$73+ Cheap flights from Illinois 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SDF
Oct 25 — Nov 11
Round-trip
1 adult, Economy
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Find cheap flights from Illinois to Kentucky with Cheapflights
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Cheapest flights from Illinois to KentuckyExplore the most affordable flight options available from Illinois to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 25, 2026.
Explore the most affordable flight options available from Illinois to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 25, 2026.
This Booking.com deal was found by Cheapflights users on 9/24. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:30 am -
Nonstop1h 30m
Mon 10/129:00 am -
Nonstop1h 50m
Deal found 9/24![Contour logo]()
$157
This Booking.com deal was found by Cheapflights users on 9/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/711:30 am -
Nonstop1h 30m
Sun 10/119:00 am -
Nonstop1h 50m
Deal found 9/23![Contour logo]()
$158
This United Airlines deal was found by Cheapflights users on 9/24. 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 10/912:02 pm -
Nonstop1h 30m
Tue 10/135:00 am -
Nonstop1h 28m
Deal found 9/24![United Airlines logo]()
$194
This American Airlines deal was found by Cheapflights users on 9/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:00 pm -
Nonstop1h 37m
Mon 11/166:27 am -
Nonstop1h 48m
Deal found 9/25![American Airlines logo]()
$196
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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
Tue 10/132:05 pm -
Nonstop1h 15m
Deal found 9/21![Southwest logo]()
$197
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/196:59 am -
Nonstop1h 33m
Mon 10/265:35 pm -
Nonstop1h 55m
Deal found 9/21![American Airlines logo]()
$197
This American Airlines deal was found by Cheapflights users on 9/23. 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 11/167:08 am -
Nonstop1h 30m
Thu 11/196:30 pm -
Nonstop1h 59m
Deal found 9/23![American Airlines logo]()
$198
This Southwest deal was found by Cheapflights users on 9/23. 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 11/57:45 am -
Nonstop1h 20m
Tue 11/107:20 am -
2 stops8h 10m
Deal found 9/23![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/246:45 am -
1 stop7h 10m
Sat 10/245:05 pm -
Nonstop1h 20m
Deal found 9/21![Southwest logo]()
$213
This Southwest deal was found by Cheapflights users on 9/23. 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 10/157:55 am -
Nonstop1h 15m
Mon 10/193:35 pm -
Nonstop1h 15m
Deal found 9/23![Southwest logo]()
$214
This United Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/209:25 pm -
Nonstop1h 34m
Fri 10/235:15 am -
Nonstop1h 41m
Deal found 9/23![United Airlines logo]()
$214
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/125:31 pm -
1 stop4h 20m
Tue 10/132:36 pm -
1 stop4h 24m
Deal found 9/21![Delta logo]()
$217
Best flights from Illinois to KentuckyDiscover carefully curated flight deals from Illinois to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 25, 2026.
Discover carefully curated flight deals from Illinois to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 25, 2026.
This Booking.com deal was found by Cheapflights users on 9/24. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:30 am -
Nonstop1h 30m
Mon 10/129:00 am -
Nonstop1h 50m
Deal found 9/24![Contour logo]()
$157
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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
Tue 10/132:05 pm -
Nonstop1h 15m
Deal found 9/21![Southwest logo]()
$197
This United Airlines deal was found by Cheapflights users on 9/24. 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.
Wed 10/215:50 pm -
Nonstop1h 41m
Fri 10/235:15 am -
Nonstop1h 41m
Deal found 9/24![United Airlines logo]()
$214
This Delta deal was found by Cheapflights users on 9/24. 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 11/96:15 pm -
1 stop4h 55m
Thu 11/127:50 am -
1 stop3h 49m
Deal found 9/24![Delta logo]()
$217
This American Airlines deal was found by Cheapflights users on 9/24. 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 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 9/24![American Airlines logo]()
$299
This Booking.com deal was found by Cheapflights users on 9/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/711:30 am -
Nonstop1h 30m
Sun 10/119:00 am -
Nonstop1h 50m
Deal found 9/23![Contour logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/33:50 pm -
2 stops27h 30m
Sat 10/109:00 am -
Nonstop1h 50m
Deal found 9/20![Multiple Airlines logo]()
$372
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/207:50 am -
Nonstop1h 15m
Tue 10/207:10 pm -
Nonstop1h 15m
Deal found 9/21![Southwest logo]()
$214
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/146:30 am -
1 stop5h 24m
Tue 11/36:00 am -
1 stop4h 25m
Deal found 9/20![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/612:02 pm -
Nonstop1h 30m
Sun 10/115:00 am -
Nonstop1h 28m
Deal found 9/20![United Airlines logo]()
$234
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:45 am -
Nonstop1h 20m
Fri 11/67:55 pm -
Nonstop1h 15m
Deal found 9/22![Southwest logo]()
$214
This Booking.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/511:30 am -
Nonstop1h 30m
Fri 10/99:00 am -
Nonstop1h 50m
Deal found 9/20![Contour logo]()
$219
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/269:30 pm -
Nonstop1h 35m
Thu 10/292:25 pm -
Nonstop1h 50m
Deal found 9/20![United Airlines logo]()
$236
This Gotogate deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:30 am -
Nonstop1h 30m
Sat 10/109:00 am -
Nonstop1h 50m
Deal found 9/21![Contour logo]()
$247
This American Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/198:05 am -
Nonstop1h 36m
Sun 1/175:10 am -
Nonstop1h 50m
Deal found 9/23![American Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/156:55 pm -
Nonstop1h 15m
Mon 10/193:35 pm -
Nonstop1h 15m
Deal found 9/20![Southwest logo]()
$248
This Delta deal was found by Cheapflights users on 9/23. 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.
Sun 11/15:27 am -
1 stop6h 27m
Wed 11/412:40 pm -
1 stop5h 00m
Deal found 9/23![Delta logo]()
$301
This United Airlines deal was found by Cheapflights users on 9/24. 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 11/144:00 pm -
Nonstop1h 32m
Sun 11/157:00 am -
Nonstop1h 45m
Deal found 9/24![United Airlines logo]()
$281
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 11/195:00 am -
1 stop6h 43m
Mon 11/236:31 pm -
1 stop6h 36m
Deal found 9/21![American Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 9/24. 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 10/249:25 pm -
Nonstop1h 34m
Sun 10/255:10 am -
Nonstop1h 45m
Deal found 9/24![United Airlines logo]()
$281
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/258:29 am -
1 stop4h 24m
Fri 10/305:57 pm -
1 stop7h 00m
Deal found 9/20![Delta logo]()
$318
This Southwest deal was found by Cheapflights users on 9/24. 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.
Sat 10/244:15 pm -
Nonstop1h 15m
Sun 10/258:00 pm -
1 stop4h 40m
Deal found 9/24![Southwest logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:30 am -
Nonstop1h 30m
Mon 10/121:55 pm -
2 stops29h 12m
Deal found 9/23![Multiple Airlines logo]()
$390
This Delta deal was found by Cheapflights users on 9/24. 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.
Fri 11/66:30 am -
1 stop4h 18m
Sun 11/87:45 am -
1 stop3h 44m
Deal found 9/24![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 9/23. 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 10/197:55 am -
Nonstop1h 15m
Thu 10/225:35 am -
1 stop4h 10m
Deal found 9/23![Southwest logo]()
$294
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:20 pm -
Nonstop1h 35m
Mon 10/196:00 am -
Nonstop1h 45m
Deal found 9/22![United Airlines logo]()
$299
This Booking.com deal was found by Cheapflights users on 9/24. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:30 am -
Nonstop1h 30m
Mon 10/59:00 am -
Nonstop1h 50m
Deal found 9/24![Contour logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/298:59 am -
2 stops48h 12m
Thu 11/58:31 pm -
1 stop21h 15m
Deal found 9/20![Multiple Airlines logo]()
$417
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/295:27 am -
1 stop5h 31m
Tue 11/312:04 pm -
1 stop5h 28m
Deal found 9/20![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:00 am -
1 stop3h 32m
Wed 10/1410:16 am -
1 stop4h 41m
Deal found 9/24![American Airlines logo]()
$394
Last-minute flights from Illinois to KentuckyDiscover last-minute flight deals from Illinois to Kentucky. Data last updated September 25, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Kentucky. Data last updated September 25, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 9/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/711:30 am -
Nonstop1h 30m
Sun 10/119:00 am -
Nonstop1h 50m
Deal found 9/23![Contour logo]()
$158
This Booking.com deal was found by Cheapflights users on 9/24. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:30 am -
Nonstop1h 30m
Mon 10/129:00 am -
Nonstop1h 50m
Deal found 9/24![Contour logo]()
$157
This United Airlines deal was found by Cheapflights users on 9/24. 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 10/912:02 pm -
Nonstop1h 30m
Tue 10/135:00 am -
Nonstop1h 28m
Deal found 9/24![United Airlines logo]()
$194
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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
Tue 10/132:05 pm -
Nonstop1h 15m
Deal found 9/21![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/125:31 pm -
1 stop4h 20m
Tue 10/132:36 pm -
1 stop4h 24m
Deal found 9/21![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 9/23. 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 10/157:55 am -
Nonstop1h 15m
Mon 10/193:35 pm -
Nonstop1h 15m
Deal found 9/23![Southwest logo]()
$214
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 10/158:29 am -
1 stop4h 24m
Mon 10/195:38 pm -
1 stop3h 52m
Deal found 9/20![Delta logo]()
$218
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/196:59 am -
Nonstop1h 33m
Mon 10/265:35 pm -
Nonstop1h 55m
Deal found 9/21![American Airlines logo]()
$197
This United Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/209:25 pm -
Nonstop1h 34m
Fri 10/235:15 am -
Nonstop1h 41m
Deal found 9/23![United Airlines logo]()
$214
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/216:30 am -
1 stop5h 24m
Wed 10/215:38 pm -
1 stop3h 52m
Deal found 9/21![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/246:45 am -
1 stop7h 10m
Sat 10/245:05 pm -
Nonstop1h 20m
Deal found 9/21![Southwest logo]()
$213
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” 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 10/277:55 am -
2 stops7h 35m
Tue 10/277:10 pm -
Nonstop1h 15m
Deal found 9/21![Southwest logo]()
$212
One-way flights from Illinois to KentuckySearch for one-way flight options from Illinois to Kentucky. Find affordable one-way fares based on user searches. Data last updated September 25, 2026.
Search for one-way flight options from Illinois to Kentucky. Find affordable one-way fares based on user searches. Data last updated September 25, 2026.
This Booking.com deal was found by Cheapflights users on 9/24. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/911:30 am -
Nonstop1h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Contour logo]()
$73
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:50 am -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Southwest logo]()
$99
This American Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:28 pm -
Nonstop1h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![American Airlines logo]()
$99
This American Airlines deal was found by Cheapflights users on 9/23. 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.
Wed 10/216:59 am -
Nonstop1h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![American Airlines logo]()
$100
This Delta deal was found by Cheapflights users on 9/23. 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.
Wed 10/217:00 am -
1 stop5h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Delta logo]()
$109
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/292:30 pm -
1 stop7h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$114
This Southwest deal was found by Cheapflights users on 9/23. 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.
Fri 10/236:55 pm -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Southwest logo]()
$116
This United Airlines deal was found by Cheapflights users on 9/24. 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 10/234:30 pm -
Nonstop1h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![United Airlines logo]()
$116
This Southwest deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:10 pm -
1 stop5h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$126
This Delta deal was found by Cheapflights users on 9/23. 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.
Fri 10/237:00 am -
1 stop5h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Delta logo]()
$126
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/267:40 am -
2 stops7h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Southwest logo]()
$131
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” 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 11/213:00 pm -
Nonstop1h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![American Airlines logo]()
$144
Find flight deals from Illinois to Kentucky
Keep the following information in mind while searching for Illinois to Kentucky flight deals. Data was last updated September 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $157 (Booking.com) |
One-way from | $73 (Booking.com) |
Popular in | September |
Cheapest in | December |
Average price | $515 |
Good round-trip deal | $129 or less |
Good one-way deal | $134 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois 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 25, 2026.
Use the filters below to find and compare flights from Illinois to Kentucky that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Thu 10/29
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
Wed 11/4
6:10 pm-8:52 pm
Nonstop1h 42m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$99
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Mon 10/19
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
Sat 10/24
4:30 pm-7:11 pm
Nonstop1h 41m
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 10/21
7:50 am-10:05 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
Thu 10/15
9:29 am-1:53 pm
1 stop3h 24m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$109
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
$109
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Wed 10/21
6:04 am-12:54 pm
1 stop5h 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
Sat 10/24
5:31 pm-10:51 pm
1 stop4h 20m
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 11/17
5:13 pm-11:13 pm
1 stop5h 00m
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 Illinois to Kentucky
Have a flexible travel schedule? Discover the best time to fly to Kentucky from Illinois with our price prediction graph.
MDW-SDF
ORD-SDF
ORD-OWB
PIA-SDF
PIA-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 Illinois to Kentucky
USIL-USKY
MDW-SDF
ORD-SDF
ORD-OWB
PIA-SDF
What is the cheapest month to book a flight from Illinois to Kentucky?
Currently, December is the cheapest month in which you can book a flight from Illinois to Kentucky (average of $272). Flying from Illinois to Kentucky in June is currently the most expensive (average of $478). 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 IL to KY?
Find hourly flight availability from Illinois 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 25, 2026.
It’s optimal to fly from Illinois to Kentucky in the morning. By choosing this option you can save up to 36% on the cost of your flight, compared to a flight in the evening.
Weekly flight availability from Illinois to Kentucky
Explore weekly flight availability from Illinois 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 25, 2026.
The most flights from USIL to USKY are scheduled on a Thursday (39 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (31 on average).
How much does it cost to fly round-trip from Illinois to Kentucky?
Airfare is below average for this route at the moment.
Illinois to Kentucky flights typically cost between $287 and $498 in November.The cheapest round-trip price found within the last 5 days was $196 on American Airlines (Nov 9-Nov 16).
How far ahead should I book a flight from Illinois to Kentucky?
The best time to book flights from Illinois to Kentucky is 33 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Illinois to Kentucky?
Use this chart to determine the cheapest time to fly round-trip from Illinois to Kentucky. Price data was last updated on September 19, 2026.
Travelers seeking maximum savings on their Illinois to Kentucky flight should consider departing on Saturday at noon 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 25, 2026.
Peruse reviews from past customers who have flown with Southwest,Contour, andUnited Airlines from Illinois to Kentucky to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Food
7.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
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 Illinois 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 Illinois 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 Illinois to Kentucky by cabin class
Find flights from Illinois to Kentucky, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Illinois and Kentucky flights
Browse other Illinois and Kentucky flight options. Last updated on September 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Kentucky
Find the right flight back to Illinois after your stay in Kentucky
Illinois to Kentucky flights
Consider these flights traveling from Illinois to Kentucky.
Top 4 airlines flying from Illinois to Kentucky
Discover the top 4 airlines that operate flights from Illinois 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 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$89 | Average$158 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$143 | Average$382 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$189 | Average$349 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$206 | Average$411 | FlexibilityNo cancel fee | On-time63% |