$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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — ORD
Jul 19 — Jul 261
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 19, 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 19, 2026.
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/147:00 am
CVG
- MDW
2 stops7h 35m
Southwest
Tue 7/215:20 pm
MDW
- CVG
1 stop3h 35m
Southwest
Deal found 6/16![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 8/84:55 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Mon 8/103:20 pm
MDW
- CVG
1 stop5h 15m
Southwest
Deal found 6/19![Southwest logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/172:30 pm
CVG
- ORD
1 stop23h 30m
Multiple Airlines
Thu 8/208:05 am
ORD
- CVG
1 stop12h 27m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$186
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/224:55 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Wed 8/261:00 pm
MDW
- CVG
2 stops6h 50m
Southwest
Deal found 6/18![Southwest logo]()
$191
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 8/66:00 am
CVG
- ORD
Nonstop1h 36m
American Airlines
Mon 8/1010:00 pm
ORD
- CVG
Nonstop1h 27m
American Airlines
Deal found 6/19![American Airlines logo]()
$194
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/67:00 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Mon 8/106:10 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 6/16![Southwest logo]()
$195
This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 9/267:00 am
CVG
- ORD
Nonstop1h 34m
United Airlines
Sat 10/174:20 pm
ORD
- CVG
Nonstop1h 36m
United Airlines
Deal found 6/16![United Airlines logo]()
$195
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.
Wed 9/23:30 pm
CVG
- MDW
1 stop6h 15m
Southwest
Sat 9/58:05 am
MDW
- CVG
1 stop4h 50m
Southwest
Deal found 6/15![Southwest logo]()
$196
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/56:10 am
CVG
- ORD
1 stop5h 32m
Delta
Mon 8/171:41 pm
ORD
- CVG
1 stop5h 13m
Delta
Deal found 6/16![Delta logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 9/2812:48 pm
CVG
- ORD
1 stop24h 14m
Frontier
Wed 10/149:33 pm
ORD
- CVG
1 stop13h 10m
Frontier
Deal found 6/16![Frontier logo]()
$207
This Frontier deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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.
Tue 8/2512:12 pm
CVG
- MDW
1 stop10h 59m
Frontier
Wed 8/266:00 am
MDW
- CVG
1 stop4h 49m
Frontier
Deal found 6/17![Frontier logo]()
$210
This Frontier deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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.
Wed 8/1912:26 pm
CVG
- ORD
1 stop8h 42m
Frontier
Wed 9/2310:40 pm
ORD
- CVG
1 stop11h 40m
Frontier
Deal found 6/18![Frontier logo]()
$210
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 19, 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 19, 2026.
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 10/74:00 pm
CVG
- ORD
1 stop3h 40m
Delta
Sat 10/108:55 am
ORD
- CVG
1 stop5h 23m
Delta
Deal found 6/16![Delta logo]()
$196
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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
Sat 8/152:25 pm
MDW
- CVG
1 stop3h 25m
Southwest
Deal found 6/17![Southwest logo]()
$205
This United Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/291:56 pm
CVG
- ORD
Nonstop1h 33m
United Airlines
Thu 7/306:56 am
ORD
- CVG
Nonstop1h 32m
United Airlines
Deal found 6/18![United Airlines logo]()
$215
This Contour 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 Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/318:00 am
BNA
- ORD
1 stop3h 30m
Contour
Wed 8/511:15 am
ORD
- BNA
1 stop4h 55m
Contour
Deal found 6/14![Contour logo]()
$247
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.
Wed 7/1511:20 am
LEX
- ORD
Nonstop1h 39m
American Airlines
Sun 7/199:43 pm
ORD
- LEX
Nonstop1h 30m
American Airlines
Deal found 6/14![American Airlines logo]()
$249
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/64:10 pm
CVG
- ORD
1 stop3h 19m
Delta
Tue 8/111:59 pm
ORD
- CVG
1 stop4h 55m
Delta
Deal found 6/14![Delta logo]()
$196
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/187:15 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Sat 7/257:40 am
MDW
- SDF
Nonstop1h 20m
Southwest
Deal found 6/18![Southwest logo]()
$223
This United Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/259:00 am
CVG
- ORD
Nonstop1h 35m
United Airlines
Wed 8/266:09 pm
ORD
- CVG
Nonstop1h 34m
United Airlines
Deal found 6/18![United Airlines logo]()
$227
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/64:10 pm
CVG
- ORD
1 stop5h 20m
Delta
Mon 8/105:20 pm
ORD
- CVG
1 stop4h 20m
Delta
Deal found 6/14![Delta logo]()
$215
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.
Tue 7/217:40 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Thu 7/237:00 pm
MDW
- CVG
1 stop4h 30m
Southwest
Deal found 6/15![Southwest logo]()
$225
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 10/236:49 am
LEX
- ORD
Nonstop1h 41m
American Airlines
Tue 10/278:00 am
ORD
- LEX
Nonstop1h 25m
American Airlines
Deal found 6/19![American Airlines logo]()
$249
This Contour deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/78:00 am
BNA
- ORD
1 stop3h 40m
Contour
Sun 8/912:30 pm
ORD
- BNA
1 stop3h 40m
Contour
Deal found 6/16![Contour logo]()
$267
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.
Sun 8/234:15 pm
CVG
- ORD
Nonstop1h 38m
United Airlines
Tue 8/2512:50 pm
ORD
- CVG
Nonstop1h 33m
United Airlines
Deal found 6/15![United Airlines logo]()
$243
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.
Thu 8/67:05 am
CVG
- MDW
2 stops9h 20m
Southwest
Mon 8/105:55 am
MDW
- CVG
1 stop5h 20m
Southwest
Deal found 6/14![Southwest logo]()
$226
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/166:53 pm
LEX
- ORD
Nonstop2h 01m
American Airlines
Sat 7/189:18 pm
ORD
- LEX
Nonstop1h 30m
American Airlines
Deal found 6/18![American Airlines logo]()
$249
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.
Tue 7/145:55 pm
LEX
- ORD
Nonstop1h 46m
United Airlines
Sat 7/185:51 pm
ORD
- LEX
Nonstop1h 38m
United Airlines
Deal found 6/15![United Airlines logo]()
$249
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/148:45 am
SDF
- MDW
Nonstop1h 15m
Southwest
Tue 7/146:15 pm
MDW
- SDF
Nonstop1h 15m
Southwest
Deal found 6/18![Southwest logo]()
$243
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 6/16![Delta logo]()
$269
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.
Fri 7/1010:48 am
LEX
- ORD
1 stop7h 51m
American Airlines
Mon 7/136:47 pm
ORD
- LEX
1 stop4h 12m
American Airlines
Deal found 6/14![American Airlines logo]()
$269
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.
Fri 7/246:00 am
TYS
- ORD
Nonstop1h 59m
United Airlines
Sun 7/265:59 pm
ORD
- TYS
Nonstop1h 49m
United Airlines
Deal found 6/15![United Airlines logo]()
$249
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/224:30 pm
LEX
- MDW
1 stop7h 06m
Delta
Wed 8/266:05 am
MDW
- LEX
1 stop5h 06m
Delta
Deal found 6/15![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/305:30 pm
CVG
- MDW
1 stop3h 40m
Southwest
Sun 10/48:05 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 6/16![Southwest logo]()
$253
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.
Wed 7/1511:15 am
BNA
- ORD
Nonstop2h 00m
United Airlines
Wed 7/157:57 pm
ORD
- BNA
Nonstop1h 48m
United Airlines
Deal found 6/15![United Airlines logo]()
$259
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:45 pm
LEX
- ORD
1 stop5h 05m
Delta
Tue 10/275:30 am
ORD
- LEX
1 stop6h 07m
Delta
Deal found 6/16![Delta logo]()
$269
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/1811:10 am
TRI
- ORD
1 stop6h 36m
American Airlines
Tue 7/214:45 pm
ORD
- TRI
1 stop5h 53m
American Airlines
Deal found 6/17![American Airlines logo]()
$305
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.
Fri 8/148:10 am
CVG
- MDW
Nonstop1h 05m
Southwest
Mon 8/175:55 am
MDW
- CVG
1 stop5h 20m
Southwest
Deal found 6/15![Southwest logo]()
$258
This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/283:01 pm
BNA
- ORD
Nonstop2h 03m
United Airlines
Tue 8/410:37 am
ORD
- BNA
Nonstop1h 52m
United Airlines
Deal found 6/16![United Airlines logo]()
$259
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/221:06 pm
LEX
- ORD
1 stop6h 53m
Delta
Wed 8/266:40 am
ORD
- LEX
1 stop4h 31m
Delta
Deal found 6/16![Delta logo]()
$269
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.
Wed 7/152:15 pm
BNA
- MDW
Nonstop1h 35m
Southwest
Wed 7/155:20 pm
MDW
- BNA
Nonstop1h 30m
Southwest
Deal found 6/15![Southwest logo]()
$259
This United Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/159:53 am
BNA
- ORD
Nonstop2h 01m
United Airlines
Wed 9/93:40 pm
ORD
- BNA
Nonstop1h 52m
United Airlines
Deal found 6/18![United Airlines logo]()
$259
Last-minute flights from Kentucky to IllinoisDiscover last-minute flight deals from Kentucky to Illinois. Data last updated June 19, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Illinois. Data last updated June 19, 2026 and is based on user searches.
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/248:00 am
BNA
- ORD
1 stop3h 30m
Contour
Sun 6/2812:20 pm
ORD
- BNA
1 stop3h 50m
Contour
Deal found 6/14![Contour logo]()
$233
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/147:00 am
CVG
- MDW
2 stops7h 35m
Southwest
Tue 7/215:20 pm
MDW
- CVG
1 stop3h 35m
Southwest
Deal found 6/16![Southwest logo]()
$182
This United Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/149:08 am
CVG
- ORD
Nonstop1h 37m
United Airlines
Tue 7/146:00 pm
ORD
- CVG
Nonstop1h 33m
United Airlines
Deal found 6/18![United Airlines logo]()
$227
This United Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:12 pm
CVG
- ORD
Nonstop1h 38m
United Airlines
Fri 7/176:56 am
ORD
- CVG
Nonstop1h 32m
United Airlines
Deal found 6/17![United Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/187:15 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Sat 7/257:40 am
MDW
- SDF
Nonstop1h 20m
Southwest
Deal found 6/18![Southwest logo]()
$223
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/208:00 am
CVG
- MDW
Nonstop1h 05m
Southwest
Wed 7/226:15 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 6/17![Southwest logo]()
$215
This United Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/217:00 am
CVG
- ORD
Nonstop1h 34m
United Airlines
Thu 7/239:20 pm
ORD
- CVG
Nonstop1h 32m
United Airlines
Deal found 6/18![United Airlines logo]()
$215
This Southwest deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/217:40 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Thu 7/237:00 pm
MDW
- CVG
1 stop4h 30m
Southwest
Deal found 6/17![Southwest logo]()
$225
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/217:40 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Fri 7/247:05 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 6/16![Southwest logo]()
$229
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2212:53 pm
CVG
- ORD
1 stop8h 00m
Frontier
Wed 7/298:05 am
ORD
- CVG
1 stop11h 30m
Frontier
Deal found 6/15![Frontier logo]()
$230
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.
Sat 7/251:40 pm
CVG
- MDW
2 stops6h 35m
Southwest
Tue 7/286:15 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 6/15![Southwest logo]()
$230
This Kissandfly.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2712:53 pm
CVG
- ORD
1 stop8h 00m
Frontier
Tue 7/289:20 pm
ORD
- CVG
Nonstop1h 32m
Frontier
Deal found 6/18![Frontier logo]()
$214
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 19, 2026.
Search for one-way flight options from Kentucky to Illinois. Find affordable one-way fares based on user searches. Data last updated June 19, 2026.
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/119:05 am
CVG
- MDW
Nonstop1h 05m
Southwest
Deal found 6/16![Southwest logo]()
$79
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.
Tue 7/147:54 pm
CVG
- ORD
Nonstop1h 40m
United Airlines
Deal found 6/15![United Airlines logo]()
$79
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.
Tue 7/2110:05 am
CVG
- ORD
Nonstop1h 32m
American Airlines
Deal found 6/15![American Airlines logo]()
$80
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:35 am
CVG
- MDW
1 stop6h 25m
Southwest
Deal found 6/16![Southwest logo]()
$89
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 7/144:00 pm
CVG
- ORD
1 stop5h 31m
Delta
Deal found 6/16![Delta logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/109:10 pm
SDF
- ORD
1 stop16h 05m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/172:30 pm
CVG
- ORD
1 stop23h 30m
Frontier
Deal found 6/17![Frontier logo]()
$92
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/138:10 am
CVG
- MDW
Nonstop1h 05m
Southwest
Deal found 6/16![Southwest logo]()
$98
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 10/2912:17 pm
CVG
- ORD
Nonstop1h 23m
American Airlines
Deal found 6/18![American Airlines logo]()
$98
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.
Wed 8/127:00 am
CVG
- MDW
2 stops10h 50m
Southwest
Deal found 6/15![Southwest logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/179:10 pm
SDF
- ORD
1 stop16h 50m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” 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 8/1511:12 am
CVG
- MDW
1 stop22h 12m
Allegiant Air
Deal found 6/16![Allegiant Air logo]()
$101
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 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $182 (Southwest) |
One-way from | $79 (Southwest) |
Popular in | January |
Cheapest in | November |
Average price | $356 |
Good round-trip deal | $121 or less |
Good one-way deal | $208 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 19, 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 - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Wed 10/7
4:00 pm-6:40 pm
1 stop3h 40m
Chicago O'Hare Intl
Sat 10/10
8:55 am-3:18 pm
1 stop5h 23m
$196
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Thu 8/6
4:10 pm-6:29 pm
1 stop3h 19m
Chicago O'Hare Intl
Tue 8/11
1:59 pm-7:54 pm
1 stop4h 55m
$196
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Thu 8/13
7:00 pm-7:10 pm
Nonstop1h 10m
Chicago Midway
Sat 8/15
2:25 pm-6:50 pm
1 stop3h 25m
$205
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Wed 7/29
1:56 pm-2:29 pm
Nonstop1h 33m
Chicago O'Hare Intl
Thu 7/30
6:56 am-9:28 am
Nonstop1h 32m
$215
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Thu 8/6
4:10 pm-8:30 pm
1 stop5h 20m
Chicago O'Hare Intl
Mon 8/10
5:20 pm-10:40 pm
1 stop4h 20m
$215
LouisvilleChicago
SDF - MDW
SDFMDW
Louisville Intl
Sat 7/18
7:15 pm-7:30 pm
Nonstop1h 15m
Chicago Midway
Sat 7/25
7:40 am-10:00 am
Nonstop1h 20m
$223
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Tue 7/21
7:40 pm-7:50 pm
Nonstop1h 10m
Chicago Midway
Thu 7/23
7:00 pm-12:30 am
1 stop4h 30m
$225
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Thu 8/6
7:05 am-3:25 pm
2 stops9h 20m
Chicago Midway
Mon 8/10
5:55 am-12:15 pm
1 stop5h 20m
$226
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Tue 8/25
9:00 am-9:35 am
Nonstop1h 35m
Chicago O'Hare Intl
Wed 8/26
6:09 pm-8:43 pm
Nonstop1h 34m
$227
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Sun 8/23
4:15 pm-4:53 pm
Nonstop1h 38m
Chicago O'Hare Intl
Tue 8/25
12:50 pm-3:23 pm
Nonstop1h 33m
$243
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
SDF-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 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 19, 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 19, 2026.
The most flights from USKY to USIL are scheduled on a Thursday (39 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (30 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 13, 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 19, 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
Entertainment
7.5
Overall
7.9
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Crew
8.6
Food
7.0
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 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 19, 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 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$97 | Average$277 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$97 | Average$250 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$108 | Average$170 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$278 | FlexibilityNo cancel fee | On-time69% |