 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$312 | Average$487 | FlexibilityNo cancel fee | On-time63% |