$65+ 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 3/24. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Apr 10 — Apr 171
Round-trip
1 adult, Economy
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Find cheap flights from Boston to Illinois with Cheapflights
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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 March 11, 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 March 11, 2026.
This Southwest deal was found by Cheapflights users on 3/8. 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 5/97:15 am
BOS
- MDW
Nonstop2h 50m
Southwest
Sat 5/92:15 pm
MDW
- BOS
2 stops8h 25m
Southwest
Deal found 3/8![Southwest logo]()
$130
This Super.com deal was found by Cheapflights users on 3/6. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Tue 4/149:41 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Deal found 3/6![JetBlue logo]()
$135
This Southwest deal was found by Cheapflights users on 3/8. 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 4/117:15 am
BOS
- MDW
Nonstop2h 50m
Southwest
Sat 4/1111:25 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/8![Southwest logo]()
$136
This United Airlines deal was found by Cheapflights users on 3/8. 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 4/16:00 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Sat 4/49:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Deal found 3/8![United Airlines logo]()
$136
This Southwest deal was found by Cheapflights users on 3/8. 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 4/76:20 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Tue 4/143:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/8![Southwest logo]()
$137
This Delta deal was found by Cheapflights users on 3/9. 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.
Wed 4/87:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Sat 4/117:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Deal found 3/9![Delta logo]()
$137
This Priceline deal was found by Cheapflights users on 3/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:05 am
BOS
- ORD
Nonstop3h 03m
Multiple Airlines
Tue 4/146:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$138
This American Airlines deal was found by Cheapflights users on 3/8. 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.
Thu 4/26:52 am
BOS
- ORD
Nonstop3h 11m
American Airlines
Sat 4/48:45 pm
ORD
- BOS
Nonstop2h 20m
American Airlines
Deal found 3/8![American Airlines logo]()
$140
This Southwest deal was found by Cheapflights users on 3/8. 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 4/117:15 am
BOS
- MDW
Nonstop2h 50m
Southwest
Tue 4/147:50 am
MDW
- BOS
2 stops7h 05m
Southwest
Deal found 3/8![Southwest logo]()
$141
This United Airlines deal was found by Cheapflights users on 3/8. 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 5/207:30 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Sat 5/237:40 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 3/8![United Airlines logo]()
$141
This Southwest deal was found by Cheapflights users on 3/8. 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 5/142:30 pm
BOS
- MDW
1 stop8h 50m
Southwest
Sat 5/163:30 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 3/8![Southwest logo]()
$142
This Priceline deal was found by Cheapflights users on 3/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/812:42 pm
BOS
- ORD
1 stop10h 57m
Multiple Airlines
Sat 4/118:58 am
ORD
- BOS
Nonstop2h 30m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$143
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 March 11, 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 March 11, 2026.
This JetBlue deal was found by Cheapflights users on 3/8. 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.
Fri 5/87:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Sat 5/96:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Deal found 3/8![JetBlue logo]()
$136
This Southwest deal was found by Cheapflights users on 3/8. 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 4/253:15 pm
BOS
- MDW
1 stop5h 50m
Southwest
Tue 4/285:30 am
MDW
- BOS
1 stop7h 10m
Southwest
Deal found 3/8![Southwest logo]()
$146
This United Airlines deal was found by Cheapflights users on 3/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/810:05 am
BOS
- ORD
1 stop5h 35m
United Airlines
Sun 4/127:30 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Deal found 3/7![United Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/158:16 pm
BOS
- RFD
1 stop14h 31m
Multiple Airlines
Sun 4/1910:37 am
RFD
- BOS
1 stop22h 38m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$246
This JetBlue deal was found by Cheapflights users on 3/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Sun 5/106:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Deal found 3/7![JetBlue logo]()
$147
This American Airlines deal was found by Cheapflights users on 3/8. 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.
Thu 4/97:40 pm
BOS
- BMI
1 stop5h 12m
American Airlines
Sat 4/1111:16 am
BMI
- BOS
1 stop6h 34m
American Airlines
Deal found 3/8![American Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 3/9. 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 6/44:45 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Sun 6/75:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 3/9![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 3/9. 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.
Wed 5/65:35 am
BOS
- ORD
1 stop10h 25m
Southwest
Fri 5/82:40 pm
ORD
- BOS
1 stop7h 35m
Southwest
Deal found 3/9![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 3/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/271:10 pm
BOS
- STL
1 stop5h 06m
Delta
Tue 6/92:18 pm
STL
- BOS
1 stop4h 27m
Delta
Deal found 3/10![Delta logo]()
$373
This JetBlue deal was found by Cheapflights users on 3/6. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:26 pm
BOS
- ORD
Nonstop3h 09m
JetBlue
Tue 6/28:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 3/6![JetBlue logo]()
$172
This United Airlines deal was found by Cheapflights users on 3/8. 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.
Fri 6/126:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sun 6/146:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 3/8![United Airlines logo]()
$211
This JetBlue deal was found by Cheapflights users on 3/8. 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 5/97:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Tue 5/128:31 am
ORD
- BOS
1 stop8h 42m
JetBlue
Deal found 3/8![JetBlue logo]()
$175
This Southwest deal was found by Cheapflights users on 3/8. 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 4/117:15 am
BOS
- MDW
Nonstop2h 50m
Southwest
Sun 4/127:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 3/8![Southwest logo]()
$186
This United Airlines deal was found by Cheapflights users on 3/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/57:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sat 6/67:40 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 3/7![United Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Mon 4/139:45 am
BOS
- EVV
1 stop10h 21m
Multiple Airlines
Fri 4/177:46 pm
EVV
- BOS
1 stop12h 43m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$267
This JetBlue deal was found by Cheapflights users on 3/6. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/238:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Sun 3/2911:00 am
ORD
- BOS
Nonstop2h 24m
JetBlue
Deal found 3/6![JetBlue logo]()
$202
This Southwest deal was found by Cheapflights users on 3/6. 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 4/67:15 am
BOS
- MDW
Nonstop2h 55m
Southwest
Wed 4/812:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/6![Southwest logo]()
$212
This American Airlines deal was found by Cheapflights users on 3/9. 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.
Sat 3/286:52 am
BOS
- CMI
1 stop5h 39m
American Airlines
Mon 3/303:47 pm
CMI
- BOS
1 stop7h 18m
American Airlines
Deal found 3/9![American Airlines logo]()
$303
This Southwest deal was found by Cheapflights users on 3/8. 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 4/236:55 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Thu 4/302:10 pm
MDW
- BOS
1 stop8h 00m
Southwest
Deal found 3/8![Southwest logo]()
$213
This American Airlines deal was found by Cheapflights users on 3/9. 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.
Thu 4/98:03 am
BOS
- CMI
1 stop14h 32m
American Airlines
Wed 7/16:09 am
CMI
- BOS
1 stop11h 37m
American Airlines
Deal found 3/9![American Airlines logo]()
$314
This JetBlue deal was found by Cheapflights users on 3/10. 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.
Fri 8/218:00 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Tue 8/259:33 am
ORD
- BOS
1 stop6h 56m
JetBlue
Deal found 3/10![JetBlue logo]()
$236
This United Airlines deal was found by Cheapflights users on 3/9. 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.
Thu 5/76:00 am
BOS
- CMI
1 stop7h 48m
United Airlines
Sat 5/91:36 pm
CMI
- BOS
2 stops9h 23m
United Airlines
Deal found 3/9![United Airlines logo]()
$294
This Southwest deal was found by Cheapflights users on 3/6. 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 4/119:00 am
BOS
- ORD
1 stop7h 30m
Southwest
Sat 4/181:55 pm
ORD
- BOS
2 stops8h 45m
Southwest
Deal found 3/6![Southwest logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2611:25 am
BOS
- RFD
1 stop22h 56m
Multiple Airlines
Fri 5/298:03 pm
RFD
- BOS
1 stop12h 26m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$328
This Delta deal was found by Cheapflights users on 3/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/75:45 am
BOS
- MLI
1 stop5h 41m
Delta
Fri 6/265:00 pm
MLI
- BOS
1 stop7h 03m
Delta
Deal found 3/7![Delta logo]()
$379
This American Airlines deal was found by Cheapflights users on 3/9. 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.
Thu 4/98:03 am
BOS
- CMI
1 stop14h 32m
American Airlines
Wed 7/1511:37 am
CMI
- BOS
1 stop10h 09m
American Airlines
Deal found 3/9![American Airlines logo]()
$314
This Southwest deal was found by Cheapflights users on 3/10. 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.
Fri 4/1010:40 am
BOS
- MDW
Nonstop2h 40m
Southwest
Tue 4/143:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/10![Southwest logo]()
$232
This United Airlines deal was found by Cheapflights users on 3/9. 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.
Sat 4/44:28 pm
BOS
- MLI
1 stop5h 43m
United Airlines
Tue 4/73:20 pm
MLI
- BOS
2 stops7h 39m
United Airlines
Deal found 3/9![United Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 3/8. 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.
Fri 4/109:00 am
BOS
- STL
1 stop12h 43m
Delta
Sat 4/1110:50 am
STL
- BOS
1 stop4h 35m
Delta
Deal found 3/8![Delta logo]()
$410
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:22 pm
BOS
- RFD
2 stops20h 23m
Multiple Airlines
Sun 5/3111:27 am
RFD
- BOS
1 stop11h 30m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$378
Last-minute flights from Boston to IllinoisDiscover last-minute flight deals from Boston to Illinois. Data last updated March 11, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Illinois. Data last updated March 11, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 3/8. 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 3/286:30 am
BOS
- MDW
Nonstop2h 50m
Southwest
Tue 3/318:00 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/8![Southwest logo]()
$144
This United Airlines deal was found by Cheapflights users on 3/8. 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 4/16:00 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Sat 4/49:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Deal found 3/8![United Airlines logo]()
$136
This Priceline deal was found by Cheapflights users on 3/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/26:05 am
BOS
- ORD
Nonstop3h 00m
Multiple Airlines
Wed 4/85:05 am
ORD
- BOS
1 stop9h 23m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$139
This American Airlines deal was found by Cheapflights users on 3/8. 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.
Thu 4/26:52 am
BOS
- ORD
Nonstop3h 11m
American Airlines
Sat 4/48:45 pm
ORD
- BOS
Nonstop2h 20m
American Airlines
Deal found 3/8![American Airlines logo]()
$140
This Super.com deal was found by Cheapflights users on 3/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Thu 4/98:55 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 3/7![JetBlue logo]()
$135
This Southwest deal was found by Cheapflights users on 3/8. 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 4/76:20 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Tue 4/143:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/8![Southwest logo]()
$137
This Priceline deal was found by Cheapflights users on 3/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:05 am
BOS
- ORD
Nonstop3h 03m
Multiple Airlines
Tue 4/146:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$138
This Delta deal was found by Cheapflights users on 3/9. 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.
Wed 4/87:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Sat 4/117:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Deal found 3/9![Delta logo]()
$137
This Priceline deal was found by Cheapflights users on 3/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/812:42 pm
BOS
- ORD
1 stop10h 57m
Multiple Airlines
Sat 4/118:58 am
ORD
- BOS
Nonstop2h 30m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$143
This Southwest deal was found by Cheapflights users on 3/8. 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 4/117:15 am
BOS
- MDW
Nonstop2h 50m
Southwest
Sat 4/1111:25 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/8![Southwest logo]()
$136
This Southwest deal was found by Cheapflights users on 3/8. 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 4/117:15 am
BOS
- MDW
Nonstop2h 50m
Southwest
Tue 4/147:50 am
MDW
- BOS
2 stops7h 05m
Southwest
Deal found 3/8![Southwest logo]()
$141
This Super.com deal was found by Cheapflights users on 3/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Sun 4/196:00 am
ORD
- BOS
Nonstop2h 13m
JetBlue
Deal found 3/9![JetBlue logo]()
$145
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 March 11, 2026.
Search for one-way flight options from Boston to Illinois. Find affordable one-way fares based on user searches. Data last updated March 11, 2026.
This Super.com deal was found by Cheapflights users on 3/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/248:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 3/8![JetBlue logo]()
$65
This Southwest deal was found by Cheapflights users on 3/8. 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 3/286:30 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 3/8![Southwest logo]()
$66
This United Airlines deal was found by Cheapflights users on 3/8. 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.
Sat 3/286:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 3/8![United Airlines logo]()
$66
This Southwest deal was found by Cheapflights users on 3/9. 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 5/23:15 pm
BOS
- MDW
1 stop5h 50m
Southwest
Deal found 3/9![Southwest logo]()
$68
This Super.com deal was found by Cheapflights users on 3/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:05 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 3/9![JetBlue logo]()
$68
This Southwest deal was found by Cheapflights users on 3/9. 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.
Sun 5/176:10 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 3/9![Southwest logo]()
$69
This Delta deal was found by Cheapflights users on 3/9. 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.
Wed 4/87:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Deal found 3/9![Delta logo]()
$69
This Cheapflightsfares deal was found by Cheapflights users on 3/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/288:16 pm
BOS
- ORD
1 stop14h 20m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$70
This Priceline deal was found by Cheapflights users on 3/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:45 am
BOS
- ORD
1 stop12h 30m
Spirit Airlines
Deal found 3/7![Spirit Airlines logo]()
$71
This Southwest deal was found by Cheapflights users on 3/9. 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 5/25:25 am
BOS
- ORD
2 stops11h 05m
Southwest
Deal found 3/9![Southwest logo]()
$73
This Jettzy deal was found by Cheapflights users on 3/10. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/154:55 pm
BOS
- ORD
Nonstop3h 04m
Delta
Deal found 3/10![Delta logo]()
$74
This Jettzy deal was found by Cheapflights users on 3/10. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/27:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Deal found 3/10![Delta logo]()
$75
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 March 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $130 (Southwest) |
One-way from | $65 (Super.com) |
Popular in | March |
Cheapest in | September |
Average price | $268 |
Good round-trip deal | $223 or less |
Good one-way deal | $116 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 March 11, 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
Fri 5/8
7:35 pm-9:36 pm
Nonstop3h 01m
Chicago O'Hare Intl
Sat 5/9
6:00 am-9:15 am
Nonstop2h 15m
$136
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 4/25
3:15 pm-8:05 pm
1 stop5h 50m
Chicago Midway
Tue 4/28
5:30 am-1:40 pm
1 stop7h 10m
$146
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 5/7
7:35 pm-9:36 pm
Nonstop3h 01m
Chicago O'Hare Intl
Sun 5/10
6:00 am-9:15 am
Nonstop2h 15m
$147
Quickest round-trip
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 6/4
4:45 pm-6:35 pm
Nonstop2h 50m
Chicago Midway
Sun 6/7
5:15 am-8:25 am
Nonstop2h 10m
$157
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/6
5:35 am-3:00 pm
1 stop10h 25m
Chicago O'Hare Intl
Fri 5/8
2:40 pm-11:15 pm
1 stop7h 35m
$157
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 4/8
10:05 am-2:40 pm
1 stop5h 35m
Chicago O'Hare Intl
Sun 4/12
7:30 am-11:01 am
Nonstop2h 31m
$161
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 5/29
5:26 pm-7:35 pm
Nonstop3h 09m
Chicago O'Hare Intl
Tue 6/2
8:30 pm-11:59 pm
Nonstop2h 29m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/9
7:35 pm-9:36 pm
Nonstop3h 01m
Chicago O'Hare Intl
Tue 5/12
8:31 am-6:13 pm
1 stop8h 42m
$175
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 4/11
7:15 am-9:05 am
Nonstop2h 50m
Chicago Midway
Sun 4/12
7:40 am-10:55 am
Nonstop2h 15m
$186
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 3/23
8:00 am-10:10 am
Nonstop3h 10m
Chicago O'Hare Intl
Sun 3/29
11:00 am-2:24 pm
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-MDW
BOS-ORD
BOS-RFD
BOS-BMI
BOS-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 Boston to Illinois
BOS-USIL
BOS-MDW
BOS-ORD
BOS-RFD
BOS-BMI
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 $91). Flying from Boston to Illinois in January is currently the most expensive (average of $123). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from 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 March 11, 2026.
One of the essential ways to save on airfare from Boston to Illinois is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 23% on airfare.
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 February 21, 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.
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 March 11, 2026.
The most flights from BOS to USIL are scheduled on a Monday (57 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).
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 March 11, 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.
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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.
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Alternative routes for Boston to Illinois
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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 March 11, 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 6 airlines flying from Boston to Illinois
Discover the top 6 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 March 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$67 | Average$172 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$82 | Average$318 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$85 | Average$162 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$117 | Average$218 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$117 | Average$387 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$127 | Average$424 | FlexibilityNo cancel fee | On-time71% |