$43+ Cheap flights from Chicago (CHI) to Kentucky
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SDF
Oct 11 — Oct 181
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
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 September 11, 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 September 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:28 pm -
1 stop15h 10m
Tue 10/612:43 pm -
1 stop6h 40m
Deal found 9/10![Frontier logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:50 pm -
1 stop17h 04m
Tue 11/312:43 pm -
1 stop6h 33m
Deal found 9/11![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/267:44 pm -
1 stop14h 59m
Mon 11/22:59 pm -
1 stop22h 52m
Deal found 9/10![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/237:44 pm -
1 stop13h 58m
Tue 10/271:10 pm -
1 stop24h 41m
Deal found 9/7![Frontier logo]()
$175
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/293:50 pm -
1 stop6h 51m
Wed 9/3012:43 pm -
1 stop6h 40m
Deal found 9/8![Frontier logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Sun 10/257:44 pm -
1 stop14h 54m
Sun 11/15:18 pm -
1 stop16h 59m
Deal found 9/10![Frontier logo]()
$179
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:00 am -
1 stop4h 38m
Wed 10/2112:43 pm -
1 stop6h 48m
Deal found 9/10![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Wed 10/77:28 pm -
1 stop11h 22m
Wed 10/1412:43 pm -
1 stop6h 48m
Deal found 9/7![Frontier logo]()
$186
This Super.com deal was found by Cheapflights users on 9/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/63:50 pm -
1 stop6h 51m
Wed 10/712:43 pm -
1 stop6h 40m
Deal found 9/8![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/87:44 pm -
1 stop14h 54m
Mon 10/1212:43 pm -
1 stop23h 49m
Deal found 9/11![Frontier logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Tue 10/206:21 am -
2 stops16h 22m
Wed 10/2112:43 pm -
1 stop12h 00m
Deal found 9/10![Frontier logo]()
$195
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:55 am -
Nonstop1h 15m
Mon 10/57:50 pm -
Nonstop1h 15m
Deal found 9/8![Southwest logo]()
$197
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 September 11, 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 September 11, 2026.
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:40 am -
1 stop4h 40m
Mon 10/55:50 pm -
1 stop3h 40m
Deal found 9/8![Delta logo]()
$235
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:55 pm -
Nonstop1h 15m
Fri 10/165:10 pm -
1 stop5h 50m
Deal found 9/10![Southwest logo]()
$243
This Frontier deal was found by Cheapflights users on 9/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/69:51 am -
1 stop9h 50m
Mon 11/95:13 pm -
1 stop5h 30m
Deal found 9/6![Frontier logo]()
$254
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 10/156:55 am -
Nonstop1h 25m
Mon 10/194:10 pm -
Nonstop1h 38m
Deal found 9/10![United Airlines logo]()
$255
This American Airlines deal was found by Cheapflights users on 9/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/118:12 am -
Nonstop1h 49m
Sun 11/158:52 pm -
Nonstop2h 06m
Deal found 9/6![American Airlines logo]()
$279
This Contour deal was found by Cheapflights users on 9/9. 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.
Thu 10/812:30 pm -
1 stop3h 40m
Mon 10/128:00 am -
1 stop3h 40m
Deal found 9/9![Contour logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:30 am -
1 stop29h 49m
Sun 11/157:30 am -
2 stops12h 38m
Deal found 9/6![Multiple Airlines logo]()
$421
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:45 am -
Nonstop1h 10m
Mon 11/28:20 pm -
Nonstop1h 10m
Deal found 9/10![Southwest logo]()
$255
This United Airlines deal was found by Cheapflights users on 9/8. 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 10/16:55 am -
Nonstop1h 39m
Mon 10/55:15 am -
Nonstop1h 41m
Deal found 9/8![United Airlines logo]()
$268
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Fri 11/63:49 pm -
Nonstop1h 35m
Sun 11/811:26 am -
Nonstop1h 48m
Deal found 9/10![American Airlines logo]()
$279
This Frontier deal was found by Cheapflights users on 9/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:30 am -
1 stop7h 57m
Sun 10/118:19 pm -
1 stop12h 12m
Deal found 9/6![Frontier logo]()
$280
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:25 pm -
1 stop4h 45m
Sun 11/18:10 am -
Nonstop1h 10m
Deal found 9/10![Southwest logo]()
$265
This KAYAK deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1912:30 pm -
1 stop3h 40m
Wed 10/218:00 am -
1 stop3h 40m
Deal found 9/8![Contour logo]()
$295
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:30 am -
1 stop6h 10m
Sat 10/317:09 am -
1 stop6h 04m
Deal found 9/9![Delta logo]()
$299
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:50 am -
Nonstop1h 38m
Sat 10/36:00 am -
Nonstop1h 45m
Deal found 9/9![United Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 9/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/59:05 pm -
Nonstop1h 46m
Sun 12/66:00 am -
Nonstop2h 11m
Deal found 9/6![American Airlines logo]()
$279
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/209:40 am -
2 stops9h 55m
Fri 10/235:35 am -
1 stop4h 10m
Deal found 9/10![Southwest logo]()
$268
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:49 pm -
1 stop4h 58m
Sat 10/317:26 am -
1 stop6h 21m
Deal found 9/9![Delta logo]()
$299
This United Airlines deal was found by Cheapflights users on 9/11. 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 10/86:50 am -
Nonstop1h 38m
Sat 10/108:50 am -
Nonstop1h 45m
Deal found 9/11![United Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/69:05 pm -
Nonstop1h 49m
Tue 10/136:03 am -
Nonstop2h 08m
Deal found 9/8![American Airlines logo]()
$279
This Southwest deal was found by Cheapflights users on 9/9. 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.
Sat 11/710:20 am -
2 stops8h 25m
Tue 11/101:00 pm -
2 stops10h 40m
Deal found 9/9![Southwest logo]()
$269
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:30 am -
1 stop6h 29m
Sun 12/61:46 pm -
1 stop4h 16m
Deal found 9/9![Delta logo]()
$299
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:50 am -
Nonstop1h 38m
Sat 10/38:50 am -
Nonstop1h 45m
Deal found 9/9![United Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 9/7. 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.
Thu 10/229:08 pm -
Nonstop1h 49m
Sun 10/256:03 am -
Nonstop2h 08m
Deal found 9/7![American Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:30 am -
1 stop6h 32m
Sat 11/141:54 pm -
1 stop4h 11m
Deal found 9/9![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/302:50 pm -
2 stops5h 45m
Tue 11/35:15 pm -
1 stop6h 25m
Deal found 9/8![Southwest logo]()
$274
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/58:40 am -
Nonstop1h 29m
Mon 12/76:35 pm -
Nonstop2h 05m
Deal found 9/9![United Airlines logo]()
$283
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/29:05 pm -
Nonstop1h 51m
Mon 10/58:26 pm -
1 stop4h 42m
Deal found 9/8![American Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 9/8. 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 10/318:05 am -
1 stop5h 36m
Sun 11/17:55 am -
1 stop6h 04m
Deal found 9/8![Delta logo]()
$301
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:55 pm -
Nonstop1h 15m
Tue 10/138:35 am -
Nonstop1h 15m
Deal found 9/8![Southwest logo]()
$277
Last-minute flights from Chicago to KentuckyDiscover last-minute flight deals from Chicago to Kentucky. Data last updated September 11, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kentucky. Data last updated September 11, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/293:50 pm -
1 stop6h 51m
Wed 9/3012:43 pm -
1 stop6h 40m
Deal found 9/8![Frontier logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:28 pm -
1 stop15h 10m
Tue 10/612:43 pm -
1 stop6h 40m
Deal found 9/10![Frontier logo]()
$121
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:55 am -
Nonstop1h 15m
Mon 10/57:50 pm -
Nonstop1h 15m
Deal found 9/8![Southwest logo]()
$197
This Super.com deal was found by Cheapflights users on 9/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/63:50 pm -
1 stop6h 51m
Wed 10/712:43 pm -
1 stop6h 40m
Deal found 9/8![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Wed 10/77:28 pm -
1 stop11h 22m
Wed 10/1412:43 pm -
1 stop6h 48m
Deal found 9/7![Frontier logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/87:44 pm -
1 stop14h 54m
Mon 10/1212:43 pm -
1 stop23h 49m
Deal found 9/11![Frontier logo]()
$189
This Priceline deal was found by Cheapflights users on 9/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:00 am -
1 stop4h 38m
Wed 10/2112:43 pm -
1 stop6h 48m
Deal found 9/10![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Tue 10/206:21 am -
2 stops16h 22m
Wed 10/2112:43 pm -
1 stop12h 00m
Deal found 9/10![Frontier logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/237:44 pm -
1 stop13h 58m
Tue 10/271:10 pm -
1 stop24h 41m
Deal found 9/7![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Sun 10/257:44 pm -
1 stop14h 54m
Sun 11/15:18 pm -
1 stop16h 59m
Deal found 9/10![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/267:44 pm -
1 stop14h 59m
Mon 11/22:59 pm -
1 stop22h 52m
Deal found 9/10![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:50 pm -
1 stop17h 04m
Tue 11/312:43 pm -
1 stop6h 33m
Deal found 9/11![Frontier logo]()
$139
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 September 11, 2026.
Search for one-way flight options from Chicago to Kentucky. Find affordable one-way fares based on user searches. Data last updated September 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 11/133:16 pm -
Nonstop1h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Allegiant Air logo]()
$43
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/302:26 pm -
Nonstop1h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Allegiant Air logo]()
$57
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Mon 10/512:56 pm -
Nonstop1h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Allegiant Air logo]()
$62
This Jetabroad deal was found by Cheapflights users on 9/9. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:30 pm -
Nonstop1h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Allegiant Air logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/22:24 pm -
Nonstop1h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Allegiant Air logo]()
$78
This Super.com deal was found by Cheapflights users on 9/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 am -
1 stop4h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$90
This Super.com deal was found by Cheapflights users on 9/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:00 am -
1 stop4h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Tue 12/82:04 pm -
1 stop24h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$93
This Priceline deal was found by Cheapflights users on 9/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/88:10 am -
1 stop6h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$93
This Super.com deal was found by Cheapflights users on 9/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:28 pm -
1 stop11h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$96
This Super.com deal was found by Cheapflights users on 9/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/63:50 pm -
1 stop6h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$99
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/127:55 am -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Southwest logo]()
$99
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 September 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $121 (Kiwi.com) |
One-way from | $43 (Kiwi.com) |
Popular in | May |
Cheapest in | November |
Average price | $401 |
Good round-trip deal | $158 or less |
Good one-way deal | $134 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 7,457,451 searches. Data last updated September 11, 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
ChicagoKnoxville
MDW Chicago Midway - TYS Knoxville McGhee Tyson
MDWTYS
Chicago Midway
Fri 11/13
3:16 pm-5:46 pm
Nonstop1h 30m
Knoxville McGhee Tyson
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$52
ChicagoKnoxville
MDW Chicago Midway - TYS Knoxville McGhee Tyson
MDWTYS
Chicago Midway
Fri 10/2
2:24 pm-4:49 pm
Nonstop1h 25m
Knoxville McGhee Tyson
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$78
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Thu 10/15
7:55 am-10:10 am
Nonstop1h 15m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$99
ChicagoLouisville
ORD Chicago O'Hare Intl - SDF Louisville Intl
ORDSDF
Chicago O'Hare Intl
Thu 10/15
9:25 pm-11:59 pm
Nonstop1h 34m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$99
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Thu 12/10
8:15 am-10:30 am
Nonstop1h 15m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$99
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Wed 10/7
6:00 pm-8:15 pm
Nonstop1h 15m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$99
ChicagoCincinnati
ORD Chicago O'Hare Intl - CVG Cincinnati Cinci./N. Kentucky
ORDCVG
Chicago O'Hare Intl
Wed 11/4
6:30 am-3:22 pm
1 stop7h 52m
Cincinnati Cinci./N. Kentucky
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$100
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Thu 12/10
6:00 am-2:04 pm
1 stop7h 04m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$109
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Tue 10/6
10:59 am-4:49 pm
1 stop4h 50m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$109
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Thu 11/5
6:04 am-12:54 pm
1 stop5h 50m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$109
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-CVG
MDW-SDF
MDW-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-CVG
MDW-SDF
MDW-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 $264). Flying from Chicago to Kentucky in June is currently the most expensive (average of $485). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to KY?
Find hourly flight availability from Chicago to Kentucky. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 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 in the evening.
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 September 11, 2026.
The most flights from CHI to USKY are scheduled on a Thursday (40 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (26 on average).
How much does it cost to fly round-trip from Chicago to Kentucky?
Airfare is below average for this route at the moment.
Chicago to Kentucky flights typically cost between $297 and $515 in October.The cheapest round-trip price found within the last 5 days was $197 on Southwest (Oct 1-Oct 5).
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 34 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 September 5, 2026.
Travelers seeking maximum savings on their Chicago to Kentucky flight should consider departing on Sunday mornings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Kentucky
Get insights into the airlines that provide service to Kentucky. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kentucky. Reviews last updated September 11, 2026.
Read reviews from past customers who have flown Southwest,Contour, andUnited Airlines from Chicago to Kentucky. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Kentucky. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Kentucky
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Kentucky by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Kentucky by cabin class
Find flights from Chicago to Kentucky, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Kentucky flights
Browse other Chicago and Kentucky flight options. Last updated on September 11, 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 7,457,451 searches. Data last updated September 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$89 | Average$158 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$129 | Average$390 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$143 | Average$376 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$189 | Average$337 | FlexibilityNo cancel fee | On-time71% |