$79+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — ORD
Jul 3 — Jul 101
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 June 3, 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 June 3, 2026.
This Southwest deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 7/147:00 am
CVG
- MDW
2 stops7h 35m
Southwest
Wed 7/156:15 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 5/31![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 9/54:55 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Mon 9/78:05 am
MDW
- CVG
Nonstop1h 20m
Southwest
Deal found 6/2![Southwest logo]()
$195
This United Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 9/52:05 pm
CVG
- ORD
Nonstop1h 34m
United Airlines
Mon 9/710:43 am
ORD
- CVG
Nonstop1h 26m
United Airlines
Deal found 6/2![United Airlines logo]()
$195
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 8/178:10 am
CVG
- MDW
Nonstop1h 05m
Southwest
Wed 8/196:30 am
MDW
- CVG
1 stop6h 10m
Southwest
Deal found 6/2![Southwest logo]()
$196
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/16:35 pm
CVG
- MDW
1 stop5h 35m
Southwest
Tue 7/73:10 pm
MDW
- CVG
1 stop5h 45m
Southwest
Deal found 6/2![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 7/142:15 pm
CVG
- ORD
1 stop5h 14m
Delta
Wed 7/157:05 am
ORD
- CVG
1 stop5h 30m
Delta
Deal found 6/1![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 8/174:10 pm
CVG
- ORD
1 stop3h 18m
Delta
Wed 8/1911:22 am
ORD
- CVG
1 stop5h 42m
Delta
Deal found 6/2![Delta logo]()
$206
This Southwest deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 7/297:00 am
CVG
- MDW
2 stops7h 35m
Southwest
Wed 8/51:00 pm
MDW
- CVG
2 stops6h 50m
Southwest
Deal found 6/1![Southwest logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 8/242:20 pm
CVG
- ORD
1 stop23h 05m
Frontier
Fri 8/287:55 am
ORD
- CVG
1 stop11h 40m
Frontier
Deal found 5/31![Frontier logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 8/32:30 pm
CVG
- ORD
1 stop22h 45m
Frontier
Wed 8/55:13 pm
ORD
- CVG
1 stop29h 33m
Frontier
Deal found 6/2![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/263:06 pm
LEX
- ORD
1 stop22h 09m
Multiple Airlines
Wed 7/295:13 pm
ORD
- LEX
1 stop13h 57m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$219
This Booking.com deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/158:00 am
BNA
- ORD
1 stop3h 30m
Contour
Wed 7/2212:20 pm
ORD
- BNA
1 stop3h 50m
Contour
Deal found 5/31![Contour logo]()
$220
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 June 3, 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 June 3, 2026.
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 8/1810:53 am
CVG
- ORD
1 stop3h 20m
Delta
Wed 8/1911:22 am
ORD
- CVG
1 stop5h 42m
Delta
Deal found 6/3![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/157:00 am
CVG
- MDW
2 stops7h 35m
Southwest
Wed 7/225:30 pm
MDW
- CVG
1 stop4h 40m
Southwest
Deal found 6/2![Southwest logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/187:00 am
BNA
- RFD
Nonstop1h 29m
Allegiant Air
Sun 6/2111:27 am
RFD
- BNA
2 stops35h 10m
Allegiant Air
Deal found 5/30![Allegiant Air logo]()
$237
This JetBlue deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:50 am
BNA
- ORD
1 stop6h 30m
JetBlue
Fri 8/289:39 am
ORD
- BNA
1 stop7h 26m
JetBlue
Deal found 5/31![JetBlue logo]()
$247
This Contour deal was found by Cheapflights users on 5/29. 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 Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/248:00 am
BNA
- ORD
1 stop3h 30m
Contour
Mon 7/2712:20 pm
ORD
- BNA
1 stop3h 50m
Contour
Deal found 5/29![Contour logo]()
$247
This United Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 7/157:00 am
LEX
- ORD
Nonstop1h 52m
United Airlines
Sat 7/185:51 pm
ORD
- LEX
Nonstop1h 38m
United Airlines
Deal found 5/31![United Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/31:08 pm
LEX
- ORD
1 stop5h 30m
American Airlines
Sun 7/58:15 am
ORD
- LEX
Nonstop1h 34m
American Airlines
Deal found 6/2![American Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/98:13 am
BNA
- RFD
1 stop23h 36m
Multiple Airlines
Mon 7/137:50 pm
RFD
- BNA
1 stop14h 27m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$275
This Southwest deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 7/17:40 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Mon 7/67:15 am
MDW
- CVG
1 stop4h 00m
Southwest
Deal found 6/1![Southwest logo]()
$235
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/138:14 am
CVG
- ORD
1 stop3h 23m
Delta
Wed 7/152:07 pm
ORD
- CVG
1 stop4h 47m
Delta
Deal found 6/2![Delta logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 8/68:13 am
BNA
- RFD
1 stop23h 36m
Allegiant Air
Sun 8/911:37 am
RFD
- BNA
1 stop8h 00m
Allegiant Air
Deal found 6/2![Allegiant Air logo]()
$247
This United Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/96:00 am
TYS
- ORD
Nonstop1h 59m
United Airlines
Sun 7/125:59 pm
ORD
- TYS
Nonstop1h 49m
United Airlines
Deal found 6/2![United Airlines logo]()
$249
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/136:55 pm
CVG
- MDW
1 stop4h 05m
Southwest
Wed 7/1512:45 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 6/2![Southwest logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 6/257:00 am
BNA
- RFD
Nonstop1h 29m
Allegiant Air
Fri 6/267:48 pm
RFD
- BNA
1 stop24h 15m
Allegiant Air
Deal found 6/1![Allegiant Air logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 6/265:19 pm
BNA
- RFD
1 stop15h 58m
Multiple Airlines
Sun 6/289:19 am
RFD
- BNA
Nonstop1h 25m
Multiple Airlines
Deal found 6/1![Multiple Airlines logo]()
$281
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 7/910:51 am
LEX
- ORD
1 stop6h 32m
Delta
Mon 7/136:35 am
ORD
- LEX
1 stop7h 07m
Delta
Deal found 6/1![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 5/29. 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 7/217:00 am
CVG
- MDW
2 stops7h 35m
Southwest
Thu 7/237:00 pm
MDW
- CVG
1 stop4h 30m
Southwest
Deal found 5/29![Southwest logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/258:35 pm
BNA
- RFD
2 stops36h 42m
Allegiant Air
Sun 6/289:19 am
RFD
- BNA
Nonstop1h 25m
Allegiant Air
Deal found 5/30![Allegiant Air logo]()
$259
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/17:45 pm
CVG
- ORD
1 stop4h 46m
United Airlines
Tue 7/77:50 pm
ORD
- CVG
Nonstop1h 36m
United Airlines
Deal found 6/3![United Airlines logo]()
$286
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 8/2210:52 am
LEX
- ORD
1 stop6h 25m
Delta
Wed 8/263:31 pm
ORD
- LEX
1 stop7h 28m
Delta
Deal found 5/30![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/17:40 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Sun 7/56:45 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 6/2![Southwest logo]()
$253
This United Airlines deal was found by Cheapflights users on 5/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/176:12 pm
CVG
- ORD
Nonstop1h 38m
United Airlines
Mon 7/206:56 am
ORD
- CVG
Nonstop1h 32m
United Airlines
Deal found 5/29![United Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/2711:32 am
BNA
- RFD
1 stop22h 18m
Allegiant Air
Sun 8/211:27 am
RFD
- BNA
1 stop8h 14m
Allegiant Air
Deal found 6/2![Allegiant Air logo]()
$262
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/27:35 am
LEX
- ORD
1 stop6h 25m
Delta
Sun 7/56:35 am
ORD
- LEX
1 stop4h 44m
Delta
Deal found 6/2![Delta logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 6/287:00 am
BNA
- RFD
Nonstop1h 29m
Allegiant Air
Sun 7/511:27 am
RFD
- BNA
1 stop8h 02m
Allegiant Air
Deal found 6/2![Allegiant Air logo]()
$264
This United Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 6/306:00 am
BNA
- ORD
Nonstop1h 58m
United Airlines
Tue 7/73:49 pm
ORD
- BNA
Nonstop1h 51m
United Airlines
Deal found 5/31![United Airlines logo]()
$293
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 8/1410:10 am
LEX
- ORD
1 stop7h 41m
Delta
Sun 8/166:40 am
ORD
- LEX
1 stop4h 31m
Delta
Deal found 5/31![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 7/214:15 pm
SDF
- MDW
1 stop6h 25m
Southwest
Wed 7/221:25 pm
MDW
- SDF
Nonstop1h 10m
Southwest
Deal found 6/1![Southwest logo]()
$285
This United Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 9/16:00 am
BNA
- ORD
Nonstop1h 58m
United Airlines
Tue 9/86:14 pm
ORD
- BNA
Nonstop1h 52m
United Airlines
Deal found 5/30![United Airlines logo]()
$293
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/247:35 am
LEX
- ORD
1 stop6h 29m
Delta
Mon 6/296:35 am
ORD
- LEX
1 stop4h 44m
Delta
Deal found 5/30![Delta logo]()
$269
Last-minute flights from Kentucky to IllinoisDiscover last-minute flight deals from Kentucky to Illinois. Data last updated June 3, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Illinois. Data last updated June 3, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/192:10 pm
BNA
- RFD
1 stop18h 07m
Allegiant Air
Sun 6/219:19 am
RFD
- BNA
Nonstop1h 25m
Allegiant Air
Deal found 5/30![Allegiant Air logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 6/257:00 am
BNA
- RFD
Nonstop1h 29m
Allegiant Air
Sun 6/2811:27 am
RFD
- BNA
1 stop8h 08m
Allegiant Air
Deal found 5/31![Allegiant Air logo]()
$223
This Mytrip deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/268:00 am
BNA
- ORD
1 stop3h 30m
Contour
Sun 6/2812:20 pm
ORD
- BNA
1 stop3h 50m
Contour
Deal found 5/31![Contour logo]()
$226
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/16:35 pm
CVG
- MDW
1 stop5h 35m
Southwest
Tue 7/73:10 pm
MDW
- CVG
1 stop5h 45m
Southwest
Deal found 6/2![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 7/17:40 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Mon 7/67:05 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 6/1![Southwest logo]()
$225
This Southwest deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 7/147:00 am
CVG
- MDW
2 stops7h 35m
Southwest
Wed 7/156:15 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 5/31![Southwest logo]()
$192
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 7/142:15 pm
CVG
- ORD
1 stop5h 14m
Delta
Wed 7/157:05 am
ORD
- CVG
1 stop5h 30m
Delta
Deal found 6/1![Delta logo]()
$197
This Booking.com deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/158:00 am
BNA
- ORD
1 stop3h 30m
Contour
Wed 7/2212:20 pm
ORD
- BNA
1 stop3h 50m
Contour
Deal found 5/31![Contour logo]()
$220
This United Airlines deal was found by Cheapflights users on 5/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:00 am
CVG
- ORD
Nonstop1h 34m
United Airlines
Thu 7/236:56 am
ORD
- CVG
Nonstop1h 32m
United Airlines
Deal found 5/29![United Airlines logo]()
$225
This Mytrip deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/248:00 am
BNA
- ORD
1 stop3h 30m
Contour
Mon 7/2712:20 pm
ORD
- BNA
1 stop3h 50m
Contour
Deal found 6/2![Contour logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/263:06 pm
LEX
- ORD
1 stop22h 09m
Multiple Airlines
Wed 7/295:13 pm
ORD
- LEX
1 stop13h 57m
Multiple Airlines
Deal found 6/2![Multiple Airlines logo]()
$219
This Southwest deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 7/297:00 am
CVG
- MDW
2 stops7h 35m
Southwest
Wed 8/51:00 pm
MDW
- CVG
2 stops6h 50m
Southwest
Deal found 6/1![Southwest logo]()
$207
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 June 3, 2026.
Search for one-way flight options from Kentucky to Illinois. Find affordable one-way fares based on user searches. Data last updated June 3, 2026.
This Delta deal was found by Cheapflights users on 5/29. 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.
Tue 8/254:10 pm
CVG
- ORD
1 stop5h 17m
Delta
Deal found 5/29![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 5/29. 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.
Mon 8/172:23 pm
CVG
- ORD
1 stop5h 05m
Delta
Deal found 5/29![Delta logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/2912:54 pm
CVG
- ORD
1 stop20h 09m
Frontier
Deal found 6/3![Frontier logo]()
$88
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 6/237:40 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 6/2![Southwest logo]()
$89
This United Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 7/147:54 pm
CVG
- ORD
Nonstop1h 40m
United Airlines
Deal found 6/1![United Airlines logo]()
$89
This American Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:54 am
CVG
- ORD
Nonstop1h 41m
American Airlines
Deal found 6/1![American Airlines logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/2312:24 pm
CVG
- ORD
1 stop20h 39m
Frontier
Deal found 6/3![Frontier logo]()
$96
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 9/58:20 am
CVG
- MDW
Nonstop1h 05m
Southwest
Deal found 6/2![Southwest logo]()
$98
This American Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:17 pm
CVG
- ORD
Nonstop1h 23m
American Airlines
Deal found 6/2![American Airlines logo]()
$98
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 8/2510:34 am
SDF
- ORD
1 stop3h 39m
Delta
Deal found 5/30![Delta logo]()
$99
This Delta deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/144:00 pm
CVG
- MDW
1 stop3h 25m
Delta
Deal found 6/3![Delta logo]()
$99
This Delta deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 6/2311:13 am
CVG
- ORD
1 stop6h 13m
Delta
Deal found 6/2![Delta logo]()
$99
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 June 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $192 (Southwest) |
One-way from | $79 (Delta) |
Popular in | January |
Cheapest in | November |
Average price | $315 |
Good round-trip deal | $118 or less |
Good one-way deal | $203 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 June 3, 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 - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Tue 8/18
10:53 am-1:13 pm
1 stop3h 20m
Chicago O'Hare Intl
Wed 8/19
11:22 am-6:04 pm
1 stop5h 42m
$197
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Wed 7/15
7:00 am-1:35 pm
2 stops7h 35m
Chicago Midway
Wed 7/22
5:30 pm-11:10 pm
1 stop4h 40m
$202
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Wed 7/1
7:40 pm-7:50 pm
Nonstop1h 10m
Chicago Midway
Mon 7/6
7:15 am-12:15 pm
1 stop4h 00m
$235
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Mon 7/13
6:55 pm-10:00 pm
1 stop4h 05m
Chicago Midway
Wed 7/15
12:45 pm-2:55 pm
Nonstop1h 10m
$235
NashvilleChicago
BNA - RFD
BNARFD
Nashville Intl
Thu 6/18
7:00 am-8:29 am
Nonstop1h 29m
Chicago Greater Rockford
Sun 6/21
11:27 am-10:37 pm
2 stops35h 10m
$237
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Mon 7/13
8:14 am-10:37 am
1 stop3h 23m
Chicago O'Hare Intl
Wed 7/15
2:07 pm-7:54 pm
1 stop4h 47m
$245
NashvilleChicago
BNA - ORD
BNAORD
Nashville Intl
Wed 8/26
10:50 am-5:20 pm
1 stop6h 30m
Chicago O'Hare Intl
Fri 8/28
9:39 am-5:05 pm
1 stop7h 26m
$247
NashvilleChicago
BNA - ORD
BNAORD
Nashville Intl
Fri 7/24
8:00 am-11:30 am
1 stop3h 30m
Chicago O'Hare Intl
Mon 7/27
12:20 pm-4:10 pm
1 stop3h 50m
$247
NashvilleChicago
BNA - RFD
BNARFD
Nashville Intl
Thu 8/6
8:13 am-7:49 am
1 stop23h 36m
Chicago Greater Rockford
Sun 8/9
11:37 am-7:37 pm
1 stop8h 00m
$247
LexingtonChicago
LEX - ORD
LEXORD
Lexington Blue Grass
Wed 7/15
7:00 am-7:52 am
Nonstop1h 52m
Chicago O'Hare Intl
Sat 7/18
5:51 pm-8:29 pm
Nonstop1h 38m
$249
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.
CVG-MDW
CVG-ORD
LEX-ORD
BNA-ORD
SDF-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
CVG-MDW
CVG-ORD
LEX-ORD
BNA-ORD
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 June is currently the most expensive (average of $121). 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 June 3, 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 33% on your trip compared to booking a flight at noon.
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 June 3, 2026.
The most flights from USKY to USIL are scheduled on a Tuesday (45 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 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 68 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 May 30, 2026.
Travelers seeking maximum savings on their Kentucky to Illinois flight should consider departing on Saturday at noon when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated June 3, 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
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
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 June 3, 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 June 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$97 | Average$277 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$97 | Average$236 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$108 | Average$170 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$290 | FlexibilityNo cancel fee | On-time69% |