$64+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SDF
Aug 26 — Sep 21
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Kentucky with Cheapflights
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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 July 27, 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 July 27, 2026.
This American Airlines deal was found by Cheapflights users on 7/22. 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.
Wed 8/199:34 am
ORD
- CVG
Nonstop1h 30m
American Airlines
Wed 8/263:44 pm
CVG
- ORD
Nonstop1h 36m
American Airlines
Deal found 7/22![American Airlines logo]()
$156
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:55 pm
MDW
- CVG
Nonstop1h 20m
Southwest
Tue 9/157:15 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 7/24![Southwest logo]()
$157
This United Airlines deal was found by Cheapflights users on 7/22. 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 9/126:59 am
ORD
- CVG
Nonstop1h 26m
United Airlines
Mon 9/145:25 am
CVG
- ORD
Nonstop1h 30m
United Airlines
Deal found 7/22![United Airlines logo]()
$157
This American Airlines deal was found by Cheapflights users on 7/22. 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.
Thu 8/136:55 pm
ORD
- CVG
Nonstop1h 23m
American Airlines
Mon 8/176:00 am
CVG
- ORD
Nonstop1h 36m
American Airlines
Deal found 7/22![American Airlines logo]()
$158
This American Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/812:54 pm
ORD
- CVG
Nonstop1h 22m
American Airlines
Tue 9/157:51 am
CVG
- ORD
Nonstop1h 37m
American Airlines
Deal found 7/24![American Airlines logo]()
$159
This Cheapflightsfares deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/912:26 pm
MDW
- TYS
Nonstop1h 25m
Allegiant Air
Mon 10/1212:04 pm
TYS
- MDW
Nonstop1h 32m
Allegiant Air
Deal found 7/26![Allegiant Air logo]()
$159
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:05 am
MDW
- CVG
Nonstop1h 20m
Southwest
Sun 9/67:30 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 7/23![Southwest logo]()
$162
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 9/312:50 pm
ORD
- CVG
Nonstop1h 31m
United Airlines
Sun 9/62:05 pm
CVG
- ORD
Nonstop1h 34m
United Airlines
Deal found 7/23![United Airlines logo]()
$162
This Cheapflightsfares deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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.
Fri 10/22:24 pm
MDW
- TYS
Nonstop1h 25m
Allegiant Air
Mon 10/511:34 am
TYS
- MDW
Nonstop1h 32m
Allegiant Air
Deal found 7/23![Allegiant Air logo]()
$166
This Cheapflightsfares deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/164:30 pm
MDW
- TYS
Nonstop1h 25m
Allegiant Air
Fri 10/231:04 pm
TYS
- MDW
Nonstop1h 32m
Allegiant Air
Deal found 7/26![Allegiant Air logo]()
$168
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/152:25 pm
MDW
- CVG
1 stop3h 25m
Southwest
Mon 8/175:25 pm
CVG
- MDW
1 stop3h 45m
Southwest
Deal found 7/24![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:05 am
ORD
- CVG
1 stop5h 23m
Delta
Tue 9/1510:52 am
CVG
- ORD
1 stop6h 21m
Delta
Deal found 7/27![Delta logo]()
$177
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 July 27, 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 July 27, 2026.
This Southwest deal was found by Cheapflights users on 7/22. 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.
Thu 8/138:05 am
MDW
- CVG
Nonstop1h 20m
Southwest
Mon 8/177:00 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 7/22![Southwest logo]()
$157
This United Airlines deal was found by Cheapflights users on 7/22. 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.
Sun 8/304:38 pm
ORD
- CVG
Nonstop1h 34m
United Airlines
Mon 9/72:05 pm
CVG
- ORD
Nonstop1h 34m
United Airlines
Deal found 7/22![United Airlines logo]()
$196
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:59 am
ORD
- CVG
1 stop5h 43m
Delta
Sun 8/236:10 am
CVG
- ORD
1 stop5h 32m
Delta
Deal found 7/25![Delta logo]()
$216
This American Airlines deal was found by Cheapflights users on 7/22. 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.
Fri 9/259:15 pm
ORD
- LEX
Nonstop1h 31m
American Airlines
Sun 9/275:23 am
LEX
- ORD
Nonstop1h 47m
American Airlines
Deal found 7/22![American Airlines logo]()
$248
This Contour deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1512:30 pm
ORD
- BNA
1 stop3h 40m
Contour
Sun 10/188:00 am
BNA
- ORD
1 stop3h 40m
Contour
Deal found 7/26![Contour logo]()
$285
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:10 pm
MDW
- CVG
Nonstop1h 20m
Southwest
Tue 9/157:15 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 7/25![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:55 pm
MDW
- CVG
Nonstop1h 20m
Southwest
Tue 9/157:15 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 7/25![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/158:00 am
MDW
- CVG
Nonstop1h 25m
Southwest
Mon 8/177:00 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 7/24![Southwest logo]()
$157
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/309:00 am
ORD
- CVG
Nonstop1h 26m
United Airlines
Mon 8/312:05 pm
CVG
- ORD
Nonstop1h 34m
United Airlines
Deal found 7/24![United Airlines logo]()
$196
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:00 am
MDW
- CVG
Nonstop1h 25m
Southwest
Sat 9/128:20 am
CVG
- MDW
Nonstop1h 05m
Southwest
Deal found 7/24![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:45 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Wed 9/167:15 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 7/26![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/811:17 am
ORD
- SDF
1 stop5h 02m
Delta
Tue 9/155:50 pm
SDF
- ORD
1 stop3h 40m
Delta
Deal found 7/26![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/153:40 pm
ORD
- BNA
Nonstop1h 52m
United Airlines
Tue 8/1811:18 am
BNA
- ORD
Nonstop2h 02m
United Airlines
Deal found 7/23![United Airlines logo]()
$217
This American Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:59 pm
ORD
- TRI
Nonstop1h 50m
American Airlines
Mon 9/77:40 am
TRI
- ORD
Nonstop2h 15m
American Airlines
Deal found 7/25![American Airlines logo]()
$259
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 10/19:46 am
ORD
- BNA
1 stop4h 53m
Delta
Mon 10/57:00 pm
BNA
- ORD
1 stop4h 59m
Delta
Deal found 7/23![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:05 am
MDW
- CVG
Nonstop1h 20m
Southwest
Sun 9/67:30 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 7/23![Southwest logo]()
$162
This United Airlines deal was found by Cheapflights users on 7/22. 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 9/52:05 pm
ORD
- BNA
Nonstop1h 52m
United Airlines
Tue 9/82:58 pm
BNA
- ORD
Nonstop2h 02m
United Airlines
Deal found 7/22![United Airlines logo]()
$217
This Contour deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/912:30 pm
ORD
- BNA
1 stop3h 40m
Contour
Sun 10/118:00 am
BNA
- ORD
1 stop3h 40m
Contour
Deal found 7/26![Contour logo]()
$285
This United Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:14 pm
ORD
- BNA
Nonstop1h 52m
United Airlines
Mon 8/316:34 pm
BNA
- ORD
Nonstop2h 00m
United Airlines
Deal found 7/26![United Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/156:59 am
ORD
- CVG
1 stop5h 43m
Delta
Mon 8/174:10 pm
CVG
- ORD
1 stop5h 20m
Delta
Deal found 7/24![Delta logo]()
$239
This American Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/198:59 am
ORD
- TRI
1 stop6h 33m
American Airlines
Sat 9/267:31 am
TRI
- ORD
Nonstop2h 16m
American Airlines
Deal found 7/24![American Airlines logo]()
$269
This Contour deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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.
Thu 8/1312:30 pm
ORD
- BNA
1 stop3h 40m
Contour
Sun 8/168:00 am
BNA
- ORD
1 stop3h 40m
Contour
Deal found 7/24![Contour logo]()
$285
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 9/115:10 pm
ORD
- BNA
1 stop5h 08m
Delta
Mon 9/147:00 pm
BNA
- ORD
1 stop4h 59m
Delta
Deal found 7/23![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 9/232:00 pm
MDW
- CVG
2 stops5h 55m
Southwest
Wed 9/305:40 am
CVG
- MDW
1 stop6h 55m
Southwest
Deal found 7/23![Southwest logo]()
$182
This United Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:14 pm
ORD
- BNA
Nonstop1h 52m
United Airlines
Sun 9/69:48 am
BNA
- ORD
Nonstop2h 00m
United Airlines
Deal found 7/25![United Airlines logo]()
$222
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:59 pm
ORD
- TRI
Nonstop1h 50m
American Airlines
Sat 8/227:22 pm
TRI
- ORD
1 stop5h 30m
American Airlines
Deal found 7/26![American Airlines logo]()
$269
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:18 am
ORD
- TRI
1 stop4h 21m
American Airlines
Mon 10/266:03 am
TRI
- ORD
Nonstop2h 08m
American Airlines
Deal found 7/26![American Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 10/17:05 am
ORD
- SDF
1 stop6h 02m
Delta
Sun 10/42:47 pm
SDF
- ORD
1 stop6h 43m
Delta
Deal found 7/23![Delta logo]()
$247
This United Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/19:25 pm
ORD
- SDF
Nonstop1h 34m
United Airlines
Sun 10/47:00 am
SDF
- ORD
Nonstop1h 40m
United Airlines
Deal found 7/26![United Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 7/22. 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.
Sat 10/318:55 am
ORD
- SDF
1 stop6h 52m
Delta
Sun 11/17:55 am
SDF
- ORD
1 stop3h 44m
Delta
Deal found 7/22![Delta logo]()
$247
Last-minute flights from Chicago to KentuckyDiscover last-minute flight deals from Chicago to Kentucky. Data last updated July 27, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kentucky. Data last updated July 27, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/92:49 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Thu 8/131:23 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 7/22![Allegiant Air logo]()
$189
This Trip.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/92:49 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Sun 8/161:23 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 7/26![Allegiant Air logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/111:50 pm
ORD
- CVG
1 stop20h 58m
Frontier
Thu 8/1312:18 pm
CVG
- ORD
1 stop8h 35m
Frontier
Deal found 7/22![Frontier logo]()
$195
This American Airlines deal was found by Cheapflights users on 7/22. 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.
Thu 8/136:55 pm
ORD
- CVG
Nonstop1h 23m
American Airlines
Mon 8/176:00 am
CVG
- ORD
Nonstop1h 36m
American Airlines
Deal found 7/22![American Airlines logo]()
$158
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/153:25 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Mon 8/177:00 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 7/24![Southwest logo]()
$157
This American Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:56 am
ORD
- CVG
Nonstop1h 28m
American Airlines
Mon 8/176:00 am
CVG
- ORD
Nonstop1h 36m
American Airlines
Deal found 7/25![American Airlines logo]()
$157
This American Airlines deal was found by Cheapflights users on 7/22. 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.
Sun 8/1610:00 pm
ORD
- CVG
Nonstop1h 27m
American Airlines
Mon 8/173:44 pm
CVG
- ORD
Nonstop1h 36m
American Airlines
Deal found 7/22![American Airlines logo]()
$191
This American Airlines deal was found by Cheapflights users on 7/22. 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.
Wed 8/199:34 am
ORD
- CVG
Nonstop1h 30m
American Airlines
Wed 8/263:44 pm
CVG
- ORD
Nonstop1h 36m
American Airlines
Deal found 7/22![American Airlines logo]()
$156
This Southwest deal was found by Cheapflights users on 7/22. 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.
Wed 8/192:00 pm
MDW
- CVG
2 stops5h 50m
Southwest
Wed 8/267:15 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 7/22![Southwest logo]()
$172
This Delta deal was found by Cheapflights users on 7/22. 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 8/199:24 am
MDW
- CVG
1 stop5h 04m
Delta
Tue 8/256:10 am
CVG
- MDW
1 stop4h 07m
Delta
Deal found 7/22![Delta logo]()
$187
This Delta deal was found by Cheapflights users on 7/22. 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 8/198:48 am
ORD
- CVG
1 stop3h 54m
Delta
Sat 8/2211:50 am
CVG
- ORD
1 stop5h 27m
Delta
Deal found 7/22![Delta logo]()
$187
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:48 am
ORD
- CVG
1 stop3h 54m
Delta
Mon 8/242:23 pm
CVG
- ORD
1 stop5h 06m
Delta
Deal found 7/26![Delta logo]()
$177
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 July 27, 2026.
Search for one-way flight options from Chicago to Kentucky. Find affordable one-way fares based on user searches. Data last updated July 27, 2026.
This Trip.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/132:49 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 7/26![Allegiant Air logo]()
$64
This CheapOair deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/232:26 pm
MDW
- TYS
Nonstop1h 25m
Allegiant Air
Deal found 7/23![Allegiant Air logo]()
$70
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/78:05 am
MDW
- CVG
Nonstop1h 20m
Southwest
Deal found 7/27![Southwest logo]()
$79
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/710:00 pm
ORD
- CVG
Nonstop1h 27m
American Airlines
Deal found 7/26![American Airlines logo]()
$79
This American Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:15 pm
ORD
- CVG
Nonstop1h 26m
American Airlines
Deal found 7/24![American Airlines logo]()
$80
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 10/307:30 pm
MDW
- CVG
Nonstop1h 05m
Southwest
Deal found 7/24![Southwest logo]()
$84
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:53 am
ORD
- CVG
Nonstop1h 33m
American Airlines
Deal found 7/26![American Airlines logo]()
$84
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/239:29 am
MDW
- CVG
1 stop4h 45m
Delta
Deal found 7/26![Delta logo]()
$89
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/222:30 pm
ORD
- CVG
1 stop4h 24m
Delta
Deal found 7/23![Delta logo]()
$89
This CheapOair deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/22:24 pm
MDW
- TYS
Nonstop1h 25m
Allegiant Air
Deal found 7/27![Allegiant Air logo]()
$89
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:24 am
MDW
- CVG
1 stop3h 18m
Delta
Deal found 7/24![Delta logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 10/12:03 pm
ORD
- CVG
1 stop20h 40m
Frontier
Deal found 7/23![Frontier logo]()
$95
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 July 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $156 (American Airlines) |
One-way from | $64 (Trip.com) |
Popular in | May |
Cheapest in | December |
Average price | $470 |
Good round-trip deal | $194 or less |
Good one-way deal | $130 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 July 27, 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
Thu 8/13
8:05 am-10:25 am
Nonstop1h 20m
Cincinnati Cinci./N. Kentucky
Mon 8/17
7:00 pm-7:10 pm
Nonstop1h 10m
$157
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Thu 9/10
6:10 pm-8:30 pm
Nonstop1h 20m
Cincinnati Cinci./N. Kentucky
Tue 9/15
7:15 pm-7:25 pm
Nonstop1h 10m
$157
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Tue 9/8
5:55 pm-8:15 pm
Nonstop1h 20m
Cincinnati Cinci./N. Kentucky
Tue 9/15
7:15 pm-7:25 pm
Nonstop1h 10m
$157
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Sat 8/15
8:00 am-10:25 am
Nonstop1h 25m
Cincinnati Cinci./N. Kentucky
Mon 8/17
7:00 pm-7:10 pm
Nonstop1h 10m
$157
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Sat 9/5
8:00 am-10:25 am
Nonstop1h 25m
Cincinnati Cinci./N. Kentucky
Sat 9/12
8:20 am-8:25 am
Nonstop1h 05m
$157
Quickest round-trip
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Wed 9/9
12:45 pm-2:55 pm
Nonstop1h 10m
Cincinnati Cinci./N. Kentucky
Wed 9/16
7:15 pm-7:25 pm
Nonstop1h 10m
$157
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Thu 9/3
8:05 am-10:25 am
Nonstop1h 20m
Cincinnati Cinci./N. Kentucky
Sun 9/6
7:30 pm-7:40 pm
Nonstop1h 10m
$162
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Wed 9/23
2:00 pm-8:55 pm
2 stops5h 55m
Cincinnati Cinci./N. Kentucky
Wed 9/30
5:40 am-11:35 am
1 stop6h 55m
$182
ChicagoCincinnati
ORD - CVG
ORDCVG
Chicago O'Hare Intl
Sun 8/30
4:38 pm-7:12 pm
Nonstop1h 34m
Cincinnati Cinci./N. Kentucky
Mon 9/7
2:05 pm-2:39 pm
Nonstop1h 34m
$196
ChicagoCincinnati
ORD - CVG
ORDCVG
Chicago O'Hare Intl
Sun 8/30
9:00 am-11:26 am
Nonstop1h 26m
Cincinnati Cinci./N. Kentucky
Mon 8/31
2:05 pm-2:39 pm
Nonstop1h 34m
$196
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-CVG
ORD-CVG
ORD-BNA
ORD-SDF
MDW-BNA
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-CVG
ORD-CVG
ORD-BNA
ORD-SDF
What is the cheapest month to book a flight from Chicago to Kentucky?
Currently, December is the cheapest month in which you can book a flight from Chicago to Kentucky (average of $247). Flying from Chicago to Kentucky in June is currently the most expensive (average of $485). 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 July 27, 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 31% versus a flight at noon.
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 July 27, 2026.
The most flights from CHI to USKY are scheduled on a Monday (39 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (33 on average).
How much does it cost to fly round-trip from Chicago to Kentucky?
Airfare is below average for this route at the moment.
Chicago to Kentucky flights typically cost between $251 and $315 in September.The cheapest round-trip price found within the last 5 days was $217 on Southwest (Sep 8-Sep 15).
How far ahead should I book a flight from Chicago to Kentucky?
To ensure you get the cheapest price possible for a flight from Chicago to Kentucky, you should look to book at least 82 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
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 July 25, 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. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 July 27, 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.
Food
7.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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 July 27, 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 July 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$104 | Average$153 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$129 | Average$360 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$137 | Average$350 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$139 | Average$320 | FlexibilityNo cancel fee | On-time71% |