$67+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — IND
Mar 12 — Mar 191
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 February 10, 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 February 10, 2026.
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:55 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Mon 5/47:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 2/8![Southwest logo]()
$132
This Priceline deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:00 am
BOS
- ORD
Nonstop3h 10m
Multiple Airlines
Wed 3/46:02 pm
ORD
- BOS
1 stop6h 11m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$132
This Southwest deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 3/45:30 am
BOS
- MDW
Nonstop2h 50m
Southwest
Sat 3/77:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/6![Southwest logo]()
$133
This Super.com deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 2/237:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Thu 2/2610:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/6![JetBlue logo]()
$133
This Southwest deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 2/282:10 pm
BOS
- MDW
1 stop6h 15m
Southwest
Mon 3/26:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/7![Southwest logo]()
$134
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Tue 5/57:00 am
ORD
- BOS
1 stop4h 51m
United Airlines
Deal found 2/8![United Airlines logo]()
$134
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 2/1110:30 am
BOS
- ORD
Nonstop3h 04m
United Airlines
Wed 2/116:05 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 2/8![United Airlines logo]()
$135
This JetBlue deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/187:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Wed 3/410:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/10![JetBlue logo]()
$136
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/146:30 am
BOS
- MDW
Nonstop2h 50m
Southwest
Tue 3/176:10 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/9![Southwest logo]()
$137
This American Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/26:52 am
BOS
- ORD
Nonstop3h 11m
American Airlines
Mon 4/68:51 pm
ORD
- BOS
Nonstop2h 20m
American Airlines
Deal found 2/7![American Airlines logo]()
$137
This CheapOair deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:00 am
BOS
- ORD
Nonstop3h 10m
Multiple Airlines
Tue 3/36:02 pm
ORD
- BOS
1 stop6h 11m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$138
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/56:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Mon 3/99:15 pm
ORD
- BOS
Nonstop2h 20m
United Airlines
Deal found 2/8![United Airlines logo]()
$139
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 February 10, 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 February 10, 2026.
This Southwest deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 2/282:10 pm
BOS
- MDW
1 stop6h 15m
Southwest
Mon 3/26:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/7![Southwest logo]()
$134
This JetBlue deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 2/277:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Tue 3/2411:00 am
ORD
- BOS
Nonstop2h 24m
JetBlue
Deal found 2/8![JetBlue logo]()
$135
This United Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 4/37:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Sun 4/56:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 2/7![United Airlines logo]()
$137
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/258:59 pm
BOS
- ORD
Nonstop2h 51m
Delta
Mon 4/276:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Deal found 2/8![Delta logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/310:19 am
BDL
- IND
1 stop22h 13m
Multiple Airlines
Wed 3/41:23 pm
IND
- BDL
1 stop21h 14m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$162
This Expedia deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:08 pm
BDL
- IND
1 stop13h 41m
Frontier
Sun 5/37:18 pm
IND
- BDL
1 stop23h 59m
Frontier
Deal found 2/8![Frontier logo]()
$271
This JetBlue deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 3/47:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Wed 3/412:59 pm
ORD
- BOS
1 stop5h 59m
JetBlue
Deal found 2/6![JetBlue logo]()
$137
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/266:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Sun 3/17:30 am
ORD
- BOS
Nonstop2h 19m
United Airlines
Deal found 2/9![United Airlines logo]()
$145
This Southwest deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 3/25:00 pm
BOS
- MDW
1 stop5h 40m
Southwest
Wed 3/42:00 pm
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 2/6![Southwest logo]()
$147
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/75:15 pm
BOS
- ORD
Nonstop3h 08m
Delta
Mon 3/97:35 pm
ORD
- BOS
Nonstop2h 27m
Delta
Deal found 2/8![Delta logo]()
$147
This American Airlines deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 4/15:28 am
BDL
- IND
1 stop5h 08m
American Airlines
Wed 4/15:30 pm
IND
- BDL
1 stop5h 47m
American Airlines
Deal found 2/7![American Airlines logo]()
$297
This Mytrip deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/86:10 pm
BOS
- SDF
2 stops18h 11m
Spirit Airlines
Thu 3/123:33 pm
SDF
- BOS
1 stop8h 26m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$302
This JetBlue deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/37:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Mon 3/96:04 am
ORD
- BOS
1 stop7h 10m
JetBlue
Deal found 2/8![JetBlue logo]()
$142
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/267:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Mon 3/307:35 pm
ORD
- BOS
Nonstop2h 27m
Delta
Deal found 2/9![Delta logo]()
$147
This United Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 3/49:40 am
BOS
- ORD
Nonstop3h 06m
United Airlines
Sat 3/74:30 pm
ORD
- BOS
1 stop4h 56m
United Airlines
Deal found 2/6![United Airlines logo]()
$152
This Sun Country Air deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/1211:58 am
BDL
- ORD
1 stop6h 31m
Sun Country Air
Wed 7/156:39 pm
ORD
- BDL
1 stop17h 02m
Sun Country Air
Deal found 2/7![Sun Country Air logo]()
$335
This Southwest deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 3/233:10 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Wed 3/2511:15 am
MDW
- BOS
1 stop10h 45m
Southwest
Deal found 2/7![Southwest logo]()
$153
This JetBlue deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 3/47:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Thu 3/56:04 am
ORD
- BOS
1 stop7h 12m
JetBlue
Deal found 2/6![JetBlue logo]()
$142
This Delta deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/411:35 am
BOS
- ORD
Nonstop3h 06m
Delta
Mon 3/910:40 am
ORD
- BOS
Nonstop2h 24m
Delta
Deal found 2/8![Delta logo]()
$147
This Southwest deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 2/225:00 am
BOS
- MDW
Nonstop2h 55m
Southwest
Wed 2/255:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/6![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/27:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Mon 4/67:35 pm
ORD
- BOS
Nonstop2h 27m
Delta
Deal found 2/9![Delta logo]()
$153
This Southwest deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 2/265:20 am
BOS
- MDW
2 stops13h 00m
Southwest
Sun 3/16:05 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 2/7![Southwest logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/2710:52 am
ALB
- ORD
1 stop25h 35m
Multiple Airlines
Thu 4/308:24 pm
ORD
- ALB
2 stops21h 05m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$235
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/216:35 pm
BOS
- MDW
Nonstop2h 55m
Southwest
Wed 3/2511:15 am
MDW
- BOS
1 stop10h 45m
Southwest
Deal found 2/9![Southwest logo]()
$163
This Southwest deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 2/207:05 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Fri 2/276:05 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 2/8![Southwest logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 5/1512:35 pm
BOS
- CVG
1 stop6h 01m
Frontier
Mon 5/187:43 pm
CVG
- BOS
2 stops14h 38m
Frontier
Deal found 2/9![Frontier logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 3/611:22 am
ALB
- ORD
1 stop25h 00m
Multiple Airlines
Tue 3/107:41 pm
ORD
- ALB
2 stops38h 40m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$262
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/275:00 am
BOS
- MDW
Nonstop2h 55m
Southwest
Mon 3/26:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/9![Southwest logo]()
$166
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/111:20 am
BOS
- CVG
Nonstop2h 42m
American Airlines
Sun 4/52:28 pm
CVG
- BOS
Nonstop2h 13m
American Airlines
Deal found 2/9![American Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 3/242:00 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Tue 3/314:45 pm
MDW
- BOS
1 stop4h 25m
Southwest
Deal found 2/7![Southwest logo]()
$167
Last-minute flights from Massachusetts to IndianaDiscover last-minute flight deals from Massachusetts to Indiana. Data last updated February 10, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Indiana. Data last updated February 10, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 2/119:30 am
BOS
- ORD
Nonstop3h 04m
United Airlines
Sun 2/157:30 am
ORD
- BOS
Nonstop2h 19m
United Airlines
Deal found 2/6![United Airlines logo]()
$135
This Cheapflightsfares deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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.
Thu 2/127:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Sat 2/1410:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/8![JetBlue logo]()
$134
This Super.com deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 2/237:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Thu 2/2610:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/6![JetBlue logo]()
$133
This CheapOair deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:00 am
BOS
- ORD
Nonstop3h 10m
Multiple Airlines
Tue 3/36:02 pm
ORD
- BOS
1 stop6h 11m
Multiple Airlines
Deal found 2/7![Multiple Airlines logo]()
$138
This JetBlue deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 2/277:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Mon 3/210:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/8![JetBlue logo]()
$136
This Southwest deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 2/285:15 am
BOS
- MDW
Nonstop2h 45m
Southwest
Sat 2/2810:15 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/7![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 2/282:10 pm
BOS
- MDW
1 stop6h 15m
Southwest
Mon 3/26:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/7![Southwest logo]()
$134
This Priceline deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:00 am
BOS
- ORD
Nonstop3h 10m
Multiple Airlines
Wed 3/46:02 pm
ORD
- BOS
1 stop6h 11m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$132
This Southwest deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” 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 3/45:30 am
BOS
- MDW
Nonstop2h 50m
Southwest
Sat 3/77:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/6![Southwest logo]()
$133
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/56:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Mon 3/99:15 pm
ORD
- BOS
Nonstop2h 20m
United Airlines
Deal found 2/8![United Airlines logo]()
$139
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/146:30 am
BOS
- MDW
Nonstop2h 50m
Southwest
Tue 3/176:10 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/9![Southwest logo]()
$137
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/307:15 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Thu 4/26:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 2/8![United Airlines logo]()
$137
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 February 10, 2026.
Search for one-way flight options from Massachusetts to Indiana. Find affordable one-way fares based on user searches. Data last updated February 10, 2026.
This Super.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” 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 2/187:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/7![JetBlue logo]()
$67
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/185:30 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/9![Southwest logo]()
$68
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/186:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 2/9![United Airlines logo]()
$68
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/188:20 am
BOS
- ORD
1 stop5h 30m
Southwest
Deal found 2/9![Southwest logo]()
$69
This Mytrip deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/410:19 am
BDL
- MDW
1 stop29h 07m
Frontier
Deal found 2/10![Frontier logo]()
$70
This Booking.com deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/410:19 am
BDL
- ORD
1 stop25h 27m
Frontier
Deal found 2/7![Frontier logo]()
$70
This Frontier deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
BOS
- ORD
1 stop11h 52m
Frontier
Deal found 2/9![Frontier logo]()
$70
This CheapOair deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:45 am
BOS
- ORD
1 stop12h 30m
Spirit Airlines
Deal found 2/8![Spirit Airlines logo]()
$71
This Trip.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/262:27 pm
BDL
- MDW
1 stop9h 02m
Frontier
Deal found 2/8![Frontier logo]()
$72
This JetBlue deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/36:00 am
BDL
- ORD
1 stop6h 49m
JetBlue
Deal found 2/9![JetBlue logo]()
$72
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/285:40 am
BOS
- ORD
1 stop16h 37m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$72
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/201:55 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/9![Southwest logo]()
$73
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 February 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $132 (Southwest) |
One-way from | $67 (Super.com) |
Popular in | October |
Cheapest in | June |
Average price | $420 |
Good round-trip deal | $377 or less |
Good one-way deal | $298 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 February 10, 2026.
Use the filters below to find and compare flights from Massachusetts to Indiana that are best for you.
Fly from
Massachusetts
Fly to
Indiana
Route
Depart
Return
Price
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 2/28
2:10 pm-7:25 pm
1 stop6h 15m
Chicago Midway
Mon 3/2
6:35 pm-9:50 pm
Nonstop2h 15m
$134
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 2/27
7:00 am-9:10 am
Nonstop3h 10m
Chicago O'Hare Intl
Tue 3/24
11:00 am-2:24 pm
Nonstop2h 24m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 4/3
7:00 am-9:00 am
Nonstop3h 00m
Chicago O'Hare Intl
Sun 4/5
6:00 am-9:25 am
Nonstop2h 25m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 3/4
7:00 am-9:10 am
Nonstop3h 10m
Chicago O'Hare Intl
Wed 3/4
12:59 pm-7:58 pm
1 stop5h 59m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 4/25
8:59 pm-10:50 pm
Nonstop2h 51m
Chicago O'Hare Intl
Mon 4/27
6:50 am-10:11 am
Nonstop2h 21m
$142
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 3/3
7:00 am-9:10 am
Nonstop3h 10m
Chicago O'Hare Intl
Mon 3/9
6:04 am-2:14 pm
1 stop7h 10m
$142
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 3/4
7:00 am-9:10 am
Nonstop3h 10m
Chicago O'Hare Intl
Thu 3/5
6:04 am-2:16 pm
1 stop7h 12m
$142
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 2/26
6:00 am-8:00 am
Nonstop3h 00m
Chicago O'Hare Intl
Sun 3/1
7:30 am-10:49 am
Nonstop2h 19m
$145
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Mon 3/2
5:00 pm-9:40 pm
1 stop5h 40m
Chicago Midway
Wed 3/4
2:00 pm-5:10 pm
Nonstop2h 10m
$147
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 3/7
5:15 pm-7:23 pm
Nonstop3h 08m
Chicago O'Hare Intl
Mon 3/9
7:35 pm-11:02 pm
Nonstop2h 27m
$147
Showing 1-10 of 60 results
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
BDL-IND
ALB-ORD
BDL-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
BDL-IND
ALB-ORD
What is the cheapest month to book a flight from Massachusetts to Indiana?
Currently, June is the cheapest month in which you can book a flight from Massachusetts to Indiana (average of $89). Flying from Massachusetts to Indiana in April is currently the most expensive (average of $254). 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 February 10, 2026.
It’s optimal to fly from Massachusetts to Indiana in the morning. By choosing this option you can save up to 57% on the cost of your flight, compared to a flight in the afternoon.
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 February 7, 2026.
Travelers seeking maximum savings on their Massachusetts to Indiana flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday evenings 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 February 10, 2026.
Peruse reviews from past customers who have flown with Southwest, Delta, and United 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.
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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 February 10, 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 7 airlines flying from Massachusetts to Indiana
Discover the top 7 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 February 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$136 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$102 | Average$225 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$106 | Average$207 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$179 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$186 | Average$429 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$196 | Average$474 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$312 | Average$429 | FlexibilityNo cancel fee | On-time63% |