$55+ Cheap flights from Chicago (CHI) to Kentucky
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 7/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SDF
May 13 — May 201
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Kentucky with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Chicago to KentuckyExplore the most affordable flight options available from Chicago to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 13, 2026.
Explore the most affordable flight options available from Chicago to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
MDW
- CVG
1 stop11h 36m
Frontier
Mon 5/47:46 pm
CVG
- MDW
1 stop16h 23m
Frontier
Deal found 4/10![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:16 am
ORD
- CVG
1 stop8h 20m
Multiple Airlines
Mon 5/47:46 pm
CVG
- ORD
1 stop13h 09m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:28 pm
ORD
- CVG
1 stop25h 08m
Frontier
Mon 5/47:46 pm
CVG
- ORD
1 stop13h 09m
Frontier
Deal found 4/9![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:04 pm
MDW
- CVG
1 stop22h 00m
Frontier
Wed 6/312:46 pm
CVG
- MDW
1 stop10h 16m
Frontier
Deal found 4/12![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 5/15:50 am
ORD
- CVG
1 stop11h 46m
Frontier
Sun 5/37:26 pm
CVG
- ORD
1 stop17h 06m
Frontier
Deal found 4/8![Frontier logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 4/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/112:04 pm
MDW
- CVG
1 stop22h 00m
Frontier
Wed 6/312:46 pm
CVG
- MDW
1 stop10h 16m
Frontier
Deal found 4/11![Frontier logo]()
$156
This Southwest deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1912:50 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Wed 5/208:35 am
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 4/9![Southwest logo]()
$157
This United Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 5/64:30 pm
ORD
- CVG
Nonstop1h 27m
United Airlines
Wed 5/132:03 pm
CVG
- ORD
Nonstop1h 32m
United Airlines
Deal found 4/8![United Airlines logo]()
$157
This American Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:30 pm
ORD
- CVG
Nonstop1h 32m
American Airlines
Wed 6/32:07 pm
CVG
- ORD
Nonstop1h 39m
American Airlines
Deal found 4/12![American Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/69:00 am
ORD
- CVG
1 stop25h 04m
Frontier
Wed 5/139:30 pm
CVG
- ORD
1 stop26h 43m
Frontier
Deal found 4/8![Frontier logo]()
$159
This Frontier deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:14 am
MDW
- CVG
1 stop12h 05m
Frontier
Sun 5/36:45 am
CVG
- MDW
1 stop9h 19m
Frontier
Deal found 4/12![Frontier logo]()
$160
This Southwest deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1212:50 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Thu 5/149:00 am
CVG
- MDW
Nonstop1h 15m
Southwest
Deal found 4/10![Southwest logo]()
$174
Best flights from Chicago to KentuckyDiscover carefully curated flight deals from Chicago to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 13, 2026.
Discover carefully curated flight deals from Chicago to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 13, 2026.
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:50 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Wed 6/37:35 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Deal found 4/12![Southwest logo]()
$157
This United Airlines deal was found by Cheapflights users on 4/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1110:44 am
ORD
- CVG
Nonstop1h 23m
United Airlines
Mon 5/189:42 pm
CVG
- ORD
Nonstop1h 38m
United Airlines
Deal found 4/11![United Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/94:05 pm
ORD
- CVG
2 stops17h 59m
Multiple Airlines
Mon 5/112:12 pm
CVG
- ORD
1 stop10h 03m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$196
This Delta deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2011:09 am
ORD
- CVG
2 stops9h 08m
Delta
Sat 5/2311:22 am
CVG
- ORD
2 stops9h 52m
Delta
Deal found 4/12![Delta logo]()
$204
This American Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 6/43:43 pm
ORD
- LEX
Nonstop1h 35m
American Airlines
Sat 6/65:19 am
LEX
- ORD
Nonstop1h 36m
American Airlines
Deal found 4/8![American Airlines logo]()
$249
This Southwest deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/197:50 am
MDW
- CVG
2 stops8h 15m
Southwest
Wed 5/205:50 pm
CVG
- MDW
1 stop5h 25m
Southwest
Deal found 4/9![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/87:05 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Wed 6/106:35 pm
CVG
- MDW
1 stop5h 35m
Southwest
Deal found 4/10![Southwest logo]()
$184
This Delta deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/48:52 am
ORD
- CVG
1 stop4h 24m
Delta
Wed 5/66:02 pm
CVG
- ORD
1 stop3h 38m
Delta
Deal found 4/10![Delta logo]()
$211
This Southwest deal was found by Cheapflights users on 4/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:10 am
MDW
- CVG
1 stop3h 50m
Southwest
Mon 5/48:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 4/11![Southwest logo]()
$185
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/192:00 pm
ORD
- CVG
1 stop4h 10m
Delta
Wed 5/205:48 am
CVG
- ORD
2 stops8h 13m
Delta
Deal found 4/9![Delta logo]()
$222
This United Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 pm
ORD
- TYS
Nonstop1h 45m
United Airlines
Tue 5/197:00 am
TYS
- ORD
Nonstop1h 56m
United Airlines
Deal found 4/12![United Airlines logo]()
$249
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/93:40 pm
MDW
- CVG
Nonstop1h 05m
Southwest
Mon 5/118:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 4/12![Southwest logo]()
$191
This United Airlines deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/84:20 pm
ORD
- LEX
Nonstop1h 29m
United Airlines
Mon 5/117:50 pm
LEX
- ORD
Nonstop1h 50m
United Airlines
Deal found 4/10![United Airlines logo]()
$249
This Southwest deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 5/233:40 pm
MDW
- CVG
Nonstop1h 05m
Southwest
Sat 5/305:00 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Deal found 4/8![Southwest logo]()
$191
This Delta deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:07 am
ORD
- CVG
1 stop6h 50m
Delta
Sat 5/98:10 am
CVG
- ORD
2 stops9h 41m
Delta
Deal found 4/8![Delta logo]()
$236
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/202:40 pm
ORD
- CVG
1 stop5h 35m
Southwest
Sat 5/2312:50 pm
CVG
- ORD
1 stop3h 40m
Southwest
Deal found 4/12![Southwest logo]()
$194
This KAYAK deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/288:01 am
ORD
- BNA
1 stop26h 11m
American Airlines
Wed 4/2912:56 pm
BNA
- ORD
Nonstop2h 02m
American Airlines
Deal found 4/8![American Airlines logo]()
$313
This United Airlines deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
ORD
- CVG
Nonstop1h 19m
United Airlines
Mon 5/48:00 pm
CVG
- ORD
Nonstop1h 43m
United Airlines
Deal found 4/10![United Airlines logo]()
$262
This American Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:41 pm
ORD
- SDF
Nonstop1h 38m
American Airlines
Sun 5/3110:47 am
SDF
- ORD
Nonstop1h 43m
American Airlines
Deal found 4/12![American Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 4/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/76:40 am
ORD
- CVG
1 stop4h 57m
Delta
Tue 6/95:48 pm
CVG
- ORD
1 stop7h 11m
Delta
Deal found 4/11![Delta logo]()
$263
This Southwest deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:30 am
MDW
- CVG
1 stop5h 20m
Southwest
Thu 5/218:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 4/8![Southwest logo]()
$201
This United Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:00 am
ORD
- SDF
Nonstop1h 25m
United Airlines
Thu 5/1410:06 am
SDF
- ORD
Nonstop1h 39m
United Airlines
Deal found 4/12![United Airlines logo]()
$272
This Delta deal was found by Cheapflights users on 4/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/198:10 am
ORD
- TYS
1 stop5h 23m
Delta
Sun 5/245:40 am
TYS
- ORD
1 stop3h 59m
Delta
Deal found 4/11![Delta logo]()
$264
This United Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:53 pm
ORD
- SDF
Nonstop1h 37m
United Airlines
Sat 5/95:40 am
SDF
- ORD
Nonstop1h 40m
United Airlines
Deal found 4/12![United Airlines logo]()
$279
This Southwest deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/72:40 pm
ORD
- CVG
1 stop6h 10m
Southwest
Sat 5/912:50 pm
CVG
- ORD
1 stop3h 40m
Southwest
Deal found 4/8![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:59 am
MDW
- LEX
1 stop5h 14m
Delta
Mon 6/11:05 pm
LEX
- MDW
1 stop4h 07m
Delta
Deal found 4/10![Delta logo]()
$269
This United Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/72:05 pm
ORD
- TYS
Nonstop1h 49m
United Airlines
Sun 5/107:00 am
TYS
- ORD
Nonstop1h 56m
United Airlines
Deal found 4/8![United Airlines logo]()
$283
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/21:29 pm
ORD
- TYS
1 stop6h 51m
Delta
Tue 5/54:38 pm
TYS
- ORD
1 stop4h 38m
Delta
Deal found 4/9![Delta logo]()
$269
This United Airlines deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 4/302:05 pm
ORD
- TYS
Nonstop1h 49m
United Airlines
Mon 5/47:00 am
TYS
- ORD
Nonstop1h 56m
United Airlines
Deal found 4/9![United Airlines logo]()
$283
This Southwest deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 6/96:00 am
MDW
- CVG
1 stop6h 20m
Southwest
Thu 6/116:50 pm
CVG
- MDW
1 stop6h 25m
Southwest
Deal found 4/9![Southwest logo]()
$235
Last-minute flights from Chicago to KentuckyDiscover last-minute flight deals from Chicago to Kentucky. Data last updated April 13, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kentucky. Data last updated April 13, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:28 pm
ORD
- CVG
1 stop25h 08m
Frontier
Mon 5/47:46 pm
CVG
- ORD
1 stop13h 09m
Frontier
Deal found 4/9![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 5/15:50 am
ORD
- CVG
1 stop11h 46m
Frontier
Sun 5/37:26 pm
CVG
- ORD
1 stop17h 06m
Frontier
Deal found 4/8![Frontier logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
MDW
- CVG
1 stop11h 36m
Frontier
Mon 5/47:46 pm
CVG
- MDW
1 stop16h 23m
Frontier
Deal found 4/10![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:16 am
ORD
- CVG
1 stop8h 20m
Multiple Airlines
Mon 5/47:46 pm
CVG
- ORD
1 stop13h 09m
Multiple Airlines
Deal found 4/10![Multiple Airlines logo]()
$137
This Frontier deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:14 am
MDW
- CVG
1 stop12h 05m
Frontier
Sun 5/36:45 am
CVG
- MDW
1 stop9h 19m
Frontier
Deal found 4/12![Frontier logo]()
$160
This Southwest deal was found by Cheapflights users on 4/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:40 am
MDW
- CVG
Nonstop1h 05m
Southwest
Mon 5/48:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 4/11![Southwest logo]()
$175
This United Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 5/64:30 pm
ORD
- CVG
Nonstop1h 27m
United Airlines
Wed 5/132:03 pm
CVG
- ORD
Nonstop1h 32m
United Airlines
Deal found 4/8![United Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/69:00 am
ORD
- CVG
1 stop25h 04m
Frontier
Wed 5/139:30 pm
CVG
- ORD
1 stop26h 43m
Frontier
Deal found 4/8![Frontier logo]()
$159
This Southwest deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1212:50 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Thu 5/149:00 am
CVG
- MDW
Nonstop1h 15m
Southwest
Deal found 4/10![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1912:50 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Wed 5/208:35 am
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 4/9![Southwest logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:04 pm
MDW
- CVG
1 stop22h 00m
Frontier
Wed 6/312:46 pm
CVG
- MDW
1 stop10h 16m
Frontier
Deal found 4/12![Frontier logo]()
$152
This American Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:30 pm
ORD
- CVG
Nonstop1h 32m
American Airlines
Wed 6/32:07 pm
CVG
- ORD
Nonstop1h 39m
American Airlines
Deal found 4/12![American Airlines logo]()
$158
One-way flights from Chicago to KentuckySearch for one-way flight options from Chicago to Kentucky. Find affordable one-way fares based on user searches. Data last updated April 13, 2026.
Search for one-way flight options from Chicago to Kentucky. Find affordable one-way fares based on user searches. Data last updated April 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 7/52:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 4/9![Allegiant Air logo]()
$55
This Kiwi.com deal was found by Cheapflights users on 4/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:52 am
ORD
- CVG
1 stop29h 03m
Multiple Airlines
Deal found 4/11![Multiple Airlines logo]()
$68
This Frontier deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/41:27 pm
ORD
- CVG
1 stop7h 24m
Frontier
Deal found 4/12![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:00 am
MDW
- CVG
1 stop28h 04m
Frontier
Deal found 4/9![Frontier logo]()
$71
This Cheapflightsfares deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/252:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Deal found 4/8![Allegiant Air logo]()
$72
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:04 pm
MDW
- CVG
1 stop22h 00m
Frontier
Deal found 4/8![Frontier logo]()
$73
This Kiwi.com deal was found by Cheapflights users on 4/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/143:44 pm
ORD
- CVG
1 stop28h 52m
Multiple Airlines
Deal found 4/11![Multiple Airlines logo]()
$73
This Kiwi.com deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:45 pm
ORD
- CVG
1 stop23h 21m
Frontier
Deal found 4/10![Frontier logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 4/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:47 pm
MDW
- TYS
Nonstop1h 26m
Allegiant Air
Deal found 4/11![Allegiant Air logo]()
$75
This Kiwi.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:15 pm
MDW
- CVG
1 stop27h 21m
Frontier
Deal found 4/9![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:55 am
ORD
- CVG
1 stop27h 09m
Frontier
Deal found 4/8![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/73:44 pm
ORD
- SDF
1 stop16h 44m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$76
Find flight deals from Chicago to Kentucky
Keep the following information in mind while searching for Chicago to Kentucky flight deals. Data was last updated April 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $130 (Kiwi.com) |
One-way from | $55 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $295 |
Good round-trip deal | $168 or less |
Good one-way deal | $59 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Kentucky 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 April 13, 2026.
Use the filters below to find and compare flights from Chicago to Kentucky that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Wed 5/27
12:50 pm-3:00 pm
Nonstop1h 10m
Cincinnati Cinci./N. Kentucky
Wed 6/3
7:35 pm-7:50 pm
Nonstop1h 15m
$157
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Tue 5/19
7:50 am-5:05 pm
2 stops8h 15m
Cincinnati Cinci./N. Kentucky
Wed 5/20
5:50 pm-10:15 pm
1 stop5h 25m
$182
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Mon 6/8
7:05 pm-9:15 pm
Nonstop1h 10m
Cincinnati Cinci./N. Kentucky
Wed 6/10
6:35 pm-11:10 pm
1 stop5h 35m
$184
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Sat 5/2
9:10 am-2:00 pm
1 stop3h 50m
Cincinnati Cinci./N. Kentucky
Mon 5/4
8:20 pm-8:30 pm
Nonstop1h 10m
$185
ChicagoCincinnati
ORD - CVG
ORDCVG
Chicago O'Hare Intl
Mon 5/11
10:44 am-1:07 pm
Nonstop1h 23m
Cincinnati Cinci./N. Kentucky
Mon 5/18
9:42 pm-10:20 pm
Nonstop1h 38m
$191
Quickest round-trip
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Sat 5/9
3:40 pm-5:45 pm
Nonstop1h 05m
Cincinnati Cinci./N. Kentucky
Mon 5/11
8:20 pm-8:30 pm
Nonstop1h 10m
$191
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Sat 5/23
3:40 pm-5:45 pm
Nonstop1h 05m
Cincinnati Cinci./N. Kentucky
Sat 5/30
5:00 pm-5:15 pm
Nonstop1h 15m
$191
ChicagoCincinnati
ORD - CVG
ORDCVG
Chicago O'Hare Intl
Wed 5/20
2:40 pm-9:15 pm
1 stop5h 35m
Cincinnati Cinci./N. Kentucky
Sat 5/23
12:50 pm-3:30 pm
1 stop3h 40m
$194
ChicagoCincinnati
ORD - CVG
ORDCVG
Chicago O'Hare Intl
Sat 5/9
4:05 pm-11:04 am
2 stops17h 59m
Cincinnati Cinci./N. Kentucky
Mon 5/11
2:12 pm-11:15 pm
1 stop10h 03m
$196
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Thu 5/14
5:30 am-11:50 am
1 stop5h 20m
Cincinnati Cinci./N. Kentucky
Thu 5/21
8:20 pm-8:30 pm
Nonstop1h 10m
$201
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Kentucky
Have a flexible travel schedule? Discover the best time to fly to Kentucky from Chicago with our price prediction graph.
MDW-TYS
ORD-CVG
MDW-CVG
ORD-SDF
ORD-LEX
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 Chicago to Kentucky
CHI-USKY
MDW-TYS
ORD-CVG
MDW-CVG
ORD-SDF
What is the cheapest month to book a flight from Chicago to Kentucky?
Currently, July is the cheapest month in which you can book a flight from Chicago to Kentucky (average of $82). Flying from Chicago to Kentucky in June is currently the most expensive (average of $176). 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 CHI to KY?
Find hourly flight availability from Chicago to Kentucky. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 13, 2026.
When flying from Chicago to Kentucky, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 34% versus a flight at noon.
What is the cheapest day to fly from Chicago to Kentucky?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Kentucky. Price data was last updated on April 11, 2026.
Travelers seeking maximum savings on their Chicago to Kentucky flight should consider departing on Sunday mornings 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.
Weekly flight availability from Chicago to Kentucky
Explore weekly flight availability from Chicago to Kentucky. 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 April 13, 2026.
The most flights from CHI to USKY are scheduled on a Friday (49 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (37 on average).
How much does it cost to fly round-trip from Chicago to Kentucky?
Reviews of airlines servicing Kentucky
Get insights into the airlines that provide service to Kentucky. 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 Kentucky. Reviews last updated April 13, 2026.
Read reviews from past customers who have flown Southwest,Contour, andUnited Airlines from Chicago to Kentucky. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Chicago to Kentucky. 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 Chicago to Kentucky
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Kentucky by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Kentucky by cabin class
Find flights from Chicago to Kentucky, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Kentucky flights
Browse other Chicago and Kentucky flight options. Last updated on April 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Kentucky flights
Consider these flights traveling from Chicago to Kentucky.
Top 4 airlines flying from Chicago to Kentucky
Discover the top 4 airlines that operate flights from Chicago to Kentucky. 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 April 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$104 | Average$148 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$124 | Average$263 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$133 | Average$350 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$136 | Average$295 | FlexibilityNo cancel fee | On-time71% |