$63+ Cheap flights from Indiana to Massachusetts
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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
IND — BOS
Aug 3 — Aug 101
Round-trip
1 adult, Economy
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Cheapest flights from Indiana to MassachusettsExplore the most affordable flight options available from Indiana to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 4, 2026.
Explore the most affordable flight options available from Indiana to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 4, 2026.
This United Airlines deal was found by Cheapflights users on 7/3. 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.
Sat 7/259:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Tue 7/287:27 pm
BOS
- ORD
1 stop5h 04m
United Airlines
Deal found 7/3![United Airlines logo]()
$172
This Delta deal was found by Cheapflights users on 7/3. 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.
Sat 9/54:30 pm
ORD
- BOS
Nonstop2h 41m
Delta
Wed 9/98:50 pm
BOS
- ORD
Nonstop2h 42m
Delta
Deal found 7/3![Delta logo]()
$173
This Jetabroad deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/69:35 am
ORD
- BOS
1 stop6h 32m
JetBlue
Tue 8/112:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Deal found 6/30![JetBlue logo]()
$174
This JetBlue deal was found by Cheapflights users on 7/3. 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.
Wed 9/28:20 pm
ORD
- BOS
Nonstop2h 56m
JetBlue
Thu 9/106:55 am
BOS
- ORD
1 stop5h 52m
JetBlue
Deal found 7/3![JetBlue logo]()
$175
This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/317:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Thu 8/138:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 7/1![Southwest logo]()
$175
This JetBlue deal was found by Cheapflights users on 7/3. 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 8/151:55 pm
ORD
- BOS
Nonstop2h 36m
JetBlue
Mon 8/175:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/3![JetBlue logo]()
$176
This JetBlue deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 8/209:35 am
ORD
- BOS
1 stop8h 24m
JetBlue
Tue 9/112:57 pm
BOS
- ORD
1 stop5h 38m
JetBlue
Deal found 6/30![JetBlue logo]()
$177
This United Airlines deal was found by Cheapflights users on 7/3. 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.
Wed 7/229:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sun 7/266:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/3![United Airlines logo]()
$178
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:45 pm
MDW
- BOS
Nonstop2h 25m
Southwest
Mon 7/275:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/29![Southwest logo]()
$178
This Delta deal was found by Cheapflights users on 7/1. 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.
Fri 7/173:19 pm
ORD
- BOS
Nonstop2h 40m
Delta
Wed 7/228:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 7/1![Delta logo]()
$179
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/195:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Tue 7/215:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/29![Southwest logo]()
$179
This United Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 8/1212:16 pm
ORD
- BOS
1 stop4h 36m
United Airlines
Fri 8/147:05 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 6/30![United Airlines logo]()
$180
Best flights from Indiana to MassachusettsDiscover carefully curated flight deals from Indiana to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 4, 2026.
Discover carefully curated flight deals from Indiana to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 4, 2026.
This JetBlue deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Wed 8/194:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 6/29![JetBlue logo]()
$177
This Southwest deal was found by Cheapflights users on 7/3. 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.
Tue 8/256:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 8/254:55 pm
BOS
- MDW
1 stop4h 50m
Southwest
Deal found 7/3![Southwest logo]()
$192
This Delta deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 11/67:30 am
ORD
- BOS
Nonstop2h 36m
Delta
Tue 11/104:10 pm
BOS
- ORD
Nonstop3h 00m
Delta
Deal found 6/30![Delta logo]()
$202
This United Airlines deal was found by Cheapflights users on 7/3. 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 7/179:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Tue 7/215:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 7/3![United Airlines logo]()
$210
This JetBlue deal was found by Cheapflights users on 7/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Wed 9/96:55 am
BOS
- ORD
1 stop5h 52m
JetBlue
Deal found 7/1![JetBlue logo]()
$201
This KAYAK deal was found by Cheapflights users on 7/2. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/37:04 pm
ORD
- BDL
Nonstop2h 22m
American Airlines
Wed 8/511:04 am
BDL
- ORD
1 stop5h 06m
American Airlines
Deal found 7/2![American Airlines logo]()
$406
This Southwest deal was found by Cheapflights users on 7/3. 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.
Fri 10/166:45 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 10/207:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/3![Southwest logo]()
$206
This Delta deal was found by Cheapflights users on 7/3. 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.
Wed 8/57:30 pm
ORD
- BOS
Nonstop2h 30m
Delta
Fri 8/78:50 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 7/3![Delta logo]()
$213
This United Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:00 am
ORD
- BOS
Nonstop2h 23m
United Airlines
Sun 11/15:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Deal found 6/29![United Airlines logo]()
$217
This JetBlue deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/159:40 am
ORD
- BOS
1 stop8h 19m
JetBlue
Mon 8/174:55 pm
BOS
- ORD
1 stop6h 03m
JetBlue
Deal found 6/30![JetBlue logo]()
$202
This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/153:10 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sat 8/225:50 am
BOS
- MDW
2 stops8h 15m
Southwest
Deal found 7/1![Southwest logo]()
$208
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:55 am
ORD
- BOS
Nonstop2h 29m
Delta
Fri 8/148:50 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 6/29![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 7/3. 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 9/189:40 pm
ORD
- BOS
Nonstop2h 30m
United Airlines
Sun 9/205:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Deal found 7/3![United Airlines logo]()
$225
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Thu 9/176:40 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/29![Southwest logo]()
$211
This JetBlue deal was found by Cheapflights users on 7/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:20 pm
ORD
- BOS
Nonstop2h 56m
JetBlue
Thu 9/106:55 am
BOS
- ORD
Nonstop2h 51m
JetBlue
Deal found 7/1![JetBlue logo]()
$215
This Southwest deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 7/317:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Fri 8/78:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/30![Southwest logo]()
$216
This JetBlue deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Thu 8/204:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 6/29![JetBlue logo]()
$221
This United Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 7/217:00 am
ORD
- BDL
Nonstop2h 21m
United Airlines
Sat 8/84:55 pm
BDL
- ORD
Nonstop2h 49m
United Airlines
Deal found 6/30![United Airlines logo]()
$289
This Southwest deal was found by Cheapflights users on 7/2. 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.
Sun 8/166:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 8/235:20 am
BOS
- MDW
2 stops9h 00m
Southwest
Deal found 7/2![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 7/2. 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.
Fri 9/44:17 pm
DAY
- BOS
1 stop6h 08m
Delta
Wed 9/910:15 am
BOS
- DAY
1 stop5h 23m
Delta
Deal found 7/2![Delta logo]()
$309
This United Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 7/226:10 pm
ORD
- BDL
Nonstop2h 23m
United Airlines
Sat 8/86:09 am
BDL
- ORD
Nonstop2h 45m
United Airlines
Deal found 6/30![United Airlines logo]()
$289
This Southwest deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/124:40 pm
MDW
- BOS
1 stop4h 35m
Southwest
Tue 8/188:15 am
BOS
- MDW
2 stops6h 15m
Southwest
Deal found 6/30![Southwest logo]()
$248
This Delta deal was found by Cheapflights users on 7/1. 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.
Wed 9/305:11 pm
MDW
- BDL
1 stop5h 47m
Delta
Tue 10/67:20 am
BDL
- MDW
1 stop5h 28m
Delta
Deal found 7/1![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 7/3. 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 10/2212:45 pm
MDW
- BOS
2 stops7h 35m
Southwest
Sun 10/2510:50 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/3![Southwest logo]()
$250
This Delta deal was found by Cheapflights users on 7/2. 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.
Thu 9/241:50 pm
ORD
- ALB
2 stops8h 09m
Delta
Sat 9/266:00 am
ALB
- ORD
2 stops10h 05m
Delta
Deal found 7/2![Delta logo]()
$314
This United Airlines deal was found by Cheapflights users on 7/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/207:45 pm
DAY
- BOS
1 stop4h 09m
United Airlines
Thu 12/3110:30 am
BOS
- DAY
2 stops8h 11m
United Airlines
Deal found 7/1![United Airlines logo]()
$314
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/207:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 9/291:20 pm
BOS
- MDW
2 stops6h 45m
Southwest
Deal found 6/29![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 9/241:00 pm
MDW
- ALB
2 stops8h 59m
Delta
Sat 9/266:50 am
ALB
- MDW
2 stops9h 35m
Delta
Deal found 6/30![Delta logo]()
$314
This United Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 8/142:29 pm
ORD
- ALB
Nonstop2h 13m
United Airlines
Mon 8/176:00 am
ALB
- ORD
Nonstop2h 33m
United Airlines
Deal found 6/30![United Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 7/1. 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.
Thu 10/11:50 pm
ORD
- BDL
1 stop5h 12m
Delta
Sat 10/103:00 pm
BDL
- ORD
1 stop7h 32m
Delta
Deal found 7/1![Delta logo]()
$317
Last-minute flights from Indiana to MassachusettsDiscover last-minute flight deals from Indiana to Massachusetts. Data last updated July 4, 2026 and is based on user searches.
Discover last-minute flight deals from Indiana to Massachusetts. Data last updated July 4, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/1. 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.
Fri 7/173:19 pm
ORD
- BOS
Nonstop2h 40m
Delta
Wed 7/228:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 7/1![Delta logo]()
$179
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/195:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Tue 7/215:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/29![Southwest logo]()
$179
This United Airlines deal was found by Cheapflights users on 7/3. 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.
Wed 7/229:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sun 7/266:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/3![United Airlines logo]()
$178
This United Airlines deal was found by Cheapflights users on 7/3. 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.
Sat 7/259:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Tue 7/287:27 pm
BOS
- ORD
1 stop5h 04m
United Airlines
Deal found 7/3![United Airlines logo]()
$172
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:45 pm
MDW
- BOS
Nonstop2h 25m
Southwest
Mon 7/275:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/29![Southwest logo]()
$178
This Southwest deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 7/317:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 8/47:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/30![Southwest logo]()
$175
This Jetabroad deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/69:35 am
ORD
- BOS
1 stop6h 32m
JetBlue
Tue 8/112:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Deal found 6/30![JetBlue logo]()
$174
This Southwest deal was found by Cheapflights users on 7/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 8/125:35 am
BOS
- MDW
1 stop7h 15m
Southwest
Deal found 7/1![Southwest logo]()
$180
This United Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 8/1212:16 pm
ORD
- BOS
1 stop4h 36m
United Airlines
Fri 8/147:05 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 6/30![United Airlines logo]()
$180
This JetBlue deal was found by Cheapflights users on 7/3. 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 8/151:55 pm
ORD
- BOS
Nonstop2h 36m
JetBlue
Mon 8/175:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/3![JetBlue logo]()
$176
This JetBlue deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 8/206:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Tue 9/18:15 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 6/30![JetBlue logo]()
$175
This American Airlines deal was found by Cheapflights users on 7/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:00 am
ORD
- BOS
Nonstop2h 32m
American Airlines
Sat 9/1210:30 am
BOS
- ORD
Nonstop3h 02m
American Airlines
Deal found 7/1![American Airlines logo]()
$173
One-way flights from Indiana to MassachusettsSearch for one-way flight options from Indiana to Massachusetts. Find affordable one-way fares based on user searches. Data last updated July 4, 2026.
Search for one-way flight options from Indiana to Massachusetts. Find affordable one-way fares based on user searches. Data last updated July 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:00 am
IND
- BOS
Nonstop2h 14m
Allegiant Air
Deal found 6/30![Allegiant Air logo]()
$63
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 10/226:00 am
IND
- BOS
Nonstop2h 14m
Allegiant Air
Deal found 6/30![Allegiant Air logo]()
$83
This CheapOair deal was found by Cheapflights users on 7/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:00 am
IND
- BOS
Nonstop2h 14m
Allegiant Air
Deal found 7/2![Allegiant Air logo]()
$85
This JetBlue deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 8/186:30 pm
ORD
- BDL
1 stop4h 50m
JetBlue
Deal found 6/30![JetBlue logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/298:05 am
ORD
- ALB
1 stop25h 20m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$92
This JetBlue deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 7/305:27 pm
ORD
- BDL
1 stop5h 32m
JetBlue
Deal found 6/30![JetBlue logo]()
$93
This SmartFares deal was found by Cheapflights users on 7/1. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 7/1![JetBlue logo]()
$94
This Cheapflightsfares deal was found by Cheapflights users on 7/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:10 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/2![JetBlue logo]()
$95
This United Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 7/159:15 am
ORD
- BOS
Nonstop2h 42m
United Airlines
Deal found 6/30![United Airlines logo]()
$96
This Southwest deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 7/146:05 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/30![Southwest logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 7/318:30 am
IND
- BOS
Nonstop2h 14m
Allegiant Air
Deal found 6/30![Allegiant Air logo]()
$96
This Super.com deal was found by Cheapflights users on 7/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/308:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 7/2![JetBlue logo]()
$97
Find flight deals from Indiana to Massachusetts
Keep the following information in mind while searching for Indiana to Massachusetts flight deals. Data was last updated July 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $172 (United Airlines) |
One-way from | $63 (Kiwi.com) |
Popular in | March |
Cheapest in | June |
Average price | $410 |
Good round-trip deal | $322 or less |
Good one-way deal | $162 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Indiana to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 4, 2026.
Use the filters below to find and compare flights from Indiana to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 8/14
5:27 pm-11:59 pm
1 stop5h 32m
Boston Logan Intl
Wed 8/19
4:30 pm-9:58 pm
1 stop6h 28m
$177
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 8/25
6:40 am-9:55 am
Nonstop2h 15m
Boston Logan Intl
Tue 8/25
4:55 pm-8:45 pm
1 stop4h 50m
$192
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 8/21
6:00 am-2:43 pm
1 stop7h 43m
Boston Logan Intl
Wed 9/9
6:55 am-11:47 am
1 stop5h 52m
$201
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 11/6
7:30 am-11:06 am
Nonstop2h 36m
Boston Logan Intl
Tue 11/10
4:10 pm-6:10 pm
Nonstop3h 00m
$202
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 8/15
9:40 am-6:59 pm
1 stop8h 19m
Boston Logan Intl
Mon 8/17
4:55 pm-9:58 pm
1 stop6h 03m
$202
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 10/16
6:45 pm-10:00 pm
Nonstop2h 15m
Boston Logan Intl
Tue 10/20
7:20 am-8:55 am
Nonstop2h 35m
$206
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 8/15
3:10 pm-6:30 pm
Nonstop2h 20m
Boston Logan Intl
Sat 8/22
5:50 am-1:05 pm
2 stops8h 15m
$208
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 7/17
9:41 pm-1:14 am
Nonstop2h 33m
Boston Logan Intl
Tue 7/21
5:45 am-9:36 am
1 stop4h 51m
$210
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sun 9/13
6:00 am-9:15 am
Nonstop2h 15m
Boston Logan Intl
Thu 9/17
6:40 pm-8:20 pm
Nonstop2h 40m
$211
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 8/5
7:30 pm-11:00 pm
Nonstop2h 30m
Boston Logan Intl
Fri 8/7
8:50 pm-10:44 pm
Nonstop2h 54m
$213
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Indiana to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Indiana with our price prediction graph.
ORD-BDL
ORD-BOS
MDW-BOS
DAY-BOS
MDW-BDL
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 Indiana to Massachusetts
USIN-USMA
ORD-BDL
ORD-BOS
MDW-BOS
DAY-BOS
What is the cheapest month to book a flight from Indiana to Massachusetts?
Currently, July is the cheapest month in which you can book a flight from Indiana to Massachusetts (average of $100). Flying from Indiana to Massachusetts in January is currently the most expensive (average of $288). 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 IN to MA?
Find hourly flight availability from Indiana to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 4, 2026.
A simple way to save on the total cost of your ticket is to fly from Indiana to Massachusetts in the evening. If you’re flexible enough to do this you can expect to save up to 48% on your trip compared to booking a flight in the afternoon.
Weekly flight availability from Indiana to Massachusetts
Explore weekly flight availability from Indiana to Massachusetts. 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 July 4, 2026.
The most flights from USIN to USMA are scheduled on a Saturday (17 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 on average).
How much does it cost to fly round-trip from Indiana to Massachusetts?
How far ahead should I book a flight from Indiana to Massachusetts?
To ensure you get the cheapest price possible for a flight from Indiana to Massachusetts, you should look to book at least 26 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Indiana to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Indiana to Massachusetts. Price data was last updated on July 4, 2026.
Travelers seeking maximum savings on their Indiana to Massachusetts flight should consider departing on Friday evenings when fares are most often at their lowest. Saturday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated July 4, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Indiana to Massachusetts have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Indiana to Massachusetts. 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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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Indiana to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Indiana to Massachusetts by cabin class
Find flights from Indiana to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Indiana and Massachusetts flights
Browse other Indiana and Massachusetts flight options. Last updated on July 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Massachusetts
Find the right flight back to Indiana after your stay in Massachusetts
Indiana to Massachusetts flights
Consider these flights traveling from Indiana to Massachusetts.
Top 6 airlines flying from Indiana to Massachusetts
Discover the top 6 airlines that operate flights from Indiana to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$202 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$127 | Average$432 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$148 | Average$216 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$172 | Average$428 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$214 | Average$404 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$259 | Average$452 | FlexibilityNo cancel fee | On-time63% |