$56+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — IND
Aug 28 — Sep 41
Round-trip
1 adult, Economy
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Find cheap flights from Massachusetts to Indiana with Cheapflights
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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 29, 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 29, 2026.
This Flysmarter deal was found by Cheapflights users on 7/28. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:00 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Sun 9/137:00 am
ORD
- BOS
1 stop7h 14m
JetBlue
Deal found 7/28![JetBlue logo]()
$203
This deal was found by Cheapflights users on 7/27. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/145:15 am
BOS
- ORD
1 stop5h 43m
JetBlue
Mon 10/129:38 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 7/27![JetBlue logo]()
$204
This Super.com deal was found by Cheapflights users on 7/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Tue 8/259:40 am
ORD
- BOS
1 stop6h 37m
JetBlue
Deal found 7/27![JetBlue logo]()
$211
This Super.com deal was found by Cheapflights users on 7/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:00 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Sat 9/1210:59 am
ORD
- BOS
1 stop5h 22m
JetBlue
Deal found 7/28![JetBlue logo]()
$212
This Super.com deal was found by Cheapflights users on 7/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:15 am
BOS
- ORD
1 stop5h 43m
JetBlue
Fri 9/117:00 am
ORD
- BOS
1 stop6h 27m
JetBlue
Deal found 7/28![JetBlue logo]()
$213
This Super.com deal was found by Cheapflights users on 7/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:15 am
BOS
- ORD
1 stop5h 43m
JetBlue
Sun 9/137:00 am
ORD
- BOS
1 stop5h 44m
JetBlue
Deal found 7/28![JetBlue logo]()
$214
This Super.com deal was found by Cheapflights users on 7/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:00 am
BOS
- ORD
Nonstop2h 48m
JetBlue
Wed 9/98:24 pm
ORD
- BOS
Nonstop2h 45m
JetBlue
Deal found 7/27![JetBlue logo]()
$215
This Super.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/1812:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Wed 9/99:38 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 7/24![JetBlue logo]()
$216
This Southwest deal was found by Cheapflights users on 7/29. 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 9/910:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Sat 9/129:05 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/29![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 7/29. 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.
Wed 9/97:30 am
BOS
- ORD
Nonstop2h 54m
Delta
Sat 9/124:35 pm
ORD
- BOS
Nonstop2h 45m
Delta
Deal found 7/29![Delta logo]()
$217
This Super.com deal was found by Cheapflights users on 7/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1812:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Thu 8/208:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/28![JetBlue logo]()
$218
This Super.com deal was found by Cheapflights users on 7/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Mon 8/248:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/27![JetBlue logo]()
$220
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 29, 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 29, 2026.
This JetBlue deal was found by Cheapflights users on 7/27. 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.
Wed 9/235:00 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Tue 9/299:38 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 7/27![JetBlue logo]()
$217
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 10/155:50 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 10/206:10 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/24![Southwest logo]()
$222
This United Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 9/173:13 pm
BOS
- ORD
Nonstop2h 52m
United Airlines
Tue 9/221:55 pm
ORD
- BOS
Nonstop2h 41m
United Airlines
Deal found 7/25![United Airlines logo]()
$222
This Delta deal was found by Cheapflights users on 7/27. 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.
Wed 9/97:30 am
BOS
- ORD
Nonstop2h 54m
Delta
Thu 9/107:30 pm
ORD
- BOS
Nonstop2h 39m
Delta
Deal found 7/27![Delta logo]()
$222
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/121:00 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 9/136:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/24![Southwest logo]()
$222
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/39:00 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Fri 9/46:15 am
ORD
- BOS
Nonstop2h 21m
United Airlines
Deal found 7/24![United Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:40 pm
BOS
- ORD
Nonstop2h 51m
Delta
Mon 10/267:25 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 7/28![Delta logo]()
$227
This JetBlue deal was found by Cheapflights users on 7/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/224:43 pm
BOS
- ORD
1 stop6h 15m
JetBlue
Thu 8/275:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Deal found 7/28![JetBlue logo]()
$231
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:30 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Mon 11/93:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/25![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 7/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:25 pm
BOS
- ORD
Nonstop3h 04m
United Airlines
Sun 11/156:15 am
ORD
- BOS
Nonstop2h 19m
United Airlines
Deal found 7/26![United Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:30 am
BOS
- ORD
Nonstop2h 54m
Delta
Mon 9/217:35 am
ORD
- BOS
Nonstop2h 33m
Delta
Deal found 7/28![Delta logo]()
$227
This JetBlue deal was found by Cheapflights users on 7/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/214:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Tue 8/259:40 am
ORD
- BOS
1 stop6h 37m
JetBlue
Deal found 7/28![JetBlue logo]()
$231
This Southwest deal was found by Cheapflights users on 7/27. 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 10/14:50 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Sun 10/45:00 am
MDW
- BOS
Nonstop2h 25m
Southwest
Deal found 7/27![Southwest logo]()
$227
This JetBlue deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 9/85:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Tue 9/157:05 am
ORD
- BOS
1 stop6h 22m
JetBlue
Deal found 7/25![JetBlue logo]()
$233
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/257:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Thu 8/277:55 am
ORD
- BOS
Nonstop2h 29m
Delta
Deal found 7/28![Delta logo]()
$235
This Southwest deal was found by Cheapflights users on 7/28. 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.
Fri 9/43:55 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 9/68:45 am
MDW
- BOS
Nonstop2h 30m
Southwest
Deal found 7/28![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/121:35 pm
BOS
- ORD
Nonstop2h 51m
Delta
Sun 9/137:35 am
ORD
- BOS
Nonstop2h 33m
Delta
Deal found 7/24![Delta logo]()
$236
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:35 pm
ALB
- ORD
1 stop4h 57m
United Airlines
Wed 10/214:00 pm
ORD
- ALB
1 stop6h 44m
United Airlines
Deal found 7/24![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 7/28. 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.
Mon 8/178:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Thu 9/106:30 pm
MDW
- BOS
Nonstop2h 25m
Southwest
Deal found 7/28![Southwest logo]()
$236
This Southwest deal was found by Cheapflights users on 7/28. 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 8/297:05 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 9/112:45 pm
MDW
- BOS
1 stop4h 50m
Southwest
Deal found 7/28![Southwest logo]()
$237
This United Airlines deal was found by Cheapflights users on 7/28. 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 8/299:40 am
BDL
- ORD
Nonstop2h 46m
United Airlines
Wed 9/26:15 pm
ORD
- BDL
1 stop4h 44m
United Airlines
Deal found 7/28![United Airlines logo]()
$287
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:23 pm
ALB
- ORD
1 stop6h 36m
Delta
Thu 10/16:00 am
ORD
- ALB
1 stop4h 49m
Delta
Deal found 7/28![Delta logo]()
$277
This JetBlue deal was found by Cheapflights users on 7/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:07 pm
BDL
- ORD
1 stop7h 37m
JetBlue
Fri 8/145:27 pm
ORD
- BDL
1 stop5h 53m
JetBlue
Deal found 7/28![JetBlue logo]()
$315
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/288:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Mon 8/313:20 pm
MDW
- BOS
1 stop6h 00m
Southwest
Deal found 7/24![Southwest logo]()
$237
This United Airlines deal was found by Cheapflights users on 7/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:00 am
BDL
- ORD
Nonstop2h 46m
United Airlines
Thu 9/178:42 am
ORD
- BDL
1 stop4h 23m
United Airlines
Deal found 7/27![United Airlines logo]()
$287
This Delta deal was found by Cheapflights users on 7/26. 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.
Sat 8/296:35 am
ALB
- MDW
2 stops10h 03m
Delta
Mon 8/315:45 pm
MDW
- ALB
1 stop4h 20m
Delta
Deal found 7/26![Delta logo]()
$282
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 9/44:30 pm
BOS
- MDW
1 stop7h 55m
Southwest
Mon 9/75:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/25![Southwest logo]()
$237
This JetBlue deal was found by Cheapflights users on 7/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:07 pm
BDL
- ORD
1 stop7h 37m
JetBlue
Tue 8/256:30 pm
ORD
- BDL
1 stop4h 50m
JetBlue
Deal found 7/28![JetBlue logo]()
$318
This United Airlines deal was found by Cheapflights users on 7/28. 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.
Fri 9/411:44 am
BDL
- ORD
Nonstop2h 45m
United Airlines
Mon 9/77:15 am
ORD
- BDL
Nonstop2h 23m
United Airlines
Deal found 7/28![United Airlines logo]()
$300
This Southwest deal was found by Cheapflights users on 7/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/191:20 pm
BOS
- MDW
1 stop6h 25m
Southwest
Sun 8/236:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/26![Southwest logo]()
$237
Last-minute flights from Massachusetts to IndianaDiscover last-minute flight deals from Massachusetts to Indiana. Data last updated July 29, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Indiana. Data last updated July 29, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 7/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/118:15 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Tue 8/186:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Deal found 7/28![JetBlue logo]()
$223
This Super.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/115:21 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Fri 8/145:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Deal found 7/24![JetBlue logo]()
$225
This Southwest deal was found by Cheapflights users on 7/28. 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.
Wed 8/127:30 am
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 8/198:45 am
MDW
- BOS
Nonstop2h 30m
Southwest
Deal found 7/28![Southwest logo]()
$236
This Super.com deal was found by Cheapflights users on 7/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:21 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Sat 8/226:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 7/27![JetBlue logo]()
$220
This Super.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/182:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Thu 8/209:35 am
ORD
- BOS
1 stop6h 32m
JetBlue
Deal found 7/24![JetBlue logo]()
$212
This Super.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/1812:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Wed 9/99:38 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 7/24![JetBlue logo]()
$216
This Super.com deal was found by Cheapflights users on 7/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/188:15 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Sat 8/226:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 7/26![JetBlue logo]()
$221
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/186:00 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Wed 9/99:07 am
ORD
- BOS
Nonstop2h 43m
United Airlines
Deal found 7/24![United Airlines logo]()
$222
This Super.com deal was found by Cheapflights users on 7/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Tue 8/259:40 am
ORD
- BOS
1 stop6h 37m
JetBlue
Deal found 7/27![JetBlue logo]()
$211
This Southwest deal was found by Cheapflights users on 7/28. 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.
Thu 8/207:30 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 8/236:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/28![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 7/27. 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.
Sat 8/225:30 am
BOS
- MDW
1 stop5h 00m
Southwest
Mon 8/245:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/27![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 7/28. 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.
Mon 8/313:55 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 8/316:30 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/28![Southwest logo]()
$222
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 29, 2026.
Search for one-way flight options from Massachusetts to Indiana. Find affordable one-way fares based on user searches. Data last updated July 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2312:45 pm
BOS
- CVG
1 stop22h 36m
Frontier
Deal found 7/27![Frontier logo]()
$56
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/239:36 am
BOS
- ORD
1 stop23h 17m
Frontier
Deal found 7/27![Frontier logo]()
$103
This Super.com deal was found by Cheapflights users on 7/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/224:43 pm
BOS
- ORD
1 stop6h 15m
JetBlue
Deal found 7/28![JetBlue logo]()
$106
This Super.com deal was found by Cheapflights users on 7/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/214:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/27![JetBlue logo]()
$107
This Cheapflightsfares deal was found by Cheapflights users on 7/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:55 am
BOS
- ORD
Nonstop2h 51m
JetBlue
Deal found 7/28![JetBlue logo]()
$108
This Southwest deal was found by Cheapflights users on 7/27. 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.
Sat 9/198:40 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/27![Southwest logo]()
$109
This Delta deal was found by Cheapflights users on 7/29. 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 9/266:00 pm
BOS
- ORD
Nonstop2h 59m
Delta
Deal found 7/29![Delta logo]()
$109
This Flysmarter deal was found by Cheapflights users on 7/29. 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 Flysmarter 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 7/29![JetBlue logo]()
$110
This Super.com deal was found by Cheapflights users on 7/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/26![JetBlue logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2910:04 am
BOS
- CVG
1 stop13h 38m
Frontier
Deal found 7/28![Frontier logo]()
$113
This Southwest deal was found by Cheapflights users on 7/28. 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.
Thu 9/248:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 7/28![Southwest logo]()
$114
This Delta deal was found by Cheapflights users on 7/27. 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 8/277:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 7/27![Delta logo]()
$114
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 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $203 (Flysmarter) |
One-way from | $56 (Kiwi.com) |
Popular in | March |
Cheapest in | February |
Average price | $437 |
Good round-trip deal | $423 or less |
Good one-way deal | $214 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 29, 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
Wed 9/23
5:00 pm-7:01 pm
Nonstop3h 01m
Chicago O'Hare Intl
Tue 9/29
9:38 am-1:06 pm
Nonstop2h 28m
$217
Quickest round-trip
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 10/15
5:50 am-7:25 am
Nonstop2h 35m
Chicago Midway
Tue 10/20
6:10 pm-9:25 pm
Nonstop2h 15m
$222
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 9/17
3:13 pm-5:05 pm
Nonstop2h 52m
Chicago O'Hare Intl
Tue 9/22
1:55 pm-5:36 pm
Nonstop2h 41m
$222
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 9/9
7:30 am-9:24 am
Nonstop2h 54m
Chicago O'Hare Intl
Thu 9/10
7:30 pm-11:09 pm
Nonstop2h 39m
$222
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 9/12
1:00 pm-2:35 pm
Nonstop2h 35m
Chicago Midway
Sun 9/13
6:00 am-9:15 am
Nonstop2h 15m
$222
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 9/3
9:00 am-10:59 am
Nonstop2h 59m
Chicago O'Hare Intl
Fri 9/4
6:15 am-9:36 am
Nonstop2h 21m
$227
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 10/23
7:40 pm-9:31 pm
Nonstop2h 51m
Chicago O'Hare Intl
Mon 10/26
7:25 am-11:00 am
Nonstop2h 35m
$227
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 11/6
6:30 pm-8:15 pm
Nonstop2h 45m
Chicago Midway
Mon 11/9
3:35 pm-6:50 pm
Nonstop2h 15m
$227
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 11/13
8:25 pm-10:29 pm
Nonstop3h 04m
Chicago O'Hare Intl
Sun 11/15
6:15 am-9:34 am
Nonstop2h 19m
$227
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 9/17
7:30 am-9:24 am
Nonstop2h 54m
Chicago O'Hare Intl
Mon 9/21
7:35 am-11:08 am
Nonstop2h 33m
$227
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-ORD
BOS-MDW
ALB-ORD
BDL-ORD
ALB-MDW
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-ORD
BOS-MDW
ALB-ORD
BDL-ORD
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 29, 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.
How much does it cost to fly round-trip from Massachusetts to Indiana?
Airfare is below average for this route at the moment.
Massachusetts to Indiana flights typically cost between $386 and $563 in October.The cheapest round-trip price found within the last 5 days was $231 on Multiple Airlines (Oct 4-Oct 5).
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 25, 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 29, 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.
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
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 29, 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 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$119 | Average$227 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$178 | Average$434 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$197 | Average$435 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$218 | Average$396 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$296 | Average$396 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$312 | Average$503 | FlexibilityNo cancel fee | On-time63% |