$94+ 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SDF
Nov 27 — Dec 41
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 October 28, 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 October 28, 2026.
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:15 pm -
Nonstop1h 20m
Mon 11/234:40 pm -
Nonstop1h 20m
Deal found 10/27![Southwest logo]()
$187
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 11/196:10 pm -
Nonstop1h 42m
Mon 11/239:02 am -
Nonstop1h 43m
Deal found 10/28![United Airlines logo]()
$187
This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:11 am -
Nonstop1h 32m
Mon 11/236:31 pm -
Nonstop1h 59m
Deal found 10/27![American Airlines logo]()
$188
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:40 pm -
Nonstop1h 25m
Mon 11/162:05 pm -
Nonstop1h 20m
Deal found 10/23![Southwest logo]()
$189
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:59 am -
Nonstop1h 39m
Mon 11/1610:27 am -
Nonstop1h 45m
Deal found 10/23![United Airlines logo]()
$189
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:40 pm -
Nonstop1h 25m
Mon 11/237:55 pm -
Nonstop1h 15m
Deal found 10/23![Southwest logo]()
$190
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:14 pm -
Nonstop1h 27m
Wed 11/115:30 am -
Nonstop1h 29m
Deal found 10/24![United Airlines logo]()
$194
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/209:30 pm -
Nonstop1h 35m
Sun 11/222:25 pm -
Nonstop1h 50m
Deal found 10/26![United Airlines logo]()
$196
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:20 pm -
Nonstop1h 40m
Mon 12/77:10 am -
Nonstop1h 45m
Deal found 10/23![United Airlines logo]()
$204
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:15 am -
Nonstop1h 15m
Tue 12/88:50 am -
Nonstop1h 15m
Deal found 10/26![Southwest logo]()
$206
This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:00 am -
Nonstop1h 40m
Fri 12/410:13 am -
Nonstop1h 47m
Deal found 10/27![American Airlines logo]()
$206
This Delta deal was found by Cheapflights users on 10/26. 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 12/15:30 pm -
1 stop4h 32m
Mon 12/73:18 pm -
1 stop3h 43m
Deal found 10/26![Delta logo]()
$207
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 October 28, 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 October 28, 2026.
This United Airlines deal was found by Cheapflights users on 10/28. 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 11/257:55 pm -
Nonstop1h 35m
Wed 12/29:00 am -
Nonstop1h 45m
Deal found 10/28![United Airlines logo]()
$187
This Southwest deal was found by Cheapflights users on 10/28. 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 11/257:40 am -
Nonstop1h 20m
Wed 12/28:50 am -
Nonstop1h 15m
Deal found 10/28![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:29 am -
1 stop4h 55m
Mon 11/163:14 pm -
1 stop4h 16m
Deal found 10/23![Delta logo]()
$239
This Southwest deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:15 pm -
Nonstop1h 20m
Sat 11/218:20 pm -
Nonstop1h 20m
Deal found 10/24![Southwest logo]()
$225
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/109:20 pm -
Nonstop1h 29m
Sun 12/139:00 am -
Nonstop1h 45m
Deal found 10/26![United Airlines logo]()
$226
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/187:05 am -
1 stop6h 43m
Sat 1/910:26 am -
1 stop6h 49m
Deal found 10/25![Delta logo]()
$245
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/297:40 am -
Nonstop1h 20m
Tue 12/298:35 pm -
Nonstop1h 25m
Deal found 10/27![Southwest logo]()
$225
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1912:14 pm -
Nonstop1h 27m
Thu 11/265:30 am -
Nonstop1h 29m
Deal found 10/23![United Airlines logo]()
$234
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:30 am -
1 stop5h 26m
Mon 11/2310:49 am -
1 stop6h 29m
Deal found 10/25![Delta logo]()
$245
This Southwest deal was found by Cheapflights users on 10/26. 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.
Thu 12/108:15 am -
Nonstop1h 15m
Sun 12/138:45 am -
Nonstop1h 15m
Deal found 10/26![Southwest logo]()
$226
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1712:14 pm -
Nonstop1h 29m
Sun 12/205:00 am -
Nonstop1h 32m
Deal found 10/23![United Airlines logo]()
$234
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/162:44 pm -
1 stop5h 29m
Sat 11/2112:40 pm -
1 stop5h 01m
Deal found 10/24![Delta logo]()
$245
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/149:30 pm -
Nonstop1h 35m
Sat 11/212:25 pm -
Nonstop1h 50m
Deal found 10/24![United Airlines logo]()
$236
This Southwest deal was found by Cheapflights users on 10/25. 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 11/1911:30 am -
2 stops8h 10m
Mon 11/237:55 pm -
Nonstop1h 15m
Deal found 10/25![Southwest logo]()
$240
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:23 am -
1 stop4h 37m
Tue 11/2410:49 am -
1 stop6h 29m
Deal found 10/25![Delta logo]()
$245
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/199:30 pm -
Nonstop1h 35m
Sun 11/222:25 pm -
Nonstop1h 50m
Deal found 10/26![United Airlines logo]()
$240
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/189:37 am -
1 stop4h 11m
Sat 1/97:30 am -
1 stop6h 47m
Deal found 10/25![Delta logo]()
$245
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:49 am -
1 stop6h 15m
Sun 12/1310:59 am -
1 stop3h 57m
Deal found 10/27![Delta logo]()
$246
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:00 am -
1 stop7h 04m
Sun 12/138:05 am -
1 stop4h 59m
Deal found 10/27![Delta logo]()
$246
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Mon 12/2112:14 pm -
Nonstop1h 29m
Fri 12/255:00 am -
Nonstop1h 32m
Deal found 10/28![United Airlines logo]()
$285
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/139:30 pm -
Nonstop1h 35m
Sun 11/152:25 pm -
Nonstop1h 50m
Deal found 10/24![United Airlines logo]()
$297
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/229:30 pm -
Nonstop1h 35m
Sun 11/292:25 pm -
Nonstop1h 50m
Deal found 10/23![United Airlines logo]()
$302
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2411:19 am -
1 stop4h 50m
Mon 11/307:35 am -
1 stop4h 04m
Deal found 10/27![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/207:40 am -
Nonstop1h 33m
Sun 11/229:00 am -
Nonstop1h 40m
Deal found 10/25![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 10/28. 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.
Wed 11/252:44 pm -
1 stop5h 34m
Wed 12/26:00 am -
1 stop7h 24m
Deal found 10/28![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1312:14 pm -
Nonstop1h 27m
Sat 11/145:30 am -
Nonstop1h 29m
Deal found 10/24![United Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 am -
1 stop4h 49m
Tue 11/247:35 am -
1 stop6h 16m
Deal found 10/27![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1012:14 pm -
Nonstop1h 27m
Sat 11/145:30 am -
Nonstop1h 29m
Deal found 10/26![United Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 10/28. 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.
Mon 11/236:00 am -
1 stop4h 49m
Fri 11/277:35 am -
1 stop4h 50m
Deal found 10/28![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/79:30 pm -
Nonstop1h 35m
Wed 11/112:25 pm -
Nonstop1h 50m
Deal found 10/23![United Airlines logo]()
$358
Last-minute flights from Chicago to KentuckyDiscover last-minute flight deals from Chicago to Kentucky. Data last updated October 28, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kentucky. Data last updated October 28, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/712:14 pm -
Nonstop1h 27m
Wed 11/115:30 am -
Nonstop1h 29m
Deal found 10/24![United Airlines logo]()
$194
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:59 am -
Nonstop1h 39m
Mon 11/1610:27 am -
Nonstop1h 45m
Deal found 10/23![United Airlines logo]()
$189
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:40 pm -
Nonstop1h 25m
Mon 11/162:05 pm -
Nonstop1h 20m
Deal found 10/23![Southwest logo]()
$189
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:55 pm -
Nonstop1h 35m
Mon 11/165:57 pm -
Nonstop1h 52m
Deal found 10/24![United Airlines logo]()
$225
This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:08 am -
Nonstop1h 30m
Sun 11/2210:01 am -
Nonstop1h 48m
Deal found 10/27![American Airlines logo]()
$226
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 11/196:10 pm -
Nonstop1h 42m
Mon 11/239:02 am -
Nonstop1h 43m
Deal found 10/28![United Airlines logo]()
$187
This Southwest deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:15 pm -
Nonstop1h 20m
Mon 11/234:40 pm -
Nonstop1h 20m
Deal found 10/27![Southwest logo]()
$187
This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:11 am -
Nonstop1h 32m
Mon 11/236:31 pm -
Nonstop1h 59m
Deal found 10/27![American Airlines logo]()
$188
This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 11/195:30 am -
1 stop5h 26m
Mon 11/2310:49 am -
1 stop6h 29m
Deal found 10/28![Delta logo]()
$207
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/209:30 pm -
Nonstop1h 35m
Sun 11/222:25 pm -
Nonstop1h 50m
Deal found 10/26![United Airlines logo]()
$196
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:40 pm -
Nonstop1h 25m
Mon 11/237:55 pm -
Nonstop1h 15m
Deal found 10/23![Southwest logo]()
$190
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:40 pm -
Nonstop1h 25m
Mon 11/308:35 pm -
Nonstop1h 25m
Deal found 10/23![Southwest logo]()
$217
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 October 28, 2026.
Search for one-way flight options from Chicago to Kentucky. Find affordable one-way fares based on user searches. Data last updated October 28, 2026.
This Southwest deal was found by Cheapflights users on 10/26. 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 11/186:15 pm -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$94
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:59 am -
Nonstop1h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![United Airlines logo]()
$94
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/3010:40 am -
Nonstop1h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![United Airlines logo]()
$95
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/246:15 pm -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Southwest logo]()
$96
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/179:30 pm -
Nonstop1h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![United Airlines logo]()
$98
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:30 am -
1 stop5h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Delta logo]()
$104
This American Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/92:42 pm -
Nonstop1h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![American Airlines logo]()
$110
This Southwest deal was found by Cheapflights users on 10/25. 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.
Sat 11/216:55 pm -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Southwest logo]()
$113
This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/106:54 am -
Nonstop1h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![American Airlines logo]()
$113
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/93:59 pm -
1 stop7h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Delta logo]()
$120
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:29 pm -
1 stop4h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Delta logo]()
$123
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/109:50 am -
1 stop6h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Delta logo]()
$123
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 October 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $187 (Southwest) |
One-way from | $94 (Southwest) |
Popular in | September |
Cheapest in | December |
Average price | $345 |
Good round-trip deal | $281 or less |
Good one-way deal | $149 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 October 28, 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
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Wed 11/18
6:15 pm-8:35 pm
Nonstop1h 20m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$94
ChicagoLouisville
ORD Chicago O'Hare Intl - SDF Louisville Intl
ORDSDF
Chicago O'Hare Intl
Wed 11/18
4:00 pm-6:32 pm
Nonstop1h 32m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$94
ChicagoLouisville
ORD Chicago O'Hare Intl - SDF Louisville Intl
ORDSDF
Chicago O'Hare Intl
Sat 1/30
10:40 am-1:26 pm
Nonstop1h 46m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$95
ChicagoOwensboro
ORD Chicago O'Hare Intl - OWB Owensboro Daviess County
ORDOWB
Chicago O'Hare Intl
Wed 11/18
9:30 pm-11:05 pm
Nonstop1h 35m
Owensboro Daviess County
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$98
ChicagoOwensboro
ORD Chicago O'Hare Intl - OWB Owensboro Daviess County
ORDOWB
Chicago O'Hare Intl
Sat 11/21
9:30 pm-11:05 pm
Nonstop1h 35m
Owensboro Daviess County
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$98
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Wed 11/18
6:00 am-11:56 am
1 stop4h 56m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$104
ChicagoLouisville
ORD Chicago O'Hare Intl - SDF Louisville Intl
ORDSDF
Chicago O'Hare Intl
Thu 11/26
11:18 am-3:59 pm
1 stop3h 41m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$104
ChicagoLouisville
ORD Chicago O'Hare Intl - SDF Louisville Intl
ORDSDF
Chicago O'Hare Intl
Wed 11/18
5:30 am-11:56 am
1 stop5h 26m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$104
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Thu 12/24
1:15 pm-10:15 pm
2 stops8h 00m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$111
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Mon 11/23
7:45 am-10:05 am
Nonstop1h 20m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$113
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-SDF
ORD-SDF
ORD-LEX
ORD-OWB
MDW-LEX
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-SDF
ORD-SDF
ORD-LEX
ORD-OWB
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 $269). 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 October 28, 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 29% versus a flight at noon.
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 $298 and $381 in November.The cheapest round-trip price found within the last 5 days was $187 on Southwest (Nov 19-Nov 23).
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 33 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 October 24, 2026.
Travelers seeking maximum savings on their Chicago to Kentucky flight should consider departing on Wednesday afternoons when fares are most often at their lowest. 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 October 28, 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
7.4
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.4
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.4
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.4
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
7.9
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.4
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
7.9
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 October 28, 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 October 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$89 | Average$159 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$379 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$197 | Average$350 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$206 | Average$411 | FlexibilityNo cancel fee | On-time63% |