$95+ Cheap flights from Boston (BOS) 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Jul 13 — Jul 201
Round-trip
1 adult, Economy
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Cheapest flights from Boston to IllinoisExplore the most affordable flight options available from Boston to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 13, 2026.
Explore the most affordable flight options available from Boston to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 13, 2026.
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/215:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 7/216:05 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/11![Southwest logo]()
$182
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/17:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Mon 7/69:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 6/8![United Airlines logo]()
$182
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Mon 8/246:30 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/8![Southwest logo]()
$183
This JetBlue deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/114:43 pm
BOS
- ORD
1 stop6h 15m
JetBlue
Wed 7/2210:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 6/8![JetBlue logo]()
$183
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/178:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Sat 8/2211:25 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/10![Southwest logo]()
$184
This United Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 9/238:31 pm
BOS
- ORD
Nonstop2h 59m
United Airlines
Sun 9/276:00 am
ORD
- BOS
1 stop4h 24m
United Airlines
Deal found 6/9![United Airlines logo]()
$184
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/48:45 am
BOS
- MDW
2 stops6h 50m
Southwest
Sat 7/115:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 6/7![Southwest logo]()
$185
This JetBlue deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:01 am
BOS
- ORD
1 stop4h 47m
JetBlue
Tue 8/189:39 am
ORD
- BOS
1 stop8h 06m
JetBlue
Deal found 6/10![JetBlue logo]()
$185
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/148:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Thu 7/166:00 am
ORD
- BOS
1 stop7h 48m
JetBlue
Deal found 6/10![JetBlue logo]()
$186
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/167:30 am
BOS
- MDW
Nonstop2h 40m
Southwest
Sun 7/195:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 6/8![Southwest logo]()
$187
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/154:31 pm
BOS
- ORD
1 stop6h 27m
JetBlue
Mon 7/208:10 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 6/10![JetBlue logo]()
$187
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 8/127:15 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Fri 8/145:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 6/11![Southwest logo]()
$188
Best flights from Boston to IllinoisDiscover carefully curated flight deals from Boston to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 13, 2026.
Discover carefully curated flight deals from Boston to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 13, 2026.
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 8/137:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Tue 8/187:55 am
ORD
- BOS
Nonstop2h 29m
Delta
Deal found 6/12![Delta logo]()
$183
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/36:45 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Mon 7/67:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/8![Southwest logo]()
$187
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 12/97:10 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sun 12/135:00 am
ORD
- BOS
1 stop4h 39m
United Airlines
Deal found 6/10![United Airlines logo]()
$188
This JetBlue deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 9/226:55 am
BOS
- ORD
1 stop5h 52m
JetBlue
Wed 9/238:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 6/12![JetBlue logo]()
$199
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/56:00 am
BOS
- BMI
2 stops8h 07m
American Airlines
Sat 8/85:00 am
BMI
- BOS
1 stop4h 32m
American Airlines
Deal found 6/9![American Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/312:37 pm
BOS
- RFD
1 stop20h 38m
Multiple Airlines
Mon 7/67:50 pm
RFD
- BOS
1 stop12h 19m
Multiple Airlines
Deal found 6/10![Multiple Airlines logo]()
$376
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/45:30 am
BOS
- MDW
1 stop4h 25m
Southwest
Mon 7/67:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/7![Southwest logo]()
$189
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/135:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Sat 8/157:59 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Deal found 6/8![United Airlines logo]()
$189
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/248:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Thu 8/610:30 am
ORD
- BOS
Nonstop2h 29m
Delta
Deal found 6/11![Delta logo]()
$201
This JetBlue deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/254:43 pm
BOS
- ORD
1 stop6h 15m
JetBlue
Mon 7/279:40 am
ORD
- BOS
1 stop6h 42m
JetBlue
Deal found 6/9![JetBlue logo]()
$213
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 11/126:00 am
BOS
- ORD
1 stop4h 37m
United Airlines
Sun 11/156:00 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 6/10![United Airlines logo]()
$198
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 10/157:30 am
BOS
- ORD
Nonstop3h 03m
Delta
Tue 10/207:00 am
ORD
- BOS
Nonstop2h 28m
Delta
Deal found 6/12![Delta logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/312:37 pm
BOS
- RFD
1 stop20h 38m
Allegiant Air
Mon 7/68:39 am
RFD
- BOS
2 stops26h 15m
Allegiant Air
Deal found 6/11![Allegiant Air logo]()
$482
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Sun 10/256:00 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 6/8![United Airlines logo]()
$202
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/410:30 am
BOS
- MDW
2 stops6h 50m
Southwest
Wed 7/85:20 pm
MDW
- BOS
1 stop5h 15m
Southwest
Deal found 6/8![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/45:05 pm
BOS
- ORD
Nonstop3h 12m
Delta
Mon 7/67:25 pm
ORD
- BOS
Nonstop2h 37m
Delta
Deal found 6/9![Delta logo]()
$213
This Southwest deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 6/196:45 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Fri 6/267:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 6/12![Southwest logo]()
$241
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/55:30 am
BOS
- ORD
1 stop6h 20m
Delta
Sat 7/114:30 pm
ORD
- BOS
Nonstop2h 41m
Delta
Deal found 6/8![Delta logo]()
$232
This American Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/266:00 am
BOS
- BMI
2 stops8h 07m
American Airlines
Sat 8/295:00 am
BMI
- BOS
1 stop4h 32m
American Airlines
Deal found 6/8![American Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/295:00 pm
BOS
- MDW
1 stop5h 40m
Southwest
Wed 8/122:00 pm
MDW
- BOS
2 stops7h 10m
Southwest
Deal found 6/11![Southwest logo]()
$254
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 9/77:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Wed 9/93:00 pm
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 6/8![Delta logo]()
$246
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/87:00 am
BOS
- CMI
1 stop5h 07m
American Airlines
Tue 7/1411:37 am
CMI
- BOS
1 stop4h 59m
American Airlines
Deal found 6/9![American Airlines logo]()
$342
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 6/175:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 6/172:40 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/8![Southwest logo]()
$267
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/91:54 pm
BOS
- BMI
1 stop4h 40m
American Airlines
Wed 7/156:04 pm
BMI
- BOS
1 stop5h 01m
American Airlines
Deal found 6/10![American Airlines logo]()
$344
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/211:30 pm
BOS
- MDW
1 stop9h 30m
Southwest
Sun 8/236:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 6/7![Southwest logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/89:15 am
BOS
- RFD
1 stop23h 47m
Multiple Airlines
Sun 10/1111:30 am
RFD
- BOS
1 stop23h 39m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$431
This United Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/176:00 am
BOS
- PIA
1 stop5h 09m
United Airlines
Sun 7/196:12 pm
PIA
- BOS
1 stop6h 02m
United Airlines
Deal found 6/9![United Airlines logo]()
$361
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/105:10 am
BOS
- CMI
1 stop13h 48m
American Airlines
Fri 7/176:28 pm
CMI
- BOS
1 stop14h 06m
American Airlines
Deal found 6/9![American Airlines logo]()
$374
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/233:55 pm
BOS
- MDW
2 stops5h 50m
Southwest
Sun 7/265:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 6/10![Southwest logo]()
$283
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:30 am
BOS
- MLI
1 stop5h 55m
Delta
Sun 9/66:00 am
MLI
- BOS
1 stop8h 13m
Delta
Deal found 6/12![Delta logo]()
$319
Last-minute flights from Boston to IllinoisDiscover last-minute flight deals from Boston to Illinois. Data last updated June 13, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Illinois. Data last updated June 13, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 6/228:45 pm
BOS
- ORD
Nonstop2h 57m
Delta
Wed 6/247:10 am
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 6/8![Delta logo]()
$200
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 6/305:25 am
BOS
- MDW
1 stop4h 15m
Southwest
Fri 7/37:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 6/11![Southwest logo]()
$188
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 6/305:25 am
BOS
- MDW
1 stop6h 35m
Southwest
Sat 7/411:10 am
MDW
- BOS
2 stops8h 25m
Southwest
Deal found 6/10![Southwest logo]()
$195
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/15:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sat 7/115:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 6/8![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/25:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 7/67:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/9![Southwest logo]()
$190
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/48:45 am
BOS
- MDW
2 stops6h 50m
Southwest
Tue 7/72:40 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/8![Southwest logo]()
$185
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/47:35 am
BOS
- MDW
1 stop7h 50m
Southwest
Mon 7/67:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/9![Southwest logo]()
$189
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/75:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 7/145:10 pm
MDW
- BOS
1 stop4h 35m
Southwest
Deal found 6/9![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/75:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Thu 7/92:30 pm
MDW
- BOS
1 stop8h 40m
Southwest
Deal found 6/9![Southwest logo]()
$198
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Thu 7/167:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/8![Southwest logo]()
$193
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/167:30 am
BOS
- MDW
Nonstop2h 40m
Southwest
Sun 7/195:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 6/8![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/215:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 7/216:05 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/11![Southwest logo]()
$182
One-way flights from Boston to IllinoisSearch for one-way flight options from Boston to Illinois. Find affordable one-way fares based on user searches. Data last updated June 13, 2026.
Search for one-way flight options from Boston to Illinois. Find affordable one-way fares based on user searches. Data last updated June 13, 2026.
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/18:37 am
BOS
- ORD
Nonstop3h 03m
American Airlines
Deal found 6/12![American Airlines logo]()
$95
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/15:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/8![Southwest logo]()
$96
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/237:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 6/8![Delta logo]()
$96
This Super.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/78:43 am
BOS
- ORD
1 stop8h 32m
JetBlue
Deal found 6/10![JetBlue logo]()
$97
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 9/28:15 am
BOS
- MDW
2 stops6h 15m
Southwest
Deal found 6/8![Southwest logo]()
$98
This Cheapflightsfares deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/35:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Deal found 6/12![JetBlue logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 8/1111:59 am
BOS
- STL
1 stop6h 38m
Frontier
Deal found 6/11![Frontier logo]()
$99
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/148:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/7![Southwest logo]()
$99
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/308:10 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 6/12![Delta logo]()
$99
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/75:00 am
BOS
- MDW
1 stop8h 15m
Southwest
Deal found 6/10![Southwest logo]()
$100
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:55 am
BOS
- ORD
1 stop5h 52m
JetBlue
Deal found 6/10![JetBlue logo]()
$100
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/108:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/8![Southwest logo]()
$101
Find flight deals from Boston to Illinois
Keep the following information in mind while searching for Boston to Illinois flight deals. Data was last updated June 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $182 (Southwest) |
One-way from | $95 (American Airlines) |
Popular in | June |
Cheapest in | September |
Average price | $263 |
Good round-trip deal | $242 or less |
Good one-way deal | $138 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Boston 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 June 13, 2026.
Use the filters below to find and compare flights from Boston to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 8/13
7:30 am-9:26 am
Nonstop2h 56m
Chicago O'Hare Intl
Tue 8/18
7:55 am-11:24 am
Nonstop2h 29m
$183
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 7/3
6:45 pm-8:35 pm
Nonstop2h 50m
Chicago Midway
Mon 7/6
7:35 pm-10:55 pm
Nonstop2h 20m
$187
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 12/9
7:10 am-9:08 am
Nonstop2h 58m
Chicago O'Hare Intl
Sun 12/13
5:00 am-10:39 am
1 stop4h 39m
$188
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 7/4
5:30 am-8:55 am
1 stop4h 25m
Chicago Midway
Mon 7/6
7:35 pm-10:55 pm
Nonstop2h 20m
$189
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 8/13
5:45 am-9:38 am
1 stop4h 53m
Chicago O'Hare Intl
Sat 8/15
7:59 pm-11:34 pm
Nonstop2h 35m
$189
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 11/12
6:00 am-9:37 am
1 stop4h 37m
Chicago O'Hare Intl
Sun 11/15
6:00 am-9:24 am
Nonstop2h 24m
$198
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 9/22
6:55 am-11:47 am
1 stop5h 52m
Chicago O'Hare Intl
Wed 9/23
8:24 pm-11:58 pm
Nonstop2h 34m
$199
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 7/24
8:45 pm-10:39 pm
Nonstop2h 54m
Chicago O'Hare Intl
Thu 8/6
10:30 am-1:59 pm
Nonstop2h 29m
$201
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 10/15
7:30 am-9:33 am
Nonstop3h 03m
Chicago O'Hare Intl
Tue 10/20
7:00 am-10:28 am
Nonstop2h 28m
$202
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 10/22
5:45 am-9:38 am
1 stop4h 53m
Chicago O'Hare Intl
Sun 10/25
6:00 am-9:24 am
Nonstop2h 24m
$202
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Boston to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Boston with our price prediction graph.
BOS-ORD
BOS-MDW
BOS-BMI
BOS-RFD
BOS-CMI
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 Boston to Illinois
BOS-USIL
BOS-ORD
BOS-MDW
BOS-BMI
BOS-RFD
What is the cheapest month to book a flight from Boston to Illinois?
Currently, September is the cheapest month in which you can book a flight from Boston to Illinois (average of $169). Flying from Boston to Illinois in July is currently the most expensive (average of $301). 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 BOS to IL?
Find hourly flight availability from Boston 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 June 13, 2026.
One of the essential ways to save on airfare from Boston to Illinois is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 23% on airfare.
Weekly flight availability from Boston to Illinois
Explore weekly flight availability from Boston 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 June 13, 2026.
The most flights from BOS to USIL are scheduled on a Monday (73 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (22 on average).
How much does it cost to fly round-trip from Boston to Illinois?
How far ahead should I book a flight from Boston to Illinois?
The best time to book flights from Boston to Illinois is 43 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Boston to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Boston to Illinois. Price data was last updated on June 8, 2026.
Travelers seeking maximum savings on their Boston 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 June 13, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Boston to Illinois to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Boarding
8.1
Overall
7.9
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Boarding
8.1
Overall
7.9
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Boarding
8.1
Overall
7.9
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Boarding
8.1
Overall
7.9
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Boarding
8.1
Overall
7.9
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Boarding
8.1
Overall
7.9
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Related info for your journey
Find useful and relevant information for your journey from Boston 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 Boston 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 Boston to Illinois by cabin class
Find flights from Boston to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Boston and Illinois flights
Browse other Boston and Illinois flight options. Last updated on June 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Boston to Illinois flights
Consider these flights traveling from Boston to Illinois.
Top 5 airlines flying from Boston to Illinois
Discover the top 5 airlines that operate flights from Boston 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 June 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$185 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$325 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$124 | Average$359 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$129 | Average$218 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$137 | Average$408 | FlexibilityNo cancel fee | On-time71% |