$53+ 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 6/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — IND
May 5 — May 121
Round-trip
1 adult, Economy
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Cheapest flights from Massachusetts to IndianaExplore the most affordable flight options available from Massachusetts to Indiana. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 5, 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 April 5, 2026.
This SmartFares deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/307:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
Sun 5/36:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Deal found 3/31![JetBlue logo]()
$138
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2812:52 pm
BOS
- MDW
1 stop10h 22m
Frontier
Tue 5/512:27 pm
MDW
- BOS
1 stop11h 57m
Frontier
Deal found 3/31![Frontier logo]()
$140
This Expedia deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Mon 4/2712:31 pm
BOS
- ORD
1 stop11h 30m
Frontier
Wed 4/296:08 pm
ORD
- BOS
1 stop6h 23m
Frontier
Deal found 3/31![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:00 am
BOS
- ORD
1 stop12h 00m
Multiple Airlines
Wed 4/2911:28 am
ORD
- BOS
1 stop13h 03m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:52 pm
BOS
- ORD
1 stop22h 31m
Multiple Airlines
Tue 5/51:59 pm
ORD
- BOS
1 stop10h 25m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
BOS
- ORD
1 stop29h 23m
Multiple Airlines
Tue 4/2811:28 am
ORD
- BOS
1 stop13h 03m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
BOS
- ORD
1 stop29h 23m
Multiple Airlines
Wed 4/2911:28 am
ORD
- BOS
1 stop13h 03m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$149
This SmartFares deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Mon 5/46:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Deal found 4/3![JetBlue logo]()
$150
This CheapOair deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Wed 5/66:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Fri 5/84:52 pm
MDW
- BOS
1 stop15h 20m
Frontier
Deal found 3/31![Frontier logo]()
$151
This SmartFares deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Sun 5/176:00 am
ORD
- BOS
Nonstop2h 17m
JetBlue
Deal found 4/3![JetBlue logo]()
$151
This Cheapflightsfares deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/297:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Sun 5/36:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Deal found 3/31![JetBlue logo]()
$152
This Expedia deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Wed 4/296:00 am
BOS
- ORD
1 stop12h 00m
Multiple Airlines
Sun 5/36:00 am
ORD
- BOS
Nonstop2h 15m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$154
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 April 5, 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 April 5, 2026.
This Southwest deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/23:30 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Mon 5/47:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 4/3![Southwest logo]()
$172
This JetBlue deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/257:35 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Thu 4/306:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Deal found 4/3![JetBlue logo]()
$172
This United Airlines deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/64:35 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Mon 5/116:23 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 4/2![United Airlines logo]()
$172
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:10 pm
BOS
- ORD
Nonstop3h 07m
Delta
Mon 5/46:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Deal found 4/4![Delta logo]()
$173
This Southwest deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:55 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Fri 5/87:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 4/3![Southwest logo]()
$177
This United Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/186:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Thu 6/189:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 4/4![United Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Thu 6/187:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/4![Southwest logo]()
$177
This United Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/207:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Thu 7/309:35 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 4/4![United Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:10 am
BOS
- ORD
Nonstop3h 05m
Delta
Wed 4/226:00 am
ORD
- BOS
Nonstop2h 26m
Delta
Deal found 4/4![Delta logo]()
$206
This Southwest deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/99:00 am
BOS
- MDW
1 stop6h 40m
Southwest
Sun 5/107:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/4![Southwest logo]()
$182
This United Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/37:30 am
BOS
- ORD
Nonstop3h 01m
United Airlines
Sun 5/105:00 am
ORD
- BOS
1 stop4h 20m
United Airlines
Deal found 4/4![United Airlines logo]()
$187
This Southwest deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/21:50 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Sun 5/37:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/4![Southwest logo]()
$182
This United Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/305:45 am
BOS
- ORD
1 stop4h 52m
United Airlines
Sun 5/37:30 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Deal found 4/4![United Airlines logo]()
$187
This Southwest deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:10 am
BOS
- MDW
Nonstop2h 50m
Southwest
Sun 5/317:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/2![Southwest logo]()
$187
This United Airlines deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/217:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sun 5/247:33 am
ORD
- BOS
Nonstop2h 32m
United Airlines
Deal found 4/3![United Airlines logo]()
$201
This Southwest deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:15 am
BOS
- ORD
1 stop10h 05m
Southwest
Tue 5/122:40 pm
ORD
- BOS
1 stop6h 50m
Southwest
Deal found 4/2![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:30 am
BOS
- ORD
2 stops11h 35m
Southwest
Wed 5/132:40 pm
ORD
- BOS
1 stop6h 50m
Southwest
Deal found 4/3![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/251:10 pm
ALB
- ORD
1 stop6h 38m
Delta
Mon 4/275:04 pm
ORD
- ALB
1 stop5h 17m
Delta
Deal found 4/2![Delta logo]()
$324
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:17 pm
BDL
- IND
1 stop3h 58m
Delta
Tue 5/56:00 am
IND
- BDL
1 stop7h 16m
Delta
Deal found 4/1![Delta logo]()
$328
This Southwest deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/47:20 am
BOS
- ORD
2 stops11h 10m
Southwest
Fri 5/82:40 pm
ORD
- BOS
2 stops8h 15m
Southwest
Deal found 4/3![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:00 pm
ALB
- ORD
1 stop6h 59m
Delta
Mon 5/45:04 pm
ORD
- ALB
1 stop5h 17m
Delta
Deal found 4/3![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1511:40 am
BOS
- MDW
2 stops8h 45m
Southwest
Fri 4/177:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/3![Southwest logo]()
$226
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
ALB
- MDW
1 stop3h 43m
Delta
Sat 5/306:36 pm
MDW
- ALB
1 stop3h 42m
Delta
Deal found 4/3![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:00 am
ALB
- ORD
Nonstop2h 34m
United Airlines
Sat 5/29:38 pm
ORD
- ALB
Nonstop2h 10m
United Airlines
Deal found 4/3![United Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/252:21 pm
BDL
- IND
1 stop6h 09m
Delta
Thu 4/306:50 pm
IND
- BDL
1 stop5h 09m
Delta
Deal found 4/4![Delta logo]()
$342
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/138:10 am
BOS
- MDW
2 stops8h 35m
Southwest
Sat 5/164:20 pm
MDW
- BOS
1 stop4h 45m
Southwest
Deal found 3/31![Southwest logo]()
$242
This United Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/284:43 pm
ALB
- ORD
Nonstop2h 36m
United Airlines
Sun 5/317:30 am
ORD
- ALB
Nonstop2h 13m
United Airlines
Deal found 4/4![United Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 6/177:35 am
BDL
- ORD
1 stop4h 56m
Delta
Wed 6/246:40 am
ORD
- BDL
1 stop5h 05m
Delta
Deal found 3/31![Delta logo]()
$353
This United Airlines deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/84:50 pm
BDL
- ORD
Nonstop2h 49m
United Airlines
Wed 6/106:45 am
ORD
- BDL
Nonstop2h 11m
United Airlines
Deal found 4/3![United Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/286:06 pm
ALB
- ORD
1 stop6h 53m
Delta
Fri 5/295:19 pm
ORD
- ALB
1 stop4h 59m
Delta
Deal found 3/31![Delta logo]()
$354
Last-minute flights from Massachusetts to IndianaDiscover last-minute flight deals from Massachusetts to Indiana. Data last updated April 5, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Indiana. Data last updated April 5, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:35 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Wed 4/159:41 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Deal found 3/31![JetBlue logo]()
$152
This CheapOair deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/147:35 pm
BOS
- ORD
Nonstop3h 04m
Multiple Airlines
Mon 4/207:15 pm
ORD
- BOS
1 stop14h 00m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$160
This JetBlue deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/157:35 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Sun 4/196:00 am
ORD
- BOS
Nonstop2h 13m
JetBlue
Deal found 3/31![JetBlue logo]()
$157
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2812:52 pm
BOS
- MDW
1 stop10h 22m
Frontier
Tue 5/512:27 pm
MDW
- BOS
1 stop11h 57m
Frontier
Deal found 3/31![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:52 pm
BOS
- MDW
1 stop10h 22m
Frontier
Mon 5/42:15 pm
MDW
- BOS
1 stop17h 19m
Frontier
Deal found 4/4![Frontier logo]()
$160
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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
Tue 5/53:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/31![Southwest logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
BOS
- MDW
1 stop17h 14m
Frontier
Mon 5/42:15 pm
MDW
- BOS
1 stop17h 19m
Frontier
Deal found 4/3![Frontier logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/59:31 am
BOS
- MDW
1 stop13h 31m
Frontier
Wed 5/1312:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Deal found 4/4![Frontier logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/59:31 am
BOS
- MDW
1 stop13h 31m
Frontier
Tue 5/1212:24 pm
MDW
- BOS
1 stop12h 00m
Frontier
Deal found 4/4![Frontier logo]()
$158
This CheapOair deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Wed 5/66:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Fri 5/84:52 pm
MDW
- BOS
1 stop15h 20m
Frontier
Deal found 3/31![Frontier logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Mon 5/116:00 am
MDW
- BOS
1 stop25h 44m
Frontier
Deal found 4/3![Frontier logo]()
$164
This Expedia deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Thu 5/76:00 am
BOS
- MDW
1 stop6h 12m
Frontier
Fri 5/84:52 pm
MDW
- BOS
1 stop15h 20m
Frontier
Deal found 3/31![Frontier logo]()
$161
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 April 5, 2026.
Search for one-way flight options from Massachusetts to Indiana. Find affordable one-way fares based on user searches. Data last updated April 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 6/511:32 am
BOS
- IND
Nonstop2h 27m
Allegiant Air
Deal found 3/31![Allegiant Air logo]()
$53
This Kiwi.com deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/19:04 am
BOS
- IND
Nonstop2h 30m
Allegiant Air
Deal found 4/3![Allegiant Air logo]()
$64
This Trip.com deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
BOS
- CVG
1 stop12h 36m
Frontier
Deal found 4/3![Frontier logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/59:31 am
BOS
- IND
1 stop25h 32m
Frontier
Deal found 4/4![Frontier logo]()
$66
This Trip.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/275:52 pm
BDL
- IND
1 stop17h 19m
Frontier
Deal found 4/4![Frontier logo]()
$67
This Kiwi.com deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
BOS
- ORD
1 stop29h 23m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$68
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/912:01 pm
BOS
- CVG
1 stop23h 03m
Frontier
Deal found 4/4![Frontier logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
BOS
- IND
1 stop29h 17m
Frontier
Deal found 4/3![Frontier logo]()
$70
This Frontier deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:52 pm
BOS
- MDW
1 stop7h 39m
Frontier
Deal found 4/1![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/29:12 am
BOS
- CVG
1 stop26h 29m
Frontier
Deal found 4/3![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/248:42 pm
BDL
- IND
1 stop13h 07m
Frontier
Deal found 4/4![Frontier logo]()
$71
This Frontier deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:00 am
BOS
- CVG
1 stop5h 41m
Frontier
Deal found 4/3![Frontier logo]()
$71
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 April 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $138 (SmartFares) |
One-way from | $53 (Kiwi.com) |
Popular in | March |
Cheapest in | July |
Average price | $467 |
Good round-trip deal | $426 or less |
Good one-way deal | $308 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 April 5, 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 - MDW
BOSMDW
Boston Logan Intl
Sat 5/2
3:30 pm-5:15 pm
Nonstop2h 45m
Chicago Midway
Mon 5/4
7:00 pm-10:20 pm
Nonstop2h 20m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 4/25
7:35 pm-9:39 pm
Nonstop3h 04m
Chicago O'Hare Intl
Thu 4/30
6:00 am-9:15 am
Nonstop2h 15m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/6
4:35 pm-6:35 pm
Nonstop3h 00m
Chicago O'Hare Intl
Mon 5/11
6:23 pm-9:59 pm
Nonstop2h 36m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/2
5:10 pm-7:17 pm
Nonstop3h 07m
Chicago O'Hare Intl
Mon 5/4
6:50 am-10:11 am
Nonstop2h 21m
$173
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Mon 5/4
6:55 pm-8:45 pm
Nonstop2h 50m
Chicago Midway
Fri 5/8
7:00 pm-10:20 pm
Nonstop2h 20m
$177
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 6/18
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Thu 6/18
9:26 pm-12:59 am
Nonstop2h 33m
$177
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 6/18
5:25 am-7:00 am
Nonstop2h 35m
Chicago Midway
Thu 6/18
7:35 pm-10:50 pm
Nonstop2h 15m
$177
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 7/20
7:19 am-9:17 am
Nonstop2h 58m
Chicago O'Hare Intl
Thu 7/30
9:35 pm-1:08 am
Nonstop2h 33m
$177
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 5/9
9:00 am-2:40 pm
1 stop6h 40m
Chicago Midway
Sun 5/10
7:40 am-10:55 am
Nonstop2h 15m
$182
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 5/2
1:50 pm-3:30 pm
Nonstop2h 40m
Chicago Midway
Sun 5/3
7:40 am-10:55 am
Nonstop2h 15m
$182
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
BOS-CVG
BOS-IND
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Massachusetts to Indiana
USMA-USIN
BOS-MDW
BOS-ORD
BDL-IND
BOS-CVG
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 $107). Flying from Massachusetts to Indiana in February is currently the most expensive (average of $284). 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 April 5, 2026.
It’s optimal to fly from Massachusetts to Indiana in the morning. By choosing this option you can save up to 55% 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 April 4, 2026.
Travelers seeking maximum savings on their Massachusetts to Indiana flight should consider departing on Saturday at noon 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.
Weekly flight availability from Massachusetts to Indiana
Explore weekly flight availability from Massachusetts to Indiana. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 5, 2026.
The most flights from USMA to USIN are scheduled on a Friday (13 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (8 on average).
How much does it cost to fly round-trip from Massachusetts to Indiana?
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 April 5, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Massachusetts to Indiana to help guide your decision. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
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 April 5, 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 April 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$60 | Average$163 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$99 | Average$202 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$102 | Average$221 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$118 | Average$402 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$178 | Average$418 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$196 | Average$449 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$318 | Average$466 | FlexibilityNo cancel fee | On-time63% |