$49+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — ORD
May 29 — Jun 51
Round-trip
1 adult, Economy
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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 April 29, 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 April 29, 2026.
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 pm
BNA
- STL
Nonstop1h 15m
Southwest
Wed 6/36:40 pm
STL
- BNA
Nonstop1h 10m
Southwest
Deal found 4/28![Southwest logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/282:35 pm
BNA
- STL
1 stop4h 01m
Southern / Mokulele
Thu 4/309:50 am
STL
- BNA
1 stop3h 58m
Southern / Mokulele
Deal found 4/27![Southern / Mokulele logo]()
$171
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/187:40 pm
BNA
- STL
1 stop4h 19m
Delta
Wed 5/207:05 am
STL
- BNA
1 stop4h 32m
Delta
Deal found 4/26![Delta logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/292:35 pm
BNA
- STL
1 stop4h 01m
Multiple Airlines
Tue 6/24:19 pm
STL
- BNA
1 stop24h 05m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$188
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/235:55 pm
BNA
- STL
Nonstop1h 15m
Southwest
Mon 5/259:55 am
STL
- BNA
Nonstop1h 10m
Southwest
Deal found 4/29![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/218:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Mon 5/257:00 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 4/27![Southwest logo]()
$191
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:00 am
CVG
- ORD
Nonstop1h 34m
American Airlines
Mon 5/253:27 pm
ORD
- CVG
Nonstop1h 29m
American Airlines
Deal found 4/27![American Airlines logo]()
$191
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2112:06 pm
CVG
- ORD
Nonstop1h 31m
American Airlines
Mon 5/256:48 pm
ORD
- CVG
Nonstop1h 34m
American Airlines
Deal found 4/28![American Airlines logo]()
$192
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/203:00 pm
CVG
- MDW
1 stop7h 09m
Delta
Thu 5/216:23 am
MDW
- CVG
1 stop5h 30m
Delta
Deal found 4/29![Delta logo]()
$194
This Delta deal was found by Cheapflights users on 4/24. 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 5/188:16 pm
CVG
- ORD
1 stop4h 43m
Delta
Tue 5/195:30 am
ORD
- CVG
1 stop4h 17m
Delta
Deal found 4/24![Delta logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/12:12 pm
CVG
- ORD
2 stops30h 39m
Frontier
Tue 6/301:50 pm
ORD
- CVG
1 stop20h 59m
Frontier
Deal found 4/26![Frontier logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:46 pm
CVG
- ORD
1 stop7h 55m
Frontier
Wed 6/36:55 am
ORD
- CVG
2 stops12h 40m
Frontier
Deal found 4/27![Frontier logo]()
$196
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 April 29, 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 April 29, 2026.
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/258:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Mon 6/17:00 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 4/25![Southwest logo]()
$191
This Delta deal was found by Cheapflights users on 4/24. 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 5/188:16 pm
CVG
- ORD
1 stop4h 43m
Delta
Tue 5/195:30 am
ORD
- CVG
1 stop4h 17m
Delta
Deal found 4/24![Delta logo]()
$194
This Southern / Mokulele deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southern / Mokulele is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/292:35 pm
BNA
- STL
1 stop4h 01m
Southern / Mokulele
Tue 6/307:20 pm
STL
- BNA
1 stop13h 43m
Southern / Mokulele
Deal found 4/26![Southern / Mokulele logo]()
$212
This Contour deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:00 am
BNA
- ORD
1 stop3h 30m
Contour
Sun 6/712:20 pm
ORD
- BNA
1 stop3h 50m
Contour
Deal found 4/25![Contour logo]()
$217
This United Airlines deal was found by Cheapflights users on 4/24. 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 6/2610:53 am
TRI
- ORD
Nonstop2h 02m
United Airlines
Sun 6/287:25 am
ORD
- TRI
Nonstop1h 53m
United Airlines
Deal found 4/24![United Airlines logo]()
$229
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/27:54 am
TRI
- ORD
Nonstop2h 11m
American Airlines
Sun 7/59:25 pm
ORD
- TRI
Nonstop1h 50m
American Airlines
Deal found 4/26![American Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:00 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Sat 5/309:10 am
MDW
- CVG
1 stop3h 50m
Southwest
Deal found 4/25![Southwest logo]()
$201
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/253:54 pm
CVG
- MDW
1 stop3h 39m
Delta
Mon 6/16:23 am
MDW
- CVG
1 stop5h 30m
Delta
Deal found 4/25![Delta logo]()
$211
This Contour deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/78:00 am
BNA
- ORD
1 stop3h 30m
Contour
Mon 8/1012:30 pm
ORD
- BNA
1 stop3h 40m
Contour
Deal found 4/26![Contour logo]()
$217
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/156:00 am
TRI
- ORD
Nonstop2h 02m
United Airlines
Mon 6/229:15 pm
ORD
- TRI
Nonstop1h 49m
United Airlines
Deal found 4/28![United Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 4/24. 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 5/255:48 am
CVG
- ORD
1 stop5h 28m
Delta
Mon 6/15:30 am
ORD
- CVG
1 stop6h 23m
Delta
Deal found 4/24![Delta logo]()
$211
This Contour deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/168:00 am
BNA
- ORD
1 stop3h 30m
Contour
Sun 7/1912:20 pm
ORD
- BNA
1 stop3h 50m
Contour
Deal found 4/25![Contour logo]()
$217
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/188:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Tue 5/197:50 am
MDW
- CVG
2 stops8h 15m
Southwest
Deal found 4/27![Southwest logo]()
$224
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:27 pm
TRI
- ORD
1 stop4h 31m
American Airlines
Tue 6/99:23 pm
ORD
- TRI
Nonstop1h 50m
American Airlines
Deal found 4/24![American Airlines logo]()
$249
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:00 am
TRI
- ORD
Nonstop2h 04m
United Airlines
Sat 8/227:27 am
ORD
- TRI
Nonstop1h 53m
United Airlines
Deal found 4/27![United Airlines logo]()
$229
This Contour deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/228:00 am
BNA
- ORD
1 stop3h 30m
Contour
Fri 6/2612:20 pm
ORD
- BNA
1 stop3h 50m
Contour
Deal found 4/25![Contour logo]()
$217
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:00 am
TRI
- ORD
Nonstop2h 02m
United Airlines
Tue 8/112:18 pm
ORD
- TRI
Nonstop1h 52m
United Airlines
Deal found 4/27![United Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/298:15 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Sat 5/303:40 pm
MDW
- CVG
Nonstop1h 05m
Southwest
Deal found 4/28![Southwest logo]()
$232
This Contour deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Sun 8/212:30 pm
ORD
- BNA
1 stop3h 40m
Contour
Deal found 4/26![Contour logo]()
$217
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/3011:00 am
CVG
- ORD
1 stop7h 02m
Delta
Tue 7/72:07 pm
ORD
- CVG
2 stops9h 32m
Delta
Deal found 4/28![Delta logo]()
$240
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/292:15 pm
BNA
- STL
1 stop4h 40m
Southwest
Tue 6/22:30 pm
STL
- BNA
Nonstop1h 10m
Southwest
Deal found 4/28![Southwest logo]()
$233
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/191:08 pm
LEX
- ORD
1 stop5h 34m
American Airlines
Sun 6/213:43 pm
ORD
- LEX
Nonstop1h 35m
American Airlines
Deal found 4/24![American Airlines logo]()
$289
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/2511:17 am
CVG
- ORD
Nonstop1h 36m
United Airlines
Tue 5/2612:46 pm
ORD
- CVG
Nonstop1h 30m
United Airlines
Deal found 4/27![United Airlines logo]()
$244
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:41 pm
TRI
- ORD
1 stop5h 18m
Delta
Wed 6/38:10 am
ORD
- TRI
1 stop5h 50m
Delta
Deal found 4/27![Delta logo]()
$249
This KAYAK deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:58 am
BNA
- ORD
Nonstop2h 11m
American Airlines
Wed 5/273:21 pm
ORD
- BNA
1 stop7h 17m
American Airlines
Deal found 4/28![American Airlines logo]()
$300
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:00 am
LEX
- ORD
Nonstop1h 45m
United Airlines
Sat 8/292:15 pm
ORD
- LEX
Nonstop1h 39m
United Airlines
Deal found 4/26![United Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/107:53 pm
TRI
- ORD
1 stop5h 00m
Delta
Sat 7/189:00 am
ORD
- TRI
1 stop5h 50m
Delta
Deal found 4/28![Delta logo]()
$249
This Contour deal was found by Cheapflights users on 4/24. 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 Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/178:00 am
BNA
- ORD
1 stop3h 30m
Contour
Sun 6/2112:20 pm
ORD
- BNA
1 stop3h 50m
Contour
Deal found 4/24![Contour logo]()
$252
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/304:30 pm
CVG
- MDW
1 stop6h 05m
Southwest
Fri 7/37:05 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 4/28![Southwest logo]()
$260
This United Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:44 pm
LEX
- ORD
Nonstop1h 51m
United Airlines
Sun 6/79:20 pm
ORD
- LEX
Nonstop1h 39m
United Airlines
Deal found 4/25![United Airlines logo]()
$249
Last-minute flights from Kentucky to IllinoisDiscover last-minute flight deals from Kentucky to Illinois. Data last updated April 29, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Illinois. Data last updated April 29, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/187:40 pm
BNA
- STL
1 stop4h 19m
Delta
Wed 5/207:05 am
STL
- BNA
1 stop4h 32m
Delta
Deal found 4/26![Delta logo]()
$179
This Delta deal was found by Cheapflights users on 4/24. 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 5/188:16 pm
CVG
- ORD
1 stop4h 43m
Delta
Tue 5/195:30 am
ORD
- CVG
1 stop4h 17m
Delta
Deal found 4/24![Delta logo]()
$194
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/203:00 pm
CVG
- MDW
1 stop7h 09m
Delta
Thu 5/216:23 am
MDW
- CVG
1 stop5h 30m
Delta
Deal found 4/29![Delta logo]()
$194
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/218:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Mon 5/257:00 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 4/27![Southwest logo]()
$191
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2112:06 pm
CVG
- ORD
Nonstop1h 31m
American Airlines
Mon 5/256:48 pm
ORD
- CVG
Nonstop1h 34m
American Airlines
Deal found 4/28![American Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2112:12 pm
CVG
- MDW
1 stop10h 50m
Frontier
Mon 5/256:00 am
MDW
- CVG
1 stop28h 04m
Frontier
Deal found 4/28![Frontier logo]()
$200
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/235:55 pm
BNA
- STL
Nonstop1h 15m
Southwest
Mon 5/259:55 am
STL
- BNA
Nonstop1h 10m
Southwest
Deal found 4/29![Southwest logo]()
$191
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:00 am
CVG
- ORD
Nonstop1h 34m
American Airlines
Mon 5/253:27 pm
ORD
- CVG
Nonstop1h 29m
American Airlines
Deal found 4/27![American Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 4/24. 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.
Mon 5/257:49 pm
CVG
- ORD
1 stop24h 52m
Frontier
Mon 6/14:05 pm
ORD
- CVG
2 stops42h 36m
Frontier
Deal found 4/24![Frontier logo]()
$197
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/276:00 pm
BNA
- STL
Nonstop1h 15m
Southwest
Wed 6/32:30 pm
STL
- BNA
Nonstop1h 10m
Southwest
Deal found 4/29![Southwest logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:46 pm
CVG
- ORD
1 stop7h 55m
Frontier
Wed 6/36:55 am
ORD
- CVG
2 stops12h 40m
Frontier
Deal found 4/27![Frontier logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/292:35 pm
BNA
- STL
1 stop4h 01m
Multiple Airlines
Tue 6/24:19 pm
STL
- BNA
1 stop24h 05m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$188
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 April 29, 2026.
Search for one-way flight options from Kentucky to Illinois. Find affordable one-way fares based on user searches. Data last updated April 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/281:22 pm
TYS
- MDW
Nonstop1h 35m
Allegiant Air
Deal found 4/26![Allegiant Air logo]()
$49
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/141:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 4/28![Allegiant Air logo]()
$66
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/311:22 pm
TYS
- MDW
Nonstop1h 35m
Allegiant Air
Deal found 4/28![Allegiant Air logo]()
$67
This Southwest deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 6/169:45 pm
BNA
- STL
Nonstop1h 15m
Southwest
Deal found 4/29![Southwest logo]()
$69
This Frontier deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:02 pm
BNA
- STL
1 stop7h 19m
Frontier
Deal found 4/25![Frontier logo]()
$70
This Expedia deal was found by Cheapflights users on 4/24. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:37 pm
CVG
- ORD
1 stop6h 36m
Frontier
Deal found 4/24![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2612:12 pm
CVG
- MDW
1 stop23h 57m
Frontier
Deal found 4/27![Frontier logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2312:46 pm
CVG
- ORD
1 stop20h 09m
Frontier
Deal found 4/25![Frontier logo]()
$73
This Delta deal was found by Cheapflights users on 4/24. 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.
Tue 5/266:43 pm
BNA
- STL
1 stop5h 16m
Delta
Deal found 4/24![Delta logo]()
$74
This Trip.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/142:35 pm
BNA
- STL
1 stop4h 01m
Southern / Mokulele
Deal found 4/25![Southern / Mokulele logo]()
$75
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/257:49 pm
CVG
- MDW
1 stop27h 13m
Frontier
Deal found 4/28![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/2812:24 pm
CVG
- MDW
1 stop23h 45m
Frontier
Deal found 4/28![Frontier logo]()
$78
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 April 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $137 (Southwest) |
One-way from | $49 (Kiwi.com) |
Popular in | January |
Cheapest in | November |
Average price | $349 |
Good round-trip deal | $138 or less |
Good one-way deal | $58 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 April 29, 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
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Mon 5/25
8:20 pm-8:30 pm
Nonstop1h 10m
Chicago Midway
Mon 6/1
7:00 pm-9:10 pm
Nonstop1h 10m
$191
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Mon 5/18
8:16 pm-11:59 pm
1 stop4h 43m
Chicago O'Hare Intl
Tue 5/19
5:30 am-10:47 am
1 stop4h 17m
$194
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Sat 5/23
5:00 pm-5:15 pm
Nonstop1h 15m
Chicago Midway
Sat 5/30
9:10 am-2:00 pm
1 stop3h 50m
$201
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Mon 5/25
3:54 pm-6:33 pm
1 stop3h 39m
Chicago Midway
Mon 6/1
6:23 am-12:53 pm
1 stop5h 30m
$211
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Mon 5/25
5:48 am-10:16 am
1 stop5h 28m
Chicago O'Hare Intl
Mon 6/1
5:30 am-12:53 pm
1 stop6h 23m
$211
NashvilleSt. Louis
BNA - STL
BNASTL
Nashville Intl
Mon 6/29
2:35 pm-6:36 pm
1 stop4h 01m
Lambert-St Louis
Tue 6/30
7:20 pm-9:03 am
1 stop13h 43m
$212
NashvilleChicago
BNA - ORD
BNAORD
Nashville Intl
Thu 6/4
8:00 am-11:30 am
1 stop3h 30m
Chicago O'Hare Intl
Sun 6/7
12:20 pm-4:10 pm
1 stop3h 50m
$217
NashvilleChicago
BNA - ORD
BNAORD
Nashville Intl
Fri 8/7
8:00 am-11:30 am
1 stop3h 30m
Chicago O'Hare Intl
Mon 8/10
12:30 pm-4:10 pm
1 stop3h 40m
$217
NashvilleChicago
BNA - ORD
BNAORD
Nashville Intl
Thu 7/16
8:00 am-11:30 am
1 stop3h 30m
Chicago O'Hare Intl
Sun 7/19
12:20 pm-4:10 pm
1 stop3h 50m
$217
NashvilleChicago
BNA - ORD
BNAORD
Nashville Intl
Mon 6/22
8:00 am-11:30 am
1 stop3h 30m
Chicago O'Hare Intl
Fri 6/26
12:20 pm-4:10 pm
1 stop3h 50m
$217
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
TYS-MDW
BNA-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 Illinois
USKY-USIL
BNA-STL
CVG-MDW
CVG-ORD
TYS-MDW
How far ahead should I book a flight from Kentucky to Illinois?
The best time to book flights from Kentucky to Illinois is 73 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 month to book a flight from Kentucky to Illinois?
Currently, April is the cheapest month in which you can book a flight from Kentucky to Illinois (average of $58). Flying from Kentucky to Illinois in February is currently the most expensive (average of $118). 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 April 29, 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.
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 April 25, 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. Wednesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 April 29, 2026.
The most flights from USKY to USIL are scheduled on a Monday (44 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Kentucky to Illinois?
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 April 29, 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.
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 April 29, 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 April 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$97 | Average$269 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$97 | Average$230 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$108 | Average$170 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$278 | FlexibilityNo cancel fee | On-time69% |