$68+ 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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
May 2 — May 91
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 April 2, 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 2, 2026.
This SmartFares deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
Sun 5/36:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Deal found 3/29![JetBlue logo]()
$137
This Frontier deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2812:52 pm
BOS
- MDW
1 stop7h 39m
Frontier
Tue 5/512:27 pm
MDW
- BOS
1 stop11h 57m
Frontier
Deal found 3/30![Frontier logo]()
$140
This Expedia deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:00 am
BOS
- ORD
1 stop12h 00m
Frontier
Tue 5/51:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 3/30![Frontier logo]()
$140
This SmartFares deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/265:25 pm
BOS
- ORD
Nonstop3h 10m
JetBlue
Thu 5/288:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 3/30![JetBlue logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
BOS
- ORD
1 stop29h 23m
Multiple Airlines
Tue 4/2811:28 am
ORD
- BOS
1 stop13h 03m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$148
This Priceline deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:35 pm
BOS
- ORD
Nonstop3h 04m
Multiple Airlines
Wed 4/296:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$149
This SmartFares deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Sun 5/176:00 am
ORD
- BOS
Nonstop2h 17m
JetBlue
Deal found 4/1![JetBlue logo]()
$150
This CheapOair deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Fri 5/84:52 pm
MDW
- BOS
1 stop15h 20m
Frontier
Deal found 3/30![Frontier logo]()
$151
This Cheapflightsfares deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/136:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Tue 5/199:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 3/31![JetBlue logo]()
$152
This Expedia deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:00 am
BOS
- ORD
1 stop12h 00m
Multiple Airlines
Sun 5/36:00 am
ORD
- BOS
Nonstop2h 15m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$154
This Super.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Wed 4/159:41 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Deal found 3/29![JetBlue logo]()
$155
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Tue 5/56:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/30![Southwest logo]()
$157
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 2, 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 2, 2026.
This Delta deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/117:15 am
BOS
- ORD
Nonstop3h 09m
Delta
Sun 4/127:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Deal found 3/28![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/253:15 pm
BOS
- MDW
1 stop5h 50m
Southwest
Wed 4/297:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 3/28![Southwest logo]()
$167
This United Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/306:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Fri 6/57:40 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 4/1![United Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/175:45 am
BOS
- RFD
1 stop29h 52m
Multiple Airlines
Mon 6/227:53 pm
RFD
- BOS
1 stop12h 52m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$328
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/138:10 am
BOS
- MDW
2 stops8h 35m
Southwest
Mon 5/187:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 3/29![Southwest logo]()
$172
This American Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/147:19 pm
BDL
- STL
1 stop5h 37m
American Airlines
Sat 5/165:21 pm
STL
- BDL
1 stop4h 36m
American Airlines
Deal found 4/1![American Airlines logo]()
$351
This United Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Mon 5/46:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 4/1![United Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/208:50 pm
BDL
- STL
2 stops35h 00m
Frontier
Sat 4/258:23 pm
STL
- BDL
1 stop17h 26m
Frontier
Deal found 4/1![Frontier logo]()
$359
This United Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/298:15 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Sat 7/46:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 3/29![United Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/237:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Sat 7/254:30 pm
ORD
- BOS
Nonstop2h 41m
Delta
Deal found 4/1![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/99:25 am
BOS
- MDW
Nonstop2h 40m
Southwest
Mon 5/115:40 pm
MDW
- BOS
1 stop4h 30m
Southwest
Deal found 4/1![Southwest logo]()
$182
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 7/25:30 am
BOS
- ORD
1 stop6h 15m
Delta
Sat 7/410:29 am
ORD
- BOS
Nonstop2h 30m
Delta
Deal found 3/31![Delta logo]()
$236
This United Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/266:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Mon 6/297:42 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 4/1![United Airlines logo]()
$216
This Southwest deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/187:30 am
BOS
- MDW
Nonstop2h 40m
Southwest
Sun 6/215:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 3/28![Southwest logo]()
$231
This United Airlines deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sun 7/126:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 3/28![United Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:10 am
BOS
- ORD
Nonstop3h 05m
Delta
Thu 4/236:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Deal found 3/29![Delta logo]()
$247
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/138:10 am
BOS
- MDW
2 stops8h 35m
Southwest
Sat 5/164:20 pm
MDW
- BOS
1 stop4h 45m
Southwest
Deal found 3/31![Southwest logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:00 am
BOS
- RFD
1 stop13h 13m
Multiple Airlines
Mon 6/18:03 pm
RFD
- BOS
1 stop22h 12m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$333
This United Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:45 am
BOS
- ORD
1 stop4h 48m
United Airlines
Sun 9/69:30 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 4/1![United Airlines logo]()
$235
This Southwest deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:45 pm
BOS
- MDW
1 stop5h 00m
Southwest
Tue 4/147:50 am
MDW
- BOS
2 stops8h 25m
Southwest
Deal found 4/1![Southwest logo]()
$250
This American Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/305:46 am
ALB
- ORD
Nonstop2h 44m
American Airlines
Sun 8/26:56 am
ORD
- ALB
Nonstop2h 16m
American Airlines
Deal found 3/27![American Airlines logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/227:00 am
BOS
- RFD
1 stop27h 21m
Multiple Airlines
Sun 5/3111:27 am
RFD
- BOS
2 stops19h 22m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$345
This United Airlines deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/316:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sun 5/319:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 3/28![United Airlines logo]()
$241
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/291:51 pm
ALB
- ORD
1 stop7h 45m
Delta
Sat 5/25:15 am
ORD
- ALB
1 stop5h 58m
Delta
Deal found 3/29![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/248:10 am
BOS
- MDW
Nonstop2h 45m
Southwest
Tue 5/267:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 3/31![Southwest logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/158:16 pm
BOS
- RFD
1 stop14h 31m
Multiple Airlines
Sun 4/1910:37 am
RFD
- BOS
1 stop22h 38m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$372
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/122:12 pm
ALB
- ORD
1 stop5h 57m
Delta
Wed 5/137:05 am
ORD
- ALB
1 stop5h 27m
Delta
Deal found 3/29![Delta logo]()
$309
This United Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:27 pm
BOS
- ORD
1 stop4h 59m
United Airlines
Sun 6/76:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 4/1![United Airlines logo]()
$263
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
ALB
- MDW
1 stop3h 43m
Delta
Wed 5/136:36 pm
MDW
- ALB
1 stop3h 42m
Delta
Deal found 3/29![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:45 am
BOS
- MDW
2 stops9h 55m
Southwest
Sun 5/39:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 3/30![Southwest logo]()
$282
Last-minute flights from Massachusetts to IllinoisDiscover last-minute flight deals from Massachusetts to Illinois. Data last updated April 2, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Illinois. Data last updated April 2, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Wed 4/159:41 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Deal found 3/29![JetBlue logo]()
$155
This Priceline deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:35 pm
BOS
- ORD
Nonstop3h 04m
Multiple Airlines
Wed 4/296:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
BOS
- ORD
1 stop29h 23m
Multiple Airlines
Tue 4/2811:28 am
ORD
- BOS
1 stop13h 03m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$148
This Frontier deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier 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
Tue 5/512:27 pm
MDW
- BOS
1 stop11h 57m
Frontier
Deal found 3/30![Frontier logo]()
$140
This Expedia deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:00 am
BOS
- ORD
1 stop12h 00m
Frontier
Tue 5/51:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 3/30![Frontier logo]()
$140
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:20 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Tue 5/53:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/30![Southwest logo]()
$157
This Expedia deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:00 am
BOS
- ORD
1 stop12h 00m
Multiple Airlines
Sun 5/36:00 am
ORD
- BOS
Nonstop2h 15m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$154
This SmartFares deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
Sun 5/36:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Deal found 3/29![JetBlue logo]()
$137
This CheapOair deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Fri 5/84:52 pm
MDW
- BOS
1 stop15h 20m
Frontier
Deal found 3/30![Frontier logo]()
$151
This Cheapflightsfares deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/136:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Tue 5/199:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 3/31![JetBlue logo]()
$152
This SmartFares deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Sun 5/176:00 am
ORD
- BOS
Nonstop2h 17m
JetBlue
Deal found 4/1![JetBlue logo]()
$150
This SmartFares deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/265:25 pm
BOS
- ORD
Nonstop3h 10m
JetBlue
Thu 5/288:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 3/30![JetBlue logo]()
$143
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 2, 2026.
Search for one-way flight options from Massachusetts to Illinois. Find affordable one-way fares based on user searches. Data last updated April 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
BOS
- ORD
1 stop29h 23m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$68
This Frontier deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:50 pm
BDL
- MDW
1 stop7h 29m
Frontier
Deal found 3/29![Frontier logo]()
$70
This Expedia deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:50 pm
BDL
- ORD
1 stop7h 49m
Frontier
Deal found 3/28![Frontier logo]()
$70
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2912:55 pm
BOS
- MDW
1 stop7h 36m
Frontier
Deal found 3/31![Frontier logo]()
$70
This SmartFares deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 3/29![JetBlue logo]()
$70
This SmartFares deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/275:25 pm
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 3/31![JetBlue logo]()
$72
This Kiwi.com deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
BOS
- MDW
1 stop17h 14m
Frontier
Deal found 4/1![Frontier logo]()
$74
This Trip.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 stop7h 39m
Frontier
Deal found 3/30![Frontier logo]()
$75
This Frontier deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/301:39 pm
BDL
- STL
1 stop10h 40m
Frontier
Deal found 3/29![Frontier logo]()
$76
This Expedia deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2712:31 pm
BOS
- ORD
1 stop11h 30m
Frontier
Deal found 3/31![Frontier logo]()
$76
This Expedia deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/38:42 pm
BDL
- STL
1 stop27h 37m
Frontier
Deal found 4/1![Frontier logo]()
$77
This Cheapflightsfares deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Sun 4/267:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 3/31![JetBlue logo]()
$78
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 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $137 (SmartFares) |
One-way from | $68 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $252 |
Good round-trip deal | $239 or less |
Good one-way deal | $129 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 2, 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 4/11
7:15 am-9:24 am
Nonstop3h 09m
Chicago O'Hare Intl
Sun 4/12
7:00 am-10:25 am
Nonstop2h 25m
$157
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 4/25
3:15 pm-8:05 pm
1 stop5h 50m
Chicago Midway
Wed 4/29
7:45 am-11:00 am
Nonstop2h 15m
$167
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/30
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Fri 6/5
7:40 pm-11:15 pm
Nonstop2h 35m
$172
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 5/13
8:10 am-3:45 pm
2 stops8h 35m
Chicago Midway
Mon 5/18
7:40 am-10:55 am
Nonstop2h 15m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 5/1
6:00 am-8:00 am
Nonstop3h 00m
Chicago O'Hare Intl
Mon 5/4
6:00 am-9:25 am
Nonstop2h 25m
$177
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 6/29
8:15 pm-10:15 pm
Nonstop3h 00m
Chicago O'Hare Intl
Sat 7/4
6:00 am-11:16 am
1 stop4h 16m
$177
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 5/9
9:25 am-11:05 am
Nonstop2h 40m
Chicago Midway
Mon 5/11
5:40 pm-11:10 pm
1 stop4h 30m
$182
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 7/23
7:30 am-9:26 am
Nonstop2h 56m
Chicago O'Hare Intl
Sat 7/25
4:30 pm-8:11 pm
Nonstop2h 41m
$197
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 6/26
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Mon 6/29
7:42 pm-11:18 pm
Nonstop2h 36m
$216
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 7/10
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Sun 7/12
6:15 am-9:39 am
Nonstop2h 24m
$217
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
BDL-MDW
BDL-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
BDL-MDW
BDL-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 $91). Flying from Massachusetts to Illinois in January is currently the most expensive (average of $123). 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 2, 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 47% 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 March 28, 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 2, 2026.
The most flights from USMA to USIL are scheduled on a Wednesday (56 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 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 2, 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
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from 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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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 April 2, 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 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$32 | Average$162 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$67 | Average$177 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$84 | Average$320 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$219 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$117 | Average$390 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$128 | Average$406 | FlexibilityNo cancel fee | On-time71% |