$70+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — IND
May 28 — Jun 41
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 28, 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 28, 2026.
This American Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
Sun 5/176:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Tue 5/196:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Deal found 4/23![American Airlines logo]()
$156
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/305:51 am
BOS
- MDW
1 stop8h 28m
Delta
Tue 6/25:15 pm
MDW
- BOS
1 stop7h 13m
Delta
Deal found 4/23![Delta logo]()
$157
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 6/35:35 am
BOS
- ORD
1 stop5h 41m
Delta
Sat 6/66:06 pm
ORD
- BOS
1 stop6h 22m
Delta
Deal found 4/23![Delta logo]()
$157
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/305:40 am
BOS
- MDW
1 stop4h 03m
Delta
Mon 6/16:36 pm
MDW
- BOS
1 stop3h 53m
Delta
Deal found 4/23![Delta logo]()
$158
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/305:40 am
BOS
- ORD
1 stop5h 49m
Delta
Mon 6/16:06 pm
ORD
- BOS
1 stop6h 22m
Delta
Deal found 4/23![Delta logo]()
$158
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:35 am
BOS
- MDW
1 stop7h 15m
Southwest
Mon 8/175:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/23![Southwest logo]()
$159
This CheapOair deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:01 pm
BOS
- ORD
1 stop8h 50m
Multiple Airlines
Tue 5/199:49 am
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$159
This Frontier deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Wed 5/2012:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Deal found 4/27![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:07 am
BOS
- ORD
1 stop14h 06m
Frontier
Tue 5/191:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/27![Frontier logo]()
$160
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/94:32 pm
BOS
- ORD
Nonstop3h 17m
American Airlines
Tue 5/1210:55 am
ORD
- BOS
Nonstop2h 31m
American Airlines
Deal found 4/24![American Airlines logo]()
$161
This Cheapflightsfares deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Tue 7/2110:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 4/28![JetBlue logo]()
$162
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:45 am
BOS
- ORD
1 stop4h 48m
United Airlines
Mon 8/177:33 am
ORD
- BOS
Nonstop2h 34m
United Airlines
Deal found 4/23![United Airlines logo]()
$163
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 28, 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 28, 2026.
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/285:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Mon 6/19:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 4/23![United Airlines logo]()
$167
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/158:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Tue 5/197:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 4/25![Delta logo]()
$182
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/185:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 6/215:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 4/25![Southwest logo]()
$191
This JetBlue deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Mon 5/49:49 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Deal found 4/24![JetBlue logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:45 am
BOS
- RFD
1 stop29h 02m
Multiple Airlines
Sun 5/1011:50 am
RFD
- BOS
1 stop21h 53m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/231:50 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Sat 5/305:25 pm
MDW
- BOS
1 stop5h 15m
Southwest
Deal found 4/25![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/206:45 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Mon 8/37:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/25![Southwest logo]()
$197
This KAYAK deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/298:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Sat 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 4/27![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 7/155:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Sun 7/199:35 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 4/23![United Airlines logo]()
$254
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/15:30 am
BOS
- ORD
1 stop6h 15m
Delta
Wed 7/87:05 am
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 4/24![Delta logo]()
$241
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/117:30 am
BOS
- MDW
Nonstop2h 40m
Southwest
Fri 6/125:05 pm
MDW
- BOS
1 stop6h 05m
Southwest
Deal found 4/27![Southwest logo]()
$242
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/73:00 pm
BOS
- ORD
Nonstop2h 58m
United Airlines
Sun 5/105:00 am
ORD
- BOS
1 stop4h 20m
United Airlines
Deal found 4/27![United Airlines logo]()
$267
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2711:00 am
BOS
- ORD
1 stop8h 03m
Delta
Wed 8/57:05 am
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 4/23![Delta logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:00 am
BOS
- RFD
1 stop29h 37m
Multiple Airlines
Sun 7/1911:27 am
RFD
- BOS
1 stop11h 31m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/24:35 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Sun 5/35:00 am
ORD
- BOS
1 stop4h 20m
United Airlines
Deal found 4/27![United Airlines logo]()
$267
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:10 am
BOS
- MDW
Nonstop2h 50m
Southwest
Sun 5/107:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/26![Southwest logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:37 pm
BOS
- RFD
1 stop20h 38m
Multiple Airlines
Thu 7/911:27 am
RFD
- BOS
1 stop11h 31m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/79:00 am
BOS
- ORD
1 stop5h 05m
Delta
Mon 7/137:05 am
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 4/24![Delta logo]()
$260
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1012:50 pm
BOS
- MDW
1 stop7h 15m
Southwest
Wed 6/177:50 am
MDW
- BOS
2 stops6h 50m
Southwest
Deal found 4/27![Southwest logo]()
$247
This United Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
BOS
- ORD
2 stops6h 36m
United Airlines
Wed 6/34:00 pm
ORD
- BOS
1 stop6h 59m
United Airlines
Deal found 4/24![United Airlines logo]()
$272
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 7/156:00 am
BOS
- RFD
1 stop29h 37m
Multiple Airlines
Mon 7/207:50 pm
RFD
- BOS
1 stop26h 48m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$308
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 7/2112:25 pm
BOS
- ORD
Nonstop2h 54m
Delta
Fri 7/245:30 pm
ORD
- BOS
1 stop5h 01m
Delta
Deal found 4/23![Delta logo]()
$260
This Southwest deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/65:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Thu 7/92:45 pm
MDW
- BOS
1 stop7h 40m
Southwest
Deal found 4/24![Southwest logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/512:33 pm
BOS
- RFD
1 stop20h 44m
Multiple Airlines
Sun 6/711:27 am
RFD
- BOS
1 stop11h 27m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$314
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/811:35 am
BOS
- MDW
2 stops6h 25m
Southwest
Sun 7/125:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 4/26![Southwest logo]()
$256
This United Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:00 am
ALB
- ORD
1 stop6h 27m
United Airlines
Tue 9/811:10 am
ORD
- ALB
Nonstop2h 13m
United Airlines
Deal found 4/25![United Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:20 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Mon 5/115:40 pm
MDW
- BOS
1 stop4h 30m
Southwest
Deal found 4/26![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:59 pm
ALB
- ORD
1 stop4h 49m
Delta
Tue 9/83:35 pm
ORD
- ALB
1 stop7h 03m
Delta
Deal found 4/25![Delta logo]()
$337
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1912:24 pm
ALB
- ORD
Nonstop2h 37m
United Airlines
Sun 6/217:30 am
ORD
- ALB
Nonstop2h 13m
United Airlines
Deal found 4/27![United Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/49:40 am
BOS
- RFD
2 stops25h 57m
Multiple Airlines
Wed 7/810:03 am
RFD
- BOS
1 stop11h 38m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$390
Last-minute flights from Massachusetts to IndianaDiscover last-minute flight deals from Massachusetts to Indiana. Data last updated April 28, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Indiana. Data last updated April 28, 2026 and is based on user searches.
This Orbitz deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Tue 5/1912:24 pm
MDW
- BOS
1 stop12h 00m
Frontier
Deal found 4/27![Frontier logo]()
$160
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/125:28 pm
BOS
- ORD
1 stop5h 12m
United Airlines
Wed 5/136:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 4/23![United Airlines logo]()
$165
This Frontier deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:07 am
BOS
- ORD
1 stop14h 06m
Frontier
Wed 5/201:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/27![Frontier logo]()
$160
This Cheapflightsfares deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/136:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Sun 5/176:00 am
ORD
- BOS
Nonstop2h 17m
JetBlue
Deal found 4/23![JetBlue logo]()
$161
This CheapOair deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:01 pm
BOS
- ORD
1 stop8h 50m
Multiple Airlines
Tue 5/199:49 am
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$159
This American Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
Sun 5/176:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Tue 5/196:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Deal found 4/23![American Airlines logo]()
$156
This CheapOair deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
Multiple Airlines
Wed 5/201:59 pm
ORD
- BOS
1 stop10h 25m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$164
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/2310:16 am
BOS
- ORD
1 stop7h 40m
Delta
Wed 5/279:36 am
ORD
- BOS
1 stop5h 52m
Delta
Deal found 4/23![Delta logo]()
$157
This Cheapflightsfares deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Sat 5/301:56 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/27![JetBlue logo]()
$162
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/305:51 am
BOS
- MDW
1 stop8h 28m
Delta
Tue 6/25:15 pm
MDW
- BOS
1 stop7h 13m
Delta
Deal found 4/23![Delta logo]()
$157
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/305:40 am
BOS
- MDW
1 stop4h 03m
Delta
Mon 6/16:36 pm
MDW
- BOS
1 stop3h 53m
Delta
Deal found 4/23![Delta logo]()
$158
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/305:40 am
BOS
- ORD
1 stop5h 49m
Delta
Mon 6/16:06 pm
ORD
- BOS
1 stop6h 22m
Delta
Deal found 4/23![Delta logo]()
$158
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 28, 2026.
Search for one-way flight options from Massachusetts to Indiana. Find affordable one-way fares based on user searches. Data last updated April 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1910:07 am
BOS
- CVG
1 stop13h 22m
Frontier
Deal found 4/24![Frontier logo]()
$70
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:35 am
BOS
- MDW
1 stop7h 15m
Southwest
Deal found 4/23![Southwest logo]()
$78
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 6/65:40 am
BOS
- MDW
1 stop4h 03m
Delta
Deal found 4/23![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/205:40 am
BOS
- ORD
1 stop5h 49m
Delta
Deal found 4/23![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:40 am
BOS
- MDW
1 stop4h 03m
Delta
Deal found 4/24![Delta logo]()
$80
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/291:00 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 4/23![Southwest logo]()
$81
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/156:39 pm
BOS
- ORD
Nonstop3h 01m
United Airlines
Deal found 4/23![United Airlines logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:45 am
BOS
- CVG
1 stop27h 03m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$81
This Super.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2311:00 am
BOS
- ORD
Nonstop3h 01m
JetBlue
Deal found 4/24![JetBlue logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/269:12 am
BOS
- CVG
1 stop26h 29m
Frontier
Deal found 4/27![Frontier logo]()
$82
This Super.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/178:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 4/27![JetBlue logo]()
$83
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/75:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 4/28![Southwest logo]()
$84
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 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $156 (American Airlines) |
One-way from | $70 (Kiwi.com) |
Popular in | March |
Cheapest in | July |
Average price | $494 |
Good round-trip deal | $466 or less |
Good one-way deal | $318 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 28, 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
Thu 5/28
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
Mon 6/1
9:26 pm-12:59 am
Nonstop2h 33m
$167
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 5/15
8:40 pm-10:35 pm
Nonstop2h 55m
Chicago O'Hare Intl
Tue 5/19
7:00 am-10:35 am
Nonstop2h 35m
$182
Quickest round-trip
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 6/18
5:25 am-7:00 am
Nonstop2h 35m
Chicago Midway
Sun 6/21
5:15 am-8:25 am
Nonstop2h 10m
$191
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 5/23
1:50 pm-3:30 pm
Nonstop2h 40m
Chicago Midway
Sat 5/30
5:25 pm-11:40 pm
1 stop5h 15m
$192
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Mon 7/20
6:45 pm-8:35 pm
Nonstop2h 50m
Chicago Midway
Mon 8/3
7:35 pm-10:50 pm
Nonstop2h 15m
$197
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 5/29
8:40 pm-10:35 pm
Nonstop2h 55m
Chicago O'Hare Intl
Sat 5/30
7:00 am-10:35 am
Nonstop2h 35m
$237
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 7/1
5:30 am-10:45 am
1 stop6h 15m
Chicago O'Hare Intl
Wed 7/8
7:05 am-10:36 am
Nonstop2h 31m
$241
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 6/11
7:30 am-9:10 am
Nonstop2h 40m
Chicago Midway
Fri 6/12
5:05 pm-12:10 am
1 stop6h 05m
$242
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 7/27
11:00 am-6:03 pm
1 stop8h 03m
Chicago O'Hare Intl
Wed 8/5
7:05 am-10:36 am
Nonstop2h 31m
$246
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 5/7
7:10 am-9:00 am
Nonstop2h 50m
Chicago Midway
Sun 5/10
7:40 am-10:55 am
Nonstop2h 15m
$247
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Massachusetts to Indiana
Have a flexible travel schedule? Discover the best time to fly to Indiana from Massachusetts with our price prediction graph.
BOS-ORD
BOS-MDW
BOS-CVG
BOS-RFD
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-ORD
BOS-MDW
BOS-CVG
BOS-RFD
How far ahead should I book a flight from Massachusetts to Indiana?
The best time to book flights from Massachusetts to Indiana is 75 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 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 April 28, 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 25, 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.
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 28, 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.
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 28, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Indiana
Find the right flight back to Massachusetts after your stay in Indiana
Massachusetts to Indiana flights
Consider these flights traveling from Massachusetts to Indiana.
Top 6 airlines flying from Massachusetts to Indiana
Discover the top 6 airlines that operate flights from Massachusetts to Indiana. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$71 | Average$175 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$102 | Average$225 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$118 | Average$435 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$178 | Average$416 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$196 | Average$355 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$318 | Average$486 | FlexibilityNo cancel fee | On-time63% |