$49+ Cheap flights from O'Hare Intl (ORD) 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 3/26. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SDF
Apr 11 — Apr 181
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl to Kentucky with Cheapflights
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Cheapest flights from O'Hare Intl to KentuckyExplore the most affordable flight options available from O'Hare Intl to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 12, 2026.
Explore the most affordable flight options available from O'Hare Intl to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 12, 2026.
This Mytrip deal was found by Cheapflights users on 3/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2510:55 am
ORD
- OWB
Nonstop1h 35m
Contour
Tue 3/312:35 pm
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/10![Contour logo]()
$103
This Booking.com deal was found by Cheapflights users on 3/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:20 am
ORD
- OWB
Nonstop1h 35m
Contour
Sun 4/269:00 am
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/12![Contour logo]()
$104
This Mytrip deal was found by Cheapflights users on 3/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/211:20 am
ORD
- OWB
Nonstop1h 35m
Contour
Sun 4/59:00 am
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/9![Contour logo]()
$106
This Mytrip deal was found by Cheapflights users on 3/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2610:55 am
ORD
- OWB
Nonstop1h 35m
Contour
Sun 3/299:00 am
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/8![Contour logo]()
$107
This Booking.com deal was found by Cheapflights users on 3/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2211:20 am
ORD
- OWB
Nonstop1h 35m
Contour
Mon 5/259:00 am
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/11![Contour logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 5/2211:20 am
ORD
- OWB
Nonstop1h 35m
Contour
Sun 5/249:00 am
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/7![Contour logo]()
$117
This Contour deal was found by Cheapflights users on 3/9. 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 Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/711:20 am
ORD
- OWB
Nonstop1h 35m
Contour
Wed 4/89:00 am
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/9![Contour logo]()
$118
This Mytrip deal was found by Cheapflights users on 3/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/2310:55 am
ORD
- OWB
Nonstop1h 35m
Contour
Tue 3/241:50 pm
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/10![Contour logo]()
$128
This Booking.com deal was found by Cheapflights users on 3/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1211:20 am
ORD
- OWB
Nonstop1h 35m
Contour
Mon 6/159:00 am
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/11![Contour logo]()
$148
This Mytrip deal was found by Cheapflights users on 3/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:20 am
ORD
- OWB
Nonstop1h 35m
Contour
Mon 4/279:00 am
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/10![Contour logo]()
$178
This United Airlines deal was found by Cheapflights users on 3/11. 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.
Thu 3/2612:00 pm
ORD
- PAH
Nonstop1h 27m
United Airlines
Mon 3/305:00 am
PAH
- ORD
Nonstop1h 43m
United Airlines
Deal found 3/11![United Airlines logo]()
$194
This Booking.com deal was found by Cheapflights users on 3/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:15 pm
ORD
- BNA
1 stop13h 20m
Multiple Airlines
Mon 4/202:00 pm
BNA
- ORD
1 stop10h 59m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$204
Best flights from O'Hare Intl to KentuckyDiscover carefully curated flight deals from O'Hare Intl to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 12, 2026.
Discover carefully curated flight deals from O'Hare Intl to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 12, 2026.
This Mytrip deal was found by Cheapflights users on 3/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2510:55 am
ORD
- OWB
Nonstop1h 35m
Contour
Tue 3/312:35 pm
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/10![Contour logo]()
$103
This United Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/612:07 pm
ORD
- PAH
Nonstop1h 28m
United Airlines
Mon 4/135:00 am
PAH
- ORD
Nonstop1h 43m
United Airlines
Deal found 3/7![United Airlines logo]()
$194
This Booking.com deal was found by Cheapflights users on 3/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/249:40 am
ORD
- OWB
Nonstop1h 35m
Contour
Sat 3/281:50 pm
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/9![Contour logo]()
$104
This Delta deal was found by Cheapflights users on 3/8. 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.
Sat 4/2512:14 pm
ORD
- SDF
1 stop5h 31m
Delta
Sat 5/23:16 pm
SDF
- ORD
1 stop4h 32m
Delta
Deal found 3/8![Delta logo]()
$227
This Booking.com deal was found by Cheapflights users on 3/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:20 am
ORD
- OWB
Nonstop1h 35m
Contour
Sun 4/269:00 am
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/12![Contour logo]()
$104
This Southwest deal was found by Cheapflights users on 3/11. 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.
Mon 4/202:40 pm
ORD
- CVG
1 stop6h 10m
Southwest
Wed 4/227:05 am
CVG
- ORD
1 stop6h 45m
Southwest
Deal found 3/11![Southwest logo]()
$231
This American Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/245:00 am
ORD
- HTS
1 stop4h 29m
American Airlines
Sun 4/266:30 am
HTS
- ORD
1 stop4h 41m
American Airlines
Deal found 3/7![American Airlines logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Sun 4/265:50 am
ORD
- CVG
1 stop10h 58m
Multiple Airlines
Sun 5/36:30 am
CVG
- ORD
1 stop15h 42m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$253
This Mytrip deal was found by Cheapflights users on 3/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2610:55 am
ORD
- OWB
Nonstop1h 35m
Contour
Sun 3/299:00 am
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/8![Contour logo]()
$107
This Spirit deal was found by Cheapflights users on 3/10. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/177:15 pm
ORD
- BNA
1 stop13h 20m
Spirit Airlines
Mon 4/203:27 pm
BNA
- ORD
1 stop8h 57m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$285
This JetBlue deal was found by Cheapflights users on 3/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/118:58 am
ORD
- BNA
1 stop10h 04m
JetBlue
Tue 4/1412:31 pm
BNA
- ORD
1 stop9h 08m
JetBlue
Deal found 3/8![JetBlue logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 5/2211:20 am
ORD
- OWB
Nonstop1h 35m
Contour
Sun 5/249:00 am
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/7![Contour logo]()
$117
This Contour deal was found by Cheapflights users on 3/12. 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 Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/2911:20 am
ORD
- OWB
Nonstop1h 35m
Contour
Thu 4/29:00 am
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/12![Contour logo]()
$118
This Contour deal was found by Cheapflights users on 3/8. 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 Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/711:20 am
ORD
- OWB
Nonstop1h 35m
Contour
Wed 4/89:00 am
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/8![Contour logo]()
$118
This United Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 3/3012:07 pm
ORD
- PAH
Nonstop1h 28m
United Airlines
Mon 4/65:00 am
PAH
- ORD
Nonstop1h 43m
United Airlines
Deal found 3/6![United Airlines logo]()
$194
This United Airlines deal was found by Cheapflights users on 3/8. 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 4/912:07 pm
ORD
- PAH
Nonstop1h 28m
United Airlines
Sun 4/125:00 am
PAH
- ORD
Nonstop1h 43m
United Airlines
Deal found 3/8![United Airlines logo]()
$194
This Delta deal was found by Cheapflights users on 3/8. 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.
Sat 4/259:48 am
ORD
- BNA
1 stop7h 02m
Delta
Sat 5/25:25 am
BNA
- ORD
1 stop4h 44m
Delta
Deal found 3/8![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/142:40 pm
ORD
- TYS
1 stop4h 00m
Southwest
Sat 4/187:45 am
TYS
- ORD
2 stops8h 45m
Southwest
Deal found 3/7![Southwest logo]()
$234
This Delta deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 8/168:15 am
ORD
- TYS
1 stop5h 52m
Delta
Sat 8/227:30 am
TYS
- ORD
1 stop6h 09m
Delta
Deal found 3/7![Delta logo]()
$229
This United Airlines deal was found by Cheapflights users on 3/8. 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.
Sun 4/57:15 am
ORD
- TYS
Nonstop1h 53m
United Airlines
Sun 4/127:00 am
TYS
- ORD
Nonstop1h 55m
United Airlines
Deal found 3/8![United Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
Mon 4/276:00 am
ORD
- EVV
1 stop13h 06m
Multiple Airlines
Fri 5/17:46 pm
EVV
- ORD
2 stops26h 53m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$256
This Southwest deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/42:40 pm
ORD
- BNA
Nonstop1h 45m
Southwest
Tue 4/146:15 am
BNA
- ORD
1 stop8h 45m
Southwest
Deal found 3/7![Southwest logo]()
$239
This American Airlines deal was found by Cheapflights users on 3/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/274:45 pm
ORD
- TRI
1 stop4h 12m
American Airlines
Sat 5/307:59 am
TRI
- ORD
Nonstop2h 11m
American Airlines
Deal found 3/10![American Airlines logo]()
$264
This Delta deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 5/137:07 am
ORD
- TYS
1 stop6h 26m
Delta
Wed 5/203:30 pm
TYS
- ORD
1 stop5h 56m
Delta
Deal found 3/7![Delta logo]()
$229
This United Airlines deal was found by Cheapflights users on 3/8. 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.
Sat 7/49:30 pm
ORD
- TYS
Nonstop2h 00m
United Airlines
Fri 7/108:20 am
TYS
- ORD
Nonstop2h 08m
United Airlines
Deal found 3/8![United Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 4/1510:31 am
ORD
- EVV
1 stop28h 01m
Multiple Airlines
Wed 5/134:29 pm
EVV
- ORD
1 stop16h 46m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$273
This Delta deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/187:10 am
ORD
- LEX
1 stop5h 28m
Delta
Wed 4/226:00 am
LEX
- ORD
1 stop5h 09m
Delta
Deal found 3/7![Delta logo]()
$229
This United Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/319:30 pm
ORD
- TYS
Nonstop2h 00m
United Airlines
Mon 8/36:30 am
TYS
- ORD
Nonstop1h 59m
United Airlines
Deal found 3/7![United Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 3/9. 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 4/72:40 pm
ORD
- BNA
Nonstop1h 40m
Southwest
Tue 4/1411:00 am
BNA
- ORD
Nonstop1h 50m
Southwest
Deal found 3/9![Southwest logo]()
$255
This Delta deal was found by Cheapflights users on 3/8. 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.
Fri 4/175:04 pm
ORD
- LEX
1 stop3h 58m
Delta
Mon 4/207:56 pm
LEX
- ORD
1 stop5h 03m
Delta
Deal found 3/8![Delta logo]()
$229
Last-minute flights from O'Hare Intl to KentuckyDiscover last-minute flight deals from O'Hare Intl to Kentucky. Data last updated March 12, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Kentucky. Data last updated March 12, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 3/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/2310:55 am
ORD
- OWB
Nonstop1h 35m
Contour
Tue 3/241:50 pm
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/10![Contour logo]()
$128
This Mytrip deal was found by Cheapflights users on 3/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2510:55 am
ORD
- OWB
Nonstop1h 35m
Contour
Tue 3/312:35 pm
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/10![Contour logo]()
$103
This Mytrip deal was found by Cheapflights users on 3/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2610:55 am
ORD
- OWB
Nonstop1h 35m
Contour
Sun 3/299:00 am
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/8![Contour logo]()
$107
This United Airlines deal was found by Cheapflights users on 3/11. 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.
Thu 3/2612:00 pm
ORD
- PAH
Nonstop1h 27m
United Airlines
Mon 3/305:00 am
PAH
- ORD
Nonstop1h 43m
United Airlines
Deal found 3/11![United Airlines logo]()
$194
This Contour deal was found by Cheapflights users on 3/9. 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 Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/2911:20 am
ORD
- OWB
Nonstop1h 35m
Contour
Thu 4/29:00 am
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/9![Contour logo]()
$195
This Mytrip deal was found by Cheapflights users on 3/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/211:20 am
ORD
- OWB
Nonstop1h 35m
Contour
Sun 4/59:00 am
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/9![Contour logo]()
$106
This Contour deal was found by Cheapflights users on 3/9. 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 Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/711:20 am
ORD
- OWB
Nonstop1h 35m
Contour
Wed 4/89:00 am
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/9![Contour logo]()
$118
This Booking.com deal was found by Cheapflights users on 3/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:15 pm
ORD
- BNA
1 stop13h 20m
Multiple Airlines
Mon 4/202:00 pm
BNA
- ORD
1 stop10h 59m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$204
This American Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/184:20 pm
ORD
- BNA
Nonstop1h 47m
American Airlines
Sat 4/257:23 pm
BNA
- ORD
Nonstop2h 06m
American Airlines
Deal found 3/7![American Airlines logo]()
$207
This Booking.com deal was found by Cheapflights users on 3/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:20 am
ORD
- OWB
Nonstop1h 35m
Contour
Sun 4/269:00 am
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/12![Contour logo]()
$104
This Mytrip deal was found by Cheapflights users on 3/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:20 am
ORD
- OWB
Nonstop1h 35m
Contour
Mon 4/279:00 am
OWB
- ORD
Nonstop1h 40m
Contour
Deal found 3/10![Contour logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 3/12. 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.
Thu 4/2312:16 pm
ORD
- OWB
1 stop6h 34m
Multiple Airlines
Sun 4/269:00 am
OWB
- ORD
Nonstop1h 40m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$193
One-way flights from O'Hare Intl to KentuckySearch for one-way flight options from O'Hare Intl to Kentucky. Find affordable one-way fares based on user searches. Data last updated March 12, 2026.
Search for one-way flight options from O'Hare Intl to Kentucky. Find affordable one-way fares based on user searches. Data last updated March 12, 2026.
This Booking.com deal was found by Cheapflights users on 3/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2610:55 am
ORD
- OWB
Nonstop1h 35m
Contour
Deal found 3/11![Contour logo]()
$49
This Contour deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/911:20 am
ORD
- OWB
Nonstop1h 35m
Contour
Deal found 3/7![Contour logo]()
$59
This Kiwi.com deal was found by Cheapflights users on 3/11. 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.
Sat 5/25:50 am
ORD
- CVG
1 stop11h 46m
Frontier
Deal found 3/11![Frontier logo]()
$64
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Wed 5/64:28 pm
ORD
- CVG
1 stop25h 08m
Frontier
Deal found 3/9![Frontier logo]()
$65
This American Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/181:17 pm
ORD
- CVG
Nonstop1h 26m
American Airlines
Deal found 3/7![American Airlines logo]()
$72
This Kiwi.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/259:16 am
ORD
- CVG
1 stop8h 20m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
Mon 4/205:50 am
ORD
- CVG
1 stop11h 46m
Frontier
Deal found 3/9![Frontier logo]()
$77
This United Airlines deal was found by Cheapflights users on 3/10. 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.
Tue 5/262:20 pm
ORD
- CVG
Nonstop1h 29m
United Airlines
Deal found 3/10![United Airlines logo]()
$79
This Booking.com deal was found by Cheapflights users on 3/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:20 am
ORD
- OWB
Nonstop1h 35m
Contour
Deal found 3/8![Contour logo]()
$79
This Frontier deal was found by Cheapflights users on 3/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:27 pm
ORD
- CVG
1 stop7h 27m
Frontier
Deal found 3/9![Frontier logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
Fri 5/84:28 pm
ORD
- CVG
1 stop25h 08m
Frontier
Deal found 3/10![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 5/201:27 pm
ORD
- CVG
1 stop18h 21m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$83
Find flight deals from O'Hare Intl to Kentucky
Keep the following information in mind while searching for O'Hare Intl to Kentucky flight deals. Data was last updated March 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $103 (Mytrip) |
One-way from | $49 (Booking.com) |
Popular in | June |
Cheapest in | August |
Average price | $445 |
Good round-trip deal | $144 or less |
Good one-way deal | $59 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl 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 March 12, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Kentucky that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoOwensboro
ORD - OWB
ORDOWB
Chicago O'Hare Intl
Wed 3/25
10:55 am-12:30 pm
Nonstop1h 35m
Owensboro Daviess County
Tue 3/31
2:35 pm-4:15 pm
Nonstop1h 40m
$103
ChicagoOwensboro
ORD - OWB
ORDOWB
Chicago O'Hare Intl
Tue 3/24
9:40 am-11:15 am
Nonstop1h 35m
Owensboro Daviess County
Sat 3/28
1:50 pm-3:30 pm
Nonstop1h 40m
$104
ChicagoOwensboro
ORD - OWB
ORDOWB
Chicago O'Hare Intl
Thu 4/23
11:20 am-12:55 pm
Nonstop1h 35m
Owensboro Daviess County
Sun 4/26
9:00 am-10:40 am
Nonstop1h 40m
$104
ChicagoOwensboro
ORD - OWB
ORDOWB
Chicago O'Hare Intl
Thu 3/26
10:55 am-12:30 pm
Nonstop1h 35m
Owensboro Daviess County
Sun 3/29
9:00 am-10:40 am
Nonstop1h 40m
$107
ChicagoOwensboro
ORD - OWB
ORDOWB
Chicago O'Hare Intl
Fri 5/22
11:20 am-12:55 pm
Nonstop1h 35m
Owensboro Daviess County
Sun 5/24
9:00 am-10:40 am
Nonstop1h 40m
$117
ChicagoOwensboro
ORD - OWB
ORDOWB
Chicago O'Hare Intl
Sun 3/29
11:20 am-12:55 pm
Nonstop1h 35m
Owensboro Daviess County
Thu 4/2
9:00 am-10:40 am
Nonstop1h 40m
$118
ChicagoOwensboro
ORD - OWB
ORDOWB
Chicago O'Hare Intl
Tue 4/7
11:20 am-12:55 pm
Nonstop1h 35m
Owensboro Daviess County
Wed 4/8
9:00 am-10:40 am
Nonstop1h 40m
$118
Quickest round-trip
ChicagoPaducah
ORD - PAH
ORDPAH
Chicago O'Hare Intl
Mon 4/6
12:07 pm-1:35 pm
Nonstop1h 28m
Paducah Barkley Regional
Mon 4/13
5:00 am-6:43 am
Nonstop1h 43m
$194
ChicagoPaducah
ORD - PAH
ORDPAH
Chicago O'Hare Intl
Mon 3/30
12:07 pm-1:35 pm
Nonstop1h 28m
Paducah Barkley Regional
Mon 4/6
5:00 am-6:43 am
Nonstop1h 43m
$194
ChicagoPaducah
ORD - PAH
ORDPAH
Chicago O'Hare Intl
Thu 4/9
12:07 pm-1:35 pm
Nonstop1h 28m
Paducah Barkley Regional
Sun 4/12
5:00 am-6:43 am
Nonstop1h 43m
$194
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from O'Hare Intl to Kentucky
Have a flexible travel schedule? Discover the best time to fly to Kentucky from O'Hare Intl with our price prediction graph.
ORD-OWB
ORD-PAH
ORD-SDF
ORD-CVG
ORD-HTS
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 O'Hare Intl Airport to Kentucky
ORD-USKY
ORD-OWB
ORD-PAH
ORD-SDF
ORD-CVG
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Kentucky?
Currently, July is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Kentucky (average of $82). Flying from Chicago O'Hare Intl Airport to Kentucky in November is currently the most expensive (average of $189). 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 ORD to KY?
Find hourly flight availability from O'Hare Intl 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 March 12, 2026.
It’s optimal to fly from Chicago O'Hare Intl Airport to Kentucky in the morning. By choosing this option you can save up to 26% on the cost of your flight, compared to a flight at noon.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to Kentucky?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Kentucky. Price data was last updated on February 21, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Kentucky
Explore weekly flight availability from O'Hare Intl 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 March 12, 2026.
The most flights from ORD to USKY are scheduled on a Monday (35 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 on average).
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 March 12, 2026.
See what other customers who have flown with Contour,United Airlines, andAmerican Airlines from Chicago O'Hare Intl Airport to Kentucky have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.6
Crew
7.9
Comfort
7.3
Boarding
7.6
Food
6.8
Entertainment
6.1
Reviews
1 / 2
10.0
ExcellentAnonymous,Oct 2025
CLT - PAH
Overall
7.6
Crew
7.9
Comfort
7.3
Boarding
7.6
Food
6.8
Entertainment
6.1
Reviews
1 / 2
10.0
ExcellentAnonymous,Oct 2025
CLT - PAH
Overall
7.6
Crew
7.9
Comfort
7.3
Boarding
7.6
Food
6.8
Entertainment
6.1
Reviews
1 / 2
10.0
ExcellentAnonymous,Oct 2025
CLT - PAH
Overall
7.6
Crew
7.9
Comfort
7.3
Boarding
7.6
Food
6.8
Entertainment
6.1
Reviews
1 / 2
10.0
ExcellentAnonymous,Oct 2025
CLT - PAH
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl 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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O'Hare Intl and Kentucky flights
Browse other O'Hare Intl and Kentucky flight options. Last updated on March 12, 2026.
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O'Hare Intl to Kentucky flights
Consider these flights traveling from O'Hare Intl to Kentucky.
Top 3 airlines flying from O'Hare Intl to Kentucky
Discover the top 3 airlines that operate flights from O'Hare Intl 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 March 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$148 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$127 | Average$317 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$139 | Average$289 | FlexibilityNo cancel fee | On-time71% |