$79+ 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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — ORD
Jul 30 — Aug 61
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 June 30, 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 June 30, 2026.
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:10 pm
CVG
- MDW
1 stop6h 10m
Southwest
Wed 7/295:30 pm
MDW
- CVG
1 stop4h 40m
Southwest
Deal found 6/25![Southwest logo]()
$177
This American Airlines deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 10/110:30 am
CVG
- ORD
Nonstop1h 40m
American Airlines
Mon 10/510:00 pm
ORD
- CVG
Nonstop1h 24m
American Airlines
Deal found 6/27![American Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/82:50 pm
CVG
- MDW
1 stop6h 40m
Southwest
Mon 8/108:05 am
MDW
- CVG
Nonstop1h 20m
Southwest
Deal found 6/26![Southwest logo]()
$178
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:40 am
CVG
- MDW
1 stop4h 20m
Southwest
Tue 8/181:00 pm
MDW
- CVG
2 stops6h 50m
Southwest
Deal found 6/29![Southwest logo]()
$182
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/82:08 pm
CVG
- MDW
1 stop3h 49m
Delta
Thu 9/109:29 am
MDW
- CVG
1 stop2h 59m
Delta
Deal found 6/29![Delta logo]()
$187
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 8/83:30 pm
CVG
- ORD
1 stop6h 00m
Delta
Mon 8/105:20 pm
ORD
- CVG
1 stop4h 20m
Delta
Deal found 6/28![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:00 am
CVG
- MDW
2 stops10h 50m
Southwest
Sat 8/298:05 am
MDW
- CVG
1 stop4h 45m
Southwest
Deal found 6/28![Southwest logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 8/317:30 am
CVG
- ORD
1 stop30h 20m
Multiple Airlines
Thu 9/38:05 am
ORD
- CVG
1 stop12h 33m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$189
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/108:10 am
CVG
- MDW
Nonstop1h 05m
Southwest
Tue 8/111:00 pm
MDW
- CVG
2 stops6h 50m
Southwest
Deal found 6/25![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:00 am
CVG
- MDW
2 stops10h 50m
Southwest
Wed 8/191:00 pm
MDW
- CVG
2 stops6h 50m
Southwest
Deal found 6/29![Southwest logo]()
$193
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:00 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Mon 8/178:05 am
MDW
- CVG
Nonstop1h 20m
Southwest
Deal found 6/26![Southwest logo]()
$195
This American Airlines deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 8/86:00 am
CVG
- ORD
Nonstop1h 36m
American Airlines
Tue 8/119:34 am
ORD
- CVG
Nonstop1h 30m
American Airlines
Deal found 6/26![American Airlines logo]()
$195
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 June 30, 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 June 30, 2026.
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/47:00 am
CVG
- MDW
1 stop4h 50m
Southwest
Sat 8/82:25 pm
MDW
- CVG
1 stop3h 25m
Southwest
Deal found 6/27![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 8/83:30 pm
CVG
- ORD
1 stop6h 00m
Delta
Mon 8/105:20 pm
ORD
- CVG
1 stop4h 20m
Delta
Deal found 6/27![Delta logo]()
$196
This United Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/159:00 am
SDF
- ORD
Nonstop1h 41m
United Airlines
Wed 8/196:56 am
ORD
- SDF
Nonstop1h 42m
United Airlines
Deal found 6/25![United Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/247:58 pm
BNA
- RFD
1 stop12h 17m
Allegiant Air
Sun 7/269:19 am
RFD
- BNA
Nonstop1h 28m
Allegiant Air
Deal found 6/27![Allegiant Air logo]()
$231
This American Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:30 am
LEX
- ORD
Nonstop1h 56m
American Airlines
Sun 8/169:15 pm
ORD
- LEX
Nonstop1h 31m
American Airlines
Deal found 6/29![American Airlines logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/307:00 am
BNA
- RFD
Nonstop1h 29m
Multiple Airlines
Sun 8/911:37 am
RFD
- BNA
3 stops22h 40m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$255
This Booking.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/49:28 am
CVG
- ORD
1 stop14h 51m
Frontier
Sat 7/115:13 pm
ORD
- CVG
1 stop19h 38m
Frontier
Deal found 6/29![Frontier logo]()
$347
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/82:50 pm
CVG
- MDW
1 stop6h 40m
Southwest
Mon 8/108:05 am
MDW
- CVG
Nonstop1h 20m
Southwest
Deal found 6/29![Southwest logo]()
$186
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 9/196:40 am
CVG
- MDW
2 stops7h 40m
Southwest
Mon 9/215:55 am
MDW
- CVG
1 stop5h 20m
Southwest
Deal found 6/28![Southwest logo]()
$201
This United Airlines deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/49:08 am
CVG
- ORD
Nonstop1h 37m
United Airlines
Tue 8/49:20 pm
ORD
- CVG
Nonstop1h 32m
United Airlines
Deal found 6/26![United Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 7/197:00 am
BNA
- RFD
Nonstop1h 29m
Allegiant Air
Fri 7/247:50 pm
RFD
- BNA
1 stop24h 18m
Allegiant Air
Deal found 6/27![Allegiant Air logo]()
$234
This United Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/87:55 pm
SDF
- ORD
Nonstop1h 45m
United Airlines
Mon 8/109:25 pm
ORD
- SDF
Nonstop1h 34m
United Airlines
Deal found 6/28![United Airlines logo]()
$224
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 8/87:55 am
SDF
- ORD
1 stop6h 55m
Delta
Mon 8/101:59 pm
ORD
- SDF
1 stop6h 20m
Delta
Deal found 6/27![Delta logo]()
$255
This American Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:18 pm
LEX
- ORD
1 stop5h 41m
American Airlines
Mon 10/53:45 pm
ORD
- LEX
Nonstop1h 39m
American Airlines
Deal found 6/29![American Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/1111:15 am
BNA
- RFD
2 stops23h 22m
Multiple Airlines
Thu 7/239:19 am
RFD
- BNA
Nonstop1h 28m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/237:00 am
BNA
- RFD
Nonstop1h 29m
Allegiant Air
Thu 7/3011:27 am
RFD
- BNA
2 stops32h 50m
Allegiant Air
Deal found 6/25![Allegiant Air logo]()
$248
This United Airlines deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 9/17:00 am
CVG
- ORD
Nonstop1h 38m
United Airlines
Wed 9/22:25 pm
ORD
- CVG
Nonstop1h 30m
United Airlines
Deal found 6/27![United Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/259:48 am
BNA
- ORD
1 stop7h 24m
Delta
Sat 8/15:30 am
ORD
- BNA
1 stop6h 00m
Delta
Deal found 6/25![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/299:40 pm
BNA
- MDW
Nonstop1h 35m
Southwest
Sat 8/18:40 pm
MDW
- BNA
Nonstop1h 35m
Southwest
Deal found 6/27![Southwest logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/267:00 am
BNA
- RFD
Nonstop1h 29m
Multiple Airlines
Sun 8/211:27 am
RFD
- BNA
3 stops22h 50m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 8/138:13 am
BNA
- RFD
1 stop23h 36m
Allegiant Air
Sun 8/1611:37 am
RFD
- BNA
1 stop8h 00m
Allegiant Air
Deal found 6/29![Allegiant Air logo]()
$248
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/212:15 pm
BNA
- MDW
Nonstop1h 35m
Southwest
Tue 7/215:20 pm
MDW
- BNA
Nonstop1h 30m
Southwest
Deal found 6/28![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 8/88:02 am
BNA
- ORD
1 stop4h 38m
Delta
Mon 8/108:48 am
ORD
- BNA
1 stop4h 25m
Delta
Deal found 6/28![Delta logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 8/812:53 pm
CVG
- ORD
1 stop8h 00m
Multiple Airlines
Mon 8/108:05 am
ORD
- CVG
2 stops10h 37m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$263
This United Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/87:00 am
CVG
- ORD
Nonstop1h 34m
United Airlines
Mon 8/102:20 pm
ORD
- CVG
Nonstop1h 29m
United Airlines
Deal found 6/29![United Airlines logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 8/277:09 pm
BNA
- RFD
2 stops21h 14m
Allegiant Air
Sun 8/303:59 pm
RFD
- BNA
Nonstop1h 25m
Allegiant Air
Deal found 6/27![Allegiant Air logo]()
$249
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/47:00 am
CVG
- MDW
1 stop4h 50m
Southwest
Tue 8/412:45 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 6/26![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:56 pm
LEX
- MDW
1 stop5h 40m
Delta
Sat 8/296:05 am
MDW
- LEX
1 stop5h 06m
Delta
Deal found 6/26![Delta logo]()
$269
This United Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 11/47:49 pm
LEX
- ORD
Nonstop1h 51m
United Airlines
Fri 12/47:49 pm
ORD
- LEX
Nonstop1h 41m
United Airlines
Deal found 6/28![United Airlines logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 7/167:00 am
BNA
- RFD
Nonstop1h 29m
Allegiant Air
Sun 7/1911:27 am
RFD
- BNA
2 stops35h 02m
Allegiant Air
Deal found 6/28![Allegiant Air logo]()
$258
Last-minute flights from Kentucky to IllinoisDiscover last-minute flight deals from Kentucky to Illinois. Data last updated June 30, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Illinois. Data last updated June 30, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/88:00 am
BNA
- ORD
1 stop3h 30m
Contour
Fri 7/1012:20 pm
ORD
- BNA
1 stop3h 50m
Contour
Deal found 6/29![Contour logo]()
$233
This American Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1510:33 am
SDF
- ORD
Nonstop1h 39m
American Airlines
Sat 7/187:29 pm
ORD
- SDF
Nonstop1h 35m
American Airlines
Deal found 6/25![American Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 7/197:00 am
BNA
- RFD
Nonstop1h 29m
Allegiant Air
Fri 7/247:50 pm
RFD
- BNA
1 stop24h 18m
Allegiant Air
Deal found 6/27![Allegiant Air logo]()
$234
This deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2211:17 am
CVG
- ORD
Nonstop1h 36m
United Airlines
Wed 7/296:00 pm
ORD
- CVG
Nonstop1h 33m
United Airlines
Deal found 6/27![United Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/247:58 pm
BNA
- RFD
1 stop12h 17m
Allegiant Air
Sun 7/269:19 am
RFD
- BNA
Nonstop1h 28m
Allegiant Air
Deal found 6/27![Allegiant Air logo]()
$231
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:10 pm
CVG
- MDW
1 stop6h 10m
Southwest
Wed 7/295:30 pm
MDW
- CVG
1 stop4h 40m
Southwest
Deal found 6/25![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/254:00 pm
CVG
- ORD
1 stop5h 31m
Delta
Wed 7/292:07 pm
ORD
- CVG
1 stop4h 47m
Delta
Deal found 6/25![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/257:10 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Mon 7/277:05 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 6/27![Southwest logo]()
$215
This American Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/258:58 am
CVG
- ORD
Nonstop1h 37m
American Airlines
Mon 7/276:46 pm
ORD
- CVG
Nonstop1h 34m
American Airlines
Deal found 6/25![American Airlines logo]()
$215
This Southwest deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/287:00 am
CVG
- MDW
2 stops7h 35m
Southwest
Tue 8/42:40 pm
MDW
- CVG
1 stop5h 10m
Southwest
Deal found 6/30![Southwest logo]()
$182
This Super.com deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2912:53 pm
CVG
- ORD
1 stop8h 00m
Frontier
Tue 8/45:13 pm
ORD
- CVG
1 stop18h 45m
Frontier
Deal found 6/26![Frontier logo]()
$226
This American Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/292:06 pm
CVG
- ORD
Nonstop1h 37m
American Airlines
Fri 7/317:06 am
ORD
- CVG
Nonstop1h 29m
American Airlines
Deal found 6/25![American Airlines logo]()
$229
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 June 30, 2026.
Search for one-way flight options from Kentucky to Illinois. Find affordable one-way fares based on user searches. Data last updated June 30, 2026.
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 9/87:15 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 6/29![Southwest logo]()
$79
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:10 am
CVG
- MDW
1 stop4h 07m
Delta
Deal found 6/29![Delta logo]()
$89
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/254:10 pm
CVG
- ORD
1 stop5h 20m
Delta
Deal found 6/28![Delta logo]()
$89
This Southwest deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:00 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 6/26![Southwest logo]()
$90
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 9/125:50 am
CVG
- MDW
2 stops8h 15m
Southwest
Deal found 6/25![Southwest logo]()
$94
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:00 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 6/29![Southwest logo]()
$98
This American Airlines deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 9/1710:30 am
CVG
- ORD
Nonstop1h 40m
American Airlines
Deal found 6/26![American Airlines logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 8/2410:39 am
SDF
- ORD
1 stop27h 11m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$99
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:10 am
CVG
- MDW
1 stop4h 07m
Delta
Deal found 6/29![Delta logo]()
$99
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/274:10 pm
CVG
- ORD
1 stop5h 20m
Delta
Deal found 6/28![Delta logo]()
$99
This Southwest deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:00 am
CVG
- MDW
2 stops10h 50m
Southwest
Deal found 6/25![Southwest logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 8/36:30 am
CVG
- ORD
1 stop30h 45m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$103
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 June 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $177 (Southwest) |
One-way from | $79 (Southwest) |
Popular in | January |
Cheapest in | November |
Average price | $356 |
Good round-trip deal | $164 or less |
Good one-way deal | $160 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 June 30, 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
Tue 8/4
7:00 am-10:50 am
1 stop4h 50m
Chicago Midway
Sat 8/8
2:25 pm-6:50 pm
1 stop3h 25m
$177
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Sat 8/8
2:50 pm-8:30 pm
1 stop6h 40m
Chicago Midway
Mon 8/10
8:05 am-10:25 am
Nonstop1h 20m
$186
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Sat 8/8
3:30 pm-8:30 pm
1 stop6h 00m
Chicago O'Hare Intl
Mon 8/10
5:20 pm-10:40 pm
1 stop4h 20m
$196
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Sat 9/19
6:40 am-1:20 pm
2 stops7h 40m
Chicago Midway
Mon 9/21
5:55 am-12:15 pm
1 stop5h 20m
$201
LouisvilleChicago
SDF - ORD
SDFORD
Louisville Intl
Sat 8/15
9:00 am-9:41 am
Nonstop1h 41m
Chicago O'Hare Intl
Wed 8/19
6:56 am-9:38 am
Nonstop1h 42m
$223
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Tue 8/4
9:08 am-9:45 am
Nonstop1h 37m
Chicago O'Hare Intl
Tue 8/4
9:20 pm-11:52 pm
Nonstop1h 32m
$223
LouisvilleChicago
SDF - ORD
SDFORD
Louisville Intl
Sat 8/8
7:55 pm-8:40 pm
Nonstop1h 45m
Chicago O'Hare Intl
Mon 8/10
9:25 pm-11:59 pm
Nonstop1h 34m
$224
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Tue 9/1
7:00 am-7:38 am
Nonstop1h 38m
Chicago O'Hare Intl
Wed 9/2
2:25 pm-4:55 pm
Nonstop1h 30m
$227
NashvilleChicago
BNA - RFD
BNARFD
Nashville Intl
Fri 7/24
7:58 pm-8:15 am
1 stop12h 17m
Chicago Greater Rockford
Sun 7/26
9:19 am-10:47 am
Nonstop1h 28m
$231
NashvilleChicago
BNA - RFD
BNARFD
Nashville Intl
Sun 7/19
7:00 am-8:29 am
Nonstop1h 29m
Chicago Greater Rockford
Fri 7/24
7:50 pm-8:08 pm
1 stop24h 18m
$234
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
SDF-ORD
BNA-RFD
BNA-ORD
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
SDF-ORD
BNA-RFD
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 June is currently the most expensive (average of $121). 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 June 30, 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 32% on your trip compared to booking a flight at noon.
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 June 30, 2026.
The most flights from USKY to USIL are scheduled on a Tuesday (39 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (9 on average).
How much does it cost to fly round-trip from Kentucky to Illinois?
How far ahead should I book a flight from Kentucky to Illinois?
The best time to book flights from Kentucky to Illinois is 68 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 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 June 27, 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. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated June 30, 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.
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Comfort
8.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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.
Browse thousands of different options on Cheapflights for your next trip
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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 June 30, 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 June 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$97 | Average$285 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$97 | Average$253 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$108 | Average$170 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$283 | FlexibilityNo cancel fee | On-time69% |