$54+ Cheap flights from Chicago (CHI) to Kentucky
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SDF
Jun 29 — Jul 61
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Kentucky with Cheapflights
1. Tell us where you want to go
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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 May 30, 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 May 30, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
Sun 6/282:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Sun 7/121:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 5/30![Allegiant Air logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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
Sun 8/161:23 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 5/30![Allegiant Air logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 5/29![Allegiant Air logo]()
$139
This Cheapflightsfares deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/42:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Thu 6/111:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 5/30![Allegiant Air logo]()
$140
This Cheapflightsfares deal was found by Cheapflights users on 5/26. 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.
Thu 6/42:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Sun 6/71:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 5/26![Allegiant Air logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/182:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Thu 6/251:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 5/30![Allegiant Air logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 10/164:30 pm
MDW
- TYS
Nonstop1h 25m
Allegiant Air
Mon 10/1912:04 pm
TYS
- MDW
Nonstop1h 32m
Allegiant Air
Deal found 5/29![Allegiant Air logo]()
$156
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 7/86:15 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Wed 7/157:40 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 5/28![Southwest logo]()
$157
This American Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/810:00 pm
ORD
- CVG
Nonstop1h 30m
American Airlines
Wed 7/151:31 pm
CVG
- ORD
Nonstop1h 37m
American Airlines
Deal found 5/28![American Airlines logo]()
$157
This Cheapflightsfares deal was found by Cheapflights users on 5/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/182:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Sun 6/211:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 5/27![Allegiant Air logo]()
$159
This Cheapflightsfares deal was found by Cheapflights users on 5/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/112:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Sun 6/141:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 5/27![Allegiant Air logo]()
$162
This United Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:50 am
ORD
- CVG
Nonstop1h 26m
United Airlines
Sat 8/222:05 pm
CVG
- ORD
Nonstop1h 34m
United Airlines
Deal found 5/28![United Airlines logo]()
$174
Best flights from Chicago to KentuckyDiscover carefully curated flight deals from Chicago to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 30, 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 May 30, 2026.
This Southwest deal was found by Cheapflights users on 5/26. 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 7/811:25 am
MDW
- CVG
2 stops9h 30m
Southwest
Wed 7/154:30 pm
CVG
- MDW
1 stop6h 10m
Southwest
Deal found 5/26![Southwest logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/712:30 pm
ORD
- BNA
1 stop3h 40m
Contour
Sun 8/98:00 am
BNA
- ORD
1 stop3h 30m
Contour
Deal found 5/30![Contour logo]()
$228
This JetBlue deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/299:40 am
ORD
- BNA
1 stop7h 23m
JetBlue
Wed 8/511:05 am
BNA
- ORD
1 stop6h 29m
JetBlue
Deal found 5/29![JetBlue logo]()
$233
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 7/149:19 am
MDW
- CVG
1 stop3h 11m
Delta
Sat 7/186:25 am
CVG
- MDW
1 stop3h 43m
Delta
Deal found 5/28![Delta logo]()
$235
This United Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 9/16:05 pm
ORD
- CVG
Nonstop1h 30m
United Airlines
Wed 9/29:00 am
CVG
- ORD
Nonstop1h 35m
United Airlines
Deal found 5/30![United Airlines logo]()
$247
This American Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 11/63:52 pm
ORD
- LEX
Nonstop1h 29m
American Airlines
Sun 11/86:51 pm
LEX
- ORD
Nonstop1h 51m
American Airlines
Deal found 5/30![American Airlines logo]()
$249
This Southwest deal was found by Cheapflights users on 5/25. 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 8/275:55 am
MDW
- CVG
1 stop5h 20m
Southwest
Mon 8/318:10 am
CVG
- MDW
Nonstop1h 05m
Southwest
Deal found 5/25![Southwest logo]()
$201
This Southwest deal was found by Cheapflights users on 5/26. 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 8/57:40 am
MDW
- CVG
1 stop3h 55m
Southwest
Mon 8/107:05 am
CVG
- MDW
2 stops6h 10m
Southwest
Deal found 5/26![Southwest logo]()
$201
This JetBlue deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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.
Thu 7/309:40 am
ORD
- BNA
1 stop7h 28m
JetBlue
Sat 8/111:07 am
BNA
- ORD
1 stop10h 23m
JetBlue
Deal found 5/29![JetBlue logo]()
$247
This United Airlines deal was found by Cheapflights users on 5/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:59 am
ORD
- TYS
Nonstop1h 46m
United Airlines
Wed 10/146:00 am
TYS
- ORD
Nonstop1h 56m
United Airlines
Deal found 5/27![United Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 5/26. 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 7/75:18 pm
ORD
- CVG
1 stop4h 26m
Delta
Thu 7/911:03 am
CVG
- ORD
1 stop6h 20m
Delta
Deal found 5/26![Delta logo]()
$263
This JetBlue deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
Tue 8/49:40 am
ORD
- BNA
1 stop7h 23m
JetBlue
Wed 8/511:05 am
BNA
- ORD
1 stop6h 29m
JetBlue
Deal found 5/30![JetBlue logo]()
$247
This United Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 7/235:55 pm
ORD
- TYS
Nonstop1h 49m
United Airlines
Sun 7/266:00 am
TYS
- ORD
Nonstop1h 59m
United Airlines
Deal found 5/29![United Airlines logo]()
$249
This Contour deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1712:20 pm
ORD
- BNA
1 stop3h 50m
Contour
Mon 6/228:00 am
BNA
- ORD
1 stop3h 30m
Contour
Deal found 5/29![Contour logo]()
$285
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:15 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Fri 7/316:55 pm
CVG
- MDW
1 stop4h 05m
Southwest
Deal found 5/28![Southwest logo]()
$239
This Delta deal was found by Cheapflights users on 5/26. 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.
Sat 7/44:25 pm
MDW
- LEX
1 stop6h 39m
Delta
Thu 7/97:35 am
LEX
- MDW
1 stop6h 03m
Delta
Deal found 5/26![Delta logo]()
$269
This United Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 8/66:55 am
ORD
- TYS
Nonstop1h 48m
United Airlines
Sun 8/96:00 am
TYS
- ORD
Nonstop1h 59m
United Airlines
Deal found 5/29![United Airlines logo]()
$249
This Contour deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 7/212:20 pm
ORD
- BNA
1 stop3h 50m
Contour
Sun 7/58:00 am
BNA
- ORD
1 stop3h 30m
Contour
Deal found 5/30![Contour logo]()
$285
This JetBlue deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
Tue 8/49:40 am
ORD
- BNA
1 stop7h 23m
JetBlue
Tue 8/1110:50 am
BNA
- ORD
1 stop6h 30m
JetBlue
Deal found 5/30![JetBlue logo]()
$264
This Southwest deal was found by Cheapflights users on 5/26. 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.
Mon 8/37:05 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Thu 8/62:10 pm
CVG
- MDW
1 stop5h 05m
Southwest
Deal found 5/26![Southwest logo]()
$244
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 7/26:00 am
MDW
- LEX
1 stop5h 19m
Delta
Sun 7/57:35 am
LEX
- MDW
1 stop6h 11m
Delta
Deal found 5/29![Delta logo]()
$269
This United Airlines deal was found by Cheapflights users on 5/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/287:45 pm
ORD
- TYS
Nonstop1h 49m
United Airlines
Sun 7/126:00 am
TYS
- ORD
Nonstop1h 59m
United Airlines
Deal found 5/27![United Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 7/195:00 am
ORD
- CVG
1 stop4h 55m
American Airlines
Wed 7/222:06 pm
CVG
- ORD
Nonstop1h 37m
American Airlines
Deal found 5/30![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:00 am
MDW
- LEX
1 stop5h 17m
Delta
Fri 7/245:56 pm
LEX
- MDW
1 stop5h 19m
Delta
Deal found 5/28![Delta logo]()
$269
This United Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 7/175:55 pm
ORD
- TYS
Nonstop1h 49m
United Airlines
Sun 7/196:00 am
TYS
- ORD
Nonstop1h 59m
United Airlines
Deal found 5/28![United Airlines logo]()
$249
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 8/206:10 pm
MDW
- SDF
Nonstop1h 15m
Southwest
Sat 8/2211:55 am
SDF
- MDW
1 stop3h 15m
Southwest
Deal found 5/29![Southwest logo]()
$254
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/34:25 pm
MDW
- LEX
1 stop6h 42m
Delta
Sun 7/57:35 am
LEX
- MDW
1 stop6h 11m
Delta
Deal found 5/30![Delta logo]()
$269
This United Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 7/215:51 pm
ORD
- LEX
Nonstop1h 38m
United Airlines
Sun 7/267:00 am
LEX
- ORD
Nonstop1h 52m
United Airlines
Deal found 5/29![United Airlines logo]()
$249
This Southwest deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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 10/17:45 am
MDW
- CVG
Nonstop1h 10m
Southwest
Sun 10/48:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 5/28![Southwest logo]()
$260
This Delta deal was found by Cheapflights users on 5/26. 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 7/305:10 pm
MDW
- LEX
1 stop5h 45m
Delta
Sat 8/87:35 am
LEX
- MDW
1 stop6h 04m
Delta
Deal found 5/26![Delta logo]()
$269
Last-minute flights from Chicago to KentuckyDiscover last-minute flight deals from Chicago to Kentucky. Data last updated May 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kentucky. Data last updated May 30, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/42:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Thu 6/111:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 5/30![Allegiant Air logo]()
$140
This Cheapflightsfares deal was found by Cheapflights users on 5/26. 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.
Thu 6/42:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Sun 6/71:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 5/26![Allegiant Air logo]()
$150
This Cheapflightsfares deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” 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.
Sun 6/72:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Thu 6/111:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 5/28![Allegiant Air logo]()
$166
This Cheapflightsfares deal was found by Cheapflights users on 5/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/112:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Sun 6/141:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 5/27![Allegiant Air logo]()
$162
This United Airlines deal was found by Cheapflights users on 5/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1710:35 am
ORD
- CVG
Nonstop1h 25m
United Airlines
Wed 6/2411:17 am
CVG
- ORD
Nonstop1h 36m
United Airlines
Deal found 5/27![United Airlines logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/182:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Thu 6/251:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 5/30![Allegiant Air logo]()
$155
This Cheapflightsfares deal was found by Cheapflights users on 5/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/182:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Sun 6/211:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 5/27![Allegiant Air logo]()
$159
This Southwest deal was found by Cheapflights users on 5/26. 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.
Tue 6/236:15 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Tue 6/307:40 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 5/26![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 5/26. 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 6/232:07 pm
ORD
- CVG
1 stop4h 51m
Delta
Tue 6/306:19 am
CVG
- ORD
1 stop5h 31m
Delta
Deal found 5/26![Delta logo]()
$177
This American Airlines deal was found by Cheapflights users on 5/26. 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.
Tue 6/236:29 am
ORD
- CVG
1 stop5h 55m
American Airlines
Tue 6/3012:06 pm
CVG
- ORD
Nonstop1h 29m
American Airlines
Deal found 5/26![American Airlines logo]()
$212
This Cheapflightsfares deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
Sun 6/282:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Sun 7/121:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 5/30![Allegiant Air logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/282:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Thu 7/21:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 5/29![Allegiant Air logo]()
$163
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 May 30, 2026.
Search for one-way flight options from Chicago to Kentucky. Find affordable one-way fares based on user searches. Data last updated May 30, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 5/27. 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 Cheapflightsfares 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 5/27![Allegiant Air logo]()
$54
This Kiwi.com deal was found by Cheapflights users on 5/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/232:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 5/27![Allegiant Air logo]()
$58
This Kiwi.com deal was found by Cheapflights users on 5/25. 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.
Thu 6/42:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Deal found 5/25![Allegiant Air logo]()
$62
This Kiwi.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/282:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Deal found 5/28![Allegiant Air logo]()
$63
This Kiwi.com deal was found by Cheapflights users on 5/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/252:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Deal found 5/26![Allegiant Air logo]()
$71
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 stop5h 04m
Delta
Deal found 5/29![Delta logo]()
$79
This United Airlines deal was found by Cheapflights users on 5/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/232:20 pm
ORD
- CVG
Nonstop1h 29m
United Airlines
Deal found 5/27![United Airlines logo]()
$79
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/241:27 pm
MDW
- CVG
1 stop3h 37m
Delta
Deal found 5/29![Delta logo]()
$87
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:51 am
ORD
- CVG
1 stop5h 51m
Delta
Deal found 5/29![Delta logo]()
$87
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/238:52 am
ORD
- CVG
1 stop5h 25m
Delta
Deal found 5/28![Delta logo]()
$89
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 8/251:00 pm
MDW
- SDF
Nonstop1h 15m
Southwest
Deal found 5/29![Southwest logo]()
$89
This American Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:06 am
ORD
- CVG
Nonstop1h 29m
American Airlines
Deal found 5/30![American Airlines logo]()
$90
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 May 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $133 (Cheapflightsfares) |
One-way from | $54 (Cheapflightsfares) |
Popular in | May |
Cheapest in | August |
Average price | $514 |
Good round-trip deal | $184 or less |
Good one-way deal | $100 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 May 30, 2026.
Use the filters below to find and compare flights from Chicago to Kentucky that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Wed 7/8
11:25 am-9:55 pm
2 stops9h 30m
Cincinnati Cinci./N. Kentucky
Wed 7/15
4:30 pm-9:40 pm
1 stop6h 10m
$182
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Thu 8/27
5:55 am-12:15 pm
1 stop5h 20m
Cincinnati Cinci./N. Kentucky
Mon 8/31
8:10 am-8:15 am
Nonstop1h 05m
$201
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Wed 8/5
7:40 am-12:35 pm
1 stop3h 55m
Cincinnati Cinci./N. Kentucky
Mon 8/10
7:05 am-12:15 pm
2 stops6h 10m
$201
ChicagoNashville
ORD - BNA
ORDBNA
Chicago O'Hare Intl
Fri 8/7
12:30 pm-4:10 pm
1 stop3h 40m
Nashville Intl
Sun 8/9
8:00 am-11:30 am
1 stop3h 30m
$228
ChicagoNashville
ORD - BNA
ORDBNA
Chicago O'Hare Intl
Wed 7/29
9:40 am-5:03 pm
1 stop7h 23m
Nashville Intl
Wed 8/5
11:05 am-5:34 pm
1 stop6h 29m
$233
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Tue 7/14
9:19 am-1:30 pm
1 stop3h 11m
Cincinnati Cinci./N. Kentucky
Sat 7/18
6:25 am-9:08 am
1 stop3h 43m
$235
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Tue 7/28
6:15 pm-8:30 pm
Nonstop1h 15m
Cincinnati Cinci./N. Kentucky
Fri 7/31
6:55 pm-10:00 pm
1 stop4h 05m
$239
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Mon 8/3
7:05 pm-9:20 pm
Nonstop1h 15m
Cincinnati Cinci./N. Kentucky
Thu 8/6
2:10 pm-6:15 pm
1 stop5h 05m
$244
ChicagoCincinnati
ORD - CVG
ORDCVG
Chicago O'Hare Intl
Tue 9/1
6:05 pm-8:35 pm
Nonstop1h 30m
Cincinnati Cinci./N. Kentucky
Wed 9/2
9:00 am-9:35 am
Nonstop1h 35m
$247
ChicagoNashville
ORD - BNA
ORDBNA
Chicago O'Hare Intl
Thu 7/30
9:40 am-5:08 pm
1 stop7h 28m
Nashville Intl
Sat 8/1
11:07 am-9:30 pm
1 stop10h 23m
$247
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Kentucky
Have a flexible travel schedule? Discover the best time to fly to Kentucky from Chicago with our price prediction graph.
MDW-TYS
MDW-CVG
ORD-CVG
MDW-SDF
ORD-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-TYS
MDW-CVG
ORD-CVG
MDW-SDF
What is the cheapest month to book a flight from Chicago to Kentucky?
Currently, July is the cheapest month in which you can book a flight from Chicago to Kentucky (average of $69). Flying from Chicago to Kentucky in May is currently the most expensive (average of $206). 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 May 30, 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 30% 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 May 30, 2026.
The most flights from CHI to USKY are scheduled on a Saturday (43 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (6 on average).
How much does it cost to fly round-trip from Chicago to Kentucky?
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 68 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 May 23, 2026.
Travelers seeking maximum savings on their Chicago to Kentucky flight should consider departing on Sunday mornings when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
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 May 30, 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.
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Boarding
8.1
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
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 May 30, 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 May 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$104 | Average$148 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$124 | Average$255 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$134 | Average$377 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$136 | Average$307 | FlexibilityNo cancel fee | On-time71% |