$82+ Cheap flights from Massachusetts to Illinois
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Jun 19 — Jun 261
Round-trip
1 adult, Economy
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Find cheap flights from Massachusetts to Illinois with Cheapflights
1. Tell us where you want to go
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Cheapest flights from Massachusetts to IllinoisExplore the most affordable flight options available from Massachusetts to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 20, 2026.
Explore the most affordable flight options available from Massachusetts to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 20, 2026.
This SmartFares deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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.
Tue 6/26:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Tue 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/15![JetBlue logo]()
$173
This Southwest deal was found by Cheapflights users on 5/17. 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.
Sat 6/65:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 6/97:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/17![Southwest logo]()
$176
This SmartFares deal was found by Cheapflights users on 5/17. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Mon 6/88:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/17![JetBlue logo]()
$176
This Southwest deal was found by Cheapflights users on 5/17. 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.
Sat 6/65:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 6/87:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/17![Southwest logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 5/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Wed 6/108:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 5/19![JetBlue logo]()
$182
This flygcity.se deal was found by Cheapflights users on 5/17. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/611:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Mon 6/88:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/17![JetBlue logo]()
$183
This SmartFares deal was found by Cheapflights users on 5/17. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Tue 8/2510:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 5/17![JetBlue logo]()
$184
This American Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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.
Tue 6/23:00 pm
BOS
- ORD
Nonstop3h 06m
American Airlines
Tue 6/91:57 pm
ORD
- BOS
Nonstop2h 35m
American Airlines
Deal found 5/16![American Airlines logo]()
$186
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Wed 6/102:40 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 5/15![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 5/18. 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.
Wed 6/37:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Wed 6/107:10 am
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 5/18![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 5/17. 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.
Sat 5/231:50 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Sat 6/65:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/17![Southwest logo]()
$188
This Frontier deal was found by Cheapflights users on 5/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:00 am
BOS
- MDW
1 stop6h 12m
Frontier
Wed 9/212:04 pm
MDW
- BOS
1 stop12h 23m
Frontier
Deal found 5/18![Frontier logo]()
$189
Best flights from Massachusetts to IllinoisDiscover carefully curated flight deals from Massachusetts to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 20, 2026.
Discover carefully curated flight deals from Massachusetts to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 20, 2026.
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 6/65:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sat 6/65:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 5/15![Southwest logo]()
$197
This JetBlue deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 8/118:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Wed 8/1910:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 5/16![JetBlue logo]()
$205
This United Airlines deal was found by Cheapflights users on 5/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/237:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Mon 7/276:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 5/19![United Airlines logo]()
$205
This Delta deal was found by Cheapflights users on 5/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/248:45 pm
BOS
- ORD
Nonstop2h 57m
Delta
Tue 6/307:10 am
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 5/17![Delta logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:37 pm
BOS
- RFD
1 stop20h 38m
Multiple Airlines
Sun 7/1211:27 am
RFD
- BOS
2 stops19h 19m
Multiple Airlines
Deal found 5/15![Multiple Airlines logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/512:33 pm
BOS
- RFD
1 stop20h 44m
Allegiant Air
Fri 6/128:35 am
RFD
- BOS
2 stops23h 28m
Allegiant Air
Deal found 5/16![Allegiant Air logo]()
$376
This KAYAK deal was found by Cheapflights users on 5/19. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/137:56 pm
ALB
- ORD
Nonstop2h 51m
American Airlines
Tue 7/144:10 pm
ORD
- ALB
Nonstop2h 16m
American Airlines
Deal found 5/19![American Airlines logo]()
$377
This Southwest deal was found by Cheapflights users on 5/18. 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.
Thu 5/287:10 am
BOS
- MDW
Nonstop2h 50m
Southwest
Thu 5/281:55 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/18![Southwest logo]()
$205
This United Airlines deal was found by Cheapflights users on 5/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:55 am
BOS
- ORD
Nonstop2h 53m
United Airlines
Sat 6/66:12 pm
ORD
- BOS
1 stop4h 47m
United Airlines
Deal found 5/19![United Airlines logo]()
$211
This Southwest deal was found by Cheapflights users on 5/18. 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.
Mon 8/177:30 am
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 8/196:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/18![Southwest logo]()
$207
This United Airlines deal was found by Cheapflights users on 5/18. 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.
Sun 6/286:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Thu 7/26:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 5/18![United Airlines logo]()
$215
This Southwest deal was found by Cheapflights users on 5/19. 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 5/278:10 am
BOS
- ORD
1 stop5h 40m
Southwest
Thu 5/282:40 pm
ORD
- BOS
1 stop7h 35m
Southwest
Deal found 5/19![Southwest logo]()
$225
This United Airlines deal was found by Cheapflights users on 5/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/187:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Thu 6/257:33 am
ORD
- BOS
Nonstop2h 32m
United Airlines
Deal found 5/19![United Airlines logo]()
$228
This Southwest deal was found by Cheapflights users on 5/19. 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 5/278:10 am
BOS
- ORD
1 stop5h 40m
Southwest
Fri 5/292:40 pm
ORD
- BOS
1 stop7h 35m
Southwest
Deal found 5/19![Southwest logo]()
$225
This United Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/57:27 pm
BOS
- ORD
1 stop4h 59m
United Airlines
Mon 6/89:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 5/16![United Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 5/19. 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 5/285:30 am
BOS
- ORD
2 stops8h 20m
Southwest
Fri 5/292:40 pm
ORD
- BOS
1 stop7h 35m
Southwest
Deal found 5/19![Southwest logo]()
$230
This United Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Sun 5/317:33 am
ORD
- BOS
Nonstop2h 32m
United Airlines
Deal found 5/15![United Airlines logo]()
$232
This Delta deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 6/305:30 am
BDL
- STL
1 stop5h 02m
Delta
Tue 7/216:00 am
STL
- BDL
1 stop5h 45m
Delta
Deal found 5/16![Delta logo]()
$347
This JetBlue deal was found by Cheapflights users on 5/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:25 am
BDL
- ORD
1 stop6h 22m
JetBlue
Wed 9/232:35 pm
ORD
- BDL
1 stop8h 20m
JetBlue
Deal found 5/17![JetBlue logo]()
$363
This Southwest deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Wed 5/273:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 5/16![Southwest logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2911:27 am
BOS
- RFD
1 stop23h 57m
Multiple Airlines
Thu 6/411:27 am
RFD
- BOS
2 stops19h 22m
Multiple Airlines
Deal found 5/17![Multiple Airlines logo]()
$380
This Delta deal was found by Cheapflights users on 5/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:05 am
ALB
- MDW
1 stop4h 03m
Delta
Sat 7/186:35 pm
MDW
- ALB
1 stop3h 46m
Delta
Deal found 5/17![Delta logo]()
$347
This American Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 6/61:41 pm
BDL
- STL
1 stop6h 38m
American Airlines
Tue 6/95:08 am
STL
- BDL
1 stop7h 35m
American Airlines
Deal found 5/16![American Airlines logo]()
$387
This JetBlue deal was found by Cheapflights users on 5/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:15 am
BDL
- ORD
1 stop8h 15m
JetBlue
Mon 6/13:27 pm
ORD
- BDL
1 stop7h 28m
JetBlue
Deal found 5/19![JetBlue logo]()
$375
This Delta deal was found by Cheapflights users on 5/18. 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.
Thu 8/136:00 am
ALB
- MDW
1 stop4h 17m
Delta
Sun 8/166:42 pm
MDW
- ALB
1 stop3h 34m
Delta
Deal found 5/18![Delta logo]()
$354
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 7/33:55 pm
BOS
- MDW
2 stops5h 45m
Southwest
Tue 7/72:35 pm
MDW
- BOS
1 stop7h 05m
Southwest
Deal found 5/15![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 5/19. 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 6/186:06 am
ALB
- ORD
1 stop5h 44m
Delta
Sat 6/205:22 pm
ORD
- ALB
1 stop5h 02m
Delta
Deal found 5/19![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 5/19. 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.
Tue 7/2111:35 am
BOS
- MDW
2 stops7h 40m
Southwest
Fri 7/247:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/19![Southwest logo]()
$256
This JetBlue deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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 6/37:15 am
BDL
- ORD
1 stop8h 15m
JetBlue
Mon 6/83:27 pm
ORD
- BDL
1 stop7h 25m
JetBlue
Deal found 5/16![JetBlue logo]()
$430
This United Airlines deal was found by Cheapflights users on 5/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 am
ALB
- STL
2 stops7h 02m
United Airlines
Wed 9/2312:59 pm
STL
- ALB
1 stop4h 49m
United Airlines
Deal found 5/17![United Airlines logo]()
$331
Last-minute flights from Massachusetts to IllinoisDiscover last-minute flight deals from Massachusetts to Illinois. Data last updated May 20, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Illinois. Data last updated May 20, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/17. 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.
Sat 5/231:50 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Sat 6/65:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/17![Southwest logo]()
$188
This SmartFares deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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.
Tue 6/26:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Tue 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/15![JetBlue logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/29:12 am
BOS
- MDW
1 stop26h 57m
Multiple Airlines
Fri 6/59:23 pm
MDW
- BOS
1 stop11h 41m
Multiple Airlines
Deal found 5/14![Multiple Airlines logo]()
$179
This American Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” 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.
Tue 6/23:00 pm
BOS
- ORD
Nonstop3h 06m
American Airlines
Tue 6/91:57 pm
ORD
- BOS
Nonstop2h 35m
American Airlines
Deal found 5/16![American Airlines logo]()
$186
This Cheapflightsfares deal was found by Cheapflights users on 5/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Wed 6/108:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 5/19![JetBlue logo]()
$182
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Wed 6/102:40 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 5/15![Southwest logo]()
$187
This JetBlue deal was found by Cheapflights users on 5/18. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Tue 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/18![JetBlue logo]()
$187
This SmartFares deal was found by Cheapflights users on 5/17. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Mon 6/88:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/17![JetBlue logo]()
$176
This Southwest deal was found by Cheapflights users on 5/17. 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.
Sat 6/65:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 6/97:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/17![Southwest logo]()
$176
This Southwest deal was found by Cheapflights users on 5/17. 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.
Sat 6/65:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 6/87:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/17![Southwest logo]()
$181
This flygcity.se deal was found by Cheapflights users on 5/17. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/611:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Mon 6/88:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/17![JetBlue logo]()
$183
This Frontier deal was found by Cheapflights users on 5/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/169:10 am
BOS
- ORD
1 stop11h 40m
Frontier
Tue 6/231:29 pm
ORD
- BOS
1 stop10h 58m
Frontier
Deal found 5/17![Frontier logo]()
$189
One-way flights from Massachusetts to IllinoisSearch for one-way flight options from Massachusetts to Illinois. Find affordable one-way fares based on user searches. Data last updated May 20, 2026.
Search for one-way flight options from Massachusetts to Illinois. Find affordable one-way fares based on user searches. Data last updated May 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/99:10 am
BOS
- STL
1 stop9h 20m
Frontier
Deal found 5/15![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1012:01 pm
BOS
- MDW
1 stop11h 10m
Frontier
Deal found 5/15![Frontier logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/29:12 am
BOS
- STL
1 stop24h 43m
Frontier
Deal found 5/18![Frontier logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
BOS
- MDW
1 stop30h 09m
Frontier
Deal found 5/14![Frontier logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
BOS
- ORD
1 stop14h 53m
Frontier
Deal found 5/15![Frontier logo]()
$88
This Super.com deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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.
Tue 6/306:00 am
BOS
- MDW
1 stop6h 12m
Frontier
Deal found 5/15![Frontier logo]()
$91
This Super.com deal was found by Cheapflights users on 5/18. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/18![JetBlue logo]()
$92
This Super.com deal was found by Cheapflights users on 5/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/19![JetBlue logo]()
$93
This Southwest deal was found by Cheapflights users on 5/18. 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.
Wed 6/310:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 5/18![Southwest logo]()
$94
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” 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 6/98:45 pm
BOS
- ORD
Nonstop2h 57m
Delta
Deal found 5/15![Delta logo]()
$94
This Frontier deal was found by Cheapflights users on 5/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:00 am
BOS
- MDW
1 stop6h 07m
Frontier
Deal found 5/18![Frontier logo]()
$95
This Expedia deal was found by Cheapflights users on 5/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:35 pm
BOS
- ORD
1 stop8h 09m
Frontier
Deal found 5/18![Frontier logo]()
$95
Find flight deals from Massachusetts to Illinois
Keep the following information in mind while searching for Massachusetts to Illinois flight deals. Data was last updated May 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $173 (SmartFares) |
One-way from | $82 (Kiwi.com) |
Popular in | May |
Cheapest in | September |
Average price | $253 |
Good round-trip deal | $238 or less |
Good one-way deal | $128 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Massachusetts to Illinois 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 May 20, 2026.
Use the filters below to find and compare flights from Massachusetts to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 6/6
5:20 am-6:55 am
Nonstop2h 35m
Chicago Midway
Sat 6/6
5:45 pm-9:05 pm
Nonstop2h 20m
$197
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 8/11
8:10 am-10:06 am
Nonstop2h 56m
Chicago O'Hare Intl
Wed 8/19
10:56 am-2:23 pm
Nonstop2h 27m
$205
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 7/23
7:19 am-9:17 am
Nonstop2h 58m
Chicago O'Hare Intl
Mon 7/27
6:05 am-9:29 am
Nonstop2h 24m
$205
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 5/28
7:10 am-9:00 am
Nonstop2h 50m
Chicago Midway
Thu 5/28
1:55 pm-5:10 pm
Nonstop2h 15m
$205
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 6/24
8:45 pm-10:42 pm
Nonstop2h 57m
Chicago O'Hare Intl
Tue 6/30
7:10 am-10:46 am
Nonstop2h 36m
$207
Quickest round-trip
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Mon 8/17
7:30 am-9:05 am
Nonstop2h 35m
Chicago Midway
Wed 8/19
6:40 am-9:55 am
Nonstop2h 15m
$207
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 5/28
10:55 am-12:48 pm
Nonstop2h 53m
Chicago O'Hare Intl
Sat 6/6
6:12 pm-11:59 pm
1 stop4h 47m
$211
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 6/28
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Thu 7/2
6:00 am-11:16 am
1 stop4h 16m
$215
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/27
8:10 am-12:50 pm
1 stop5h 40m
Chicago O'Hare Intl
Thu 5/28
2:40 pm-11:15 pm
1 stop7h 35m
$225
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/27
8:10 am-12:50 pm
1 stop5h 40m
Chicago O'Hare Intl
Fri 5/29
2:40 pm-11:15 pm
1 stop7h 35m
$225
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Massachusetts to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Massachusetts with our price prediction graph.
BOS-ORD
BOS-MDW
BOS-RFD
ALB-ORD
BDL-STL
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Massachusetts to Illinois
USMA-USIL
BOS-ORD
BOS-MDW
BOS-RFD
ALB-ORD
What is the cheapest month to book a flight from Massachusetts to Illinois?
Currently, September is the cheapest month in which you can book a flight from Massachusetts to Illinois (average of $168). Flying from Massachusetts to Illinois in April is currently the most expensive (average of $290). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MA to IL?
Find hourly flight availability from Massachusetts to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 20, 2026.
A simple way to save on the total cost of your ticket is to fly from Massachusetts to Illinois in the evening. If you’re flexible enough to do this you can expect to save up to 44% on your trip compared to booking a flight in the afternoon.
How much does it cost to fly round-trip from Massachusetts to Illinois?
How far ahead should I book a flight from Massachusetts to Illinois?
Booking 74 days in advance of your planned departure date is, on average, the best time to get cheap flights from Massachusetts to Illinois. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Massachusetts to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Illinois. Price data was last updated on May 16, 2026.
Travelers seeking maximum savings on their Massachusetts to Illinois flight should consider departing on Thursday evenings 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 Illinois
Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated May 20, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Massachusetts to Illinois have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Massachusetts to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Massachusetts to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Massachusetts to Illinois by cabin class
Find flights from Massachusetts to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Massachusetts and Illinois flights
Browse other Massachusetts and Illinois flight options. Last updated on May 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Illinois
Find the right flight back to Massachusetts after your stay in Illinois
Massachusetts to Illinois flights
Consider these flights traveling from Massachusetts to Illinois.
Top 6 airlines flying from Massachusetts to Illinois
Discover the top 6 airlines that operate flights from Massachusetts to Illinois. 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 May 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$177 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$323 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$95 | Average$187 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$121 | Average$357 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$128 | Average$219 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$137 | Average$413 | FlexibilityNo cancel fee | On-time71% |