$94+ 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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — IND
Aug 16 — Aug 231
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 17, 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 17, 2026.
This SmartFares deal was found by Cheapflights users on 7/13. 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.
Mon 8/244:55 pm
BOS
- ORD
1 stop6h 03m
JetBlue
Mon 8/319:35 am
ORD
- BOS
1 stop8h 22m
JetBlue
Deal found 7/13![JetBlue logo]()
$176
This deal was found by Cheapflights users on 7/14. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:05 am
BOS
- ORD
1 stop5h 51m
JetBlue
Sat 11/148:24 pm
ORD
- BOS
Nonstop2h 32m
JetBlue
Deal found 7/14![JetBlue logo]()
$178
This Super.com deal was found by Cheapflights users on 7/13. 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.
Tue 8/45:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Thu 8/69:35 am
ORD
- BOS
1 stop8h 22m
JetBlue
Deal found 7/13![JetBlue logo]()
$179
This Super.com deal was found by Cheapflights users on 7/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:01 am
BOS
- ORD
1 stop4h 45m
JetBlue
Mon 8/315:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Deal found 7/14![JetBlue logo]()
$183
This SmartFares deal was found by Cheapflights users on 7/15. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Sat 8/296:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 7/15![JetBlue logo]()
$184
This SmartFares deal was found by Cheapflights users on 7/14. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/264:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Thu 8/276:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 7/14![JetBlue logo]()
$186
This Super.com deal was found by Cheapflights users on 7/13. 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 10/224:00 pm
BOS
- ORD
1 stop6h 56m
JetBlue
Sat 10/248:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 7/13![JetBlue logo]()
$187
This Super.com deal was found by Cheapflights users on 7/13. 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.
Tue 9/155:15 am
BOS
- ORD
1 stop7h 32m
JetBlue
Wed 9/168:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 7/13![JetBlue logo]()
$188
This SmartFares deal was found by Cheapflights users on 7/15. 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 SmartFares 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 7/15![JetBlue logo]()
$190
This Southwest deal was found by Cheapflights users on 7/14. 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.
Sat 10/179:40 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 10/206:10 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/14![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 7/14. 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.
Sat 9/267:05 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 9/276:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/14![Southwest logo]()
$206
This Southwest deal was found by Cheapflights users on 7/14. 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 9/227:15 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 9/233:05 pm
MDW
- BOS
1 stop5h 20m
Southwest
Deal found 7/14![Southwest logo]()
$207
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 17, 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 17, 2026.
This JetBlue deal was found by Cheapflights users on 7/15. 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.
Sat 9/195:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Tue 9/229:38 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 7/15![JetBlue logo]()
$197
This Southwest deal was found by Cheapflights users on 7/15. 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.
Sun 8/239:05 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Thu 8/275:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/15![Southwest logo]()
$215
This United Airlines deal was found by Cheapflights users on 7/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/193:30 pm
BOS
- ORD
Nonstop2h 52m
United Airlines
Thu 8/209:40 pm
ORD
- BOS
Nonstop2h 31m
United Airlines
Deal found 7/14![United Airlines logo]()
$215
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/164:15 pm
ORH
- ORD
1 stop6h 57m
Delta
Sun 10/187:00 am
ORD
- ORH
1 stop6h 59m
Delta
Deal found 7/17![Delta logo]()
$230
This JetBlue deal was found by Cheapflights users on 7/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Thu 8/206:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Deal found 7/12![JetBlue logo]()
$201
This Southwest deal was found by Cheapflights users on 7/12. 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 9/48:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Mon 9/75:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/12![Southwest logo]()
$215
This United Airlines deal was found by Cheapflights users on 7/13. 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.
Thu 9/245:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Sun 9/277:30 am
ORD
- BOS
Nonstop2h 34m
United Airlines
Deal found 7/13![United Airlines logo]()
$225
This Delta deal was found by Cheapflights users on 7/12. 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 8/178:50 pm
BOS
- ORD
Nonstop2h 54m
Delta
Fri 8/217:30 pm
ORD
- BOS
Nonstop2h 30m
Delta
Deal found 7/12![Delta logo]()
$236
This JetBlue deal was found by Cheapflights users on 7/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:15 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Fri 8/218:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/12![JetBlue logo]()
$215
This Southwest deal was found by Cheapflights users on 7/14. 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.
Sun 8/165:30 am
BOS
- MDW
1 stop5h 25m
Southwest
Wed 8/196:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/14![Southwest logo]()
$225
This United Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/129:00 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Sat 8/1510:25 am
ORD
- BOS
Nonstop2h 42m
United Airlines
Deal found 7/17![United Airlines logo]()
$225
This Southwest deal was found by Cheapflights users on 7/14. 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 8/47:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Fri 8/73:20 pm
MDW
- BOS
1 stop6h 00m
Southwest
Deal found 7/14![Southwest logo]()
$225
This Southwest deal was found by Cheapflights users on 7/13. 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.
Wed 8/193:20 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 8/256:00 am
MDW
- BOS
1 stop6h 45m
Southwest
Deal found 7/13![Southwest logo]()
$225
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 9/55:06 pm
ALB
- ORD
1 stop4h 24m
Delta
Sun 9/66:40 am
ORD
- ALB
1 stop5h 46m
Delta
Deal found 7/17![Delta logo]()
$277
This United Airlines deal was found by Cheapflights users on 7/13. 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.
Thu 7/235:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Thu 7/309:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 7/13![United Airlines logo]()
$261
This Southwest deal was found by Cheapflights users on 7/13. 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.
Wed 8/1210:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Fri 8/147:55 am
MDW
- BOS
2 stops7h 15m
Southwest
Deal found 7/13![Southwest logo]()
$230
This United Airlines deal was found by Cheapflights users on 7/15. 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.
Tue 7/287:27 pm
BOS
- ORD
1 stop5h 04m
United Airlines
Mon 8/106:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 7/15![United Airlines logo]()
$261
This Delta deal was found by Cheapflights users on 7/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Mon 8/248:48 am
ORD
- ORH
2 stops7h 12m
Delta
Deal found 7/16![Delta logo]()
$292
This Southwest deal was found by Cheapflights users on 7/15. 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.
Wed 8/268:15 am
BOS
- MDW
2 stops6h 15m
Southwest
Thu 8/275:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/15![Southwest logo]()
$230
This JetBlue deal was found by Cheapflights users on 7/15. 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.
Fri 9/186:25 am
BDL
- ORD
1 stop6h 22m
JetBlue
Sun 9/203:00 pm
ORD
- BDL
1 stop7h 14m
JetBlue
Deal found 7/15![JetBlue logo]()
$321
This United Airlines deal was found by Cheapflights users on 7/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/277:27 pm
BOS
- ORD
1 stop5h 04m
United Airlines
Mon 8/39:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 7/14![United Airlines logo]()
$274
This Delta deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 9/1112:35 pm
ALB
- ORD
2 stops8h 55m
Delta
Mon 9/1411:17 am
ORD
- ALB
1 stop4h 01m
Delta
Deal found 7/17![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 7/12. 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 8/287:30 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 9/18:40 am
MDW
- BOS
2 stops6h 20m
Southwest
Deal found 7/12![Southwest logo]()
$230
This JetBlue deal was found by Cheapflights users on 7/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:07 pm
BDL
- ORD
1 stop7h 37m
JetBlue
Sun 9/65:27 pm
ORD
- BDL
1 stop5h 32m
JetBlue
Deal found 7/16![JetBlue logo]()
$338
This United Airlines deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/76:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sun 8/99:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 7/17![United Airlines logo]()
$280
This Southwest deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 8/125:35 am
BOS
- MDW
1 stop7h 15m
Southwest
Sat 8/153:10 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/17![Southwest logo]()
$235
This Delta deal was found by Cheapflights users on 7/15. 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.
Fri 10/24:20 pm
ORH
- ORD
2 stops8h 39m
Delta
Sun 10/47:00 am
ORD
- ORH
1 stop7h 37m
Delta
Deal found 7/15![Delta logo]()
$321
This United Airlines deal was found by Cheapflights users on 7/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Wed 8/56:20 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 7/14![United Airlines logo]()
$290
This Southwest deal was found by Cheapflights users on 7/13. 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 8/218:40 am
BOS
- MDW
2 stops9h 25m
Southwest
Mon 8/245:55 am
MDW
- BOS
1 stop6h 40m
Southwest
Deal found 7/13![Southwest logo]()
$240
This Delta deal was found by Cheapflights users on 7/15. 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.
Fri 9/256:23 pm
ALB
- MDW
1 stop5h 22m
Delta
Wed 9/301:19 pm
MDW
- ALB
2 stops8h 40m
Delta
Deal found 7/15![Delta logo]()
$328
Last-minute flights from Massachusetts to IndianaDiscover last-minute flight deals from Massachusetts to Indiana. Data last updated July 17, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Indiana. Data last updated July 17, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/315:16 pm
ORH
- ORD
1 stop16h 54m
American Airlines
Tue 8/46:37 am
ORD
- ORH
1 stop9h 14m
American Airlines
Deal found 7/16![American Airlines logo]()
$230
This Super.com deal was found by Cheapflights users on 7/13. 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.
Tue 8/45:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Thu 8/69:35 am
ORD
- BOS
1 stop8h 22m
JetBlue
Deal found 7/13![JetBlue logo]()
$179
This Super.com deal was found by Cheapflights users on 7/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:01 am
BOS
- ORD
1 stop4h 46m
JetBlue
Sat 8/85:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Deal found 7/15![JetBlue logo]()
$193
This Super.com deal was found by Cheapflights users on 7/12. 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.
Wed 8/55:01 am
BOS
- ORD
1 stop4h 46m
JetBlue
Tue 8/118:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/12![JetBlue logo]()
$195
This Southwest deal was found by Cheapflights users on 7/13. 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.
Thu 8/137:30 am
BOS
- MDW
Nonstop2h 35m
Southwest
Thu 8/205:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/13![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 7/12. 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 8/143:25 pm
BOS
- MDW
1 stop7h 55m
Southwest
Thu 8/205:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/12![Southwest logo]()
$225
This SmartFares deal was found by Cheapflights users on 7/15. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Sat 8/296:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 7/15![JetBlue logo]()
$184
This SmartFares deal was found by Cheapflights users on 7/13. 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.
Mon 8/244:55 pm
BOS
- ORD
1 stop6h 03m
JetBlue
Mon 8/319:35 am
ORD
- BOS
1 stop8h 22m
JetBlue
Deal found 7/13![JetBlue logo]()
$176
This SmartFares deal was found by Cheapflights users on 7/15. 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 SmartFares 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 7/15![JetBlue logo]()
$190
This SmartFares deal was found by Cheapflights users on 7/14. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/264:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Thu 8/276:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 7/14![JetBlue logo]()
$186
This Super.com deal was found by Cheapflights users on 7/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:01 am
BOS
- ORD
1 stop4h 45m
JetBlue
Mon 8/315:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Deal found 7/14![JetBlue logo]()
$183
This SmartFares deal was found by Cheapflights users on 7/16. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/305:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Sun 9/65:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Deal found 7/16![JetBlue logo]()
$194
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 17, 2026.
Search for one-way flight options from Massachusetts to Indiana. Find affordable one-way fares based on user searches. Data last updated July 17, 2026.
This Super.com deal was found by Cheapflights users on 7/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/284:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/14![JetBlue logo]()
$94
This Flysmarter deal was found by Cheapflights users on 7/14. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:55 am
BOS
- ORD
Nonstop2h 51m
JetBlue
Deal found 7/14![JetBlue logo]()
$96
This Cheapflightsfares deal was found by Cheapflights users on 7/13. 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 9/225:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Deal found 7/13![JetBlue logo]()
$97
This Southwest deal was found by Cheapflights users on 7/13. 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.
Sat 9/267:05 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/13![Southwest logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 7/13. 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.
Mon 9/286:55 am
BOS
- ORD
1 stop5h 52m
JetBlue
Deal found 7/13![JetBlue logo]()
$99
This American Airlines deal was found by Cheapflights users on 7/15. 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.
Sat 9/127:17 pm
BOS
- ORD
Nonstop3h 18m
American Airlines
Deal found 7/15![American Airlines logo]()
$100
This JetBlue deal was found by Cheapflights users on 7/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/104:00 pm
BOS
- ORD
1 stop7h 06m
JetBlue
Deal found 7/12![JetBlue logo]()
$101
This Cheapflightsfares deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” 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 9/165:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Deal found 7/17![JetBlue logo]()
$102
This Southwest deal was found by Cheapflights users on 7/16. 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.
Wed 9/1610:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Deal found 7/16![Southwest logo]()
$104
This Delta deal was found by Cheapflights users on 7/15. 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.
Tue 10/134:15 pm
ORH
- ORD
1 stop5h 28m
Delta
Deal found 7/15![Delta logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 7/13. 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.
Thu 10/112:34 pm
BOS
- CVG
1 stop24h 40m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$104
This Super.com deal was found by Cheapflights users on 7/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/28:07 am
BOS
- ORD
Nonstop2h 58m
JetBlue
Deal found 7/14![JetBlue logo]()
$105
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 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $176 (SmartFares) |
One-way from | $94 (Super.com) |
Popular in | March |
Cheapest in | August |
Average price | $439 |
Good round-trip deal | $319 or less |
Good one-way deal | $157 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 17, 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
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 9/19
5:00 pm-7:22 pm
Nonstop3h 22m
Chicago O'Hare Intl
Tue 9/22
9:38 am-1:06 pm
Nonstop2h 28m
$197
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 8/18
2:45 pm-9:58 pm
1 stop8h 13m
Chicago O'Hare Intl
Thu 8/20
6:00 am-2:43 pm
1 stop7h 43m
$201
Quickest round-trip
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sun 8/23
9:05 pm-10:40 pm
Nonstop2h 35m
Chicago Midway
Thu 8/27
5:45 am-9:00 am
Nonstop2h 15m
$215
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 8/19
3:30 pm-5:22 pm
Nonstop2h 52m
Chicago O'Hare Intl
Thu 8/20
9:40 pm-1:11 am
Nonstop2h 31m
$215
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 9/4
8:20 pm-10:00 pm
Nonstop2h 40m
Chicago Midway
Mon 9/7
5:45 am-9:00 am
Nonstop2h 15m
$215
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 8/19
8:15 am-10:11 am
Nonstop2h 56m
Chicago O'Hare Intl
Fri 8/21
8:20 pm-11:51 pm
Nonstop2h 31m
$215
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 9/24
5:45 am-9:38 am
1 stop4h 53m
Chicago O'Hare Intl
Sun 9/27
7:30 am-11:04 am
Nonstop2h 34m
$225
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sun 8/16
5:30 am-9:55 am
1 stop5h 25m
Chicago Midway
Wed 8/19
6:40 am-9:55 am
Nonstop2h 15m
$225
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 8/12
9:00 am-10:59 am
Nonstop2h 59m
Chicago O'Hare Intl
Sat 8/15
10:25 am-2:07 pm
Nonstop2h 42m
$225
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 8/4
7:20 pm-9:00 pm
Nonstop2h 40m
Chicago Midway
Fri 8/7
3:20 pm-10:20 pm
1 stop6h 00m
$225
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.
BOS-MDW
BOS-ORD
ORH-ORD
BOS-CVG
ALB-ORD
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
BOS-MDW
BOS-ORD
ORH-ORD
BOS-CVG
What is the cheapest month to book a flight from Massachusetts to Indiana?
Currently, January is the cheapest month in which you can book a flight from Massachusetts to Indiana (average of $415). Flying from Massachusetts to Indiana in March is currently the most expensive (average of $531). 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 17, 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 17, 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 July 11, 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 17, 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.
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
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 17, 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 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$116 | Average$225 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$178 | Average$430 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$197 | Average$442 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$218 | Average$360 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$296 | Average$396 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$312 | Average$487 | FlexibilityNo cancel fee | On-time63% |