$98+ Cheap flights from Kentucky to Illinois
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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — ORD
Oct 22 — Oct 291
Round-trip
1 adult, Economy
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Find cheap flights from Kentucky to Illinois with Cheapflights
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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 Kentucky to IllinoisExplore the most affordable flight options available from Kentucky to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 22, 2026.
Explore the most affordable flight options available from Kentucky to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 22, 2026.
This Booking.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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.
Sun 10/49:00 am -
Nonstop1h 50m
Thu 10/811:30 am -
Nonstop1h 30m
Deal found 9/19![Contour logo]()
$161
This Booking.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/89:00 am -
Nonstop1h 50m
Sun 10/1111:30 am -
Nonstop1h 30m
Deal found 9/17![Contour logo]()
$162
This Contour deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Sat 10/39:00 am -
Nonstop1h 50m
Wed 10/711:30 am -
Nonstop1h 30m
Deal found 9/18![Contour logo]()
$178
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/15:00 am -
Nonstop1h 28m
Mon 10/512:02 pm -
Nonstop1h 30m
Deal found 9/17![United Airlines logo]()
$194
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/62:25 pm -
Nonstop1h 50m
Mon 11/99:30 pm -
Nonstop1h 35m
Deal found 9/18![United Airlines logo]()
$196
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.
Thu 10/227:00 am -
Nonstop1h 40m
Mon 10/267:55 pm -
Nonstop1h 35m
Deal found 9/22![United Airlines logo]()
$197
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 10/157:50 pm -
Nonstop1h 15m
Mon 10/197:55 am -
Nonstop1h 15m
Deal found 9/22![Southwest logo]()
$197
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.
Thu 10/156:29 am -
Nonstop1h 42m
Mon 10/196:55 pm -
Nonstop1h 40m
Deal found 9/20![American Airlines logo]()
$198
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/610:25 am -
Nonstop1h 40m
Wed 10/76:55 am -
Nonstop1h 39m
Deal found 9/17![United Airlines logo]()
$207
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.
Thu 10/2210:25 am -
Nonstop1h 40m
Thu 10/224:30 pm -
Nonstop1h 41m
Deal found 9/22![United Airlines logo]()
$208
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/263:35 pm -
Nonstop1h 15m
Wed 10/283:05 pm -
2 stops7h 00m
Deal found 9/19![Southwest logo]()
$212
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.
Sat 10/175:05 pm -
Nonstop1h 20m
Sat 10/246:45 am -
1 stop7h 10m
Deal found 9/22![Southwest logo]()
$213
Best flights from Kentucky to IllinoisDiscover carefully curated flight deals from Kentucky to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 22, 2026.
Discover carefully curated flight deals from Kentucky to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 22, 2026.
This Contour deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Sat 10/39:00 am -
Nonstop1h 50m
Wed 10/711:30 am -
Nonstop1h 30m
Deal found 9/18![Contour logo]()
$178
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 11/202:25 pm -
Nonstop1h 50m
Sun 11/229:30 pm -
Nonstop1h 35m
Deal found 9/19![United Airlines logo]()
$196
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 11/192:05 pm -
Nonstop1h 20m
Sat 11/217:55 am -
Nonstop1h 20m
Deal found 9/22![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/316:00 am -
1 stop4h 25m
Wed 11/46:20 am -
1 stop4h 37m
Deal found 9/18![Delta logo]()
$217
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 9/307:18 pm -
1 stop4h 39m
Sat 10/36:00 am -
1 stop3h 42m
Deal found 9/19![American Airlines logo]()
$389
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.
Fri 11/62:25 pm -
Nonstop1h 50m
Mon 11/99:30 pm -
Nonstop1h 35m
Deal found 9/20![United Airlines logo]()
$196
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:25 pm -
Nonstop1h 50m
Wed 11/49:30 pm -
Nonstop1h 35m
Deal found 9/21![United Airlines logo]()
$196
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 11/127:59 pm -
1 stop4h 55m
Sat 11/141:30 pm -
1 stop4h 44m
Deal found 9/19![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/247:05 am -
2 stops8h 45m
Sat 10/244:15 pm -
Nonstop1h 15m
Deal found 9/19![Southwest logo]()
$218
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 10/125:38 pm -
1 stop3h 52m
Wed 10/146:30 am -
1 stop5h 24m
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.
Wed 10/283:00 pm -
1 stop6h 40m
Wed 11/41:15 pm -
2 stops8h 00m
Deal found 9/21![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/282:36 pm -
1 stop4h 24m
Sat 10/319:29 am -
1 stop3h 11m
Deal found 9/18![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/265:10 pm -
1 stop5h 50m
Wed 10/287:55 am -
2 stops7h 35m
Deal found 9/19![Southwest logo]()
$222
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.
Wed 10/145:00 am -
Nonstop1h 28m
Mon 11/212:14 pm -
Nonstop1h 27m
Deal found 9/22![United Airlines logo]()
$234
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/312:20 pm -
1 stop4h 40m
Tue 11/39:29 am -
1 stop3h 11m
Deal found 9/18![Delta logo]()
$217
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/29:00 am -
Nonstop1h 50m
Sun 10/411:30 am -
Nonstop1h 30m
Deal found 9/21![Contour logo]()
$293
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/265:10 pm -
1 stop5h 50m
Tue 10/279:40 am -
2 stops9h 55m
Deal found 9/19![Southwest logo]()
$222
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.
Fri 11/134:40 pm -
Nonstop1h 20m
Sat 11/148:00 am -
2 stops7h 25m
Deal found 9/21![Southwest logo]()
$229
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 12/252:05 pm -
Nonstop1h 20m
Fri 12/256:15 pm -
Nonstop1h 15m
Deal found 9/19![Southwest logo]()
$231
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/238:45 am -
Nonstop1h 49m
Sun 12/272:40 pm -
Nonstop1h 40m
Deal found 9/21![United Airlines logo]()
$281
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/295:10 am -
Nonstop1h 45m
Mon 11/26:59 am -
Nonstop1h 39m
Deal found 9/18![United Airlines logo]()
$287
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/311:59 pm -
1 stop4h 48m
Sun 11/16:20 am -
1 stop4h 37m
Deal found 9/18![Delta logo]()
$301
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/277:00 am -
Nonstop1h 45m
Wed 11/46:59 am -
Nonstop1h 39m
Deal found 9/18![United Airlines logo]()
$287
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.
Fri 10/237:50 pm -
Nonstop1h 15m
Tue 10/277:55 am -
2 stops7h 35m
Deal found 9/20![Southwest logo]()
$263
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/246:00 am -
1 stop5h 18m
Mon 10/265:04 pm -
1 stop5h 55m
Deal found 9/19![Delta logo]()
$319
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/275:57 pm -
Nonstop1h 52m
Sat 11/284:00 pm -
Nonstop1h 32m
Deal found 9/21![United Airlines logo]()
$298
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/308:34 am -
2 stops9h 25m
Sun 11/16:02 am -
1 stop5h 41m
Deal found 9/19![American Airlines logo]()
$547
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 12/125:00 pm -
Nonstop1h 20m
Sun 12/1312:50 pm -
Nonstop1h 15m
Deal found 9/18![Southwest logo]()
$281
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.
Fri 12/1112:45 pm -
1 stop7h 20m
Sun 12/138:04 am -
1 stop5h 43m
Deal found 9/21![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/257:10 am -
Nonstop1h 46m
Sat 11/287:40 am -
Nonstop1h 33m
Deal found 9/18![United Airlines logo]()
$299
Last-minute flights from Kentucky to IllinoisDiscover last-minute flight deals from Kentucky to Illinois. Data last updated September 22, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Illinois. Data last updated September 22, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/15:00 am -
Nonstop1h 28m
Mon 10/512:02 pm -
Nonstop1h 30m
Deal found 9/17![United Airlines logo]()
$194
This Contour deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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.
Sat 10/39:00 am -
Nonstop1h 50m
Wed 10/711:30 am -
Nonstop1h 30m
Deal found 9/18![Contour logo]()
$178
This Booking.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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.
Sun 10/49:00 am -
Nonstop1h 50m
Thu 10/811:30 am -
Nonstop1h 30m
Deal found 9/19![Contour logo]()
$161
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/610:25 am -
Nonstop1h 40m
Wed 10/76:55 am -
Nonstop1h 39m
Deal found 9/17![United Airlines logo]()
$207
This Booking.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/89:00 am -
Nonstop1h 50m
Sun 10/1111:30 am -
Nonstop1h 30m
Deal found 9/17![Contour logo]()
$162
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 10/157:50 pm -
Nonstop1h 15m
Mon 10/197:55 am -
Nonstop1h 15m
Deal found 9/22![Southwest logo]()
$197
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.
Thu 10/156:29 am -
Nonstop1h 42m
Mon 10/196:55 pm -
Nonstop1h 40m
Deal found 9/20![American Airlines logo]()
$198
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.
Sat 10/175:05 pm -
Nonstop1h 20m
Sat 10/246:45 am -
1 stop7h 10m
Deal found 9/22![Southwest logo]()
$213
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.
Thu 10/227:00 am -
Nonstop1h 40m
Mon 10/267:55 pm -
Nonstop1h 35m
Deal found 9/22![United Airlines logo]()
$197
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.
Thu 10/2210:25 am -
Nonstop1h 40m
Thu 10/224:30 pm -
Nonstop1h 41m
Deal found 9/22![United Airlines logo]()
$208
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/263:35 pm -
Nonstop1h 15m
Wed 10/283:05 pm -
2 stops7h 00m
Deal found 9/19![Southwest logo]()
$212
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:27 am -
Nonstop1h 45m
Mon 11/26:10 pm -
Nonstop1h 42m
Deal found 9/21![United Airlines logo]()
$214
One-way flights from Kentucky to IllinoisSearch for one-way flight options from Kentucky to Illinois. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
Search for one-way flight options from Kentucky to Illinois. Find affordable one-way fares based on user searches. Data last updated September 22, 2026.
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/36:16 pm -
Nonstop1h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![American Airlines logo]()
$98
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 11/182:25 pm -
Nonstop1h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![United Airlines logo]()
$98
This American Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/2812:46 pm -
Nonstop1h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![American Airlines logo]()
$99
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 10/245:05 pm -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![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.
Thu 10/226:29 am -
Nonstop1h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![American Airlines logo]()
$100
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/610:25 am -
Nonstop1h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![United Airlines logo]()
$104
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 12/167:35 pm -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$104
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 10/285:57 pm -
1 stop7h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$109
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.
Tue 10/205:57 pm -
1 stop5h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Delta logo]()
$109
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” 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 10/196:15 pm -
1 stop6h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Southwest logo]()
$114
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:27 am -
Nonstop1h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![United Airlines logo]()
$116
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.
Fri 10/307:50 pm -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Southwest logo]()
$116
Find flight deals from Kentucky to Illinois
Keep the following information in mind while searching for Kentucky to Illinois flight deals. Data was last updated September 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $161 (Booking.com) |
One-way from | $98 (American Airlines) |
Popular in | January |
Cheapest in | December |
Average price | $374 |
Good round-trip deal | $164 or less |
Good one-way deal | $98 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Kentucky to Illinois 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 22, 2026.
Use the filters below to find and compare flights from Kentucky to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OwensboroChicago
OWB Owensboro Daviess County - ORD Chicago O'Hare Intl
OWBORD
Owensboro Daviess County
Fri 12/4
2:40 pm-4:27 pm
Nonstop1h 47m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$98
Quickest round-trip
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Thu 10/15
3:35 pm-3:50 pm
Nonstop1h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$99
LouisvilleChicago
SDF Louisville Intl - ORD Chicago O'Hare Intl
SDFORD
Louisville Intl
Thu 10/15
9:04 am-9:45 am
Nonstop1h 41m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$99
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Tue 11/3
7:35 pm-7:50 pm
Nonstop1h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$99
LouisvilleChicago
SDF Louisville Intl - ORD Chicago O'Hare Intl
SDFORD
Louisville Intl
Tue 10/6
10:25 am-11:05 am
Nonstop1h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$104
LouisvilleChicago
SDF Louisville Intl - ORD Chicago O'Hare Intl
SDFORD
Louisville Intl
Tue 10/13
7:00 am-7:40 am
Nonstop1h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$104
LouisvilleChicago
SDF Louisville Intl - ORD Chicago O'Hare Intl
SDFORD
Louisville Intl
Wed 11/18
3:00 pm-8:49 pm
1 stop6h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$109
LouisvilleChicago
SDF Louisville Intl - ORD Chicago O'Hare Intl
SDFORD
Louisville Intl
Mon 11/23
5:59 pm-11:54 pm
1 stop6h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$109
LouisvilleChicago
SDF Louisville Intl - ORD Chicago O'Hare Intl
SDFORD
Louisville Intl
Mon 10/19
2:36 pm-8:30 pm
1 stop6h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$109
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Tue 10/20
3:00 pm-10:20 pm
1 stop8h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$109
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Kentucky to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Kentucky with our price prediction graph.
OWB-ORD
PAH-ORD
SDF-ORD
SDF-MDW
SDF-PIA
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 Kentucky to Illinois
USKY-USIL
OWB-ORD
PAH-ORD
SDF-ORD
SDF-MDW
What is the cheapest month to book a flight from Kentucky to Illinois?
Currently, October is the cheapest month in which you can book a flight from Kentucky to Illinois (average of $254). Flying from Kentucky to Illinois in June is currently the most expensive (average of $367). 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 KY to IL?
Find hourly flight availability from Kentucky to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 22, 2026.
A simple way to save on the total cost of your ticket is to fly from Kentucky to Illinois in the morning. If you’re flexible enough to do this you can expect to save up to 36% on your trip compared to booking a flight in the evening.
Weekly flight availability from Kentucky to Illinois
Explore weekly flight availability from Kentucky to Illinois. 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 22, 2026.
The most flights from USKY to USIL are scheduled on a Monday (44 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (11 on average).
How much does it cost to fly round-trip from Kentucky to Illinois?
Airfare is below average for this route at the moment.
Kentucky to Illinois flights typically cost between $266 and $459 in October.The cheapest round-trip price found within the last 5 days was $197 on United Airlines (Oct 22-Oct 26).
How far ahead should I book a flight from Kentucky to Illinois?
The best time to book flights from Kentucky to Illinois is 41 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 Kentucky to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Kentucky to Illinois. Price data was last updated on September 19, 2026.
Travelers seeking maximum savings on their Kentucky to Illinois flight should consider departing on Saturday at noon when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated September 22, 2026.
Read through reviews of airlines operating flights from Kentucky to Illinois, such as Southwest,Contour, andUnited Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Kentucky to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Kentucky to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Kentucky to Illinois by cabin class
Find flights from Kentucky to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Kentucky and Illinois flights
Browse other Kentucky and Illinois flight options. Last updated on September 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Illinois
Find the right flight back to Kentucky after your stay in Illinois
Kentucky to Illinois flights
Consider these flights traveling from Kentucky to Illinois.
Top 4 airlines flying from Kentucky to Illinois
Discover the top 4 airlines that operate flights from Kentucky to Illinois. 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 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$104 | Average$170 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$171 | Average$305 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$178 | Average$326 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$187 | Average$315 | FlexibilityNo cancel fee | On-time63% |