$82+ Cheap flights from Massachusetts to Illinois
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Jun 4 — Jun 111
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 May 5, 2026.
Explore the most affordable flight options available from Massachusetts to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:26 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Wed 6/108:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 4/30![JetBlue logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Tue 5/265:45 am
BOS
- ORD
1 stop31h 52m
Multiple Airlines
Tue 6/91:29 pm
ORD
- BOS
1 stop10h 58m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$164
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 7/215:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Wed 7/2210:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 5/2![JetBlue logo]()
$165
This Southwest deal was found by Cheapflights users on 4/30. 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.
Wed 6/32:25 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Sat 6/65:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/30![Southwest logo]()
$167
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Tue 6/91:55 pm
ORD
- BOS
Nonstop2h 34m
United Airlines
Deal found 4/30![United Airlines logo]()
$167
This Super.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Fri 6/58:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/4![JetBlue logo]()
$169
This Super.com deal was found by Cheapflights users on 5/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/158:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Mon 7/208:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 5/1![JetBlue logo]()
$170
This Southwest deal was found by Cheapflights users on 4/30. 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.
Mon 6/84:45 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Wed 6/106:05 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/30![Southwest logo]()
$172
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Fri 6/53:50 pm
ORD
- BOS
Nonstop2h 37m
Delta
Deal found 4/30![Delta logo]()
$172
This CheapOair deal was found by Cheapflights users on 4/30. 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.
Tue 6/95:26 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Thu 6/1110:56 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 4/30![JetBlue logo]()
$173
This Delta deal was found by Cheapflights users on 5/1. 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.
Sat 5/235:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Sun 5/247:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 5/1![Delta logo]()
$174
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/2![JetBlue logo]()
$175
Best flights from Massachusetts to IllinoisDiscover carefully curated flight deals from Massachusetts to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 5, 2026.
Discover carefully curated flight deals from Massachusetts to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 5, 2026.
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 7/137:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Tue 7/149:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 5/2![United Airlines logo]()
$172
This Southwest deal was found by Cheapflights users on 5/1. 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.
Tue 6/26:20 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Wed 6/36:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 5/1![Southwest logo]()
$182
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/207:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Thu 5/2810:25 am
ORD
- BOS
Nonstop2h 24m
Delta
Deal found 4/30![Delta logo]()
$182
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Fri 6/127:46 pm
BOS
- BMI
1 stop5h 49m
American Airlines
Mon 6/156:02 pm
BMI
- BOS
1 stop5h 26m
American Airlines
Deal found 5/1![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/227:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Thu 6/256:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 5/4![United Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/185:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 6/295:05 pm
MDW
- BOS
1 stop6h 05m
Southwest
Deal found 5/4![Southwest logo]()
$187
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/106:40 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Wed 6/176:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 5/4![United Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/247:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Wed 6/247:25 pm
ORD
- BOS
Nonstop2h 37m
Delta
Deal found 5/2![Delta logo]()
$202
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:10 am
BOS
- MDW
Nonstop2h 50m
Southwest
Tue 6/26:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 5/3![Southwest logo]()
$187
This Sun Country Air deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/911:04 am
BDL
- ORD
1 stop7h 15m
Sun Country Air
Sat 7/116:19 pm
ORD
- BDL
1 stop15h 38m
Sun Country Air
Deal found 5/2![Sun Country Air logo]()
$425
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Mon 7/138:15 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Thu 7/167:33 am
ORD
- BOS
Nonstop2h 32m
United Airlines
Deal found 5/1![United Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 5/1. 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.
Mon 6/227:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Wed 7/17:10 am
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 5/1![Delta logo]()
$202
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/272:25 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Sat 5/306:10 am
MDW
- BOS
1 stop4h 50m
Southwest
Deal found 5/2![Southwest logo]()
$192
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 7/136:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Wed 7/156:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 5/2![United Airlines logo]()
$182
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:10 am
BOS
- MDW
Nonstop2h 50m
Southwest
Sat 5/306:10 am
MDW
- BOS
1 stop6h 25m
Southwest
Deal found 5/3![Southwest logo]()
$197
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/25:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Fri 6/59:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 5/4![United Airlines logo]()
$182
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/295:30 am
BOS
- ORD
2 stops9h 50m
Southwest
Tue 6/22:40 pm
ORD
- BOS
1 stop6h 50m
Southwest
Deal found 5/3![Southwest logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Sun 5/175:45 am
BOS
- BMI
2 stops27h 54m
Multiple Airlines
Thu 5/218:14 pm
BMI
- BOS
1 stop24h 28m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$616
This United Airlines deal was found by Cheapflights users on 5/1. 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 7/35:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Wed 7/87:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 5/1![United Airlines logo]()
$196
This Southwest deal was found by Cheapflights users on 5/1. 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.
Wed 7/155:25 am
BOS
- MDW
1 stop4h 15m
Southwest
Mon 7/207:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 5/1![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 8/15:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 8/41:55 pm
MDW
- BOS
2 stops7h 15m
Southwest
Deal found 5/4![Southwest logo]()
$207
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Wed 7/155:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Mon 7/207:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 5/1![United Airlines logo]()
$207
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/175:45 am
ALB
- ORD
1 stop4h 29m
Delta
Wed 6/245:22 pm
ORD
- ALB
1 stop5h 02m
Delta
Deal found 5/4![Delta logo]()
$305
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” 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 6/197:46 pm
BOS
- BMI
1 stop5h 49m
American Airlines
Thu 6/256:02 pm
BMI
- BOS
1 stop5h 26m
American Airlines
Deal found 5/5![American Airlines logo]()
$413
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 6/2810:05 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Tue 6/305:20 pm
MDW
- BOS
1 stop5h 10m
Southwest
Deal found 5/4![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 5/1. 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 5/286:06 pm
ALB
- STL
1 stop6h 53m
Delta
Mon 6/16:04 pm
STL
- ALB
1 stop4h 14m
Delta
Deal found 5/1![Delta logo]()
$335
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/233:30 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Sun 5/246:05 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 5/2![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 8/306:00 am
ALB
- ORD
1 stop5h 44m
Delta
Wed 9/27:10 am
ORD
- ALB
1 stop3h 41m
Delta
Deal found 5/3![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 4/30. 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.
Mon 7/65:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Fri 7/105:20 pm
MDW
- BOS
1 stop5h 45m
Southwest
Deal found 4/30![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 8/1112:25 pm
ALB
- ORD
1 stop7h 47m
Delta
Thu 8/135:20 pm
ORD
- ALB
1 stop4h 56m
Delta
Deal found 5/4![Delta logo]()
$337
Last-minute flights from Massachusetts to IllinoisDiscover last-minute flight deals from Massachusetts to Illinois. Data last updated May 5, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Illinois. Data last updated May 5, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/2![JetBlue logo]()
$175
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Sun 5/247:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 4/30![Delta logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Tue 5/265:45 am
BOS
- ORD
1 stop31h 52m
Multiple Airlines
Tue 6/91:29 pm
ORD
- BOS
1 stop10h 58m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$164
This Super.com deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 5/266:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Fri 5/298:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/3![JetBlue logo]()
$170
This JetBlue deal was found by Cheapflights users on 4/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Wed 6/108:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 4/30![JetBlue logo]()
$167
This Southwest deal was found by Cheapflights users on 4/30. 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.
Wed 6/32:25 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Sat 6/65:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/30![Southwest logo]()
$167
This Super.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Fri 6/58:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/4![JetBlue logo]()
$169
This Southwest deal was found by Cheapflights users on 4/30. 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.
Mon 6/86:45 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Wed 6/106:05 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/30![Southwest logo]()
$172
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:26 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Wed 6/108:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 4/30![JetBlue logo]()
$162
This CheapOair deal was found by Cheapflights users on 4/30. 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.
Tue 6/95:26 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Thu 6/1110:56 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 4/30![JetBlue logo]()
$173
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Mon 6/155:00 am
BOS
- ORD
Nonstop2h 58m
American Airlines
Mon 6/226:04 am
ORD
- BOS
Nonstop2h 26m
American Airlines
Deal found 5/1![American Airlines logo]()
$178
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/186:40 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Mon 6/229:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 5/2![United Airlines logo]()
$177
One-way flights from Massachusetts to IllinoisSearch for one-way flight options from Massachusetts to Illinois. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
Search for one-way flight options from Massachusetts to Illinois. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Tue 5/269:12 am
BOS
- STL
1 stop24h 43m
Frontier
Deal found 5/1![Frontier logo]()
$82
This Super.com deal was found by Cheapflights users on 4/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/30![JetBlue logo]()
$82
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/178:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 4/30![JetBlue logo]()
$83
This Southwest deal was found by Cheapflights users on 4/30. 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.
Sat 6/65:45 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 4/30![Southwest logo]()
$84
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 4/30![United Airlines logo]()
$84
This Super.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/256:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/4![JetBlue logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” 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 5/266:00 am
BOS
- MDW
1 stop17h 02m
Frontier
Deal found 5/4![Frontier logo]()
$88
This Cheapflightsfares deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 5/5![JetBlue logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 5/2712:01 pm
BOS
- STL
1 stop30h 32m
Frontier
Deal found 4/30![Frontier logo]()
$89
This Southwest deal was found by Cheapflights users on 4/30. 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.
Sun 5/248:10 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 4/30![Southwest logo]()
$89
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Deal found 4/30![Delta logo]()
$89
This Priceline deal was found by Cheapflights users on 5/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/185:44 pm
BDL
- STL
1 stop7h 37m
Frontier
Deal found 5/1![Frontier logo]()
$90
Find flight deals from Massachusetts to Illinois
Keep the following information in mind while searching for Massachusetts to Illinois flight deals. Data was last updated May 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $162 (Cheapflightsfares) |
One-way from | $82 (Kiwi.com) |
Popular in | April |
Cheapest in | September |
Average price | $243 |
Good round-trip deal | $227 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 May 5, 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
Mon 7/13
7:19 am-9:17 am
Nonstop2h 58m
Chicago O'Hare Intl
Tue 7/14
9:41 pm-1:14 am
Nonstop2h 33m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 6/22
7:19 am-9:17 am
Nonstop2h 58m
Chicago O'Hare Intl
Thu 6/25
6:05 am-9:29 am
Nonstop2h 24m
$177
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 6/10
6:40 pm-8:40 pm
Nonstop3h 00m
Chicago O'Hare Intl
Wed 6/17
6:00 am-11:16 am
1 stop4h 16m
$177
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 7/13
8:15 pm-10:15 pm
Nonstop3h 00m
Chicago O'Hare Intl
Thu 7/16
7:33 am-11:05 am
Nonstop2h 32m
$177
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 6/2
6:20 pm-8:10 pm
Nonstop2h 50m
Chicago Midway
Wed 6/3
6:00 pm-9:20 pm
Nonstop2h 20m
$182
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/20
7:35 am-9:27 am
Nonstop2h 52m
Chicago O'Hare Intl
Thu 5/28
10:25 am-1:49 pm
Nonstop2h 24m
$182
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 7/13
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Wed 7/15
6:00 am-11:16 am
1 stop4h 16m
$182
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/2
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
Fri 6/5
9:41 pm-1:14 am
Nonstop2h 33m
$182
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 6/18
5:25 am-7:00 am
Nonstop2h 35m
Chicago Midway
Mon 6/29
5:05 pm-12:10 am
1 stop6h 05m
$187
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 5/28
7:10 am-9:00 am
Nonstop2h 50m
Chicago Midway
Tue 6/2
6:00 pm-9:20 pm
Nonstop2h 20m
$187
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-BMI
BDL-ORD
ALB-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
BOS-BMI
BDL-ORD
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 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 May 5, 2026.
A simple way to save on the total cost of your ticket is to fly from Massachusetts to Illinois in the evening. If you’re flexible enough to do this you can expect to save up to 44% on your trip compared to booking a flight in the afternoon.
What is the cheapest day to fly from Massachusetts to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Illinois. Price data was last updated on May 2, 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 May 5, 2026.
The most flights from USMA to USIL are scheduled on a Monday (70 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (38 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 May 5, 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
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from 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 May 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Illinois
Find the right flight back to Massachusetts after your stay in Illinois
Massachusetts to Illinois flights
Consider these flights traveling from Massachusetts to Illinois.
Top 6 airlines flying from Massachusetts to Illinois
Discover the top 6 airlines that operate flights from Massachusetts to Illinois. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$176 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$87 | Average$321 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$95 | Average$187 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$119 | Average$380 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$125 | Average$218 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$133 | Average$416 | FlexibilityNo cancel fee | On-time71% |