$76+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
May 18 — May 251
Round-trip
1 adult, Economy
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Find cheap flights from Massachusetts to Illinois with Cheapflights
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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 April 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 April 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/510:07 am
BOS
- ORD
1 stop14h 06m
Frontier
Sat 5/95:30 pm
ORD
- BOS
1 stop14h 42m
Frontier
Deal found 4/13![Frontier logo]()
$150
This CheapOair deal was found by Cheapflights users on 4/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Fri 5/84:52 pm
MDW
- BOS
1 stop15h 20m
Frontier
Deal found 4/14![Frontier logo]()
$151
This CheapOair deal was found by Cheapflights users on 4/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:01 pm
BOS
- ORD
1 stop8h 50m
Frontier
Fri 5/85:30 pm
ORD
- BOS
1 stop14h 42m
Frontier
Deal found 4/14![Frontier logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/610:07 am
BOS
- ORD
1 stop14h 06m
Frontier
Sat 5/95:30 pm
ORD
- BOS
1 stop14h 42m
Frontier
Deal found 4/13![Frontier logo]()
$153
This Trip.com deal was found by Cheapflights users on 4/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Thu 5/1412:19 pm
MDW
- BOS
1 stop12h 05m
Frontier
Deal found 4/15![Frontier logo]()
$154
This Expedia deal was found by Cheapflights users on 4/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:01 pm
BOS
- ORD
1 stop8h 50m
Multiple Airlines
Sat 5/97:20 am
ORD
- BOS
Nonstop2h 26m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$154
This flygcity.se deal was found by Cheapflights users on 4/14. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Sun 5/106:00 am
ORD
- BOS
Nonstop2h 16m
JetBlue
Deal found 4/14![JetBlue logo]()
$156
This Expedia deal was found by Cheapflights users on 4/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:35 pm
BOS
- ORD
Nonstop3h 01m
Multiple Airlines
Fri 5/85:30 pm
ORD
- BOS
1 stop14h 42m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$159
This Frontier deal was found by Cheapflights users on 4/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/312:28 pm
BOS
- MDW
1 stop8h 03m
Frontier
Tue 5/512:24 pm
MDW
- BOS
1 stop12h 00m
Frontier
Deal found 4/14![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 4/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/912:01 pm
BOS
- ORD
1 stop8h 50m
Frontier
Tue 5/121:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/14![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 4/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/59:31 am
BOS
- ORD
1 stop11h 20m
Frontier
Wed 5/61:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/15![Frontier logo]()
$161
This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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.
Tue 5/126:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Wed 5/139:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/14![JetBlue logo]()
$162
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 April 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 April 18, 2026.
This Delta deal was found by Cheapflights users on 4/17. 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.
Tue 6/27:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Tue 6/97:10 am
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 4/17![Delta logo]()
$167
This Southwest deal was found by Cheapflights users on 4/15. 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.
Thu 7/235:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 7/282:40 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 4/15![Southwest logo]()
$172
This United Airlines deal was found by Cheapflights users on 4/13. 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 7/85:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Wed 7/81:55 pm
ORD
- BOS
Nonstop2h 34m
United Airlines
Deal found 4/13![United Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Sun 5/177:00 am
BOS
- RFD
1 stop27h 59m
Multiple Airlines
Thu 5/2111:27 am
RFD
- BOS
1 stop11h 27m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$275
This United Airlines deal was found by Cheapflights users on 4/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/73:08 pm
BOS
- ORD
Nonstop2h 52m
United Airlines
Thu 7/96:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 4/14![United Airlines logo]()
$182
This Southwest deal was found by Cheapflights users on 4/14. 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 7/145:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 7/2112:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 4/14![Southwest logo]()
$192
This Delta deal was found by Cheapflights users on 4/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:10 am
BOS
- ORD
Nonstop3h 05m
Delta
Sat 5/26:00 am
ORD
- BOS
Nonstop2h 26m
Delta
Deal found 4/13![Delta logo]()
$192
This United Airlines deal was found by Cheapflights users on 4/15. 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.
Wed 7/158:00 am
BOS
- ORD
1 stop5h 06m
United Airlines
Mon 7/206:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 4/15![United Airlines logo]()
$182
This Southwest deal was found by Cheapflights users on 4/15. 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 5/99:25 am
BOS
- MDW
Nonstop2h 40m
Southwest
Tue 5/121:55 pm
MDW
- BOS
1 stop7h 25m
Southwest
Deal found 4/15![Southwest logo]()
$202
This United Airlines deal was found by Cheapflights users on 4/13. 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 4/2911:00 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Sun 5/37:30 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Deal found 4/13![United Airlines logo]()
$192
This Southwest deal was found by Cheapflights users on 4/13. 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 6/117:30 am
BOS
- MDW
Nonstop2h 40m
Southwest
Mon 6/154:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 4/13![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 4/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/287:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Sat 7/410:29 am
ORD
- BOS
Nonstop2h 30m
Delta
Deal found 4/13![Delta logo]()
$236
This United Airlines deal was found by Cheapflights users on 4/17. 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 5/207:30 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Sun 5/246:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 4/17![United Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 4/17. 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.
Sat 5/212:25 pm
BOS
- RFD
2 stops22h 22m
Multiple Airlines
Thu 5/710:37 am
RFD
- BOS
1 stop12h 17m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$291
This Southwest deal was found by Cheapflights users on 4/17. 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 6/165:00 pm
BOS
- MDW
1 stop5h 35m
Southwest
Sat 6/205:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 4/17![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 4/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:50 pm
BOS
- ORD
1 stop6h 09m
Delta
Sat 5/26:00 am
ORD
- BOS
Nonstop2h 26m
Delta
Deal found 4/13![Delta logo]()
$251
This United Airlines deal was found by Cheapflights users on 4/13. 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 6/266:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Mon 7/67:42 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 4/13![United Airlines logo]()
$220
This Southwest deal was found by Cheapflights users on 4/15. 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 5/29:25 am
BOS
- MDW
Nonstop2h 40m
Southwest
Tue 5/55:30 am
MDW
- BOS
1 stop7h 10m
Southwest
Deal found 4/15![Southwest logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 7/156:00 am
BOS
- RFD
1 stop29h 37m
Multiple Airlines
Mon 7/207:50 pm
RFD
- BOS
1 stop26h 48m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$301
This Southwest deal was found by Cheapflights users on 4/14. 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 5/95:25 am
BOS
- MDW
1 stop8h 45m
Southwest
Sun 5/107:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/14![Southwest logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Wed 5/205:45 am
BOS
- RFD
1 stop29h 52m
Multiple Airlines
Sun 5/2411:27 am
RFD
- BOS
1 stop11h 27m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 4/13. 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 5/295:50 pm
BOS
- MDW
1 stop7h 05m
Southwest
Fri 6/57:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/13![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 4/17. 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.
Fri 5/227:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Mon 5/256:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 4/17![United Airlines logo]()
$250
This Delta deal was found by Cheapflights users on 4/14. 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.
Mon 6/86:29 pm
ALB
- ORD
1 stop6h 30m
Delta
Tue 6/95:22 pm
ORD
- ALB
1 stop4h 47m
Delta
Deal found 4/14![Delta logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Thu 8/278:41 pm
BOS
- RFD
1 stop19h 12m
Multiple Airlines
Mon 8/317:04 pm
RFD
- BOS
1 stop13h 41m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 4/14. 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 6/139:20 am
BOS
- MDW
1 stop8h 45m
Southwest
Sat 6/205:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/14![Southwest logo]()
$228
This United Airlines deal was found by Cheapflights users on 4/17. 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 5/910:00 am
BOS
- ORD
1 stop5h 36m
United Airlines
Wed 5/136:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 4/17![United Airlines logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 4/17. 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 6/1212:33 pm
BOS
- RFD
1 stop20h 44m
Multiple Airlines
Mon 6/157:53 pm
RFD
- BOS
1 stop22h 22m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 4/14. 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.
Thu 5/215:15 pm
BDL
- STL
1 stop7h 44m
Delta
Thu 5/281:27 pm
STL
- BDL
1 stop6h 45m
Delta
Deal found 4/14![Delta logo]()
$351
This Southwest deal was found by Cheapflights users on 4/17. 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 6/45:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 6/107:50 am
MDW
- BOS
2 stops6h 50m
Southwest
Deal found 4/17![Southwest logo]()
$242
Last-minute flights from Massachusetts to IllinoisDiscover last-minute flight deals from Massachusetts to Illinois. Data last updated April 18, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Illinois. Data last updated April 18, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 4/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/312:28 pm
BOS
- MDW
1 stop8h 03m
Frontier
Tue 5/512:24 pm
MDW
- BOS
1 stop12h 00m
Frontier
Deal found 4/14![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/510:07 am
BOS
- ORD
1 stop14h 06m
Frontier
Sat 5/95:30 pm
ORD
- BOS
1 stop14h 42m
Frontier
Deal found 4/13![Frontier logo]()
$150
This Expedia deal was found by Cheapflights users on 4/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:35 pm
BOS
- ORD
Nonstop3h 01m
Multiple Airlines
Fri 5/85:30 pm
ORD
- BOS
1 stop14h 42m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$159
This Frontier deal was found by Cheapflights users on 4/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/59:31 am
BOS
- ORD
1 stop11h 20m
Frontier
Wed 5/61:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/15![Frontier logo]()
$161
This CheapOair deal was found by Cheapflights users on 4/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Fri 5/84:52 pm
MDW
- BOS
1 stop15h 20m
Frontier
Deal found 4/14![Frontier logo]()
$151
This CheapOair deal was found by Cheapflights users on 4/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:01 pm
BOS
- ORD
1 stop8h 50m
Frontier
Fri 5/85:30 pm
ORD
- BOS
1 stop14h 42m
Frontier
Deal found 4/14![Frontier logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/610:07 am
BOS
- ORD
1 stop14h 06m
Frontier
Sat 5/95:30 pm
ORD
- BOS
1 stop14h 42m
Frontier
Deal found 4/13![Frontier logo]()
$153
This Expedia deal was found by Cheapflights users on 4/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:01 pm
BOS
- ORD
1 stop8h 50m
Multiple Airlines
Sat 5/97:20 am
ORD
- BOS
Nonstop2h 26m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$154
This flygcity.se deal was found by Cheapflights users on 4/14. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Sun 5/106:00 am
ORD
- BOS
Nonstop2h 16m
JetBlue
Deal found 4/14![JetBlue logo]()
$156
This Frontier deal was found by Cheapflights users on 4/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/912:01 pm
BOS
- ORD
1 stop8h 50m
Frontier
Tue 5/121:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/14![Frontier logo]()
$160
This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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.
Tue 5/126:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Wed 5/139:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/14![JetBlue logo]()
$162
This Trip.com deal was found by Cheapflights users on 4/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Thu 5/1412:19 pm
MDW
- BOS
1 stop12h 05m
Frontier
Deal found 4/15![Frontier logo]()
$154
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 April 18, 2026.
Search for one-way flight options from Massachusetts to Illinois. Find affordable one-way fares based on user searches. Data last updated April 18, 2026.
This Frontier deal was found by Cheapflights users on 4/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Deal found 4/14![Frontier logo]()
$76
This Expedia deal was found by Cheapflights users on 4/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/129:31 am
BOS
- ORD
1 stop11h 20m
Frontier
Deal found 4/14![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 5/199:31 am
BOS
- STL
1 stop9h 02m
Frontier
Deal found 4/15![Frontier logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 4/2912:55 pm
BOS
- MDW
1 stop7h 36m
Frontier
Deal found 4/15![Frontier logo]()
$78
This KAYAK deal was found by Cheapflights users on 4/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 4/14![JetBlue logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
BOS
- STL
1 stop12h 36m
Frontier
Deal found 4/13![Frontier logo]()
$79
This Kissandfly.com deal was found by Cheapflights users on 4/15. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Deal found 4/15![Frontier logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 4/2912:55 pm
BOS
- ORD
1 stop22h 28m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$79
This Frontier deal was found by Cheapflights users on 4/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/109:31 am
BOS
- STL
1 stop8h 23m
Frontier
Deal found 4/13![Frontier logo]()
$80
This Orbitz deal was found by Cheapflights users on 4/17. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/199:31 am
BOS
- ORD
1 stop11h 20m
Frontier
Deal found 4/17![Frontier logo]()
$80
This Trip.com deal was found by Cheapflights users on 4/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:52 pm
BOS
- MDW
1 stop10h 22m
Frontier
Deal found 4/13![Frontier logo]()
$82
This KAYAK deal was found by Cheapflights users on 4/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:25 pm
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 4/14![JetBlue logo]()
$82
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 April 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $150 (Kiwi.com) |
One-way from | $76 (Frontier) |
Popular in | April |
Cheapest in | September |
Average price | $252 |
Good round-trip deal | $232 or less |
Good one-way deal | $126 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 April 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
Tue 6/2
7:35 am-9:27 am
Nonstop2h 52m
Chicago O'Hare Intl
Tue 6/9
7:10 am-10:46 am
Nonstop2h 36m
$167
Quickest round-trip
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 7/23
5:25 am-7:00 am
Nonstop2h 35m
Chicago Midway
Tue 7/28
2:40 pm-6:00 pm
Nonstop2h 20m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 7/8
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
Wed 7/8
1:55 pm-5:29 pm
Nonstop2h 34m
$177
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 7/7
3:08 pm-5:00 pm
Nonstop2h 52m
Chicago O'Hare Intl
Thu 7/9
6:00 am-11:16 am
1 stop4h 16m
$182
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 7/15
8:00 am-12:06 pm
1 stop5h 06m
Chicago O'Hare Intl
Mon 7/20
6:15 am-9:39 am
Nonstop2h 24m
$182
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 7/14
5:35 am-7:10 am
Nonstop2h 35m
Chicago Midway
Tue 7/21
12:45 pm-4:05 pm
Nonstop2h 20m
$192
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 4/30
7:10 am-9:15 am
Nonstop3h 05m
Chicago O'Hare Intl
Sat 5/2
6:00 am-9:26 am
Nonstop2h 26m
$192
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 4/29
11:00 am-12:59 pm
Nonstop2h 59m
Chicago O'Hare Intl
Sun 5/3
7:30 am-11:01 am
Nonstop2h 31m
$192
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/20
7:30 am-9:30 am
Nonstop3h 00m
Chicago O'Hare Intl
Sun 5/24
6:00 am-11:16 am
1 stop4h 16m
$200
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 5/9
9:25 am-11:05 am
Nonstop2h 40m
Chicago Midway
Tue 5/12
1:55 pm-10:20 pm
1 stop7h 25m
$202
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-STL
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-STL
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 $166). Flying from Massachusetts to Illinois in April is currently the most expensive (average of $295). 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 April 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 46% on your trip compared to booking a flight in the afternoon.
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 April 11, 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.
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 April 18, 2026.
The most flights from USMA to USIL are scheduled on a Friday (59 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (35 on average).
How much does it cost to fly round-trip from Massachusetts to Illinois?
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 April 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.
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
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 April 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 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 April 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$32 | Average$162 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$67 | Average$176 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$85 | Average$320 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$386 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$122 | Average$218 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$129 | Average$405 | FlexibilityNo cancel fee | On-time71% |