$70+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Apr 21 — Apr 281
Round-trip
1 adult, Economy
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Find cheap flights from Illinois to Massachusetts with Cheapflights
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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 March 22, 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 March 22, 2026.
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:34 pm
ORD
- BOS
1 stop7h 52m
Frontier
Wed 4/156:00 am
BOS
- ORD
1 stop12h 00m
Frontier
Deal found 3/20![Frontier logo]()
$140
This Frontier deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/612:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Wed 5/1312:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Deal found 3/22![Frontier logo]()
$140
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/42:15 pm
MDW
- BOS
1 stop10h 16m
Frontier
Mon 5/116:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Deal found 3/20![Frontier logo]()
$141
This Cheapflightsfares deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 3/20![JetBlue logo]()
$152
This American Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/111:11 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Sat 4/116:48 pm
BOS
- ORD
Nonstop3h 12m
American Airlines
Deal found 3/21![American Airlines logo]()
$153
This SmartFares deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/20![JetBlue logo]()
$154
This SmartFares deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:55 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Mon 4/136:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/18![JetBlue logo]()
$155
This American Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/28:56 pm
ORD
- BOS
Nonstop2h 29m
American Airlines
Sun 5/36:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 3/22![American Airlines logo]()
$156
This Delta deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:59 pm
ORD
- BOS
Nonstop2h 28m
Delta
Sun 5/36:00 am
BOS
- ORD
Nonstop3h 09m
Delta
Deal found 3/20![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/99:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 4/126:10 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 3/20![Southwest logo]()
$157
This American Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/111:11 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Sun 4/126:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 3/21![American Airlines logo]()
$158
This Priceline deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Fri 5/16:52 am
BOS
- ORD
Nonstop2h 59m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$159
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 March 22, 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 March 22, 2026.
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/87:00 am
ORD
- BOS
Nonstop2h 28m
Delta
Tue 7/2111:00 am
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 3/19![Delta logo]()
$157
This United Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 5/89:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Sun 5/106:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 3/21![United Airlines logo]()
$157
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/87:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Mon 5/116:45 pm
BOS
- MDW
1 stop5h 00m
Southwest
Deal found 3/21![Southwest logo]()
$167
This KAYAK deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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.
Sat 6/209:33 am
ORD
- ACK
1 stop4h 50m
JetBlue
Sat 6/274:20 pm
ACK
- ORD
1 stop5h 24m
JetBlue
Deal found 3/22![JetBlue logo]()
$284
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/87:00 am
ORD
- BOS
Nonstop2h 28m
Delta
Wed 7/227:00 am
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 3/19![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/205:40 pm
MDW
- BOS
1 stop4h 30m
Southwest
Mon 4/2710:40 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 3/21![Southwest logo]()
$167
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Wed 6/38:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Deal found 3/22![Delta logo]()
$157
This United Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 5/89:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Mon 5/117:26 pm
BOS
- ORD
1 stop5h 11m
United Airlines
Deal found 3/21![United Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 5/282:10 pm
MDW
- BOS
2 stops8h 45m
Southwest
Sun 5/316:10 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 3/21![Southwest logo]()
$172
This Delta deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/283:30 pm
ORD
- BOS
Nonstop2h 28m
Delta
Wed 4/297:35 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 3/18![Delta logo]()
$157
This American Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/208:00 am
ORD
- ACK
Nonstop2h 46m
American Airlines
Sat 6/275:09 pm
ACK
- ORD
1 stop5h 28m
American Airlines
Deal found 3/19![American Airlines logo]()
$403
This United Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Fri 8/146:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 3/18![United Airlines logo]()
$187
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/292:40 pm
ORD
- BOS
1 stop7h 35m
Southwest
Wed 6/38:10 am
BOS
- ORD
1 stop5h 40m
Southwest
Deal found 3/18![Southwest logo]()
$177
This United Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 7/249:35 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Tue 8/46:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 3/21![United Airlines logo]()
$189
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:40 pm
MDW
- BOS
1 stop4h 30m
Southwest
Sun 5/35:30 am
BOS
- MDW
1 stop4h 15m
Southwest
Deal found 3/19![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Fri 5/298:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Deal found 3/19![Delta logo]()
$187
This United Airlines deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/29:15 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Wed 4/87:15 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 3/22![United Airlines logo]()
$191
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/88:15 am
MDW
- BOS
1 stop4h 35m
Southwest
Sat 4/119:25 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 3/21![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:45 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 4/57:05 am
BOS
- MDW
Nonstop2h 55m
Southwest
Deal found 3/19![Southwest logo]()
$177
This United Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 7/26:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Tue 7/75:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 3/21![United Airlines logo]()
$201
This Southwest deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/123:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 5/196:20 am
BOS
- MDW
1 stop5h 20m
Southwest
Deal found 3/17![Southwest logo]()
$187
This KAYAK deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/139:33 am
ORD
- ACK
1 stop4h 50m
JetBlue
Sat 6/204:20 pm
ACK
- ORD
1 stop5h 24m
JetBlue
Deal found 3/18![JetBlue logo]()
$353
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/42:45 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 4/75:55 pm
BOS
- MDW
1 stop4h 55m
Southwest
Deal found 3/21![Southwest logo]()
$187
This KAYAK deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/18:57 am
ORD
- ALB
Nonstop2h 10m
American Airlines
Fri 4/36:16 pm
ALB
- ORD
Nonstop2h 52m
American Airlines
Deal found 3/17![American Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 4/2610:35 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 3/17![Southwest logo]()
$197
This United Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/229:35 pm
ORD
- ALB
Nonstop2h 18m
United Airlines
Sat 4/256:05 am
ALB
- ORD
Nonstop2h 33m
United Airlines
Deal found 3/18![United Airlines logo]()
$287
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/35:40 pm
MDW
- BOS
1 stop4h 30m
Southwest
Wed 4/87:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 3/21![Southwest logo]()
$201
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/139:49 am
ORD
- BDL
1 stop6h 07m
Delta
Wed 5/206:00 am
BDL
- ORD
1 stop5h 16m
Delta
Deal found 3/19![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/13:35 pm
MDW
- BOS
1 stop6h 50m
Southwest
Sun 4/58:10 am
BOS
- MDW
1 stop5h 10m
Southwest
Deal found 3/19![Southwest logo]()
$206
This American Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/137:00 am
ORD
- ACK
1 stop6h 02m
American Airlines
Sat 6/2012:16 pm
ACK
- ORD
Nonstop3h 08m
American Airlines
Deal found 3/18![American Airlines logo]()
$488
Last-minute flights from Illinois to MassachusettsDiscover last-minute flight deals from Illinois to Massachusetts. Data last updated March 22, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Massachusetts. Data last updated March 22, 2026 and is based on user searches.
This SmartFares deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:55 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/18![JetBlue logo]()
$155
This SmartFares deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:55 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Mon 4/136:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/19![JetBlue logo]()
$156
This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/99:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 4/126:10 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 3/20![Southwest logo]()
$157
This SmartFares deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/20![JetBlue logo]()
$154
This American Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/111:11 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Sat 4/116:48 pm
BOS
- ORD
Nonstop3h 12m
American Airlines
Deal found 3/21![American Airlines logo]()
$153
This American Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/111:11 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Sun 4/126:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 3/21![American Airlines logo]()
$158
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:34 pm
ORD
- BOS
1 stop7h 52m
Frontier
Wed 4/156:00 am
BOS
- ORD
1 stop12h 00m
Frontier
Deal found 3/20![Frontier logo]()
$140
This Expedia deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:30 am
MDW
- BOS
1 stop27h 51m
Frontier
Tue 4/1412:40 pm
BOS
- MDW
1 stop10h 34m
Frontier
Deal found 3/20![Frontier logo]()
$140
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/222:15 pm
MDW
- BOS
1 stop10h 16m
Frontier
Tue 4/2812:52 pm
BOS
- MDW
1 stop10h 22m
Frontier
Deal found 3/20![Frontier logo]()
$160
This Priceline deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Fri 5/16:52 am
BOS
- ORD
Nonstop2h 59m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$159
This Expedia deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:08 pm
ORD
- BOS
1 stop6h 23m
Frontier
Fri 5/112:42 pm
BOS
- ORD
1 stop10h 57m
Frontier
Deal found 3/20![Frontier logo]()
$160
This Delta deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Sun 5/36:00 am
BOS
- ORD
Nonstop3h 09m
Delta
Deal found 3/20![Delta logo]()
$157
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 March 22, 2026.
Search for one-way flight options from Illinois to Massachusetts. Find affordable one-way fares based on user searches. Data last updated March 22, 2026.
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:08 pm
ORD
- BOS
1 stop6h 23m
Frontier
Deal found 3/20![Frontier logo]()
$70
This Priceline deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:15 am
ORD
- BDL
1 stop5h 49m
Frontier
Deal found 3/21![Frontier logo]()
$70
This Priceline deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/61:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 3/20![Frontier logo]()
$76
This Frontier deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/152:15 pm
MDW
- BOS
1 stop10h 16m
Frontier
Deal found 3/22![Frontier logo]()
$76
This Frontier deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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.
Thu 4/162:15 pm
MDW
- BOS
1 stop10h 16m
Frontier
Deal found 3/21![Frontier logo]()
$77
This Super.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/158:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 3/20![JetBlue logo]()
$78
This Expedia deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:30 am
MDW
- BOS
1 stop27h 51m
Frontier
Deal found 3/20![Frontier logo]()
$78
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Deal found 3/19![Delta logo]()
$79
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 3/19![Southwest logo]()
$79
This Super.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/812:45 pm
ORD
- BOS
1 stop7h 48m
Spirit Airlines
Deal found 3/20![Spirit Airlines logo]()
$80
This Frontier deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/56:41 pm
STL
- BOS
1 stop5h 43m
Frontier
Deal found 3/22![Frontier logo]()
$80
This Cheapflightsfares deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/712:45 pm
ORD
- BOS
1 stop7h 48m
Spirit Airlines
Deal found 3/20![Spirit Airlines logo]()
$81
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 March 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $140 (Frontier) |
One-way from | $70 (Frontier) |
Popular in | April |
Cheapest in | January |
Average price | $225 |
Good round-trip deal | $167 or less |
Good one-way deal | $88 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 March 22, 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
Wed 7/8
7:00 am-10:28 am
Nonstop2h 28m
Boston Logan Intl
Tue 7/21
11:00 am-12:52 pm
Nonstop2h 52m
$157
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 5/8
9:30 pm-12:59 am
Nonstop2h 29m
Boston Logan Intl
Sun 5/10
6:00 am-8:00 am
Nonstop3h 00m
$157
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 7/8
7:00 am-10:28 am
Nonstop2h 28m
Boston Logan Intl
Wed 7/22
7:00 am-8:58 am
Nonstop2h 58m
$157
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/30
7:00 am-10:35 am
Nonstop2h 35m
Boston Logan Intl
Wed 6/3
8:40 pm-10:35 pm
Nonstop2h 55m
$157
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 4/28
3:30 pm-6:58 pm
Nonstop2h 28m
Boston Logan Intl
Wed 4/29
7:35 pm-9:29 pm
Nonstop2h 54m
$157
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 5/8
7:00 pm-10:20 pm
Nonstop2h 20m
Boston Logan Intl
Mon 5/11
6:45 pm-10:45 pm
1 stop5h 00m
$167
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Mon 4/20
5:40 pm-11:10 pm
1 stop4h 30m
Boston Logan Intl
Mon 4/27
10:40 am-12:20 pm
Nonstop2h 40m
$167
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Thu 5/28
2:10 pm-11:55 pm
2 stops8h 45m
Boston Logan Intl
Sun 5/31
6:10 am-7:55 am
Nonstop2h 45m
$172
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 5/8
9:30 pm-12:59 am
Nonstop2h 29m
Boston Logan Intl
Mon 5/11
7:26 pm-11:37 pm
1 stop5h 11m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 5/29
2:40 pm-11:15 pm
1 stop7h 35m
Boston Logan Intl
Wed 6/3
8:10 am-12:50 pm
1 stop5h 40m
$177
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-BOS
MDW-BOS
ORD-ACK
ORD-ALB
ORD-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 Illinois to Massachusetts
USIL-USMA
ORD-BOS
MDW-BOS
ORD-ACK
ORD-ALB
What is the cheapest month to book a flight from Illinois to Massachusetts?
Currently, September is the cheapest month in which you can book a flight from Illinois to Massachusetts (average of $91). Flying from Illinois to Massachusetts in January is currently the most expensive (average of $117). 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 March 22, 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 44% versus a flight in the morning.
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 March 14, 2026.
Travelers seeking maximum savings on their Illinois to Massachusetts flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 March 22, 2026.
The most flights from USIL to USMA are scheduled on a Sunday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (43 on average).
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 March 22, 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.
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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.
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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 March 22, 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 6 airlines flying from Illinois to Massachusetts
Discover the top 6 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 March 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$62 | Average$365 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$86 | Average$253 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$91 | Average$158 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$117 | Average$355 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$117 | Average$431 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$124 | Average$244 | FlexibilityNo cancel fee | On-time63% |