$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 6/11. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — ORD
Jun 21 — Jun 281
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 May 22, 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 May 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/2812:24 pm
CVG
- STL
1 stop21h 28m
Frontier
Wed 7/15:06 pm
STL
- CVG
1 stop17h 08m
Frontier
Deal found 5/19![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1612:24 pm
CVG
- STL
1 stop6h 06m
Frontier
Tue 6/236:31 pm
STL
- CVG
1 stop16h 18m
Frontier
Deal found 5/19![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:54 pm
CVG
- STL
1 stop20h 58m
Frontier
Fri 7/104:52 pm
STL
- CVG
1 stop17h 56m
Frontier
Deal found 5/19![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 5/18. 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.
Tue 6/912:24 pm
CVG
- STL
1 stop21h 23m
Frontier
Thu 6/116:31 pm
STL
- CVG
1 stop16h 18m
Frontier
Deal found 5/18![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 5/17. 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.
Thu 6/1812:24 pm
CVG
- STL
1 stop6h 06m
Frontier
Sun 6/216:31 pm
STL
- CVG
1 stop16h 18m
Frontier
Deal found 5/17![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/1112:24 pm
CVG
- STL
1 stop6h 06m
Frontier
Sun 6/146:31 pm
STL
- CVG
1 stop16h 18m
Frontier
Deal found 5/20![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 5/18. 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.
Tue 6/3012:24 pm
CVG
- STL
1 stop6h 06m
Multiple Airlines
Wed 7/15:06 pm
STL
- CVG
2 stops18h 01m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/212:24 pm
CVG
- STL
1 stop6h 06m
Frontier
Sun 7/56:33 pm
STL
- CVG
1 stop16h 15m
Frontier
Deal found 5/19![Frontier logo]()
$179
This Southwest deal was found by Cheapflights users on 5/18. 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.
Mon 8/177:00 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Thu 8/206:10 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 5/18![Southwest logo]()
$191
This American Airlines deal was found by Cheapflights users on 5/18. 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.
Mon 8/179:53 am
CVG
- ORD
Nonstop1h 41m
American Airlines
Thu 8/206:58 am
ORD
- CVG
Nonstop1h 25m
American Airlines
Deal found 5/18![American Airlines logo]()
$191
This Southwest deal was found by Cheapflights users on 5/17. 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 6/167:00 am
CVG
- MDW
2 stops7h 35m
Southwest
Tue 6/236:15 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 5/17![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 5/18. 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 8/222:50 pm
CVG
- MDW
1 stop6h 30m
Southwest
Wed 8/265:55 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 5/18![Southwest logo]()
$194
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 May 22, 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 May 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:54 pm
CVG
- STL
1 stop20h 58m
Frontier
Fri 7/104:52 pm
STL
- CVG
1 stop17h 56m
Frontier
Deal found 5/19![Frontier logo]()
$125
This Southwest deal was found by Cheapflights users on 5/18. 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.
Mon 8/178:10 am
CVG
- MDW
Nonstop1h 05m
Southwest
Thu 8/203:20 pm
MDW
- CVG
1 stop5h 15m
Southwest
Deal found 5/18![Southwest logo]()
$201
This United Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 8/184:15 pm
CVG
- ORD
Nonstop1h 38m
United Airlines
Wed 8/194:38 pm
ORD
- CVG
Nonstop1h 34m
United Airlines
Deal found 5/22![United Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 5/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/248:23 am
CVG
- ORD
1 stop5h 41m
Delta
Wed 6/245:22 pm
ORD
- CVG
1 stop4h 31m
Delta
Deal found 5/18![Delta logo]()
$238
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/186:36 pm
LEX
- ORD
Nonstop1h 59m
American Airlines
Mon 6/226:29 am
ORD
- LEX
1 stop5h 09m
American Airlines
Deal found 5/20![American Airlines logo]()
$259
This JetBlue deal was found by Cheapflights users on 5/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1710:52 am
BNA
- ORD
1 stop6h 30m
JetBlue
Sat 6/2010:12 am
ORD
- BNA
1 stop6h 23m
JetBlue
Deal found 5/17![JetBlue logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 7/212:24 pm
CVG
- STL
1 stop6h 06m
Multiple Airlines
Sun 7/56:34 pm
STL
- CVG
2 stops27h 57m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$273
This Contour deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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.
Wed 6/178:00 am
BNA
- ORD
1 stop3h 30m
Contour
Sun 6/2112:20 pm
ORD
- BNA
1 stop3h 50m
Contour
Deal found 5/21![Contour logo]()
$277
This Southwest deal was found by Cheapflights users on 5/19. 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.
Tue 6/96:35 pm
CVG
- MDW
1 stop3h 35m
Southwest
Wed 6/1011:25 am
MDW
- CVG
2 stops9h 25m
Southwest
Deal found 5/19![Southwest logo]()
$202
This United Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 10/29:00 am
LEX
- ORD
Nonstop1h 45m
United Airlines
Sun 10/46:50 am
ORD
- LEX
Nonstop1h 38m
United Airlines
Deal found 5/20![United Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 7/294:00 pm
CVG
- ORD
1 stop3h 29m
Delta
Fri 7/315:18 pm
ORD
- CVG
1 stop4h 36m
Delta
Deal found 5/22![Delta logo]()
$249
This Priceline deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/212:24 pm
CVG
- STL
1 stop6h 06m
Frontier
Sun 7/54:09 pm
STL
- CVG
1 stop6h 37m
Frontier
Deal found 5/22![Frontier logo]()
$269
This United Airlines deal was found by Cheapflights users on 5/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2611:05 am
LEX
- ORD
Nonstop1h 49m
United Airlines
Sat 8/2910:36 am
ORD
- LEX
Nonstop1h 40m
United Airlines
Deal found 5/19![United Airlines logo]()
$249
This Southwest deal was found by Cheapflights users on 5/19. 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.
Fri 6/198:25 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Tue 6/237:25 am
MDW
- CVG
1 stop4h 55m
Southwest
Deal found 5/19![Southwest logo]()
$249
This Delta deal was found by Cheapflights users on 5/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/153:46 pm
TRI
- ORD
1 stop6h 00m
Delta
Sun 8/166:40 am
ORD
- TRI
1 stop5h 23m
Delta
Deal found 5/19![Delta logo]()
$249
This American Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 7/227:54 am
TRI
- ORD
Nonstop2h 11m
American Airlines
Sat 7/254:51 pm
ORD
- TRI
1 stop6h 37m
American Airlines
Deal found 5/21![American Airlines logo]()
$295
This United Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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
LEX
- ORD
Nonstop1h 50m
United Airlines
Mon 8/179:20 pm
ORD
- LEX
Nonstop1h 35m
United Airlines
Deal found 5/22![United Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 5/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/14:36 pm
TRI
- ORD
1 stop4h 57m
Delta
Sat 8/228:02 am
ORD
- TRI
1 stop5h 57m
Delta
Deal found 5/18![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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
Fri 7/172:45 pm
MDW
- CVG
2 stops7h 20m
Southwest
Deal found 5/22![Southwest logo]()
$259
This United Airlines deal was found by Cheapflights users on 5/18. 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.
Fri 6/196:00 am
TYS
- ORD
Nonstop1h 59m
United Airlines
Sat 6/206:07 pm
ORD
- TYS
Nonstop1h 49m
United Airlines
Deal found 5/18![United Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 5/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/143:46 pm
TRI
- ORD
1 stop6h 00m
Delta
Sun 8/165:28 am
ORD
- TRI
1 stop6h 35m
Delta
Deal found 5/19![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 5/18. 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.
Sun 7/267:25 pm
CVG
- MDW
1 stop3h 20m
Southwest
Wed 7/296:15 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 5/18![Southwest logo]()
$263
This American Airlines deal was found by Cheapflights users on 5/17. 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.
Wed 7/157:54 am
TRI
- ORD
Nonstop2h 11m
American Airlines
Sat 7/185:07 am
ORD
- TRI
1 stop4h 15m
American Airlines
Deal found 5/17![American Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 5/18. 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.
Thu 6/256:00 am
TYS
- ORD
Nonstop1h 59m
United Airlines
Sun 7/56:55 am
ORD
- TYS
Nonstop1h 48m
United Airlines
Deal found 5/18![United Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 5/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/14:36 pm
TRI
- ORD
1 stop4h 57m
Delta
Fri 8/218:02 am
ORD
- TRI
1 stop4h 01m
Delta
Deal found 5/19![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/258:25 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Mon 7/277:05 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 5/21![Southwest logo]()
$273
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 7/174:00 pm
CVG
- ORD
1 stop3h 29m
Delta
Wed 7/227:05 am
ORD
- CVG
1 stop5h 25m
Delta
Deal found 5/22![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/248:45 am
SDF
- MDW
Nonstop1h 15m
Southwest
Sat 6/2711:30 am
MDW
- SDF
Nonstop1h 10m
Southwest
Deal found 5/20![Southwest logo]()
$275
This American Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 6/192:16 pm
CVG
- STL
1 stop6h 20m
American Airlines
Sun 6/215:29 am
STL
- CVG
1 stop6h 36m
American Airlines
Deal found 5/21![American Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 5/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:00 pm
TRI
- ORD
1 stop4h 32m
Delta
Sun 7/55:30 am
ORD
- TRI
1 stop6h 29m
Delta
Deal found 5/19![Delta logo]()
$259
Last-minute flights from Kentucky to IllinoisDiscover last-minute flight deals from Kentucky to Illinois. Data last updated May 22, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Illinois. Data last updated May 22, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/18. 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.
Tue 6/912:24 pm
CVG
- STL
1 stop21h 23m
Frontier
Thu 6/116:31 pm
STL
- CVG
1 stop16h 18m
Frontier
Deal found 5/18![Frontier logo]()
$126
This Delta deal was found by Cheapflights users on 5/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/94:00 pm
CVG
- MDW
1 stop3h 31m
Delta
Tue 6/169:17 am
MDW
- CVG
1 stop3h 18m
Delta
Deal found 5/18![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 5/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/94:00 pm
CVG
- ORD
1 stop3h 29m
Delta
Tue 6/168:52 am
ORD
- CVG
1 stop3h 43m
Delta
Deal found 5/18![Delta logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/1112:24 pm
CVG
- STL
1 stop6h 06m
Frontier
Sun 6/146:31 pm
STL
- CVG
1 stop16h 18m
Frontier
Deal found 5/20![Frontier logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1612:24 pm
CVG
- STL
1 stop6h 06m
Frontier
Tue 6/236:31 pm
STL
- CVG
1 stop16h 18m
Frontier
Deal found 5/19![Frontier logo]()
$124
This Southwest deal was found by Cheapflights users on 5/19. 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.
Tue 6/167:00 am
CVG
- MDW
2 stops7h 35m
Southwest
Tue 6/166:15 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 5/19![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 5/19. 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.
Tue 6/167:00 am
CVG
- MDW
2 stops7h 35m
Southwest
Tue 6/2311:25 am
MDW
- CVG
2 stops9h 25m
Southwest
Deal found 5/19![Southwest logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 5/17. 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.
Thu 6/1812:24 pm
CVG
- STL
1 stop6h 06m
Frontier
Sun 6/216:31 pm
STL
- CVG
1 stop16h 18m
Frontier
Deal found 5/17![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 6/2212:54 pm
CVG
- MDW
1 stop10h 17m
Frontier
Thu 6/2512:27 pm
MDW
- CVG
1 stop22h 22m
Frontier
Deal found 5/18![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/2512:24 pm
CVG
- STL
1 stop21h 28m
Multiple Airlines
Tue 6/306:31 pm
STL
- CVG
2 stops18h 21m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/2812:24 pm
CVG
- STL
1 stop21h 28m
Frontier
Wed 7/15:06 pm
STL
- CVG
1 stop17h 08m
Frontier
Deal found 5/19![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 5/18. 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.
Tue 6/3012:24 pm
CVG
- STL
1 stop6h 06m
Multiple Airlines
Wed 7/15:06 pm
STL
- CVG
2 stops18h 01m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$175
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 May 22, 2026.
Search for one-way flight options from Kentucky to Illinois. Find affordable one-way fares based on user searches. Data last updated May 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/1112:24 pm
CVG
- STL
1 stop6h 06m
Frontier
Deal found 5/20![Frontier logo]()
$63
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1912:54 pm
CVG
- STL
1 stop20h 58m
Frontier
Deal found 5/19![Frontier logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 8/1712:53 pm
CVG
- MDW
1 stop23h 19m
Frontier
Deal found 5/20![Frontier logo]()
$70
This Southwest deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 7/147:40 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 5/22![Southwest logo]()
$79
This American Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 6/169:00 pm
CVG
- ORD
Nonstop1h 41m
American Airlines
Deal found 5/22![American Airlines logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 5/18. 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.
Tue 7/1412:27 pm
CVG
- ORD
1 stop8h 26m
Frontier
Deal found 5/18![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:54 pm
CVG
- MDW
1 stop10h 14m
Frontier
Deal found 5/19![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/1612:24 pm
CVG
- ORD
1 stop20h 39m
Frontier
Deal found 5/20![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 8/1512:53 pm
CVG
- MDW
1 stop10h 10m
Frontier
Deal found 5/20![Frontier logo]()
$84
This American Airlines deal was found by Cheapflights users on 5/18. 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.
Tue 7/142:06 pm
CVG
- ORD
Nonstop1h 37m
American Airlines
Deal found 5/18![American Airlines logo]()
$88
This Delta deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” 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 6/164:00 pm
CVG
- ORD
1 stop3h 29m
Delta
Deal found 5/22![Delta logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 5/18. 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.
Fri 8/712:54 pm
CVG
- STL
1 stop21h 03m
Frontier
Deal found 5/18![Frontier logo]()
$94
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 May 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $123 (Kiwi.com) |
One-way from | $63 (Kiwi.com) |
Popular in | January |
Cheapest in | November |
Average price | $373 |
Good round-trip deal | $110 or less |
Good one-way deal | $58 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 May 22, 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
CincinnatiSt. Louis
CVG - STL
CVGSTL
Cincinnati Cinci./N. Kentucky
Fri 7/3
12:54 pm-8:52 am
1 stop20h 58m
Lambert-St Louis
Fri 7/10
4:52 pm-11:48 am
1 stop17h 56m
$125
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Mon 8/17
8:10 am-8:15 am
Nonstop1h 05m
Chicago Midway
Thu 8/20
3:20 pm-9:35 pm
1 stop5h 15m
$201
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Tue 6/9
6:35 pm-9:10 pm
1 stop3h 35m
Chicago Midway
Wed 6/10
11:25 am-9:50 pm
2 stops9h 25m
$202
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Tue 8/18
4:15 pm-4:53 pm
Nonstop1h 38m
Chicago O'Hare Intl
Wed 8/19
4:38 pm-7:12 pm
Nonstop1h 34m
$227
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Wed 6/24
8:23 am-1:04 pm
1 stop5h 41m
Chicago O'Hare Intl
Wed 6/24
5:22 pm-10:53 pm
1 stop4h 31m
$238
LexingtonChicago
LEX - ORD
LEXORD
Lexington Blue Grass
Fri 10/2
9:00 am-9:45 am
Nonstop1h 45m
Chicago O'Hare Intl
Sun 10/4
6:50 am-9:28 am
Nonstop1h 38m
$249
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Wed 7/29
4:00 pm-6:29 pm
1 stop3h 29m
Chicago O'Hare Intl
Fri 7/31
5:18 pm-10:54 pm
1 stop4h 36m
$249
LexingtonChicago
LEX - ORD
LEXORD
Lexington Blue Grass
Wed 8/26
11:05 am-11:54 am
Nonstop1h 49m
Chicago O'Hare Intl
Sat 8/29
10:36 am-1:16 pm
Nonstop1h 40m
$249
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Fri 6/19
8:25 pm-8:35 pm
Nonstop1h 10m
Chicago Midway
Tue 6/23
7:25 am-1:20 pm
1 stop4h 55m
$249
BlountvilleChicago
TRI - ORD
TRIORD
Blountville Tri Cities TN/VA
Sat 8/15
3:46 pm-8:46 pm
1 stop6h 00m
Chicago O'Hare Intl
Sun 8/16
6:40 am-1:03 pm
1 stop5h 23m
$249
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-STL
CVG-MDW
CVG-ORD
BNA-ORD
TRI-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-STL
CVG-MDW
CVG-ORD
BNA-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 February is currently the most expensive (average of $118). 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 May 22, 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 in the evening.
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 May 22, 2026.
The most flights from USKY to USIL are scheduled on a Thursday (45 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (24 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 74 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 May 16, 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.
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 May 22, 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.
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
7.9
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 May 22, 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 May 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$77 | Average$215 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$97 | Average$275 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$108 | Average$170 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$286 | FlexibilityNo cancel fee | On-time69% |