$94+ 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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Aug 17 — Aug 241
Round-trip
1 adult, Economy
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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 July 18, 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 July 18, 2026.
This deal was found by Cheapflights users on 7/14. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:05 am
BOS
- ORD
1 stop5h 51m
JetBlue
Sat 11/148:24 pm
ORD
- BOS
Nonstop2h 32m
JetBlue
Deal found 7/14![JetBlue logo]()
$178
This Super.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/45:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Fri 8/76:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Deal found 7/13![JetBlue logo]()
$179
This Super.com deal was found by Cheapflights users on 7/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/42:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Thu 8/66:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 7/14![JetBlue logo]()
$182
This Super.com deal was found by Cheapflights users on 7/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:01 am
BOS
- ORD
1 stop4h 45m
JetBlue
Mon 8/315:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Deal found 7/14![JetBlue logo]()
$183
This SmartFares deal was found by Cheapflights users on 7/15. 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.
Sun 8/235:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Sat 8/296:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 7/15![JetBlue logo]()
$184
This SmartFares deal was found by Cheapflights users on 7/14. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/264:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Thu 8/276:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 7/14![JetBlue logo]()
$186
This Super.com deal was found by Cheapflights users on 7/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:55 am
BOS
- ORD
Nonstop2h 51m
JetBlue
Sat 9/126:30 am
ORD
- BOS
1 stop7h 10m
JetBlue
Deal found 7/14![JetBlue logo]()
$187
This Super.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 9/155:15 am
BOS
- ORD
1 stop7h 32m
JetBlue
Wed 9/168:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 7/13![JetBlue logo]()
$188
This SmartFares deal was found by Cheapflights users on 7/15. 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.
Mon 8/245:21 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Thu 8/278:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/15![JetBlue logo]()
$190
This Super.com deal was found by Cheapflights users on 7/18. 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 8/1912:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Wed 8/266:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Deal found 7/18![JetBlue logo]()
$192
This Super.com deal was found by Cheapflights users on 7/15. 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.
Wed 8/55:01 am
BOS
- ORD
1 stop4h 46m
JetBlue
Sat 8/85:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Deal found 7/15![JetBlue logo]()
$193
This Southwest deal was found by Cheapflights users on 7/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/179:40 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 10/206:10 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/14![Southwest logo]()
$197
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 July 18, 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 July 18, 2026.
This JetBlue deal was found by Cheapflights users on 7/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Tue 9/229:38 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 7/15![JetBlue logo]()
$197
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:50 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 10/209:10 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/13![Southwest logo]()
$206
This Delta deal was found by Cheapflights users on 7/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:40 pm
BOS
- ORD
Nonstop2h 48m
Delta
Mon 10/267:30 am
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 7/14![Delta logo]()
$215
This United Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 7/299:50 am
BOS
- ORD
Nonstop2h 53m
United Airlines
Fri 8/712:53 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 7/13![United Airlines logo]()
$215
This American Airlines deal was found by Cheapflights users on 7/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/75:23 pm
ORH
- ORD
1 stop6h 07m
American Airlines
Sun 8/96:45 am
ORD
- ORH
1 stop9h 13m
American Airlines
Deal found 7/17![American Airlines logo]()
$310
This JetBlue deal was found by Cheapflights users on 7/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/124:00 pm
BOS
- ORD
1 stop7h 06m
JetBlue
Wed 9/169:38 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 7/14![JetBlue logo]()
$199
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/257:15 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 8/318:15 am
MDW
- BOS
Nonstop2h 25m
Southwest
Deal found 7/13![Southwest logo]()
$215
This United Airlines deal was found by Cheapflights users on 7/18. 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.
Thu 10/1512:45 pm
BOS
- ORD
Nonstop2h 52m
United Airlines
Tue 10/209:05 am
ORD
- BOS
Nonstop2h 43m
United Airlines
Deal found 7/18![United Airlines logo]()
$216
This Delta deal was found by Cheapflights users on 7/16. 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.
Fri 9/48:50 pm
BOS
- ORD
Nonstop2h 54m
Delta
Tue 9/87:05 pm
ORD
- BOS
Nonstop2h 42m
Delta
Deal found 7/16![Delta logo]()
$225
This Southwest deal was found by Cheapflights users on 7/15. 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 8/193:20 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 8/236:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/15![Southwest logo]()
$215
This JetBlue deal was found by Cheapflights users on 7/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:15 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Wed 8/268:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/14![JetBlue logo]()
$215
This United Airlines deal was found by Cheapflights users on 7/17. 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.
Wed 8/129:00 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Sat 8/1510:25 am
ORD
- BOS
Nonstop2h 42m
United Airlines
Deal found 7/17![United Airlines logo]()
$225
This Delta deal was found by Cheapflights users on 7/18. 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.
Fri 11/208:10 pm
BOS
- ORD
Nonstop2h 54m
Delta
Tue 11/247:00 am
ORD
- BOS
Nonstop2h 28m
Delta
Deal found 7/18![Delta logo]()
$225
This Southwest deal was found by Cheapflights users on 7/17. 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.
Thu 10/156:35 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 10/201:10 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/17![Southwest logo]()
$216
This JetBlue deal was found by Cheapflights users on 7/17. 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.
Tue 8/182:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Fri 8/218:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/17![JetBlue logo]()
$218
This United Airlines deal was found by Cheapflights users on 7/16. 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.
Thu 10/158:31 pm
BOS
- ORD
Nonstop2h 58m
United Airlines
Sun 10/186:10 am
ORD
- BOS
Nonstop2h 23m
United Airlines
Deal found 7/16![United Airlines logo]()
$225
This Delta deal was found by Cheapflights users on 7/17. 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.
Fri 10/164:15 pm
ORH
- ORD
1 stop6h 57m
Delta
Sun 10/187:00 am
ORD
- ORH
1 stop6h 59m
Delta
Deal found 7/17![Delta logo]()
$230
This Southwest deal was found by Cheapflights users on 7/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/47:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Fri 8/73:20 pm
MDW
- BOS
1 stop6h 00m
Southwest
Deal found 7/14![Southwest logo]()
$225
This Delta deal was found by Cheapflights users on 7/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/285:40 pm
ORH
- ORD
1 stop5h 56m
Delta
Wed 7/299:30 am
ORD
- ORH
1 stop6h 30m
Delta
Deal found 7/14![Delta logo]()
$230
This United Airlines deal was found by Cheapflights users on 7/18. 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.
Mon 8/177:05 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Wed 8/196:00 am
ORD
- BOS
1 stop4h 17m
United Airlines
Deal found 7/18![United Airlines logo]()
$235
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/1910:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Tue 8/2512:45 pm
MDW
- BOS
2 stops7h 40m
Southwest
Deal found 7/13![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 7/15. 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 8/288:40 am
BOS
- MDW
2 stops9h 25m
Southwest
Sun 8/306:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/15![Southwest logo]()
$240
This Delta deal was found by Cheapflights users on 7/15. 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.
Wed 8/51:27 pm
ALB
- MDW
1 stop6h 06m
Delta
Wed 8/1210:54 am
MDW
- ALB
2 stops11h 23m
Delta
Deal found 7/15![Delta logo]()
$282
This Southwest deal was found by Cheapflights users on 7/15. 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 9/43:35 pm
BOS
- MDW
1 stop6h 25m
Southwest
Wed 9/911:55 am
MDW
- BOS
2 stops5h 40m
Southwest
Deal found 7/15![Southwest logo]()
$241
This JetBlue deal was found by Cheapflights users on 7/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:25 am
BDL
- ORD
1 stop6h 22m
JetBlue
Sun 9/203:00 pm
ORD
- BDL
1 stop7h 14m
JetBlue
Deal found 7/15![JetBlue logo]()
$321
This United Airlines deal was found by Cheapflights users on 7/16. 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.
Sat 9/265:00 pm
ALB
- STL
1 stop6h 59m
United Airlines
Mon 9/288:00 am
STL
- ALB
1 stop6h 04m
United Airlines
Deal found 7/16![United Airlines logo]()
$297
This Delta deal was found by Cheapflights users on 7/16. 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.
Sat 8/296:00 am
ALB
- ORD
2 stops9h 48m
Delta
Tue 9/11:59 pm
ORD
- ALB
2 stops8h 58m
Delta
Deal found 7/16![Delta logo]()
$288
This Southwest deal was found by Cheapflights users on 7/15. 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 8/145:25 am
BOS
- MDW
1 stop6h 35m
Southwest
Fri 8/215:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/15![Southwest logo]()
$245
This United Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 10/212:45 pm
ALB
- ORD
Nonstop2h 34m
United Airlines
Sat 10/32:30 pm
ORD
- ALB
Nonstop2h 12m
United Airlines
Deal found 7/13![United Airlines logo]()
$303
This JetBlue deal was found by Cheapflights users on 7/16. 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.
Thu 9/35:07 pm
BDL
- ORD
1 stop7h 37m
JetBlue
Sun 9/65:27 pm
ORD
- BDL
1 stop5h 32m
JetBlue
Deal found 7/16![JetBlue logo]()
$338
Last-minute flights from Massachusetts to IllinoisDiscover last-minute flight deals from Massachusetts to Illinois. Data last updated July 18, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Illinois. Data last updated July 18, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 7/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/28:07 am
BOS
- ORD
Nonstop2h 58m
JetBlue
Wed 8/56:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Deal found 7/14![JetBlue logo]()
$195
This Super.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/45:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Fri 8/76:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Deal found 7/13![JetBlue logo]()
$179
This Super.com deal was found by Cheapflights users on 7/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/42:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Thu 8/66:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 7/14![JetBlue logo]()
$182
This Super.com deal was found by Cheapflights users on 7/15. 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.
Wed 8/55:01 am
BOS
- ORD
1 stop4h 46m
JetBlue
Sat 8/85:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Deal found 7/15![JetBlue logo]()
$193
This Super.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/125:21 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Sat 8/159:40 am
ORD
- BOS
1 stop6h 37m
JetBlue
Deal found 7/13![JetBlue logo]()
$196
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/138:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Sun 8/166:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/13![Southwest logo]()
$215
This Super.com deal was found by Cheapflights users on 7/18. 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 8/1912:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Wed 8/266:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Deal found 7/18![JetBlue logo]()
$192
This SmartFares deal was found by Cheapflights users on 7/15. 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.
Sun 8/235:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Sat 8/296:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 7/15![JetBlue logo]()
$184
This SmartFares deal was found by Cheapflights users on 7/15. 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.
Mon 8/245:21 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Thu 8/278:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/15![JetBlue logo]()
$190
This SmartFares deal was found by Cheapflights users on 7/14. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/264:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Thu 8/276:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 7/14![JetBlue logo]()
$186
This Super.com deal was found by Cheapflights users on 7/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:01 am
BOS
- ORD
1 stop4h 45m
JetBlue
Mon 8/315:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Deal found 7/14![JetBlue logo]()
$183
This SmartFares deal was found by Cheapflights users on 7/16. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/305:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Sun 9/65:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Deal found 7/16![JetBlue logo]()
$194
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 July 18, 2026.
Search for one-way flight options from Massachusetts to Illinois. Find affordable one-way fares based on user searches. Data last updated July 18, 2026.
This Super.com deal was found by Cheapflights users on 7/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/284:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/14![JetBlue logo]()
$94
This Super.com deal was found by Cheapflights users on 7/18. 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.
Tue 8/1112:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Deal found 7/18![JetBlue logo]()
$96
This Cheapflightsfares deal was found by Cheapflights users on 7/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/36:55 am
BOS
- ORD
Nonstop2h 51m
JetBlue
Deal found 7/14![JetBlue logo]()
$97
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 9/267:05 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/13![Southwest logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 7/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:55 am
BOS
- ORD
1 stop5h 52m
JetBlue
Deal found 7/15![JetBlue logo]()
$99
This Flysmarter deal was found by Cheapflights users on 7/18. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:15 am
BOS
- ORD
1 stop7h 32m
JetBlue
Deal found 7/18![JetBlue logo]()
$100
This JetBlue deal was found by Cheapflights users on 7/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:55 am
BOS
- ORD
1 stop5h 52m
JetBlue
Deal found 7/14![JetBlue logo]()
$101
This Super.com deal was found by Cheapflights users on 7/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/411:52 am
BOS
- STL
1 stop6h 45m
Frontier
Deal found 7/14![Frontier logo]()
$104
This Southwest deal was found by Cheapflights users on 7/16. 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 9/1610:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Deal found 7/16![Southwest logo]()
$104
This Delta deal was found by Cheapflights users on 7/15. 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 10/134:15 pm
ORH
- ORD
1 stop5h 28m
Delta
Deal found 7/15![Delta logo]()
$104
This Super.com deal was found by Cheapflights users on 7/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/28:07 am
BOS
- ORD
Nonstop2h 58m
JetBlue
Deal found 7/14![JetBlue logo]()
$105
This JetBlue deal was found by Cheapflights users on 7/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/274:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/15![JetBlue logo]()
$106
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 July 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $178 |
One-way from | $94 (Super.com) |
Popular in | June |
Cheapest in | January |
Average price | $243 |
Good round-trip deal | $224 or less |
Good one-way deal | $143 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 July 18, 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 - ORD
BOSORD
Boston Logan Intl
Sat 9/19
5:00 pm-7:22 pm
Nonstop3h 22m
Chicago O'Hare Intl
Tue 9/22
9:38 am-1:06 pm
Nonstop2h 28m
$197
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 9/12
4:00 pm-10:06 pm
1 stop7h 06m
Chicago O'Hare Intl
Wed 9/16
9:38 am-1:06 pm
Nonstop2h 28m
$199
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 10/16
5:50 am-7:25 am
Nonstop2h 35m
Chicago Midway
Tue 10/20
9:10 am-12:30 pm
Nonstop2h 20m
$206
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 10/23
7:40 pm-9:28 pm
Nonstop2h 48m
Chicago O'Hare Intl
Mon 10/26
7:30 am-11:06 am
Nonstop2h 36m
$215
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 7/29
9:50 am-11:43 am
Nonstop2h 53m
Chicago O'Hare Intl
Fri 8/7
12:53 pm-4:29 pm
Nonstop2h 36m
$215
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 8/25
7:15 pm-8:50 pm
Nonstop2h 35m
Chicago Midway
Mon 8/31
8:15 am-11:40 am
Nonstop2h 25m
$215
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 8/19
3:20 pm-4:55 pm
Nonstop2h 35m
Chicago Midway
Sun 8/23
6:00 am-9:15 am
Nonstop2h 15m
$215
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 8/19
8:15 am-10:11 am
Nonstop2h 56m
Chicago O'Hare Intl
Wed 8/26
8:20 pm-11:51 pm
Nonstop2h 31m
$215
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 10/15
12:45 pm-2:37 pm
Nonstop2h 52m
Chicago O'Hare Intl
Tue 10/20
9:05 am-12:48 pm
Nonstop2h 43m
$216
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 10/15
6:35 pm-8:10 pm
Nonstop2h 35m
Chicago Midway
Tue 10/20
1:10 pm-4:30 pm
Nonstop2h 20m
$216
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
ORH-ORD
ALB-MDW
BDL-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Massachusetts to Illinois
USMA-USIL
BOS-ORD
BOS-MDW
ORH-ORD
ALB-MDW
What is the cheapest month to book a flight from Massachusetts to Illinois?
Currently, January is the cheapest month in which you can book a flight from Massachusetts to Illinois (average of $197). Flying from Massachusetts to Illinois in June is currently the most expensive (average of $276). 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 July 18, 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 43% on your trip compared to booking a flight in the afternoon.
Weekly flight availability from Massachusetts to Illinois
Explore weekly flight availability from Massachusetts to Illinois. 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 18, 2026.
The most flights from USMA to USIL are scheduled on a Friday (73 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (45 on average).
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 77 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 June 8, 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 July 18, 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.
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Massachusetts to 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 July 18, 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 5 airlines flying from Massachusetts to Illinois
Discover the top 5 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 July 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$186 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$323 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$124 | Average$359 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$134 | Average$282 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$137 | Average$416 | FlexibilityNo cancel fee | On-time71% |