$59+ Cheap flights from Kentucky to Illinois
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/8. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — ORD
Aug 17 — Aug 241
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Kentucky to Illinois 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Kentucky to Illinois
Cheapest
Best
Last-minute
One-way
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 July 18, 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 July 18, 2026.
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/116:45 am
BNA
- STL
Nonstop1h 10m
Southwest
Wed 8/127:15 am
STL
- BNA
Nonstop1h 10m
Southwest
Deal found 7/13![Southwest logo]()
$117
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/105:40 am
BNA
- STL
1 stop4h 50m
Southwest
Mon 8/172:20 pm
STL
- BNA
1 stop3h 30m
Southwest
Deal found 7/13![Southwest logo]()
$137
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/85:14 am
BNA
- STL
1 stop4h 06m
Delta
Mon 8/1012:52 pm
STL
- BNA
1 stop4h 04m
Delta
Deal found 7/13![Delta logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 7/239:30 am
BNA
- STL
1 stop3h 51m
Southern / Mokulele
Mon 7/272:00 pm
STL
- BNA
1 stop4h 03m
Southern / Mokulele
Deal found 7/13![Southern / Mokulele logo]()
$171
This Southern / Mokulele deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southern / Mokulele is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:30 am
BNA
- STL
1 stop3h 51m
Southern / Mokulele
Mon 9/72:00 pm
STL
- BNA
1 stop4h 03m
Southern / Mokulele
Deal found 7/13![Southern / Mokulele logo]()
$172
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/104:10 pm
CVG
- MDW
1 stop3h 23m
Delta
Mon 8/171:25 pm
MDW
- CVG
1 stop5h 29m
Delta
Deal found 7/13![Delta logo]()
$177
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 8/48:10 am
CVG
- ORD
1 stop5h 58m
Delta
Wed 8/58:48 am
ORD
- CVG
1 stop3h 54m
Delta
Deal found 7/12![Delta logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:53 pm
CVG
- ORD
1 stop20h 09m
Frontier
Fri 8/141:50 pm
ORD
- CVG
1 stop20h 58m
Frontier
Deal found 7/15![Frontier logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 9/1712:48 pm
CVG
- ORD
1 stop7h 56m
Frontier
Sun 9/202:03 pm
ORD
- CVG
1 stop20h 40m
Frontier
Deal found 7/16![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/207:05 am
CVG
- MDW
2 stops6h 10m
Southwest
Sat 8/225:55 am
MDW
- CVG
1 stop5h 45m
Southwest
Deal found 7/13![Southwest logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2312:48 pm
CVG
- ORD
1 stop24h 14m
Frontier
Wed 10/219:33 pm
ORD
- CVG
1 stop13h 10m
Frontier
Deal found 7/12![Frontier logo]()
$184
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 9/216:00 am
CVG
- MDW
1 stop4h 30m
Southwest
Mon 9/216:10 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 7/16![Southwest logo]()
$186
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 July 18, 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 July 18, 2026.
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/248:50 pm
BNA
- STL
Nonstop1h 15m
Southwest
Thu 8/273:45 pm
STL
- BNA
Nonstop1h 10m
Southwest
Deal found 7/16![Southwest logo]()
$117
This Southern / Mokulele deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southern / Mokulele is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/139:30 am
BNA
- STL
1 stop3h 51m
Southern / Mokulele
Thu 10/152:00 pm
STL
- BNA
1 stop4h 03m
Southern / Mokulele
Deal found 7/15![Southern / Mokulele logo]()
$172
This United Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 8/107:15 am
SDF
- ORD
Nonstop1h 41m
United Airlines
Thu 8/132:00 pm
ORD
- SDF
Nonstop1h 38m
United Airlines
Deal found 7/14![United Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 9/38:50 pm
BNA
- STL
Nonstop1h 15m
Southwest
Mon 9/75:40 pm
STL
- BNA
Nonstop1h 10m
Southwest
Deal found 7/13![Southwest logo]()
$117
This CheapOair deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1111:12 am
BNA
- ORD
1 stop11h 58m
Frontier
Sat 8/155:13 pm
ORD
- BNA
1 stop17h 09m
Frontier
Deal found 7/12![Frontier logo]()
$235
This KAYAK deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/510:52 am
CVG
- ORD
1 stop6h 22m
Delta
Wed 10/78:55 am
ORD
- CVG
1 stop5h 25m
Delta
Deal found 7/14![Delta logo]()
$235
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 8/176:00 pm
BNA
- STL
Nonstop1h 10m
Southwest
Thu 8/205:40 pm
STL
- BNA
Nonstop1h 10m
Southwest
Deal found 7/14![Southwest logo]()
$117
This American Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 9/1711:13 am
LEX
- ORD
Nonstop1h 46m
American Airlines
Sat 9/191:19 pm
ORD
- LEX
1 stop6h 31m
American Airlines
Deal found 7/12![American Airlines logo]()
$259
This Contour deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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.
Fri 7/318:00 am
BNA
- ORD
1 stop3h 30m
Contour
Fri 8/712:30 pm
ORD
- BNA
1 stop3h 40m
Contour
Deal found 7/13![Contour logo]()
$267
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 10/215:45 pm
BNA
- STL
Nonstop1h 15m
Southwest
Mon 10/262:30 pm
STL
- BNA
Nonstop1h 10m
Southwest
Deal found 7/16![Southwest logo]()
$117
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 10/2212:35 pm
BNA
- STL
Nonstop1h 15m
Southwest
Mon 10/265:50 pm
STL
- BNA
Nonstop1h 10m
Southwest
Deal found 7/16![Southwest logo]()
$117
This Southern / Mokulele deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southern / Mokulele is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/299:30 am
BNA
- STL
1 stop3h 51m
Southern / Mokulele
Sun 8/22:00 pm
STL
- BNA
1 stop4h 03m
Southern / Mokulele
Deal found 7/13![Southern / Mokulele logo]()
$172
This Southwest deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 8/126:05 am
BNA
- STL
1 stop3h 30m
Southwest
Wed 8/194:45 pm
STL
- BNA
Nonstop1h 10m
Southwest
Deal found 7/15![Southwest logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 8/133:05 pm
LEX
- MDW
2 stops19h 46m
Multiple Airlines
Sun 8/169:14 am
MDW
- LEX
1 stop21h 59m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$387
This United Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 8/1110:23 am
SDF
- ORD
Nonstop1h 40m
United Airlines
Tue 8/184:30 pm
ORD
- SDF
Nonstop1h 37m
United Airlines
Deal found 7/12![United Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/1112:45 pm
BNA
- STL
1 stop5h 10m
Southwest
Tue 8/186:30 am
STL
- BNA
2 stops5h 40m
Southwest
Deal found 7/16![Southwest logo]()
$142
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/2210:34 am
SDF
- ORD
1 stop6h 43m
Delta
Mon 8/241:59 pm
ORD
- SDF
1 stop6h 20m
Delta
Deal found 7/16![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/235:25 am
CVG
- ORD
Nonstop1h 30m
United Airlines
Wed 10/214:30 pm
ORD
- CVG
Nonstop1h 36m
United Airlines
Deal found 7/14![United Airlines logo]()
$227
This American Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 9/411:57 am
LEX
- ORD
Nonstop1h 47m
American Airlines
Tue 9/88:54 am
ORD
- LEX
1 stop6h 31m
American Airlines
Deal found 7/14![American Airlines logo]()
$259
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 8/115:25 pm
SDF
- ORD
1 stop4h 05m
Delta
Tue 8/181:59 pm
ORD
- SDF
1 stop6h 20m
Delta
Deal found 7/12![Delta logo]()
$237
This Contour deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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.
Fri 7/318:00 am
BNA
- ORD
1 stop3h 30m
Contour
Wed 8/511:15 am
ORD
- BNA
1 stop4h 55m
Contour
Deal found 7/13![Contour logo]()
$267
This Delta deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 8/102:34 pm
SDF
- MDW
1 stop4h 59m
Delta
Thu 8/139:24 am
MDW
- SDF
1 stop3h 27m
Delta
Deal found 7/14![Delta logo]()
$237
This American Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 7/305:35 am
LEX
- ORD
Nonstop1h 35m
American Airlines
Sun 8/29:43 pm
ORD
- LEX
Nonstop1h 30m
American Airlines
Deal found 7/12![American Airlines logo]()
$264
This United Airlines deal was found by Cheapflights users on 7/17. 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.
Mon 8/247:30 am
BNA
- ORD
Nonstop2h 00m
United Airlines
Wed 8/267:45 pm
ORD
- BNA
Nonstop1h 52m
United Airlines
Deal found 7/17![United Airlines logo]()
$247
This Delta deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 8/116:05 am
BNA
- ORD
1 stop4h 37m
Delta
Tue 8/181:50 pm
ORD
- BNA
1 stop5h 01m
Delta
Deal found 7/15![Delta logo]()
$237
This American Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 8/297:04 am
TYS
- ORD
1 stop5h 34m
American Airlines
Sun 8/307:30 am
ORD
- TYS
1 stop4h 07m
American Airlines
Deal found 7/12![American Airlines logo]()
$269
This Southwest deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 9/56:40 am
CVG
- MDW
2 stops7h 40m
Southwest
Wed 9/91:00 pm
MDW
- CVG
2 stops6h 50m
Southwest
Deal found 7/16![Southwest logo]()
$187
This United Airlines deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 9/249:00 am
LEX
- ORD
Nonstop1h 45m
United Airlines
Sun 9/276:50 am
ORD
- LEX
Nonstop1h 38m
United Airlines
Deal found 7/12![United Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 10/55:15 am
BNA
- ORD
1 stop5h 04m
Delta
Mon 10/55:10 pm
ORD
- BNA
1 stop5h 08m
Delta
Deal found 7/13![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/217:00 am
LEX
- ORD
Nonstop1h 45m
United Airlines
Sat 8/229:20 pm
ORD
- LEX
Nonstop1h 35m
United Airlines
Deal found 7/13![United Airlines logo]()
$249
Last-minute flights from Kentucky to IllinoisDiscover last-minute flight deals from Kentucky to Illinois. Data last updated July 18, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Illinois. Data last updated July 18, 2026 and is based on user searches.
This Southern / Mokulele deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southern / Mokulele is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/219:30 am
BNA
- STL
1 stop3h 51m
Southern / Mokulele
Fri 7/242:00 pm
STL
- BNA
1 stop4h 03m
Southern / Mokulele
Deal found 7/13![Southern / Mokulele logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 7/239:30 am
BNA
- STL
1 stop3h 51m
Southern / Mokulele
Mon 7/272:00 pm
STL
- BNA
1 stop4h 03m
Southern / Mokulele
Deal found 7/13![Southern / Mokulele logo]()
$171
This Delta deal was found by Cheapflights users on 7/12. Clicking the “Pick Dates” 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 8/48:10 am
CVG
- ORD
1 stop5h 58m
Delta
Wed 8/58:48 am
ORD
- CVG
1 stop3h 54m
Delta
Deal found 7/12![Delta logo]()
$177
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/85:14 am
BNA
- STL
1 stop4h 06m
Delta
Mon 8/1012:52 pm
STL
- BNA
1 stop4h 04m
Delta
Deal found 7/13![Delta logo]()
$147
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/105:40 am
BNA
- STL
1 stop4h 50m
Southwest
Mon 8/172:20 pm
STL
- BNA
1 stop3h 30m
Southwest
Deal found 7/13![Southwest logo]()
$137
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/104:10 pm
CVG
- MDW
1 stop3h 23m
Delta
Mon 8/171:25 pm
MDW
- CVG
1 stop5h 29m
Delta
Deal found 7/13![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/107:05 am
CVG
- MDW
2 stops9h 20m
Southwest
Mon 8/173:20 pm
MDW
- CVG
1 stop5h 15m
Southwest
Deal found 7/13![Southwest logo]()
$188
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/116:45 am
BNA
- STL
Nonstop1h 10m
Southwest
Wed 8/127:15 am
STL
- BNA
Nonstop1h 10m
Southwest
Deal found 7/13![Southwest logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:53 pm
CVG
- ORD
1 stop20h 09m
Frontier
Fri 8/141:50 pm
ORD
- CVG
1 stop20h 58m
Frontier
Deal found 7/15![Frontier logo]()
$179
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/207:05 am
CVG
- MDW
2 stops6h 10m
Southwest
Sat 8/225:55 am
MDW
- CVG
1 stop5h 45m
Southwest
Deal found 7/13![Southwest logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/2712:26 pm
CVG
- ORD
1 stop8h 33m
Frontier
Sun 8/307:05 am
ORD
- CVG
1 stop27h 16m
Frontier
Deal found 7/16![Frontier logo]()
$187
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/295:50 am
CVG
- MDW
2 stops8h 15m
Southwest
Mon 8/312:35 pm
MDW
- CVG
2 stops6h 45m
Southwest
Deal found 7/13![Southwest logo]()
$187
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 July 18, 2026.
Search for one-way flight options from Kentucky to Illinois. Find affordable one-way fares based on user searches. Data last updated July 18, 2026.
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/87:00 am
BNA
- STL
Nonstop1h 15m
Southwest
Deal found 7/13![Southwest logo]()
$59
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/1312:18 pm
CVG
- ORD
1 stop8h 35m
Frontier
Deal found 7/16![Frontier logo]()
$62
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:26 pm
CVG
- ORD
1 stop8h 42m
Frontier
Deal found 7/17![Frontier logo]()
$63
This Kiwi.com deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1612:48 pm
CVG
- ORD
1 stop24h 14m
Frontier
Deal found 7/15![Frontier logo]()
$64
This Southwest deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 9/113:50 pm
BNA
- STL
1 stop4h 05m
Southwest
Deal found 7/13![Southwest logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” 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 8/2312:26 pm
CVG
- ORD
1 stop8h 33m
Frontier
Deal found 7/15![Frontier logo]()
$72
This Delta deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/136:02 pm
BNA
- STL
1 stop5h 56m
Delta
Deal found 7/13![Delta logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 9/1212:48 pm
CVG
- ORD
1 stop24h 14m
Frontier
Deal found 7/16![Frontier logo]()
$75
This Delta deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” 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 8/85:14 am
BNA
- STL
1 stop4h 06m
Delta
Deal found 7/16![Delta logo]()
$79
This Southwest deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 8/138:10 am
CVG
- MDW
Nonstop1h 05m
Southwest
Deal found 7/14![Southwest logo]()
$79
This United Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” 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 8/67:00 am
CVG
- ORD
Nonstop1h 34m
United Airlines
Deal found 7/14![United Airlines logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” 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 8/149:30 am
BNA
- STL
1 stop3h 51m
Southern / Mokulele
Deal found 7/13![Southern / Mokulele logo]()
$82
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 July 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $117 (Southwest) |
One-way from | $59 (Southwest) |
Popular in | January |
Cheapest in | November |
Average price | $337 |
Good round-trip deal | $163 or less |
Good one-way deal | $206 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 2,558,603 searches. Data last updated July 18, 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
NashvilleSt. Louis
BNA - STL
BNASTL
Nashville Intl
Mon 8/24
8:50 pm-10:05 pm
Nonstop1h 15m
Lambert-St Louis
Thu 8/27
3:45 pm-4:55 pm
Nonstop1h 10m
$117
NashvilleSt. Louis
BNA - STL
BNASTL
Nashville Intl
Thu 9/3
8:50 pm-10:05 pm
Nonstop1h 15m
Lambert-St Louis
Mon 9/7
5:40 pm-6:50 pm
Nonstop1h 10m
$117
Quickest round-trip
NashvilleSt. Louis
BNA - STL
BNASTL
Nashville Intl
Mon 8/17
6:00 pm-7:10 pm
Nonstop1h 10m
Lambert-St Louis
Thu 8/20
5:40 pm-6:50 pm
Nonstop1h 10m
$117
NashvilleSt. Louis
BNA - STL
BNASTL
Nashville Intl
Wed 10/21
5:45 pm-7:00 pm
Nonstop1h 15m
Lambert-St Louis
Mon 10/26
2:30 pm-3:40 pm
Nonstop1h 10m
$117
NashvilleSt. Louis
BNA - STL
BNASTL
Nashville Intl
Thu 10/22
12:35 pm-1:50 pm
Nonstop1h 15m
Lambert-St Louis
Mon 10/26
5:50 pm-7:00 pm
Nonstop1h 10m
$117
NashvilleSt. Louis
BNA - STL
BNASTL
Nashville Intl
Wed 8/12
6:05 am-9:35 am
1 stop3h 30m
Lambert-St Louis
Wed 8/19
4:45 pm-5:55 pm
Nonstop1h 10m
$127
NashvilleSt. Louis
BNA - STL
BNASTL
Nashville Intl
Tue 8/11
12:45 pm-5:55 pm
1 stop5h 10m
Lambert-St Louis
Tue 8/18
6:30 am-12:10 pm
2 stops5h 40m
$142
NashvilleSt. Louis
BNA - STL
BNASTL
Nashville Intl
Tue 10/13
9:30 am-1:21 pm
1 stop3h 51m
Lambert-St Louis
Thu 10/15
2:00 pm-6:03 pm
1 stop4h 03m
$172
NashvilleSt. Louis
BNA - STL
BNASTL
Nashville Intl
Wed 7/29
9:30 am-1:21 pm
1 stop3h 51m
Lambert-St Louis
Sun 8/2
2:00 pm-6:03 pm
1 stop4h 03m
$172
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Sat 9/5
6:40 am-1:20 pm
2 stops7h 40m
Chicago Midway
Wed 9/9
1:00 pm-8:50 pm
2 stops6h 50m
$187
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.
BNA-STL
CVG-MDW
CVG-ORD
BNA-ORD
LEX-MDW
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
BNA-STL
CVG-MDW
CVG-ORD
BNA-ORD
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 $227). 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 July 18, 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 32% 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 July 18, 2026.
The most flights from USKY to USIL are scheduled on a Friday (39 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 on average).
How much does it cost to fly round-trip from Kentucky to Illinois?
How far ahead should I book a flight from Kentucky to Illinois?
The best time to book flights from Kentucky to Illinois is 78 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 July 11, 2026.
Travelers seeking maximum savings on their Kentucky to Illinois 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.
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 July 18, 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.
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
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
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Return Flight Options
Top destinations
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 July 18, 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 2,558,603 searches. Data last updated July 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$77 | Average$266 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$97 | Average$287 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$104 | Average$170 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$285 | FlexibilityNo cancel fee | On-time69% |