$63+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SDF
Mar 28 — Apr 41
1 adult, Economy
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Find cheap flights from Chicago to Kentucky with Cheapflights
1. Tell us where you want to go
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 February 26, 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 February 26, 2026.
This United Airlines deal was found by Cheapflights users on 2/22. 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 4/410:45 am
ORD
- SDF
Nonstop1h 32m
United Airlines
Sat 4/1110:07 am
SDF
- ORD
Nonstop1h 40m
United Airlines
Deal found 2/22![United Airlines logo]()
$103
This United Airlines deal was found by Cheapflights users on 2/22. 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 3/285:50 pm
ORD
- SDF
Nonstop1h 24m
United Airlines
Wed 4/110:00 am
SDF
- ORD
Nonstop1h 38m
United Airlines
Deal found 2/22![United Airlines logo]()
$140
This United Airlines deal was found by Cheapflights users on 2/24. 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.
Thu 4/161:00 pm
ORD
- CVG
Nonstop1h 25m
United Airlines
Thu 4/169:12 pm
CVG
- ORD
Nonstop1h 41m
United Airlines
Deal found 2/24![United Airlines logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 2/22. 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.
Wed 4/221:40 pm
ORD
- CVG
1 stop26h 53m
Multiple Airlines
Mon 4/277:46 pm
CVG
- ORD
1 stop24h 08m
Multiple Airlines
Deal found 2/22![Multiple Airlines logo]()
$143
This Southwest deal was found by Cheapflights users on 2/22. 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.
Sat 4/47:45 am
MDW
- SDF
Nonstop1h 15m
Southwest
Sat 4/118:40 am
SDF
- MDW
Nonstop1h 20m
Southwest
Deal found 2/22![Southwest logo]()
$151
This United Airlines deal was found by Cheapflights users on 2/24. 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.
Tue 3/245:55 pm
ORD
- CVG
Nonstop1h 18m
United Airlines
Wed 3/257:45 pm
CVG
- ORD
Nonstop1h 33m
United Airlines
Deal found 2/24![United Airlines logo]()
$157
This Frontier deal was found by Cheapflights users on 2/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/141:27 pm
ORD
- CVG
1 stop7h 27m
Frontier
Sun 5/178:48 pm
CVG
- ORD
1 stop10h 59m
Frontier
Deal found 2/23![Frontier logo]()
$160
This Delta deal was found by Cheapflights users on 2/25. 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.
Thu 4/161:24 pm
MDW
- CVG
1 stop5h 49m
Delta
Sat 4/186:30 pm
CVG
- MDW
1 stop4h 58m
Delta
Deal found 2/25![Delta logo]()
$161
This United Airlines deal was found by Cheapflights users on 2/23. 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.
Fri 4/310:45 pm
ORD
- CVG
Nonstop1h 28m
United Airlines
Wed 4/88:30 am
CVG
- ORD
Nonstop1h 36m
United Airlines
Deal found 2/23![United Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/245:50 am
ORD
- CVG
1 stop11h 46m
Multiple Airlines
Sun 4/266:53 pm
CVG
- ORD
1 stop20h 27m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$162
This Southwest deal was found by Cheapflights users on 2/24. 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 3/311:20 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Wed 4/17:35 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 2/24![Southwest logo]()
$164
This United Airlines deal was found by Cheapflights users on 2/25. 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.
Mon 3/307:00 am
ORD
- CVG
Nonstop1h 19m
United Airlines
Tue 3/318:30 am
CVG
- ORD
Nonstop1h 36m
United Airlines
Deal found 2/25![United Airlines logo]()
$164
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 February 26, 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 February 26, 2026.
This United Airlines deal was found by Cheapflights users on 2/23. 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.
Tue 3/249:22 pm
ORD
- CVG
Nonstop1h 24m
United Airlines
Tue 3/316:10 pm
CVG
- ORD
Nonstop1h 41m
United Airlines
Deal found 2/23![United Airlines logo]()
$157
This Southwest deal was found by Cheapflights users on 2/22. 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.
Sat 4/47:45 am
MDW
- SDF
1 stop4h 15m
Southwest
Sat 4/118:40 am
SDF
- MDW
Nonstop1h 20m
Southwest
Deal found 2/22![Southwest logo]()
$161
This Delta deal was found by Cheapflights users on 2/25. 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.
Thu 4/161:36 pm
ORD
- CVG
1 stop5h 37m
Delta
Sat 4/188:14 am
CVG
- ORD
2 stops10h 57m
Delta
Deal found 2/25![Delta logo]()
$166
This United Airlines deal was found by Cheapflights users on 2/25. 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.
Wed 4/110:45 am
ORD
- CVG
Nonstop1h 23m
United Airlines
Sat 4/42:08 pm
CVG
- ORD
Nonstop1h 36m
United Airlines
Deal found 2/25![United Airlines logo]()
$164
This Southwest deal was found by Cheapflights users on 2/22. 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.
Sat 3/217:15 pm
MDW
- SDF
Nonstop1h 15m
Southwest
Sun 3/222:15 pm
SDF
- MDW
Nonstop1h 20m
Southwest
Deal found 2/22![Southwest logo]()
$164
This Delta deal was found by Cheapflights users on 2/22. 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 4/86:34 pm
MDW
- CVG
1 stop3h 03m
Delta
Wed 4/155:35 am
CVG
- MDW
1 stop5h 21m
Delta
Deal found 2/22![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 2/22. 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 4/2212:50 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Mon 4/278:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 2/22![Southwest logo]()
$169
This United Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/2110:55 am
ORD
- CVG
Nonstop1h 27m
United Airlines
Sat 3/287:45 pm
CVG
- ORD
Nonstop1h 35m
United Airlines
Deal found 2/25![United Airlines logo]()
$171
This Southwest deal was found by Cheapflights users on 2/24. 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.
Thu 3/267:15 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Thu 4/28:15 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Deal found 2/24![Southwest logo]()
$171
This Delta deal was found by Cheapflights users on 2/24. 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 4/149:29 am
MDW
- SDF
1 stop5h 32m
Delta
Mon 4/205:36 pm
SDF
- MDW
1 stop5h 52m
Delta
Deal found 2/24![Delta logo]()
$195
This United Airlines deal was found by Cheapflights users on 2/22. 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 4/257:15 am
ORD
- TYS
Nonstop1h 51m
United Airlines
Tue 4/287:00 am
TYS
- ORD
Nonstop1h 55m
United Airlines
Deal found 2/22![United Airlines logo]()
$189
This Delta deal was found by Cheapflights users on 2/22. 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 3/1810:45 am
MDW
- SDF
1 stop4h 45m
Delta
Sat 3/217:45 am
SDF
- MDW
1 stop5h 44m
Delta
Deal found 2/22![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 2/22. 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.
Fri 5/157:00 am
ORD
- SDF
Nonstop1h 25m
United Airlines
Sun 5/175:40 am
SDF
- ORD
Nonstop1h 40m
United Airlines
Deal found 2/22![United Airlines logo]()
$192
This Southwest deal was found by Cheapflights users on 2/22. 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 4/85:00 pm
MDW
- CVG
1 stop4h 55m
Southwest
Wed 4/157:35 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Deal found 2/22![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 2/24. 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 4/141:36 pm
ORD
- SDF
2 stops9h 23m
Delta
Mon 4/207:56 am
SDF
- ORD
1 stop5h 49m
Delta
Deal found 2/24![Delta logo]()
$200
This United Airlines deal was found by Cheapflights users on 2/22. 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 4/255:45 pm
ORD
- SDF
Nonstop1h 31m
United Airlines
Sun 5/249:00 am
SDF
- ORD
Nonstop1h 38m
United Airlines
Deal found 2/22![United Airlines logo]()
$199
This Delta deal was found by Cheapflights users on 2/22. 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.
Sun 5/106:24 am
ORD
- SDF
2 stops6h 27m
Delta
Sun 5/107:59 pm
SDF
- ORD
1 stop5h 00m
Delta
Deal found 2/22![Delta logo]()
$202
This Southwest deal was found by Cheapflights users on 2/26. 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.
Fri 4/1712:45 pm
MDW
- SDF
Nonstop1h 15m
Southwest
Mon 4/202:40 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Deal found 2/26![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 2/25. 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 4/167:00 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Sat 4/188:45 am
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 2/25![Southwest logo]()
$207
This United Airlines deal was found by Cheapflights users on 2/23. 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.
Wed 4/17:05 am
ORD
- CVG
Nonstop1h 24m
United Airlines
Thu 4/99:12 pm
CVG
- ORD
Nonstop1h 41m
United Airlines
Deal found 2/23![United Airlines logo]()
$209
This Delta deal was found by Cheapflights users on 2/22. 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 3/185:30 am
ORD
- LEX
1 stop5h 24m
Delta
Wed 3/255:49 pm
LEX
- ORD
1 stop3h 28m
Delta
Deal found 2/22![Delta logo]()
$209
This United Airlines deal was found by Cheapflights users on 2/23. 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.
Mon 5/48:05 pm
ORD
- BNA
Nonstop1h 47m
United Airlines
Mon 5/186:39 pm
BNA
- ORD
Nonstop1h 59m
United Airlines
Deal found 2/23![United Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 2/23. 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 3/253:35 pm
MDW
- SDF
1 stop6h 55m
Southwest
Wed 4/16:35 am
SDF
- MDW
1 stop9h 00m
Southwest
Deal found 2/23![Southwest logo]()
$209
This Delta deal was found by Cheapflights users on 2/22. 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 4/245:53 pm
ORD
- LEX
1 stop5h 01m
Delta
Sun 4/267:40 am
LEX
- ORD
1 stop6h 05m
Delta
Deal found 2/22![Delta logo]()
$209
This United Airlines deal was found by Cheapflights users on 2/23. 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 5/76:05 am
ORD
- BNA
Nonstop1h 48m
United Airlines
Fri 5/158:00 pm
BNA
- ORD
Nonstop1h 59m
United Airlines
Deal found 2/23![United Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 2/23. 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.
Tue 3/242:40 pm
ORD
- BNA
Nonstop1h 45m
Southwest
Tue 3/315:50 am
BNA
- ORD
1 stop5h 20m
Southwest
Deal found 2/23![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 2/22. 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 5/207:07 am
ORD
- CVG
1 stop4h 46m
Delta
Mon 5/2511:05 am
CVG
- ORD
1 stop6h 46m
Delta
Deal found 2/22![Delta logo]()
$225
This United Airlines deal was found by Cheapflights users on 2/23. 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 4/210:45 am
ORD
- CVG
Nonstop1h 23m
United Airlines
Wed 4/86:10 pm
CVG
- ORD
Nonstop1h 36m
United Airlines
Deal found 2/23![United Airlines logo]()
$216
This Southwest deal was found by Cheapflights users on 2/22. 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 3/257:45 am
MDW
- TYS
2 stops8h 55m
Southwest
Wed 4/17:50 am
TYS
- MDW
2 stops7h 00m
Southwest
Deal found 2/22![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 2/22. 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 3/211:10 pm
MDW
- SDF
1 stop3h 05m
Delta
Sun 3/222:17 pm
SDF
- MDW
1 stop4h 37m
Delta
Deal found 2/22![Delta logo]()
$228
Last-minute flights from Chicago to KentuckyDiscover last-minute flight deals from Chicago to Kentucky. Data last updated February 26, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kentucky. Data last updated February 26, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 2/24. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/109:28 am
ORD
- CVG
1 stop8h 05m
Frontier
Wed 3/115:45 am
CVG
- ORD
1 stop10h 53m
Frontier
Deal found 2/24![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 2/23. 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 3/195:01 am
ORD
- CVG
1 stop12h 30m
Frontier
Mon 3/232:45 pm
CVG
- ORD
1 stop20h 51m
Frontier
Deal found 2/23![Frontier logo]()
$173
This United Airlines deal was found by Cheapflights users on 2/23. 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 3/215:55 pm
ORD
- CVG
Nonstop1h 18m
United Airlines
Mon 3/237:45 pm
CVG
- ORD
Nonstop1h 33m
United Airlines
Deal found 2/23![United Airlines logo]()
$171
This United Airlines deal was found by Cheapflights users on 2/23. 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.
Tue 3/249:22 pm
ORD
- CVG
Nonstop1h 24m
United Airlines
Tue 3/316:10 pm
CVG
- ORD
Nonstop1h 41m
United Airlines
Deal found 2/23![United Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/246:36 pm
ORD
- CVG
1 stop22h 08m
Multiple Airlines
Tue 3/317:43 pm
CVG
- ORD
1 stop27h 56m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$170
This American Airlines deal was found by Cheapflights users on 2/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/243:12 pm
ORD
- CVG
Nonstop1h 20m
American Airlines
Fri 3/275:00 am
CVG
- ORD
Nonstop1h 31m
American Airlines
Deal found 2/23![American Airlines logo]()
$174
This United Airlines deal was found by Cheapflights users on 2/23. 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.
Wed 3/259:22 pm
ORD
- CVG
Nonstop1h 24m
United Airlines
Fri 3/274:25 pm
CVG
- ORD
Nonstop1h 35m
United Airlines
Deal found 2/23![United Airlines logo]()
$169
This Southwest deal was found by Cheapflights users on 2/24. 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.
Thu 3/267:15 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Thu 4/28:15 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Deal found 2/24![Southwest logo]()
$171
This United Airlines deal was found by Cheapflights users on 2/22. 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 3/285:50 pm
ORD
- SDF
Nonstop1h 24m
United Airlines
Wed 4/110:00 am
SDF
- ORD
Nonstop1h 38m
United Airlines
Deal found 2/22![United Airlines logo]()
$140
This Southwest deal was found by Cheapflights users on 2/22. 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.
Sat 3/287:15 pm
MDW
- SDF
Nonstop1h 15m
Southwest
Wed 4/17:05 pm
SDF
- MDW
Nonstop1h 20m
Southwest
Deal found 2/22![Southwest logo]()
$164
This United Airlines deal was found by Cheapflights users on 2/25. 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.
Mon 3/307:00 am
ORD
- CVG
Nonstop1h 19m
United Airlines
Tue 3/318:30 am
CVG
- ORD
Nonstop1h 36m
United Airlines
Deal found 2/25![United Airlines logo]()
$164
This Southwest deal was found by Cheapflights users on 2/24. 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 3/311:20 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Wed 4/17:35 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 2/24![Southwest logo]()
$164
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 February 26, 2026.
Search for one-way flight options from Chicago to Kentucky. Find affordable one-way fares based on user searches. Data last updated February 26, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:00 am
MDW
- CVG
1 stop11h 36m
Frontier
Deal found 2/25![Frontier logo]()
$63
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/222:15 pm
MDW
- CVG
1 stop26h 18m
Frontier
Deal found 2/25![Frontier logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/62:20 pm
MDW
- CVG
1 stop27h 16m
Frontier
Deal found 2/25![Frontier logo]()
$66
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/254:28 pm
ORD
- CVG
1 stop24h 20m
Frontier
Deal found 2/25![Frontier logo]()
$66
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:00 am
MDW
- CVG
1 stop10h 48m
Frontier
Deal found 2/25![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/195:59 am
ORD
- CVG
1 stop10h 49m
Frontier
Deal found 2/25![Frontier logo]()
$70
This Southwest deal was found by Cheapflights users on 2/24. 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 4/76:10 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 2/24![Southwest logo]()
$71
This United Airlines deal was found by Cheapflights users on 2/24. 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.
Fri 5/87:00 am
ORD
- CVG
Nonstop1h 15m
United Airlines
Deal found 2/24![United Airlines logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 2/22. 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.
Thu 7/162:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 2/22![Allegiant Air logo]()
$71
This Southwest deal was found by Cheapflights users on 2/23. 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.
Sat 4/257:40 am
MDW
- CVG
Nonstop1h 05m
Southwest
Deal found 2/23![Southwest logo]()
$72
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/151:40 pm
ORD
- CVG
1 stop26h 53m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$73
This American Airlines deal was found by Cheapflights users on 2/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:40 am
ORD
- SDF
Nonstop1h 35m
American Airlines
Deal found 2/23![American Airlines logo]()
$74
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 February 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $103 (United Airlines) |
One-way from | $63 (Kiwi.com) |
Popular in | June |
Cheapest in | August |
Average price | $376 |
Good round-trip deal | $118 or less |
Good one-way deal | $118 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 February 26, 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
ChicagoCincinnati
ORD - CVG
ORDCVG
Chicago O'Hare Intl
Tue 3/24
9:22 pm-11:46 pm
Nonstop1h 24m
Cincinnati Cinci./N. Kentucky
Tue 3/31
6:10 pm-6:51 pm
Nonstop1h 41m
$157
ChicagoLouisville
MDW - SDF
MDWSDF
Chicago Midway
Sat 4/4
7:45 am-1:00 pm
1 stop4h 15m
Louisville Intl
Sat 4/11
8:40 am-9:00 am
Nonstop1h 20m
$161
ChicagoCincinnati
ORD - CVG
ORDCVG
Chicago O'Hare Intl
Wed 4/1
10:45 am-1:08 pm
Nonstop1h 23m
Cincinnati Cinci./N. Kentucky
Sat 4/4
2:08 pm-2:44 pm
Nonstop1h 36m
$164
ChicagoLouisville
MDW - SDF
MDWSDF
Chicago Midway
Sat 3/21
7:15 pm-9:30 pm
Nonstop1h 15m
Louisville Intl
Sun 3/22
2:15 pm-2:35 pm
Nonstop1h 20m
$164
ChicagoCincinnati
ORD - CVG
ORDCVG
Chicago O'Hare Intl
Thu 4/16
1:36 pm-8:13 pm
1 stop5h 37m
Cincinnati Cinci./N. Kentucky
Sat 4/18
8:14 am-6:11 pm
2 stops10h 57m
$166
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Wed 4/22
12:50 pm-3:00 pm
Nonstop1h 10m
Cincinnati Cinci./N. Kentucky
Mon 4/27
8:20 pm-8:30 pm
Nonstop1h 10m
$169
ChicagoCincinnati
ORD - CVG
ORDCVG
Chicago O'Hare Intl
Sat 3/21
10:55 am-1:22 pm
Nonstop1h 27m
Cincinnati Cinci./N. Kentucky
Sat 3/28
7:45 pm-8:20 pm
Nonstop1h 35m
$171
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Thu 3/26
7:15 pm-9:30 pm
Nonstop1h 15m
Cincinnati Cinci./N. Kentucky
Thu 4/2
8:15 pm-8:30 pm
Nonstop1h 15m
$171
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Wed 4/8
6:34 pm-10:37 pm
1 stop3h 03m
Cincinnati Cinci./N. Kentucky
Wed 4/15
5:35 am-9:56 am
1 stop5h 21m
$177
ChicagoKnoxville
ORD - TYS
ORDTYS
Chicago O'Hare Intl
Sat 4/25
7:15 am-10:06 am
Nonstop1h 51m
Knoxville McGhee Tyson
Tue 4/28
7:00 am-7:55 am
Nonstop1h 55m
$189
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.
ORD-CVG
MDW-SDF
MDW-CVG
ORD-TYS
ORD-SDF
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
ORD-CVG
MDW-SDF
MDW-CVG
ORD-TYS
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 $98). Flying from Chicago to Kentucky in June is currently the most expensive (average of $177). 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 February 26, 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 27% 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 February 21, 2026.
Travelers seeking maximum savings on their Chicago to Kentucky flight should consider departing on Wednesday afternoons 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 February 26, 2026.
The most flights from CHI to USKY are scheduled on a Wednesday (36 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 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 February 26, 2026.
Read reviews from past customers who have flown Southwest, Contour, and United Airlines from Chicago to Kentucky. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
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 February 26, 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 February 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$148 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$124 | Average$318 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$127 | Average$320 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$136 | Average$289 | FlexibilityNo cancel fee | On-time71% |