$91+ Cheap flights from Massachusetts to Illinois
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/7. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Aug 5 — Aug 121
Round-trip
1 adult, Economy
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Find cheap flights from Massachusetts to Illinois with Cheapflights
1. Tell us where you want to go
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Cheapest flights from Massachusetts to IllinoisExplore the most affordable flight options available from Massachusetts to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 6, 2026.
Explore the most affordable flight options available from Massachusetts to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 6, 2026.
This Southwest deal was found by Cheapflights users on 7/1. 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 7/255:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 7/277:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/1![Southwest logo]()
$170
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Wed 7/1512:01 pm
BOS
- ORD
Nonstop3h 01m
American Airlines
Wed 7/226:00 am
ORD
- BOS
Nonstop2h 34m
American Airlines
Deal found 7/1![American Airlines logo]()
$170
This Southwest deal was found by Cheapflights users on 7/1. 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 8/245:50 pm
BOS
- MDW
1 stop5h 05m
Southwest
Wed 8/266:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/1![Southwest logo]()
$172
This United Airlines deal was found by Cheapflights users on 7/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/287:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Wed 7/296:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 7/3![United Airlines logo]()
$172
This Southwest deal was found by Cheapflights users on 7/2. 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.
Tue 8/257:15 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 9/96:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/2![Southwest logo]()
$173
This United Airlines deal was found by Cheapflights users on 7/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/258:20 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Sat 9/193:35 pm
ORD
- BOS
Nonstop2h 44m
United Airlines
Deal found 7/3![United Airlines logo]()
$173
This Flysmarter deal was found by Cheapflights users on 7/2. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:41 am
BOS
- ORD
1 stop8h 36m
JetBlue
Mon 8/248:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/2![JetBlue logo]()
$174
This JetBlue deal was found by Cheapflights users on 7/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:15 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Thu 8/209:35 am
ORD
- BOS
1 stop6h 32m
JetBlue
Deal found 7/2![JetBlue logo]()
$175
This Jettzy deal was found by Cheapflights users on 7/3. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/174:55 pm
BOS
- ORD
1 stop6h 03m
JetBlue
Mon 8/248:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/3![JetBlue logo]()
$177
This Southwest deal was found by Cheapflights users on 7/1. 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 7/185:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 7/277:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/1![Southwest logo]()
$178
This Delta deal was found by Cheapflights users on 7/2. 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.
Tue 7/217:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Thu 7/3010:28 am
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 7/2![Delta logo]()
$178
This United Airlines deal was found by Cheapflights users on 7/2. 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 7/207:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Tue 7/289:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 7/2![United Airlines logo]()
$179
Best flights from Massachusetts to IllinoisDiscover carefully curated flight deals from Massachusetts to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 6, 2026.
Discover carefully curated flight deals from Massachusetts to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 6, 2026.
This United Airlines deal was found by Cheapflights users on 7/1. 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 7/186:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Wed 7/227:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 7/1![United Airlines logo]()
$170
This JetBlue deal was found by Cheapflights users on 7/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:40 pm
BOS
- ORD
1 stop8h 18m
JetBlue
Sat 9/51:49 pm
ORD
- BOS
Nonstop3h 10m
JetBlue
Deal found 7/4![JetBlue logo]()
$175
This Delta deal was found by Cheapflights users on 7/3. 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.
Mon 8/317:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Sat 9/1211:30 am
ORD
- BOS
Nonstop2h 45m
Delta
Deal found 7/3![Delta logo]()
$181
This Southwest deal was found by Cheapflights users on 7/2. 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.
Fri 7/175:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 7/207:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/2![Southwest logo]()
$209
This United Airlines deal was found by Cheapflights users on 7/1. 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 7/186:43 pm
BOS
- ORD
Nonstop2h 57m
United Airlines
Sat 7/256:20 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 7/1![United Airlines logo]()
$170
This JetBlue deal was found by Cheapflights users on 7/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2211:05 am
BOS
- ORD
Nonstop2h 54m
JetBlue
Mon 8/246:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Deal found 7/3![JetBlue logo]()
$176
This United Airlines deal was found by Cheapflights users on 7/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Sat 8/226:15 am
ORD
- BOS
Nonstop2h 21m
United Airlines
Deal found 7/3![United Airlines logo]()
$172
This Delta deal was found by Cheapflights users on 7/2. 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.
Fri 7/245:40 pm
ORH
- ORD
1 stop5h 56m
Delta
Wed 8/510:30 am
ORD
- ORH
1 stop5h 30m
Delta
Deal found 7/2![Delta logo]()
$192
This United Airlines deal was found by Cheapflights users on 7/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:15 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Tue 8/116:00 am
ORD
- BOS
1 stop4h 17m
United Airlines
Deal found 7/5![United Airlines logo]()
$172
This Southwest deal was found by Cheapflights users on 7/4. 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.
Mon 7/205:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 7/2212:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/4![Southwest logo]()
$212
This JetBlue deal was found by Cheapflights users on 7/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/214:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Mon 8/246:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Deal found 7/2![JetBlue logo]()
$201
This Delta deal was found by Cheapflights users on 7/2. 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.
Tue 9/224:20 pm
ORH
- ORD
1 stop5h 11m
Delta
Tue 10/68:36 am
ORD
- ORH
1 stop5h 23m
Delta
Deal found 7/2![Delta logo]()
$212
This Southwest deal was found by Cheapflights users on 7/4. 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 7/185:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 7/195:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 7/4![Southwest logo]()
$214
This United Airlines deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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 7/217:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Thu 7/309:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 7/6![United Airlines logo]()
$178
This Southwest deal was found by Cheapflights users on 7/4. 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 10/152:45 pm
BOS
- MDW
1 stop8h 15m
Southwest
Tue 10/203:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/4![Southwest logo]()
$216
This Delta deal was found by Cheapflights users on 7/4. 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 8/55:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Tue 8/116:59 am
ORD
- ORH
2 stops9h 01m
Delta
Deal found 7/4![Delta logo]()
$218
This United Airlines deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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 8/225:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Sat 8/297:45 am
ORD
- BOS
Nonstop2h 34m
United Airlines
Deal found 7/6![United Airlines logo]()
$181
This Southwest deal was found by Cheapflights users on 7/1. 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 8/247:40 am
BOS
- MDW
2 stops8h 15m
Southwest
Wed 8/266:30 am
MDW
- BOS
1 stop5h 10m
Southwest
Deal found 7/1![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 7/2. 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.
Tue 9/294:20 pm
ORH
- ORD
1 stop6h 58m
Delta
Thu 10/19:30 am
ORD
- ORH
1 stop5h 07m
Delta
Deal found 7/2![Delta logo]()
$221
This United Airlines deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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 7/266:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Thu 7/309:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 7/6![United Airlines logo]()
$187
This Southwest deal was found by Cheapflights users on 7/2. 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.
Mon 8/35:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Thu 8/63:20 pm
MDW
- BOS
1 stop6h 00m
Southwest
Deal found 7/2![Southwest logo]()
$225
This United Airlines deal was found by Cheapflights users on 7/2. 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 7/237:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sun 7/269:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 7/2![United Airlines logo]()
$196
This Southwest deal was found by Cheapflights users on 7/3. 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 9/38:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Fri 9/45:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/3![Southwest logo]()
$226
This Delta deal was found by Cheapflights users on 7/3. 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.
Tue 7/145:40 pm
ORH
- ORD
1 stop5h 56m
Delta
Fri 7/177:05 am
ORD
- ORH
2 stops8h 55m
Delta
Deal found 7/3![Delta logo]()
$273
This Southwest deal was found by Cheapflights users on 7/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:15 am
BOS
- MDW
2 stops6h 15m
Southwest
Tue 8/118:45 am
MDW
- BOS
Nonstop2h 30m
Southwest
Deal found 7/5![Southwest logo]()
$230
This Delta deal was found by Cheapflights users on 7/3. 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.
Fri 7/175:40 pm
ORH
- ORD
1 stop5h 56m
Delta
Tue 7/215:30 am
ORD
- ORH
2 stops10h 30m
Delta
Deal found 7/3![Delta logo]()
$284
This Southwest deal was found by Cheapflights users on 7/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/292:25 pm
BOS
- MDW
1 stop4h 30m
Southwest
Fri 7/317:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/5![Southwest logo]()
$236
This Delta deal was found by Cheapflights users on 7/2. 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 8/126:58 pm
ALB
- STL
1 stop5h 23m
Delta
Sat 8/156:00 am
STL
- ALB
1 stop6h 26m
Delta
Deal found 7/2![Delta logo]()
$297
This Southwest deal was found by Cheapflights users on 7/3. 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 10/1610:00 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 10/196:25 pm
MDW
- BOS
1 stop4h 40m
Southwest
Deal found 7/3![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 7/1. 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.
Tue 8/115:45 am
ALB
- ORD
2 stops9h 24m
Delta
Mon 8/175:20 pm
ORD
- ALB
1 stop4h 45m
Delta
Deal found 7/1![Delta logo]()
$309
Last-minute flights from Massachusetts to IllinoisDiscover last-minute flight deals from Massachusetts to Illinois. Data last updated July 6, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Illinois. Data last updated July 6, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/1. 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.
Wed 7/1512:01 pm
BOS
- ORD
Nonstop3h 01m
American Airlines
Wed 7/226:00 am
ORD
- BOS
Nonstop2h 34m
American Airlines
Deal found 7/1![American Airlines logo]()
$170
This Southwest deal was found by Cheapflights users on 7/1. 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 7/255:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 7/277:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/1![Southwest logo]()
$170
This United Airlines deal was found by Cheapflights users on 7/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/258:20 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Tue 7/286:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 7/3![United Airlines logo]()
$172
This United Airlines deal was found by Cheapflights users on 7/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/258:20 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Sat 9/193:35 pm
ORD
- BOS
Nonstop2h 44m
United Airlines
Deal found 7/3![United Airlines logo]()
$173
This Southwest deal was found by Cheapflights users on 7/3. 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.
Sat 7/255:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sat 7/255:45 pm
MDW
- BOS
Nonstop2h 25m
Southwest
Deal found 7/3![Southwest logo]()
$175
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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 7/257:59 pm
BOS
- ORD
Nonstop3h 00m
Delta
Thu 7/303:19 pm
ORD
- BOS
Nonstop2h 40m
Delta
Deal found 7/6![Delta logo]()
$178
This JetBlue deal was found by Cheapflights users on 7/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:15 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Thu 8/209:35 am
ORD
- BOS
1 stop6h 32m
JetBlue
Deal found 7/2![JetBlue logo]()
$175
This Jettzy deal was found by Cheapflights users on 7/3. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/174:55 pm
BOS
- ORD
1 stop6h 03m
JetBlue
Mon 8/248:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/3![JetBlue logo]()
$177
This Southwest deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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 8/225:30 am
BOS
- MDW
1 stop5h 00m
Southwest
Sat 8/293:10 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/6![Southwest logo]()
$172
This Flysmarter deal was found by Cheapflights users on 7/2. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:41 am
BOS
- ORD
1 stop8h 36m
JetBlue
Mon 8/248:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/2![JetBlue logo]()
$174
This Southwest deal was found by Cheapflights users on 7/2. 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.
Mon 8/246:40 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Wed 8/266:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/2![Southwest logo]()
$179
This Southwest deal was found by Cheapflights users on 7/2. 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.
Tue 8/257:15 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 9/96:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/2![Southwest logo]()
$173
One-way flights from Massachusetts to IllinoisSearch for one-way flight options from Massachusetts to Illinois. Find affordable one-way fares based on user searches. Data last updated July 6, 2026.
Search for one-way flight options from Massachusetts to Illinois. Find affordable one-way fares based on user searches. Data last updated July 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/78:02 pm
ALB
- ORD
1 stop17h 13m
Multiple Airlines
Deal found 7/3![Multiple Airlines logo]()
$91
This American Airlines deal was found by Cheapflights users on 7/5. 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.
Sun 8/25:16 pm
ORH
- ORD
1 stop7h 14m
American Airlines
Deal found 7/5![American Airlines logo]()
$94
This United Airlines deal was found by Cheapflights users on 7/1. 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 8/226:00 pm
BOS
- ORD
1 stop5h 15m
United Airlines
Deal found 7/1![United Airlines logo]()
$98
This Southwest deal was found by Cheapflights users on 7/4. 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.
Wed 9/910:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Deal found 7/4![Southwest logo]()
$99
This Super.com deal was found by Cheapflights users on 7/1. 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.
Mon 8/105:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/1![JetBlue logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 7/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:01 am
BOS
- ORD
1 stop4h 45m
JetBlue
Deal found 7/2![JetBlue logo]()
$100
This Delta deal was found by Cheapflights users on 7/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/215:40 pm
ORH
- ORD
1 stop5h 56m
Delta
Deal found 7/5![Delta logo]()
$101
This JetBlue deal was found by Cheapflights users on 7/5. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Deal found 7/5![JetBlue logo]()
$101
This Southwest deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:00 am
BOS
- MDW
1 stop8h 15m
Southwest
Deal found 7/6![Southwest logo]()
$103
This Super.com deal was found by Cheapflights users on 7/2. 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.
Wed 7/2212:45 pm
BOS
- ORD
1 stop5h 49m
JetBlue
Deal found 7/2![JetBlue logo]()
$103
This Delta deal was found by Cheapflights users on 7/2. 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.
Tue 9/224:20 pm
ORH
- ORD
1 stop6h 58m
Delta
Deal found 7/2![Delta logo]()
$104
This Southwest deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” 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 7/205:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/6![Southwest logo]()
$105
Find flight deals from Massachusetts to Illinois
Keep the following information in mind while searching for Massachusetts to Illinois flight deals. Data was last updated July 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $170 (Southwest) |
One-way from | $91 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $240 |
Good round-trip deal | $237 or less |
Good one-way deal | $139 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Massachusetts to Illinois that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 6, 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 7/18
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Wed 7/22
7:45 pm-11:21 pm
Nonstop2h 36m
$170
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 7/18
6:43 pm-8:40 pm
Nonstop2h 57m
Chicago O'Hare Intl
Sat 7/25
6:20 pm-9:56 pm
Nonstop2h 36m
$170
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 8/20
5:45 am-9:38 am
1 stop4h 53m
Chicago O'Hare Intl
Sat 8/22
6:15 am-9:36 am
Nonstop2h 21m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 8/4
8:15 pm-10:15 pm
Nonstop3h 00m
Chicago O'Hare Intl
Tue 8/11
6:00 am-11:17 am
1 stop4h 17m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 9/1
2:40 pm-9:58 pm
1 stop8h 18m
Chicago O'Hare Intl
Sat 9/5
1:49 pm-5:59 pm
Nonstop3h 10m
$175
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 8/22
11:05 am-12:59 pm
Nonstop2h 54m
Chicago O'Hare Intl
Mon 8/24
6:00 am-2:43 pm
1 stop7h 43m
$176
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 7/21
7:19 am-9:17 am
Nonstop2h 58m
Chicago O'Hare Intl
Thu 7/30
9:41 pm-1:14 am
Nonstop2h 33m
$178
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 8/31
7:30 am-9:26 am
Nonstop2h 56m
Chicago O'Hare Intl
Sat 9/12
11:30 am-3:15 pm
Nonstop2h 45m
$181
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 8/22
5:45 am-9:38 am
1 stop4h 53m
Chicago O'Hare Intl
Sat 8/29
7:45 am-11:19 am
Nonstop2h 34m
$181
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 7/26
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Thu 7/30
9:41 pm-1:14 am
Nonstop2h 33m
$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.
ALB-ORD
ORH-ORD
BOS-ORD
BOS-MDW
ALB-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
ALB-ORD
ORH-ORD
BOS-ORD
BOS-MDW
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 $167). Flying from Massachusetts to Illinois in July is currently the most expensive (average of $293). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MA to IL?
Find hourly flight availability from Massachusetts to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 6, 2026.
A simple way to save on the total cost of your ticket is to fly from Massachusetts to Illinois in the evening. If you’re flexible enough to do this you can expect to save up to 43% on your trip compared to booking a flight in the afternoon.
Weekly flight availability from Massachusetts to Illinois
Explore weekly flight availability from Massachusetts to Illinois. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 6, 2026.
The most flights from USMA to USIL are scheduled on a Monday (74 on average). You will have fewer flight options on Saturday, 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?
How far ahead should I book a flight from Massachusetts to Illinois?
Booking 77 days in advance of your planned departure date is, on average, the best time to get cheap flights from Massachusetts to Illinois. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Massachusetts to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Illinois. Price data was last updated on June 8, 2026.
Travelers seeking maximum savings on their Massachusetts to Illinois flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated July 6, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Massachusetts to Illinois have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Massachusetts to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Massachusetts to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Massachusetts to Illinois by cabin class
Find flights from Massachusetts to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Massachusetts and Illinois flights
Browse other Massachusetts and Illinois flight options. Last updated on July 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Illinois
Find the right flight back to Massachusetts after your stay in Illinois
Massachusetts to Illinois flights
Consider these flights traveling from Massachusetts to Illinois.
Top 5 airlines flying from Massachusetts to Illinois
Discover the top 5 airlines that operate flights from Massachusetts to Illinois. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$185 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$323 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$125 | Average$361 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$134 | Average$219 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$137 | Average$420 | FlexibilityNo cancel fee | On-time71% |