$81+ 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 6/10. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — IND
Jun 20 — Jun 271
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 May 21, 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 May 21, 2026.
This Southwest deal was found by Cheapflights users on 5/17. 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.
Sat 6/65:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 6/97:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/17![Southwest logo]()
$176
This SmartFares deal was found by Cheapflights users on 5/17. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Mon 6/88:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/17![JetBlue logo]()
$176
This Southwest deal was found by Cheapflights users on 5/17. 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.
Sat 6/65:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 6/87:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/17![Southwest logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Tue 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/19![JetBlue logo]()
$182
This flygcity.se deal was found by Cheapflights users on 5/17. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/611:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Mon 6/88:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/17![JetBlue logo]()
$183
This SmartFares deal was found by Cheapflights users on 5/17. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Tue 8/2510:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 5/17![JetBlue logo]()
$184
This American Airlines deal was found by Cheapflights users on 5/16. 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.
Tue 6/23:00 pm
BOS
- ORD
Nonstop3h 06m
American Airlines
Tue 6/91:57 pm
ORD
- BOS
Nonstop2h 35m
American Airlines
Deal found 5/16![American Airlines logo]()
$186
This Southwest deal was found by Cheapflights users on 5/17. 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 6/37:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Wed 6/106:05 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/17![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/37:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Wed 6/107:10 am
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 5/18![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 5/17. 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.
Sat 5/231:50 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Sat 6/65:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/17![Southwest logo]()
$188
This Frontier deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 8/256:00 am
BOS
- MDW
1 stop6h 12m
Frontier
Wed 9/212:04 pm
MDW
- BOS
1 stop12h 23m
Frontier
Deal found 5/18![Frontier logo]()
$189
This Frontier deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 8/259:12 am
BOS
- ORD
1 stop11h 43m
Frontier
Tue 9/11:50 pm
ORD
- BOS
1 stop10h 37m
Frontier
Deal found 5/18![Frontier logo]()
$189
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 May 21, 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 May 21, 2026.
This United Airlines deal was found by Cheapflights users on 5/17. 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.
Sun 5/317:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Wed 6/37:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 5/17![United Airlines logo]()
$192
This Southwest deal was found by Cheapflights users on 5/16. 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 6/105:30 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Sun 6/145:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 5/16![Southwest logo]()
$196
This JetBlue deal was found by Cheapflights users on 5/16. 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.
Tue 8/118:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Wed 8/1910:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 5/16![JetBlue logo]()
$205
This KAYAK deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/812:20 pm
BOS
- ORD
Nonstop2h 55m
Delta
Tue 6/910:29 am
ORD
- BOS
Nonstop2h 30m
Delta
Deal found 5/20![Delta logo]()
$243
This KAYAK deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/137:56 pm
ALB
- ORD
Nonstop2h 51m
American Airlines
Tue 7/144:10 pm
ORD
- ALB
Nonstop2h 16m
American Airlines
Deal found 5/19![American Airlines logo]()
$377
This Southwest deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 7/215:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Fri 7/247:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/19![Southwest logo]()
$201
This United Airlines deal was found by Cheapflights users on 5/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/17:27 pm
BOS
- ORD
1 stop4h 59m
United Airlines
Tue 6/27:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 5/16![United Airlines logo]()
$202
This Southwest deal was found by Cheapflights users on 5/16. 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.
Fri 10/28:40 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 10/45:15 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/16![Southwest logo]()
$205
This United Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/126:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Mon 6/159:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 5/20![United Airlines logo]()
$205
This Sun Country Air deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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.
Fri 6/1211:31 am
BDL
- ORD
1 stop6h 53m
Sun Country Air
Sun 6/148:19 pm
ORD
- BDL
1 stop13h 18m
Sun Country Air
Deal found 5/19![Sun Country Air logo]()
$475
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/105:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 7/137:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/18![Southwest logo]()
$205
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 5/2810:55 am
BOS
- ORD
Nonstop2h 53m
United Airlines
Sat 6/66:12 pm
ORD
- BOS
1 stop4h 47m
United Airlines
Deal found 5/19![United Airlines logo]()
$211
This Southwest deal was found by Cheapflights users on 5/17. 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.
Thu 8/205:55 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Sat 8/227:40 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 5/17![Southwest logo]()
$211
This United Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/225:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Sun 7/266:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 5/20![United Airlines logo]()
$215
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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.
Sun 6/286:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Thu 7/26:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 5/18![United Airlines logo]()
$215
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 5/278:10 am
BOS
- ORD
1 stop5h 40m
Southwest
Thu 5/282:40 pm
ORD
- BOS
1 stop7h 35m
Southwest
Deal found 5/20![Southwest logo]()
$225
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 7/285:30 am
BDL
- IND
1 stop4h 18m
Delta
Tue 8/47:55 am
IND
- BDL
1 stop3h 57m
Delta
Deal found 5/20![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 5/275:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Thu 5/289:15 am
ORD
- BOS
Nonstop2h 42m
United Airlines
Deal found 5/20![United Airlines logo]()
$215
This Southwest deal was found by Cheapflights users on 5/17. 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.
Thu 6/185:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 6/215:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 5/17![Southwest logo]()
$226
This Delta deal was found by Cheapflights users on 5/17. 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.
Wed 7/156:05 am
ALB
- MDW
1 stop4h 03m
Delta
Sat 7/186:35 pm
MDW
- ALB
1 stop3h 46m
Delta
Deal found 5/17![Delta logo]()
$347
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/13:45 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Sun 6/75:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 5/20![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/187:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Thu 6/259:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 5/20![United Airlines logo]()
$228
This JetBlue deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/47:15 am
BDL
- ORD
1 stop8h 15m
JetBlue
Mon 6/83:27 pm
ORD
- BDL
1 stop7h 25m
JetBlue
Deal found 5/18![JetBlue logo]()
$405
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/38:10 am
BOS
- MDW
2 stops8h 35m
Southwest
Wed 6/107:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/20![Southwest logo]()
$227
This JetBlue deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 5/307:15 am
BDL
- ORD
1 stop8h 01m
JetBlue
Mon 6/83:27 pm
ORD
- BDL
1 stop7h 25m
JetBlue
Deal found 5/20![JetBlue logo]()
$410
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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.
Sun 6/145:30 am
BDL
- IND
1 stop4h 20m
Delta
Tue 6/167:47 am
IND
- BDL
1 stop4h 28m
Delta
Deal found 5/19![Delta logo]()
$373
This KAYAK deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/17:00 am
BDL
- ORD
Nonstop2h 46m
American Airlines
Thu 6/47:26 pm
ORD
- BDL
Nonstop2h 20m
American Airlines
Deal found 5/20![American Airlines logo]()
$456
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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.
Sun 8/26:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Tue 8/46:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 5/18![United Airlines logo]()
$241
This Delta deal was found by Cheapflights users on 5/17. 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.
Tue 6/305:30 am
BDL
- MDW
1 stop4h 44m
Delta
Tue 6/306:58 pm
MDW
- BDL
1 stop3h 37m
Delta
Deal found 5/17![Delta logo]()
$373
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 9/35:50 pm
BOS
- MDW
1 stop5h 05m
Southwest
Mon 9/75:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/20![Southwest logo]()
$251
Last-minute flights from Massachusetts to IndianaDiscover last-minute flight deals from Massachusetts to Indiana. Data last updated May 21, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Indiana. Data last updated May 21, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/17. 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.
Sat 5/231:50 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Sat 6/65:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/17![Southwest logo]()
$188
This Cheapflightsfares deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 5/276:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Thu 5/288:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/20![JetBlue logo]()
$200
This United Airlines deal was found by Cheapflights users on 5/17. 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.
Thu 5/289:40 am
BOS
- ORD
Nonstop2h 53m
United Airlines
Tue 6/29:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 5/17![United Airlines logo]()
$196
This United Airlines deal was found by Cheapflights users on 5/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/309:50 am
BOS
- ORD
Nonstop2h 53m
United Airlines
Tue 6/27:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 5/16![United Airlines logo]()
$192
This United Airlines deal was found by Cheapflights users on 5/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/306:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Mon 6/19:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 5/16![United Airlines logo]()
$197
This Southwest deal was found by Cheapflights users on 5/17. 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.
Tue 6/210:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Tue 6/97:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/17![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 5/16. 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 6/38:10 am
BOS
- MDW
2 stops8h 35m
Southwest
Sat 6/65:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 5/16![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/45:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 6/75:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 5/18![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 5/17. 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.
Sat 6/65:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 6/97:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/17![Southwest logo]()
$176
This Southwest deal was found by Cheapflights users on 5/17. 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.
Sat 6/65:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 6/87:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/17![Southwest logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/99:10 am
BOS
- MDW
1 stop14h 01m
Frontier
Wed 6/106:00 am
MDW
- BOS
1 stop18h 27m
Frontier
Deal found 5/19![Frontier logo]()
$193
This Frontier deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/236:00 am
BOS
- MDW
1 stop6h 12m
Frontier
Wed 6/2412:04 pm
MDW
- BOS
1 stop12h 23m
Frontier
Deal found 5/18![Frontier logo]()
$190
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 May 21, 2026.
Search for one-way flight options from Massachusetts to Indiana. Find affordable one-way fares based on user searches. Data last updated May 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:00 am
BOS
- CVG
1 stop5h 49m
Frontier
Deal found 5/19![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 5/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/99:10 am
BOS
- IND
1 stop26h 09m
Frontier
Deal found 5/16![Frontier logo]()
$82
This Super.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/18![JetBlue logo]()
$92
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 5/18![Southwest logo]()
$94
This Delta deal was found by Cheapflights users on 5/16. 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.
Tue 6/94:15 pm
BOS
- ORD
Nonstop3h 05m
Delta
Deal found 5/16![Delta logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2611:32 am
BOS
- IND
Nonstop2h 27m
Allegiant Air
Deal found 5/17![Allegiant Air logo]()
$95
This Super.com deal was found by Cheapflights users on 5/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Deal found 5/16![Frontier logo]()
$95
This Frontier deal was found by Cheapflights users on 5/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1012:01 pm
BOS
- ORD
1 stop8h 49m
Frontier
Deal found 5/16![Frontier logo]()
$95
This Frontier deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 8/256:00 am
BOS
- MDW
1 stop6h 12m
Frontier
Deal found 5/18![Frontier logo]()
$96
This Super.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/16:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/18![JetBlue logo]()
$96
This Trip.com deal was found by Cheapflights users on 5/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:00 am
BOS
- MDW
1 stop6h 12m
Frontier
Deal found 5/16![Frontier logo]()
$97
This Southwest deal was found by Cheapflights users on 5/16. 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.
Sat 5/306:00 am
BOS
- MDW
1 stop10h 15m
Southwest
Deal found 5/16![Southwest logo]()
$98
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 May 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $176 (Southwest) |
One-way from | $81 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $489 |
Good round-trip deal | $407 or less |
Good one-way deal | $149 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Massachusetts to Indiana that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 21, 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
Sun 5/31
7:19 am-9:17 am
Nonstop2h 58m
Chicago O'Hare Intl
Wed 6/3
7:45 pm-11:21 pm
Nonstop2h 36m
$192
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 6/10
5:30 pm-7:20 pm
Nonstop2h 50m
Chicago Midway
Sun 6/14
5:15 am-8:25 am
Nonstop2h 10m
$196
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 7/21
5:35 am-7:10 am
Nonstop2h 35m
Chicago Midway
Fri 7/24
7:35 pm-10:50 pm
Nonstop2h 15m
$201
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 6/1
7:27 pm-11:26 pm
1 stop4h 59m
Chicago O'Hare Intl
Tue 6/2
7:45 pm-11:21 pm
Nonstop2h 36m
$202
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 8/11
8:10 am-10:06 am
Nonstop2h 56m
Chicago O'Hare Intl
Wed 8/19
10:56 am-2:23 pm
Nonstop2h 27m
$205
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 10/2
8:40 am-10:15 am
Nonstop2h 35m
Chicago Midway
Sun 10/4
5:15 am-8:30 am
Nonstop2h 15m
$205
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 6/12
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Mon 6/15
9:41 pm-1:14 am
Nonstop2h 33m
$205
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 7/10
5:25 am-7:00 am
Nonstop2h 35m
Chicago Midway
Mon 7/13
7:35 pm-10:50 pm
Nonstop2h 15m
$205
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 5/28
10:55 am-12:48 pm
Nonstop2h 53m
Chicago O'Hare Intl
Sat 6/6
6:12 pm-11:59 pm
1 stop4h 47m
$211
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 8/20
5:55 pm-7:35 pm
Nonstop2h 40m
Chicago Midway
Sat 8/22
7:40 am-11:00 am
Nonstop2h 20m
$211
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
BDL-IND
BDL-ORD
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
BDL-IND
BDL-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 $58). Flying from Massachusetts to Indiana in April is currently the most expensive (average of $218). 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 May 21, 2026.
It’s optimal to fly from Massachusetts to Indiana in the morning. By choosing this option you can save up to 54% 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?
How far ahead should I book a flight from Massachusetts to Indiana?
The best time to book flights from Massachusetts to Indiana is 62 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 May 16, 2026.
Travelers seeking maximum savings on their Massachusetts to Indiana flight should consider departing on Saturday 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 May 21, 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.
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 May 21, 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 May 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$74 | Average$193 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$102 | Average$223 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$118 | Average$432 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$178 | Average$416 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$196 | Average$348 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$296 | Average$394 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$318 | Average$486 | FlexibilityNo cancel fee | On-time63% |