$95+ Cheap flights from Kentucky to Chicago (CHI)
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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — CHI
Nov 24 — Dec 11
Round-trip
1 adult, Economy
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Find cheap flights from Kentucky to Chicago 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 Kentucky to ChicagoExplore the most affordable flight options available from Kentucky to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
Explore the most affordable flight options available from Kentucky to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
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 11/96:31 pm -
Nonstop1h 59m
Thu 11/126:59 pm -
Nonstop1h 37m
Deal found 10/23![American Airlines logo]()
$189
This Southwest deal was found by Cheapflights users on 10/20. 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 11/127:55 pm -
Nonstop1h 15m
Sun 11/1512:50 pm -
Nonstop1h 15m
Deal found 10/20![Southwest logo]()
$191
This United Airlines deal was found by Cheapflights users on 10/22. 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 11/65:30 am -
Nonstop1h 29m
Tue 11/1012:14 pm -
Nonstop1h 27m
Deal found 10/22![United Airlines logo]()
$194
This United Airlines deal was found by Cheapflights users on 10/22. 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 12/302:13 pm -
Nonstop1h 46m
Sat 1/29:23 pm -
Nonstop1h 36m
Deal found 10/22![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.
Tue 11/105:57 pm -
Nonstop1h 52m
Wed 11/117:55 pm -
Nonstop1h 35m
Deal found 10/23![United Airlines logo]()
$205
This Southwest deal was found by Cheapflights users on 10/21. 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 11/108:50 am -
Nonstop1h 15m
Wed 11/111:15 pm -
2 stops8h 00m
Deal found 10/21![Southwest logo]()
$206
This Southwest deal was found by Cheapflights users on 10/22. 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.
Mon 12/73:50 pm -
1 stop7h 55m
Thu 12/108:15 am -
Nonstop1h 15m
Deal found 10/22![Southwest logo]()
$207
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 11/93:14 pm -
1 stop4h 16m
Thu 11/121:30 pm -
1 stop6h 24m
Deal found 10/23![Delta logo]()
$209
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 11/93:14 pm -
1 stop3h 50m
Thu 11/129:30 am -
1 stop3h 54m
Deal found 10/23![Delta logo]()
$209
This Southwest deal was found by Cheapflights users on 10/21. 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 12/43:10 pm -
1 stop7h 20m
Sun 12/67:20 am -
1 stop7h 05m
Deal found 10/21![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 10/20. 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 11/138:45 am -
Nonstop1h 15m
Fri 11/1311:10 am -
2 stops10h 05m
Deal found 10/20![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 10/21. 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 11/105:40 am -
1 stop4h 20m
Tue 11/101:15 pm -
2 stops8h 00m
Deal found 10/21![Southwest logo]()
$216
Best flights from Kentucky to ChicagoDiscover carefully curated flight deals from Kentucky to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
Discover carefully curated flight deals from Kentucky to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
This Southwest deal was found by Cheapflights users on 10/20. 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 11/127:55 pm -
Nonstop1h 15m
Sun 11/1512:50 pm -
Nonstop1h 15m
Deal found 10/20![Southwest logo]()
$191
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 11/75:30 am -
Nonstop1h 29m
Wed 11/1112:14 pm -
Nonstop1h 27m
Deal found 10/23![United Airlines logo]()
$194
This Delta deal was found by Cheapflights users on 10/20. 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 11/255:40 pm -
1 stop3h 37m
Wed 12/28:39 am -
1 stop4h 50m
Deal found 10/20![Delta logo]()
$239
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/63:42 pm -
1 stop18h 36m
Mon 12/75:24 pm -
1 stop16h 10m
Deal found 10/24![Multiple Airlines logo]()
$363
This Southwest deal was found by Cheapflights users on 10/22. 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 11/128:45 am -
Nonstop1h 15m
Thu 11/126:40 pm -
Nonstop1h 25m
Deal found 10/22![Southwest logo]()
$191
This United Airlines deal was found by Cheapflights users on 10/22. 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 11/65:30 am -
Nonstop1h 29m
Tue 11/1012:14 pm -
Nonstop1h 27m
Deal found 10/22![United Airlines logo]()
$194
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Thu 11/122:25 pm -
Nonstop1h 50m
Sun 11/159:30 pm -
Nonstop1h 35m
Deal found 10/21![United Airlines logo]()
$196
This Southwest deal was found by Cheapflights users on 10/19. 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.
Tue 2/168:40 am -
Nonstop1h 30m
Thu 2/187:50 am -
Nonstop1h 25m
Deal found 10/19![Southwest logo]()
$205
This Delta deal was found by Cheapflights users on 10/20. 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.
Sat 12/53:12 pm -
1 stop4h 57m
Sat 12/1210:36 am -
1 stop5h 17m
Deal found 10/20![Delta logo]()
$239
This Delta deal was found by Cheapflights users on 10/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:49 am -
1 stop6h 29m
Sat 11/142:44 pm -
1 stop5h 29m
Deal found 10/22![Delta logo]()
$239
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 12/187:00 am -
Nonstop1h 49m
Mon 12/217:55 pm -
Nonstop1h 44m
Deal found 10/24![United Airlines logo]()
$225
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.
Fri 12/187:15 pm -
1 stop6h 05m
Mon 12/217:10 pm -
Nonstop1h 15m
Deal found 10/24![Southwest logo]()
$235
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.
Tue 11/2410:49 am -
1 stop6h 29m
Thu 11/2611:18 am -
1 stop3h 41m
Deal found 10/23![Delta logo]()
$239
This United Airlines deal was found by Cheapflights users on 10/22. 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 11/117:00 am -
Nonstop1h 45m
Fri 11/136:59 am -
Nonstop1h 39m
Deal found 10/22![United Airlines logo]()
$231
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 11/121:01 pm -
1 stop4h 17m
Sat 11/1410:34 am -
1 stop6h 46m
Deal found 10/23![Delta logo]()
$239
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Wed 11/255:30 am -
Nonstop1h 29m
Sun 11/2912:14 pm -
Nonstop1h 27m
Deal found 10/20![United Airlines logo]()
$234
This Delta deal was found by Cheapflights users on 10/20. 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.
Sat 11/2110:49 am -
1 stop4h 10m
Thu 11/2611:18 am -
1 stop3h 41m
Deal found 10/20![Delta logo]()
$251
This Southwest deal was found by Cheapflights users on 10/20. 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 2/127:55 pm -
Nonstop1h 20m
Mon 2/157:40 am -
Nonstop1h 20m
Deal found 10/20![Southwest logo]()
$280
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.
Thu 12/245:00 am -
Nonstop1h 32m
Fri 1/811:59 am -
Nonstop1h 29m
Deal found 10/24![United Airlines logo]()
$234
This Delta deal was found by Cheapflights users on 10/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:50 am -
1 stop6h 01m
Mon 11/165:13 pm -
1 stop5h 57m
Deal found 10/22![Delta logo]()
$251
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.
Wed 11/45:30 am -
Nonstop1h 29m
Wed 11/1112:14 pm -
Nonstop1h 27m
Deal found 10/24![United Airlines logo]()
$244
This Delta deal was found by Cheapflights users on 10/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:59 pm -
1 stop4h 57m
Thu 12/105:30 am -
1 stop5h 27m
Deal found 10/22![Delta logo]()
$265
This United Airlines deal was found by Cheapflights users on 10/22. 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 12/27:10 am -
Nonstop1h 45m
Sun 12/66:20 pm -
Nonstop1h 40m
Deal found 10/22![United Airlines logo]()
$245
This Delta deal was found by Cheapflights users on 10/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/31:04 pm -
1 stop5h 02m
Sun 12/68:39 am -
1 stop4h 50m
Deal found 10/22![Delta logo]()
$265
This Delta deal was found by Cheapflights users on 10/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:05 am -
1 stop5h 54m
Sun 11/159:30 am -
1 stop3h 54m
Deal found 10/22![Delta logo]()
$265
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.
Tue 1/510:20 am -
Nonstop1h 49m
Sat 1/91:55 pm -
Nonstop1h 40m
Deal found 10/23![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 10/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:59 pm -
1 stop5h 55m
Mon 11/235:29 pm -
1 stop4h 17m
Deal found 10/22![Delta logo]()
$265
This United Airlines deal was found by Cheapflights users on 10/20. 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 11/135:10 am -
Nonstop1h 45m
Fri 11/137:55 pm -
Nonstop1h 35m
Deal found 10/20![United Airlines logo]()
$281
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.
Sun 11/2210:33 am -
1 stop6h 45m
Tue 12/111:39 am -
1 stop4h 40m
Deal found 10/24![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 10/21. 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 11/62:25 pm -
Nonstop1h 50m
Tue 11/109:30 pm -
Nonstop1h 35m
Deal found 10/21![United Airlines logo]()
$358
Last-minute flights from Kentucky to ChicagoDiscover last-minute flight deals from Kentucky to Chicago. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Chicago. Data last updated October 25, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/22. 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 11/65:30 am -
Nonstop1h 29m
Tue 11/1012:14 pm -
Nonstop1h 27m
Deal found 10/22![United Airlines logo]()
$194
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 11/96:31 pm -
Nonstop1h 59m
Thu 11/126:59 pm -
Nonstop1h 37m
Deal found 10/23![American Airlines logo]()
$189
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 11/93:14 pm -
1 stop4h 16m
Thu 11/121:30 pm -
1 stop6h 24m
Deal found 10/23![Delta logo]()
$209
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 11/93:14 pm -
1 stop3h 50m
Thu 11/129:30 am -
1 stop3h 54m
Deal found 10/23![Delta logo]()
$209
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.
Tue 11/105:57 pm -
Nonstop1h 52m
Wed 11/117:55 pm -
Nonstop1h 35m
Deal found 10/23![United Airlines logo]()
$205
This Southwest deal was found by Cheapflights users on 10/21. 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 11/108:50 am -
Nonstop1h 15m
Wed 11/111:15 pm -
2 stops8h 00m
Deal found 10/21![Southwest logo]()
$206
This Southwest deal was found by Cheapflights users on 10/20. 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 11/127:55 pm -
Nonstop1h 15m
Sun 11/1512:50 pm -
Nonstop1h 15m
Deal found 10/20![Southwest logo]()
$191
This United Airlines deal was found by Cheapflights users on 10/21. 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.
Thu 11/122:25 pm -
Nonstop1h 50m
Sun 11/159:30 pm -
Nonstop1h 35m
Deal found 10/21![United Airlines logo]()
$196
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/126:27 am -
Nonstop1h 48m
Sat 11/146:59 pm -
Nonstop1h 37m
Deal found 10/21![American Airlines logo]()
$219
This Southwest deal was found by Cheapflights users on 10/20. 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 11/138:45 am -
Nonstop1h 15m
Fri 11/1311:10 am -
2 stops10h 05m
Deal found 10/20![Southwest logo]()
$212
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 11/137:00 am -
Nonstop1h 45m
Sun 11/152:30 pm -
Nonstop1h 32m
Deal found 10/23![United Airlines logo]()
$230
This American Airlines deal was found by Cheapflights users on 10/22. 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 11/216:24 am -
Nonstop1h 51m
Mon 11/232:42 pm -
Nonstop1h 31m
Deal found 10/22![American Airlines logo]()
$228
One-way flights from Kentucky to ChicagoSearch for one-way flight options from Kentucky to Chicago. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
Search for one-way flight options from Kentucky to Chicago. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
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.
Fri 12/255:45 am -
Nonstop1h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![American Airlines logo]()
$95
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.
Wed 11/182:05 pm -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Southwest logo]()
$95
This Southwest deal was found by Cheapflights users on 10/21. 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 11/107:35 pm -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Southwest logo]()
$96
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 12/32:40 pm -
Nonstop1h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![United Airlines logo]()
$98
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 11/163:00 pm -
1 stop6h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Delta logo]()
$105
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 11/163:14 pm -
1 stop3h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Delta logo]()
$105
This American Airlines deal was found by Cheapflights users on 10/21. 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 1/181:11 pm -
Nonstop1h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$110
This Southwest deal was found by Cheapflights users on 10/22. 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.
Sun 12/612:05 pm -
2 stops9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$111
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.
Sat 1/912:53 pm -
1 stop4h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Delta logo]()
$113
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.
Fri 12/114:40 pm -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Southwest logo]()
$113
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.
Fri 12/257:20 am -
2 stops9h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Southwest logo]()
$117
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2510:49 am -
1 stop4h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Delta logo]()
$118
Find flight deals from Kentucky to Chicago
Keep the following information in mind while searching for Kentucky to Chicago flight deals. Data was last updated October 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $189 (American Airlines) |
One-way from | $95 (American Airlines) |
Popular in | August |
Cheapest in | January |
Average price | $291 |
Good round-trip deal | $196 or less |
Good one-way deal | $213 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Kentucky to Chicago 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 25, 2026.
Use the filters below to find and compare flights from Kentucky to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Fri 12/25
2:05 pm-2:25 pm
Nonstop1h 20m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$96
Quickest round-trip
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Tue 11/10
7:35 pm-7:50 pm
Nonstop1h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$96
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Thu 11/12
8:45 am-9:00 am
Nonstop1h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$96
OwensboroChicago
OWB Owensboro Daviess County - ORD Chicago O'Hare Intl
OWBORD
Owensboro Daviess County
Fri 1/15
2:37 pm-4:23 pm
Nonstop1h 46m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$98
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Thu 11/19
6:00 am-11:59 am
1 stop6h 59m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$105
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Sat 12/5
12:45 pm-3:35 pm
1 stop3h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$106
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Thu 11/26
7:15 am-2:30 pm
1 stop8h 15m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$106
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Sun 12/6
12:05 pm-8:05 pm
2 stops9h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$111
LouisvilleChicago
SDF Louisville Intl - ORD Chicago O'Hare Intl
SDFORD
Louisville Intl
Wed 11/18
5:10 am-5:55 am
Nonstop1h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$113
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Sat 1/9
7:20 am-12:33 pm
1 stop6h 13m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$113
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Kentucky to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Kentucky with our price prediction graph.
SDF-ORD
SDF-MDW
PAH-ORD
OWB-ORD
LEX-ORD
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 Chicago
USKY-CHI
SDF-ORD
SDF-MDW
PAH-ORD
OWB-ORD
What is the cheapest month to book a flight from Kentucky to Chicago?
Currently, March is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $277). Flying from Kentucky to Chicago 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 CHI?
Find hourly flight availability from Kentucky to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 25, 2026.
One of the essential ways to save on airfare from Kentucky to Chicago is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 40% on airfare.
Weekly flight availability from Kentucky to Chicago
Explore weekly flight availability from Kentucky to Chicago. 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 October 25, 2026.
The most flights from USKY to CHI are scheduled on a Friday (48 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (9 on average).
How much does it cost to fly round-trip from Kentucky to Chicago?
Airfare is below average for this route at the moment.
Kentucky to Chicago flights typically cost between $274 and $362 in November.The cheapest round-trip price found within the last 5 days was $189 on American Airlines (Nov 9-Nov 12).
How far ahead should I book a flight from Kentucky to Chicago?
To ensure you get the cheapest price possible for a flight from Kentucky to Chicago, you should look to book at least 39 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 Kentucky to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Kentucky to Chicago. Price data was last updated on October 24, 2026.
Travelers seeking maximum savings on their Kentucky to Chicago flight should consider departing on Sunday mornings when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Kentucky to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Kentucky to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 25, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Kentucky to Chicago by cabin class
Find flights from Kentucky to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Kentucky and Chicago flights
Browse other Kentucky and Chicago flight options. Last updated on October 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Kentucky to Chicago flights
Consider these flights traveling from Kentucky to Chicago.
Top 4 airlines flying from Kentucky to Chicago
Discover the top 4 airlines that operate flights from Kentucky to Chicago. 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 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$100 | Average$170 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$178 | Average$340 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$187 | Average$325 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$204 | Average$317 | FlexibilityNo cancel fee | On-time71% |