$63+ Cheap flights from Kentucky to Illinois
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — ORD
Apr 15 — Apr 221
Round-trip
1 adult, Economy
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Cheapest flights from Kentucky to IllinoisExplore the most affordable flight options available from Kentucky to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 16, 2026.
Explore the most affordable flight options available from Kentucky to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 16, 2026.
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/225:59 am
CVG
- MDW
1 stop3h 48m
Delta
Tue 4/281:24 pm
MDW
- CVG
1 stop5h 49m
Delta
Deal found 3/11![Delta logo]()
$177
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.
Fri 4/177:46 pm
CVG
- ORD
1 stop26h 26m
Multiple Airlines
Fri 4/247:15 pm
ORD
- CVG
2 stops22h 21m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$177
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.
Sat 4/187:46 pm
CVG
- ORD
1 stop15h 37m
Multiple Airlines
Sat 4/259:16 am
ORD
- CVG
1 stop8h 20m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$178
This Southwest deal was found by Cheapflights users on 3/12. 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.
Mon 4/208:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Wed 4/227:50 am
MDW
- CVG
2 stops8h 15m
Southwest
Deal found 3/12![Southwest logo]()
$179
This Frontier deal was found by Cheapflights users on 3/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1012:19 pm
CVG
- MDW
1 stop11h 00m
Frontier
Fri 4/179:14 am
MDW
- CVG
1 stop13h 06m
Frontier
Deal found 3/13![Frontier logo]()
$180
This Frontier deal was found by Cheapflights users on 3/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1312:19 pm
CVG
- ORD
1 stop11h 20m
Frontier
Thu 4/165:50 am
ORD
- CVG
1 stop10h 43m
Frontier
Deal found 3/12![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 3/12. 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.
Sat 4/118:45 am
CVG
- MDW
Nonstop1h 10m
Southwest
Sat 4/185:25 pm
MDW
- CVG
1 stop4h 55m
Southwest
Deal found 3/12![Southwest logo]()
$181
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.
Sun 4/196:53 pm
CVG
- ORD
1 stop16h 30m
Multiple Airlines
Mon 4/2711:28 am
ORD
- CVG
1 stop6h 08m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$181
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/215:59 am
CVG
- MDW
2 stops7h 44m
Delta
Wed 4/295:21 pm
MDW
- CVG
1 stop5h 50m
Delta
Deal found 3/11![Delta logo]()
$182
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/16:30 am
CVG
- ORD
1 stop7h 20m
Southwest
Wed 4/12:40 pm
ORD
- CVG
1 stop5h 55m
Southwest
Deal found 3/11![Southwest logo]()
$182
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.
Sun 4/266:53 pm
CVG
- ORD
1 stop16h 30m
Multiple Airlines
Fri 5/15:50 am
ORD
- CVG
1 stop11h 46m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$183
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/228:14 am
CVG
- MDW
1 stop5h 29m
Delta
Mon 4/276:00 am
MDW
- CVG
1 stop5h 30m
Delta
Deal found 3/11![Delta logo]()
$184
Best flights from Kentucky to IllinoisDiscover carefully curated flight deals from Kentucky to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 16, 2026.
Discover carefully curated flight deals from Kentucky to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 16, 2026.
This Southwest deal was found by Cheapflights users on 3/14. 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.
Thu 5/146:50 pm
CVG
- MDW
1 stop5h 40m
Southwest
Sat 5/166:10 am
MDW
- CVG
1 stop5h 00m
Southwest
Deal found 3/14![Southwest logo]()
$211
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/163:30 pm
CVG
- ORD
1 stop5h 54m
Delta
Mon 5/187:07 am
ORD
- CVG
1 stop4h 46m
Delta
Deal found 3/11![Delta logo]()
$211
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/189:00 am
LEX
- ORD
Nonstop1h 45m
United Airlines
Sat 7/117:49 pm
ORD
- LEX
Nonstop1h 41m
United Airlines
Deal found 3/11![United Airlines logo]()
$229
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:00 am
CVG
- ORD
Nonstop1h 33m
American Airlines
Fri 5/88:15 am
ORD
- CVG
Nonstop1h 26m
American Airlines
Deal found 3/11![American Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 4/239:31 am
LEX
- MDW
2 stops11h 00m
Multiple Airlines
Sun 4/269:16 am
MDW
- LEX
1 stop22h 26m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 3/12. 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.
Sat 5/236:00 pm
CVG
- ORD
1 stop3h 14m
Delta
Mon 6/17:07 am
ORD
- CVG
1 stop4h 46m
Delta
Deal found 3/12![Delta logo]()
$211
This Southwest deal was found by Cheapflights users on 3/15. 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.
Mon 4/68:15 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Wed 4/86:10 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 3/15![Southwest logo]()
$221
This United Airlines deal was found by Cheapflights users on 3/12. 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.
Thu 5/146:01 pm
TYS
- ORD
Nonstop1h 54m
United Airlines
Tue 5/192:10 pm
ORD
- TYS
Nonstop1h 58m
United Airlines
Deal found 3/12![United Airlines logo]()
$229
This United Airlines deal was found by Cheapflights users on 3/12. 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.
Tue 4/2110:49 am
TYS
- ORD
Nonstop2h 04m
United Airlines
Mon 5/42:05 pm
ORD
- TYS
Nonstop1h 49m
United Airlines
Deal found 3/12![United Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 3/12. 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.
Tue 5/1212:50 pm
TYS
- ORD
1 stop6h 35m
Southwest
Tue 5/192:40 pm
ORD
- TYS
1 stop4h 00m
Southwest
Deal found 3/12![Southwest logo]()
$229
This Delta deal was found by Cheapflights users on 3/12. 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.
Wed 5/67:40 am
LEX
- MDW
1 stop6h 03m
Delta
Mon 5/115:10 pm
MDW
- LEX
1 stop5h 48m
Delta
Deal found 3/12![Delta logo]()
$249
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/188:20 am
TYS
- ORD
Nonstop2h 08m
United Airlines
Wed 7/222:12 pm
ORD
- TYS
Nonstop2h 00m
United Airlines
Deal found 3/11![United Airlines logo]()
$229
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:40 am
LEX
- ORD
1 stop6h 05m
Delta
Mon 4/208:15 am
ORD
- LEX
1 stop6h 52m
Delta
Deal found 3/11![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 3/13. 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.
Thu 4/162:45 pm
TYS
- MDW
1 stop7h 30m
Southwest
Mon 4/203:50 pm
MDW
- TYS
1 stop3h 30m
Southwest
Deal found 3/13![Southwest logo]()
$249
This United Airlines deal was found by Cheapflights users on 3/12. 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.
Mon 4/136:15 pm
CVG
- ORD
Nonstop1h 36m
United Airlines
Thu 4/166:59 am
ORD
- CVG
Nonstop1h 24m
United Airlines
Deal found 3/12![United Airlines logo]()
$231
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/247:56 pm
LEX
- ORD
1 stop5h 03m
Delta
Mon 4/275:04 pm
ORD
- LEX
1 stop4h 30m
Delta
Deal found 3/11![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 3/14. 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.
Wed 4/812:50 pm
TYS
- ORD
1 stop6h 35m
Southwest
Mon 4/132:40 pm
ORD
- TYS
1 stop4h 40m
Southwest
Deal found 3/14![Southwest logo]()
$249
This United Airlines deal was found by Cheapflights users on 3/12. 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.
Fri 6/267:00 am
LEX
- ORD
Nonstop1h 50m
United Airlines
Mon 6/299:20 pm
ORD
- LEX
Nonstop1h 39m
United Airlines
Deal found 3/12![United Airlines logo]()
$244
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/213:30 pm
TYS
- MDW
1 stop6h 39m
Delta
Tue 5/269:22 am
MDW
- TYS
1 stop3h 58m
Delta
Deal found 3/11![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 3/12. 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.
Wed 5/67:05 am
CVG
- MDW
2 stops8h 50m
Southwest
Thu 5/72:10 pm
MDW
- CVG
2 stops8h 15m
Southwest
Deal found 3/12![Southwest logo]()
$251
This United Airlines deal was found by Cheapflights users on 3/15. 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.
Fri 4/109:00 pm
LEX
- ORD
Nonstop1h 47m
United Airlines
Mon 4/139:30 pm
ORD
- LEX
Nonstop1h 29m
United Airlines
Deal found 3/15![United Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 3/12. 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 5/143:05 pm
TYS
- ORD
1 stop4h 00m
Delta
Mon 5/187:07 am
ORD
- TYS
1 stop6h 26m
Delta
Deal found 3/12![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 3/15. 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.
Fri 4/106:45 pm
TYS
- MDW
1 stop5h 45m
Southwest
Mon 4/2011:45 am
MDW
- TYS
2 stops7h 35m
Southwest
Deal found 3/15![Southwest logo]()
$254
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/175:54 pm
TYS
- ORD
1 stop7h 05m
Delta
Mon 4/201:36 pm
ORD
- TYS
1 stop6h 44m
Delta
Deal found 3/11![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 3/13. 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.
Thu 4/166:35 am
TYS
- ORD
2 stops9h 55m
Southwest
Mon 4/202:40 pm
ORD
- TYS
1 stop4h 40m
Southwest
Deal found 3/13![Southwest logo]()
$254
This United Airlines deal was found by Cheapflights users on 3/12. 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.
Tue 6/95:20 am
SDF
- ORD
Nonstop1h 41m
United Airlines
Tue 6/165:50 pm
ORD
- SDF
Nonstop1h 33m
United Airlines
Deal found 3/12![United Airlines logo]()
$258
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/265:59 am
CVG
- MDW
1 stop3h 48m
Delta
Tue 4/286:00 am
MDW
- CVG
1 stop4h 15m
Delta
Deal found 3/11![Delta logo]()
$253
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:35 am
CVG
- ORD
1 stop7h 15m
Southwest
Fri 5/12:40 pm
ORD
- CVG
1 stop6h 10m
Southwest
Deal found 3/11![Southwest logo]()
$261
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:00 am
BNA
- ORD
Nonstop1h 59m
United Airlines
Sat 6/67:00 am
ORD
- BNA
Nonstop1h 42m
United Airlines
Deal found 3/11![United Airlines logo]()
$288
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1511:00 am
BNA
- ORD
Nonstop1h 50m
Southwest
Sat 4/181:55 pm
ORD
- BNA
Nonstop1h 45m
Southwest
Deal found 3/11![Southwest logo]()
$265
Last-minute flights from Kentucky to IllinoisDiscover last-minute flight deals from Kentucky to Illinois. Data last updated March 16, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Illinois. Data last updated March 16, 2026 and is based on user searches.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/16:30 am
CVG
- ORD
1 stop7h 20m
Southwest
Wed 4/12:40 pm
ORD
- CVG
1 stop5h 55m
Southwest
Deal found 3/11![Southwest logo]()
$182
This Frontier deal was found by Cheapflights users on 3/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1012:19 pm
CVG
- MDW
1 stop11h 00m
Frontier
Fri 4/179:14 am
MDW
- CVG
1 stop13h 06m
Frontier
Deal found 3/13![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 3/12. 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.
Sat 4/118:45 am
CVG
- MDW
Nonstop1h 10m
Southwest
Sat 4/185:25 pm
MDW
- CVG
1 stop4h 55m
Southwest
Deal found 3/12![Southwest logo]()
$181
This Frontier deal was found by Cheapflights users on 3/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1312:19 pm
CVG
- ORD
1 stop11h 20m
Frontier
Thu 4/165:50 am
ORD
- CVG
1 stop10h 43m
Frontier
Deal found 3/12![Frontier logo]()
$180
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.
Fri 4/177:46 pm
CVG
- ORD
1 stop26h 26m
Multiple Airlines
Fri 4/247:15 pm
ORD
- CVG
2 stops22h 21m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$177
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.
Sat 4/187:46 pm
CVG
- ORD
1 stop15h 37m
Multiple Airlines
Sat 4/259:16 am
ORD
- CVG
1 stop8h 20m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$178
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.
Sun 4/196:53 pm
CVG
- ORD
1 stop16h 30m
Multiple Airlines
Mon 4/2711:28 am
ORD
- CVG
1 stop6h 08m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$181
This Southwest deal was found by Cheapflights users on 3/12. 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.
Mon 4/208:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Wed 4/227:50 am
MDW
- CVG
2 stops8h 15m
Southwest
Deal found 3/12![Southwest logo]()
$179
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/215:59 am
CVG
- MDW
2 stops7h 44m
Delta
Wed 4/295:21 pm
MDW
- CVG
1 stop5h 50m
Delta
Deal found 3/11![Delta logo]()
$182
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/225:59 am
CVG
- MDW
1 stop3h 48m
Delta
Tue 4/281:24 pm
MDW
- CVG
1 stop5h 49m
Delta
Deal found 3/11![Delta logo]()
$177
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/225:59 am
CVG
- MDW
1 stop3h 48m
Delta
Sat 4/255:21 pm
MDW
- CVG
1 stop5h 50m
Delta
Deal found 3/11![Delta logo]()
$184
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.
Sun 4/266:53 pm
CVG
- ORD
1 stop16h 30m
Multiple Airlines
Fri 5/15:50 am
ORD
- CVG
1 stop11h 46m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$183
One-way flights from Kentucky to IllinoisSearch for one-way flight options from Kentucky to Illinois. Find affordable one-way fares based on user searches. Data last updated March 16, 2026.
Search for one-way flight options from Kentucky to Illinois. Find affordable one-way fares based on user searches. Data last updated March 16, 2026.
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.
Tue 5/1212:12 pm
CVG
- MDW
1 stop10h 50m
Frontier
Deal found 3/11![Frontier logo]()
$63
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.
Tue 5/512:12 pm
CVG
- MDW
1 stop23h 57m
Frontier
Deal found 3/11![Frontier logo]()
$65
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.
Tue 5/1212:12 pm
CVG
- ORD
1 stop20h 43m
Frontier
Deal found 3/11![Frontier logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Mon 5/1112:46 pm
CVG
- MDW
1 stop23h 26m
Frontier
Deal found 3/12![Frontier logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 3/13. 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.
Mon 5/1112:46 pm
CVG
- ORD
1 stop20h 09m
Frontier
Deal found 3/13![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 7/21:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 3/12![Allegiant Air logo]()
$72
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Fri 4/177:46 pm
CVG
- ORD
1 stop26h 26m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 3/14. 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.
Fri 4/177:46 pm
CVG
- ORD
1 stop16h 47m
Frontier
Deal found 3/14![Frontier logo]()
$75
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:35 am
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 3/11![Southwest logo]()
$79
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/52:03 pm
CVG
- ORD
Nonstop1h 32m
United Airlines
Deal found 3/11![United Airlines logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 3/13. 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.
Sat 5/912:46 pm
CVG
- MDW
1 stop23h 26m
Frontier
Deal found 3/13![Frontier logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Wed 5/1312:46 pm
CVG
- ORD
1 stop23h 00m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$80
Find flight deals from Kentucky to Illinois
Keep the following information in mind while searching for Kentucky to Illinois flight deals. Data was last updated March 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $177 (Delta) |
One-way from | $63 (Kiwi.com) |
Popular in | January |
Cheapest in | November |
Average price | $286 |
Good round-trip deal | $180 or less |
Good one-way deal | $178 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Kentucky 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 16, 2026.
Use the filters below to find and compare flights from Kentucky to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Thu 5/14
6:50 pm-11:30 pm
1 stop5h 40m
Chicago Midway
Sat 5/16
6:10 am-12:10 pm
1 stop5h 00m
$211
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Sat 5/16
3:30 pm-8:24 pm
1 stop5h 54m
Chicago O'Hare Intl
Mon 5/18
7:07 am-12:53 pm
1 stop4h 46m
$211
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Sat 5/23
6:00 pm-8:14 pm
1 stop3h 14m
Chicago O'Hare Intl
Mon 6/1
7:07 am-12:53 pm
1 stop4h 46m
$211
Quickest round-trip
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Mon 4/6
8:15 pm-8:30 pm
Nonstop1h 15m
Chicago Midway
Wed 4/8
6:10 pm-8:20 pm
Nonstop1h 10m
$221
LexingtonChicago
LEX - ORD
LEXORD
Lexington Blue Grass
Thu 6/18
9:00 am-9:45 am
Nonstop1h 45m
Chicago O'Hare Intl
Sat 7/11
7:49 pm-10:30 pm
Nonstop1h 41m
$229
KnoxvilleChicago
TYS - ORD
TYSORD
Knoxville McGhee Tyson
Thu 5/14
6:01 pm-6:55 pm
Nonstop1h 54m
Chicago O'Hare Intl
Tue 5/19
2:10 pm-5:08 pm
Nonstop1h 58m
$229
KnoxvilleChicago
TYS - ORD
TYSORD
Knoxville McGhee Tyson
Tue 4/21
10:49 am-11:53 am
Nonstop2h 04m
Chicago O'Hare Intl
Mon 5/4
2:05 pm-4:54 pm
Nonstop1h 49m
$229
KnoxvilleChicago
TYS - ORD
TYSORD
Knoxville McGhee Tyson
Tue 5/12
12:50 pm-6:25 pm
1 stop6h 35m
Chicago O'Hare Intl
Tue 5/19
2:40 pm-7:40 pm
1 stop4h 00m
$229
KnoxvilleChicago
TYS - ORD
TYSORD
Knoxville McGhee Tyson
Sat 7/18
8:20 am-9:28 am
Nonstop2h 08m
Chicago O'Hare Intl
Wed 7/22
2:12 pm-5:12 pm
Nonstop2h 00m
$229
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Mon 4/13
6:15 pm-6:51 pm
Nonstop1h 36m
Chicago O'Hare Intl
Thu 4/16
6:59 am-9:23 am
Nonstop1h 24m
$231
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Kentucky to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Kentucky with our price prediction graph.
CVG-MDW
CVG-ORD
BNA-ORD
LEX-ORD
LEX-MDW
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 Kentucky to Illinois
USKY-USIL
CVG-MDW
CVG-ORD
BNA-ORD
LEX-ORD
What is the cheapest month to book a flight from Kentucky to Illinois?
Currently, April is the cheapest month in which you can book a flight from Kentucky to Illinois (average of $58). Flying from Kentucky to Illinois in March is currently the most expensive (average of $180). 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 KY to IL?
Find hourly flight availability from Kentucky 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 16, 2026.
A simple way to save on the total cost of your ticket is to fly from Kentucky to Illinois in the morning. If you’re flexible enough to do this you can expect to save up to 34% on your trip compared to booking a flight at noon.
What is the cheapest day to fly from Kentucky to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Kentucky to Illinois. Price data was last updated on March 14, 2026.
Travelers seeking maximum savings on their Kentucky to Illinois flight should consider departing on Saturday at noon when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Kentucky to Illinois
Explore weekly flight availability from Kentucky 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 16, 2026.
The most flights from USKY to USIL are scheduled on a Monday (38 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (31 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 16, 2026.
Read through reviews of airlines operating flights from Kentucky to Illinois, such as Southwest,Contour, andUnited Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Crew
8.6
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Related info for your journey
Find useful and relevant information for your journey from Kentucky 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 Kentucky 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 Kentucky to Illinois by cabin class
Find flights from Kentucky to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Kentucky and Illinois flights
Browse other Kentucky and Illinois flight options. Last updated on March 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Illinois
Find the right flight back to Kentucky after your stay in Illinois
Kentucky to Illinois flights
Consider these flights traveling from Kentucky to Illinois.
Top 4 airlines flying from Kentucky to Illinois
Discover the top 4 airlines that operate flights from Kentucky 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 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$97 | Average$265 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$97 | Average$264 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$97 | Average$250 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$108 | Average$170 | FlexibilityNo cancel fee | On-timeN/A |