$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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
juil. 16 — juil. 231
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 juin 16, 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 juin 16, 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.
mar. 7/215:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
mar. 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 6/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 7/48:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
lun. 7/69:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 6/12![United Airlines logo]()
$182
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.
sam. 8/298:40 am
BOS
- MDW
Nonstop2h 35m
Southwest
mar. 9/12:00 pm
MDW
- BOS
2 stops7h 10m
Southwest
Deal found 6/11![Southwest logo]()
$183
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.
sam. 7/115:01 am
BOS
- ORD
1 stop4h 50m
JetBlue
mar. 7/218:10 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 6/12![JetBlue logo]()
$183
This Cheapflightsfares deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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.
mer. 7/1512:45 pm
BOS
- ORD
1 stop5h 49m
JetBlue
ven. 7/178:10 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 6/14![JetBlue logo]()
$184
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.
mar. 6/305:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
sam. 7/412:50 pm
MDW
- BOS
2 stops6h 35m
Southwest
Deal found 6/10![Southwest logo]()
$185
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/712:45 pm
BOS
- ORD
1 stop5h 49m
JetBlue
mar. 7/146:00 am
ORD
- BOS
1 stop7h 48m
JetBlue
Deal found 6/11![JetBlue logo]()
$185
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/72:45 pm
BOS
- ORD
1 stop7h 18m
JetBlue
ven. 7/1010:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 6/11![JetBlue logo]()
$186
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.
jeu. 7/165:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
lun. 7/207:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/12![Southwest logo]()
$187
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 7/35:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
mar. 7/76:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Deal found 6/11![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.
jeu. 10/16:30 pm
BOS
- MDW
Nonstop2h 50m
Southwest
dim. 10/45:15 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 6/11![Southwest logo]()
$188
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.
jeu. 8/135:01 am
BOS
- ORD
1 stop4h 47m
JetBlue
ven. 8/149:39 am
ORD
- BOS
1 stop6h 36m
JetBlue
Deal found 6/10![JetBlue 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 juin 16, 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 juin 16, 2026.
This JetBlue deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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.
mar. 7/712:45 pm
BOS
- ORD
1 stop5h 49m
JetBlue
lun. 7/278:10 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 6/14![JetBlue logo]()
$189
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 7/158:15 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
sam. 7/186:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 6/11![United Airlines logo]()
$198
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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.
jeu. 7/25:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
sam. 7/46:30 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/15![Southwest logo]()
$200
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 8/78:50 pm
BOS
- ORD
Nonstop2h 54m
Delta
ven. 8/147:30 pm
ORD
- BOS
Nonstop2h 30m
Delta
Deal found 6/10![Delta logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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.
jeu. 9/311:05 am
BOS
- RFD
1 stop21h 57m
Multiple Airlines
dim. 9/611:55 am
RFD
- BOS
1 stop22h 41m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$342
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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.
mer. 7/11:03 pm
BOS
- BMI
1 stop5h 20m
American Airlines
mar. 7/76:04 pm
BMI
- BOS
1 stop5h 01m
American Airlines
Deal found 6/15![American Airlines logo]()
$344
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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.
sam. 7/115:20 am
BOS
- MDW
Nonstop2h 35m
Southwest
lun. 7/137:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/13![Southwest logo]()
$200
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.
ven. 7/248:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
jeu. 8/610:30 am
ORD
- BOS
Nonstop2h 29m
Delta
Deal found 6/11![Delta logo]()
$201
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 7/17:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
dim. 7/56:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 6/12![United Airlines logo]()
$203
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.
ven. 7/178:41 am
BOS
- ORD
1 stop8h 35m
JetBlue
mar. 7/219:40 am
ORD
- BOS
1 stop6h 37m
JetBlue
Deal found 6/10![JetBlue logo]()
$213
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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.
sam. 7/47:35 am
BOS
- MDW
1 stop7h 50m
Southwest
mer. 7/156:05 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/13![Southwest logo]()
$203
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.
jeu. 8/68:50 pm
BOS
- ORD
Nonstop2h 54m
Delta
mar. 8/117:55 am
ORD
- BOS
Nonstop2h 29m
Delta
Deal found 6/12![Delta logo]()
$203
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.
sam. 8/112:56 pm
BOS
- STL
2 stops12h 03m
Frontier
dim. 8/26:34 pm
STL
- BOS
1 stop12h 12m
Frontier
Deal found 6/10![Frontier logo]()
$456
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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.
jeu. 8/65:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
dim. 8/99:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 6/14![United Airlines logo]()
$216
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.
ven. 7/312:37 pm
BOS
- RFD
1 stop20h 38m
Allegiant Air
lun. 7/68:39 am
RFD
- BOS
2 stops26h 15m
Allegiant Air
Deal found 6/11![Allegiant Air logo]()
$482
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 7/197:30 am
BOS
- ORD
Nonstop2h 56m
Delta
lun. 7/2010:28 am
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 6/10![Delta logo]()
$211
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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.
mar. 8/114:55 pm
BOS
- MDW
1 stop4h 50m
Southwest
ven. 8/149:20 am
MDW
- BOS
1 stop6h 45m
Southwest
Deal found 6/15![Southwest logo]()
$223
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.
ven. 7/108:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
dim. 7/196:59 am
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 6/12![Delta logo]()
$211
This Southwest deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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.
jeu. 7/305:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
mer. 8/512:50 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/13![Southwest logo]()
$235
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.
ven. 6/196:45 pm
BOS
- MDW
Nonstop2h 50m
Southwest
ven. 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 6/12. 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.
ven. 7/108:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
lun. 7/205:54 pm
ORD
- BOS
1 stop5h 01m
Delta
Deal found 6/12![Delta logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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.
mer. 7/2910:04 am
BOS
- SPI
1 stop9h 47m
Multiple Airlines
mer. 8/57:31 pm
SPI
- BOS
1 stop12h 38m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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.
ven. 9/47:17 pm
BOS
- MLI
1 stop5h 51m
American Airlines
dim. 9/66:00 am
MLI
- BOS
2 stops7h 26m
American Airlines
Deal found 6/15![American Airlines logo]()
$374
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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.
sam. 8/2212:27 pm
BOS
- DEC
1 stop6h 32m
United Airlines
lun. 8/247:20 pm
DEC
- BOS
1 stop4h 54m
United Airlines
Deal found 6/15![United Airlines logo]()
$314
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.
sam. 7/116:45 pm
BOS
- MDW
1 stop4h 45m
Southwest
dim. 7/125:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 6/12![Southwest logo]()
$243
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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.
lun. 6/295:05 pm
BOS
- BMI
2 stops8h 30m
American Airlines
ven. 7/35:00 am
BMI
- BOS
1 stop4h 28m
American Airlines
Deal found 6/14![American Airlines logo]()
$374
This United Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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.
mer. 8/1210:38 am
BOS
- PIA
1 stop5h 22m
United Airlines
mer. 8/195:45 am
PIA
- BOS
1 stop7h 22m
United Airlines
Deal found 6/13![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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.
jeu. 9/35:25 am
BOS
- MDW
1 stop6h 35m
Southwest
lun. 9/75:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 6/14![Southwest logo]()
$246
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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.
mer. 7/81:01 pm
BOS
- PIA
1 stop12h 21m
American Airlines
mer. 7/156:00 am
PIA
- BOS
1 stop11h 47m
American Airlines
Deal found 6/15![American Airlines logo]()
$377
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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.
mer. 7/18:15 am
BOS
- MLI
1 stop6h 41m
United Airlines
lun. 7/66:30 pm
MLI
- BOS
1 stop5h 44m
United Airlines
Deal found 6/14![United Airlines logo]()
$322
Last-minute flights from Boston to IllinoisDiscover last-minute flight deals from Boston to Illinois. Data last updated juin 16, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Illinois. Data last updated juin 16, 2026 and is based on user searches.
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.
mar. 6/305:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
sam. 7/412:50 pm
MDW
- BOS
2 stops6h 35m
Southwest
Deal found 6/10![Southwest logo]()
$185
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.
mar. 6/305:25 am
BOS
- MDW
1 stop4h 15m
Southwest
ven. 7/37:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 6/11![Southwest logo]()
$188
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 7/35:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
mar. 7/76:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Deal found 6/11![JetBlue logo]()
$187
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 7/48:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
lun. 7/69:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 6/12![United Airlines logo]()
$182
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/712:45 pm
BOS
- ORD
1 stop5h 49m
JetBlue
mar. 7/146:00 am
ORD
- BOS
1 stop7h 48m
JetBlue
Deal found 6/11![JetBlue logo]()
$185
This JetBlue deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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.
mar. 7/75:25 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
jeu. 7/166:00 am
ORD
- BOS
1 stop7h 48m
JetBlue
Deal found 6/14![JetBlue 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.
sam. 7/115:01 am
BOS
- ORD
1 stop4h 50m
JetBlue
mar. 7/218:10 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 6/12![JetBlue logo]()
$183
This Cheapflightsfares deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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.
mer. 7/155:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
lun. 7/208:10 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 6/15![JetBlue logo]()
$184
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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.
mer. 7/155:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
ven. 7/176:00 pm
MDW
- BOS
1 stop4h 30m
Southwest
Deal found 6/14![Southwest logo]()
$189
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.
jeu. 7/165:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
lun. 7/207:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/12![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.
mar. 7/215:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
mar. 7/216:05 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 6/11![Southwest logo]()
$182
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.
mer. 7/228:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
ven. 7/249:42 am
ORD
- BOS
1 stop6h 40m
JetBlue
Deal found 6/12![JetBlue logo]()
$186
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 juin 16, 2026.
Search for one-way flight options from Boston to Illinois. Find affordable one-way fares based on user searches. Data last updated juin 16, 2026.
This Super.com deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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.
mar. 6/3012:42 pm
BOS
- ORD
1 stop5h 39m
JetBlue
Deal found 6/13![JetBlue logo]()
$95
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.
mar. 6/305:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/11![Southwest logo]()
$96
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 7/19:50 am
BOS
- ORD
Nonstop2h 53m
United Airlines
Deal found 6/11![United Airlines logo]()
$96
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 7/34:40 pm
BOS
- ORD
1 stop5h 50m
JetBlue
Deal found 6/11![JetBlue logo]()
$97
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.
mer. 8/268:15 am
BOS
- MDW
2 stops6h 15m
Southwest
Deal found 6/11![Southwest logo]()
$98
This Cheapflightsfares deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” 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.
mar. 7/78:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 6/13![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.
mar. 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 6/12. 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.
mer. 9/910:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Deal found 6/12![Southwest logo]()
$99
This JetBlue deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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.
sam. 9/125:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Deal found 6/14![JetBlue logo]()
$99
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.
sam. 7/255:01 am
BOS
- ORD
1 stop4h 50m
JetBlue
Deal found 6/12![JetBlue logo]()
$100
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.
lun. 8/178:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/11![Southwest logo]()
$101
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 9/96:55 am
BOS
- ORD
1 stop5h 52m
JetBlue
Deal found 6/11![JetBlue 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 juin 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $182 (Southwest) |
One-way from | $95 (Super.com) |
Popular in | June |
Cheapest in | September |
Average price | $267 |
Good round-trip deal | $247 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 juin 16, 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
mar. 7/7
12:45 pm-5:34 pm
1 stop5h 49m
Chicago O'Hare Intl
lun. 7/27
8:10 pm-11:41 pm
Nonstop2h 31m
$189
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
mer. 7/15
8:15 pm-10:15 pm
Nonstop3h 00m
Chicago O'Hare Intl
sam. 7/18
6:00 am-11:16 am
1 stop4h 16m
$198
Quickest round-trip
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
jeu. 7/2
5:25 am-7:00 am
Nonstop2h 35m
Chicago Midway
sam. 7/4
6:30 am-9:50 am
Nonstop2h 20m
$200
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
sam. 7/11
5:20 am-6:55 am
Nonstop2h 35m
Chicago Midway
lun. 7/13
7:35 pm-10:55 pm
Nonstop2h 20m
$200
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
ven. 8/7
8:50 pm-10:44 pm
Nonstop2h 54m
Chicago O'Hare Intl
ven. 8/14
7:30 pm-11:00 pm
Nonstop2h 30m
$201
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
ven. 7/24
8:45 pm-10:39 pm
Nonstop2h 54m
Chicago O'Hare Intl
jeu. 8/6
10:30 am-1:59 pm
Nonstop2h 29m
$201
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
mer. 7/1
7:19 am-9:17 am
Nonstop2h 58m
Chicago O'Hare Intl
dim. 7/5
6:05 am-9:29 am
Nonstop2h 24m
$203
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
sam. 7/4
7:35 am-2:25 pm
1 stop7h 50m
Chicago Midway
mer. 7/15
6:05 pm-9:25 pm
Nonstop2h 20m
$203
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
jeu. 8/6
8:50 pm-10:44 pm
Nonstop2h 54m
Chicago O'Hare Intl
mar. 8/11
7:55 am-11:24 am
Nonstop2h 29m
$203
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
dim. 7/19
7:30 am-9:26 am
Nonstop2h 56m
Chicago O'Hare Intl
lun. 7/20
10:28 am-1:59 pm
Nonstop2h 31m
$211
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-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-ORD
BOS-MDW
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 $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 juin 16, 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 juin 16, 2026.
The most flights from BOS 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 (36 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 13, 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 juin 16, 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
Crew
8.6
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Food
7.0
Boarding
8.1
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
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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 juin 16, 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 juin 16, 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$360 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$130 | Average$219 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$137 | Average$408 | FlexibilityNo cancel fee | On-time71% |