$85+ Cheap flights from Illinois 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Aug 1 — Aug 81
Round-trip
1 adult, Economy
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Cheapest flights from Illinois to MassachusettsExplore the most affordable flight options available from Illinois to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 2, 2026.
Explore the most affordable flight options available from Illinois to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 2, 2026.
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.
Mon 8/316:00 am
ORD
- ACK
1 stop8h 24m
JetBlue
Wed 9/212:02 pm
ACK
- ORD
1 stop6h 33m
JetBlue
Deal found 6/30![JetBlue logo]()
$166
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.
Sat 9/54:30 pm
ORD
- BOS
Nonstop2h 41m
Delta
Wed 9/98:50 pm
BOS
- ORD
Nonstop2h 42m
Delta
Deal found 7/1![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 7/1. 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.
Sat 9/51:49 pm
ORD
- BOS
Nonstop3h 10m
JetBlue
Sun 9/65:01 am
BOS
- ORD
1 stop4h 47m
JetBlue
Deal found 7/1![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
Tue 8/47:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 7/1![Southwest logo]()
$175
This Jetabroad deal was found by Cheapflights users on 6/28. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Sun 7/265:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Deal found 6/28![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 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.
Sat 9/57:30 am
ORD
- BOS
Nonstop2h 29m
Delta
Thu 9/107:30 am
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 6/30![Delta 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 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 7/282:40 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Fri 7/315:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/1![Southwest logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 6/28. 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 7/159:40 am
ORD
- BOS
1 stop6h 37m
JetBlue
Sun 7/198:07 am
BOS
- ORD
Nonstop2h 58m
JetBlue
Deal found 6/28![JetBlue logo]()
$180
Best flights from Illinois to MassachusettsDiscover carefully curated flight deals from Illinois to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 2, 2026.
Discover carefully curated flight deals from Illinois to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 2, 2026.
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 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.
Wed 8/194:40 pm
MDW
- BOS
1 stop4h 35m
Southwest
Fri 8/218:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 7/1![Southwest logo]()
$180
This Delta deal was found by Cheapflights users on 6/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/77:30 pm
ORD
- BOS
Nonstop2h 30m
Delta
Mon 8/107:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/27![Delta logo]()
$191
This United Airlines deal was found by Cheapflights users on 6/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1410:30 am
ORD
- BOS
Nonstop2h 37m
United Airlines
Wed 7/158:15 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 6/28![United Airlines logo]()
$191
This United Airlines deal was found by Cheapflights users on 6/27. 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.
Tue 7/1410:30 am
ORD
- BOS
Nonstop2h 37m
United Airlines
Tue 7/215:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 6/27![United Airlines logo]()
$193
This JetBlue deal was found by Cheapflights users on 6/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:30 am
ORD
- BOS
1 stop7h 10m
JetBlue
Tue 9/296:55 am
BOS
- ORD
1 stop5h 52m
JetBlue
Deal found 6/28![JetBlue logo]()
$201
This Southwest deal was found by Cheapflights users on 6/27. 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.
Fri 7/176:00 pm
MDW
- BOS
1 stop4h 30m
Southwest
Mon 7/205:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/27![Southwest logo]()
$205
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 7/1. 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.
Mon 7/276:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Thu 7/306:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/1![United Airlines logo]()
$199
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 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 United Airlines deal was found by Cheapflights users on 6/27. 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 9/1012:52 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Sun 9/136:00 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 6/27![United Airlines logo]()
$207
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 8/78:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sun 8/162:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Deal found 6/29![JetBlue logo]()
$211
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 8/252:00 pm
MDW
- BOS
2 stops7h 10m
Southwest
Thu 8/276:40 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/30![Southwest logo]()
$221
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.
Fri 7/179:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sun 7/196:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/1![United Airlines logo]()
$209
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 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.
Thu 7/234:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Fri 7/245:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/1![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 6/28. 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.
Fri 7/242:30 pm
MDW
- BOS
1 stop6h 10m
Southwest
Mon 7/275:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/28![Southwest logo]()
$231
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 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 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 7/256:00 am
ORD
- ACK
1 stop8h 19m
JetBlue
Tue 7/2811:25 am
ACK
- ORD
1 stop8h 50m
JetBlue
Deal found 6/30![JetBlue logo]()
$262
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 7/228:10 am
MDW
- BOS
1 stop4h 35m
Southwest
Tue 7/2811:35 am
BOS
- MDW
2 stops7h 40m
Southwest
Deal found 6/30![Southwest logo]()
$241
This Delta deal was found by Cheapflights users on 6/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:45 pm
STL
- BDL
1 stop4h 52m
Delta
Wed 12/21:00 pm
BDL
- STL
1 stop4h 50m
Delta
Deal found 6/28![Delta logo]()
$317
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 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.
Sat 9/53:10 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Fri 9/112:15 pm
BOS
- MDW
2 stops6h 20m
Southwest
Deal found 6/30![Southwest logo]()
$246
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 7/296:30 am
STL
- BDL
1 stop4h 43m
Delta
Wed 8/125:24 pm
BDL
- STL
1 stop6h 57m
Delta
Deal found 7/1![Delta logo]()
$317
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 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.
Sun 8/166:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 8/235:20 am
BOS
- MDW
2 stops9h 00m
Southwest
Deal found 7/1![Southwest logo]()
$247
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 8/16:00 am
ORD
- ACK
1 stop8h 19m
JetBlue
Sat 8/84:22 pm
ACK
- ORD
1 stop6h 36m
JetBlue
Deal found 6/30![JetBlue logo]()
$316
This Delta deal was found by Cheapflights users on 6/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/85:09 pm
MLI
- BOS
1 stop5h 32m
Delta
Thu 8/138:55 am
BOS
- MLI
1 stop8h 30m
Delta
Deal found 6/28![Delta logo]()
$319
Last-minute flights from Illinois to MassachusettsDiscover last-minute flight deals from Illinois to Massachusetts. Data last updated July 2, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Massachusetts. Data last updated July 2, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/157:29 pm
ORD
- BOS
Nonstop2h 37m
American Airlines
Sun 7/197:00 am
BOS
- ORD
Nonstop3h 01m
American Airlines
Deal found 6/28![American Airlines logo]()
$178
This Cheapflightsfares deal was found by Cheapflights users on 6/28. 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 7/159:40 am
ORD
- BOS
1 stop6h 37m
JetBlue
Sun 7/198:07 am
BOS
- ORD
Nonstop2h 58m
JetBlue
Deal found 6/28![JetBlue logo]()
$180
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 Jetabroad deal was found by Cheapflights users on 6/28. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Sun 7/265:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Deal found 6/28![JetBlue logo]()
$176
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 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 7/282:40 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Fri 7/315:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/1![Southwest logo]()
$179
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 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 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.
Fri 8/145:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Fri 8/215:21 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 6/30![JetBlue logo]()
$175
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 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
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.
Mon 8/316:00 am
ORD
- ACK
1 stop8h 24m
JetBlue
Wed 9/212:02 pm
ACK
- ORD
1 stop6h 33m
JetBlue
Deal found 6/30![JetBlue logo]()
$166
One-way flights from Illinois to MassachusettsSearch for one-way flight options from Illinois to Massachusetts. Find affordable one-way fares based on user searches. Data last updated July 2, 2026.
Search for one-way flight options from Illinois to Massachusetts. Find affordable one-way fares based on user searches. Data last updated July 2, 2026.
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 8/256:30 pm
ORD
- BDL
1 stop4h 50m
JetBlue
Deal found 6/30![JetBlue logo]()
$85
This JetBlue deal was found by Cheapflights users on 6/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
ORD
- ACK
1 stop8h 24m
JetBlue
Deal found 6/27![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 6/29. 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 7/245:27 pm
ORD
- BDL
1 stop5h 32m
JetBlue
Deal found 6/29![JetBlue logo]()
$93
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.
Mon 8/246:00 am
ORD
- ACK
1 stop8h 24m
JetBlue
Deal found 6/29![JetBlue logo]()
$93
This Super.com deal was found by Cheapflights users on 6/27. 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.
Sat 7/115:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Deal found 6/27![JetBlue logo]()
$94
This Cheapflightsfares deal was found by Cheapflights users on 6/27. 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.
Tue 7/1410:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 6/27![JetBlue logo]()
$95
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.
Sat 8/299:40 am
ORD
- ACK
1 stop4h 44m
JetBlue
Deal found 6/29![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 Cheapflightsfares deal was found by Cheapflights users on 6/27. 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.
Fri 8/76:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Deal found 6/27![JetBlue logo]()
$97
This Cheapflightsfares deal was found by Cheapflights users on 6/28. 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.
Sat 9/268:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 6/28![JetBlue logo]()
$98
Find flight deals from Illinois to Massachusetts
Keep the following information in mind while searching for Illinois to Massachusetts flight deals. Data was last updated July 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $166 (JetBlue) |
One-way from | $85 (JetBlue) |
Popular in | April |
Cheapest in | January |
Average price | $241 |
Good round-trip deal | $212 or less |
Good one-way deal | $128 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois 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 2, 2026.
Use the filters below to find and compare flights from Illinois 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
Thu 8/20
9:35 am-6:59 pm
1 stop8h 24m
Boston Logan Intl
Tue 9/1
12:57 pm-5:35 pm
1 stop5h 38m
$177
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 8/19
4:40 pm-10:15 pm
1 stop4h 35m
Boston Logan Intl
Fri 8/21
8:20 pm-10:00 pm
Nonstop2h 40m
$180
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 8/7
7:30 pm-11:00 pm
Nonstop2h 30m
Boston Logan Intl
Mon 8/10
7:30 am-9:26 am
Nonstop2h 56m
$191
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 7/14
10:30 am-2:07 pm
Nonstop2h 37m
Boston Logan Intl
Wed 7/15
8:15 pm-10:15 pm
Nonstop3h 00m
$191
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 7/14
10:30 am-2:07 pm
Nonstop2h 37m
Boston Logan Intl
Tue 7/21
5:45 am-9:36 am
1 stop4h 51m
$193
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 7/27
6:05 am-9:29 am
Nonstop2h 24m
Boston Logan Intl
Thu 7/30
6:00 am-7:58 am
Nonstop2h 58m
$199
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 9/26
6:30 am-2:40 pm
1 stop7h 10m
Boston Logan Intl
Tue 9/29
6:55 am-11:47 am
1 stop5h 52m
$201
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
MDW - BOS
MDWBOS
Chicago Midway
Fri 7/17
6:00 pm-11:30 pm
1 stop4h 30m
Boston Logan Intl
Mon 7/20
5:25 am-7:00 am
Nonstop2h 35m
$205
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 9/10
12:52 pm-4:27 pm
Nonstop2h 35m
Boston Logan Intl
Sun 9/13
6:00 am-7:59 am
Nonstop2h 59m
$207
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Illinois to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Illinois with our price prediction graph.
ORD-ACK
ORD-BOS
MDW-BOS
ORD-BDL
ORD-ALB
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 Illinois to Massachusetts
USIL-USMA
ORD-ACK
ORD-BOS
MDW-BOS
ORD-BDL
What is the cheapest month to book a flight from Illinois to Massachusetts?
Currently, November is the cheapest month in which you can book a flight from Illinois to Massachusetts (average of $183). Flying from Illinois to Massachusetts in June is currently the most expensive (average of $316). 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 IL to MA?
Find hourly flight availability from Illinois 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 2, 2026.
When flying from Illinois to Massachusetts, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 42% versus a flight in the morning.
Weekly flight availability from Illinois to Massachusetts
Explore weekly flight availability from Illinois 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 2, 2026.
The most flights from USIL to USMA are scheduled on a Wednesday (76 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).
How much does it cost to fly round-trip from Illinois to Massachusetts?
How far ahead should I book a flight from Illinois to Massachusetts?
To ensure you get the cheapest price possible for a flight from Illinois to Massachusetts, you should look to book at least 60 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 Illinois to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Illinois to Massachusetts. Price data was last updated on June 27, 2026.
Travelers seeking maximum savings on their Illinois to Massachusetts flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday at noon 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 2, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Illinois to Massachusetts have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Comfort
8.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Comfort
8.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Comfort
8.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Comfort
8.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Comfort
8.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Comfort
8.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Related info for your journey
Find useful and relevant information for your journey from Illinois to Massachusetts. 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 Illinois 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 Illinois to Massachusetts by cabin class
Find flights from Illinois to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Illinois and Massachusetts flights
Browse other Illinois and Massachusetts flight options. Last updated on July 2, 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 Illinois after your stay in Massachusetts
Illinois to Massachusetts flights
Consider these flights traveling from Illinois to Massachusetts.
Top 5 airlines flying from Illinois to Massachusetts
Discover the top 5 airlines that operate flights from Illinois 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 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$285 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$81 | Average$308 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$114 | Average$253 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$127 | Average$363 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$136 | Average$432 | FlexibilityNo cancel fee | On-time71% |