$53+ 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 5/31. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — ORD
May 9 — May 161
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 9, 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 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/276:06 pm
SDF
- ORD
1 stop28h 11m
Multiple Airlines
Thu 5/73:44 pm
ORD
- SDF
1 stop16h 44m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 5/17:48 pm
SDF
- ORD
1 stop26h 29m
Multiple Airlines
Thu 5/73:44 pm
ORD
- SDF
1 stop26h 14m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/276:06 pm
SDF
- ORD
1 stop28h 11m
Multiple Airlines
Fri 5/15:05 am
ORD
- SDF
1 stop10h 59m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/1510:33 am
SDF
- ORD
1 stop14h 26m
Multiple Airlines
Tue 5/191:18 pm
ORD
- SDF
1 stop21h 16m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/17:46 pm
CVG
- ORD
1 stop26h 26m
Multiple Airlines
Sun 5/108:39 am
ORD
- CVG
2 stops26h 02m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$176
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/57:05 am
CVG
- ORD
1 stop6h 45m
Southwest
Tue 5/122:40 pm
ORD
- CVG
1 stop5h 35m
Southwest
Deal found 4/7![Southwest logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/306:45 am
CVG
- MDW
1 stop17h 58m
Frontier
Fri 5/16:00 am
MDW
- CVG
1 stop11h 36m
Frontier
Deal found 4/7![Frontier logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/16:06 pm
SDF
- ORD
1 stop16h 30m
Multiple Airlines
Sun 5/31:00 pm
ORD
- SDF
1 stop19h 28m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/17:46 pm
CVG
- MDW
1 stop23h 51m
Frontier
Tue 5/53:07 pm
MDW
- CVG
2 stops19h 53m
Frontier
Deal found 4/7![Frontier logo]()
$180
This Frontier deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Fri 4/243:32 pm
CVG
- ORD
1 stop9h 22m
Frontier
Sun 4/265:50 am
ORD
- CVG
1 stop10h 58m
Frontier
Deal found 4/5![Frontier logo]()
$180
This Frontier deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Fri 4/171:10 pm
CVG
- MDW
1 stop9h 27m
Frontier
Mon 4/276:00 am
MDW
- CVG
1 stop11h 36m
Frontier
Deal found 4/6![Frontier logo]()
$181
This Frontier deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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.
Wed 5/61:05 pm
CVG
- ORD
1 stop8h 27m
Frontier
Sat 5/99:37 pm
ORD
- CVG
1 stop12h 07m
Frontier
Deal found 4/8![Frontier logo]()
$181
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 9, 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 9, 2026.
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/127:05 am
CVG
- ORD
1 stop6h 45m
Southwest
Tue 5/122:40 pm
ORD
- CVG
1 stop5h 35m
Southwest
Deal found 4/5![Southwest logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 4/206:06 pm
SDF
- ORD
1 stop28h 11m
Multiple Airlines
Fri 5/15:05 am
ORD
- SDF
1 stop10h 59m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$193
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/279:59 am
CVG
- MDW
1 stop7h 13m
Delta
Thu 5/289:23 am
MDW
- CVG
1 stop5h 20m
Delta
Deal found 4/9![Delta logo]()
$194
This Mytrip deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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.
Mon 4/206:06 pm
SDF
- ORD
2 stops17h 17m
Spirit Airlines
Fri 5/15:05 am
ORD
- SDF
1 stop10h 59m
Spirit Airlines
Deal found 4/4![Spirit Airlines logo]()
$203
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/52:03 pm
CVG
- ORD
Nonstop1h 32m
United Airlines
Wed 5/612:50 pm
ORD
- CVG
Nonstop1h 28m
United Airlines
Deal found 4/5![United Airlines logo]()
$227
This American Airlines deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 6/277:59 am
TRI
- ORD
Nonstop2h 11m
American Airlines
Wed 7/19:23 pm
ORD
- TRI
Nonstop1h 53m
American Airlines
Deal found 4/8![American Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/219:00 am
CVG
- MDW
Nonstop1h 15m
Southwest
Thu 5/287:00 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 4/5![Southwest logo]()
$191
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/66:02 pm
CVG
- ORD
1 stop3h 38m
Delta
Thu 5/75:30 am
ORD
- CVG
1 stop4h 17m
Delta
Deal found 4/5![Delta logo]()
$194
This Southwest deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 4/308:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Sat 5/25:25 pm
MDW
- CVG
1 stop4h 55m
Southwest
Deal found 4/9![Southwest logo]()
$201
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/25:35 am
CVG
- MDW
2 stops8h 08m
Delta
Wed 5/69:29 am
MDW
- CVG
2 stops9h 44m
Delta
Deal found 4/6![Delta logo]()
$204
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/67:05 am
CVG
- MDW
2 stops8h 50m
Southwest
Sat 5/97:45 am
MDW
- CVG
1 stop5h 15m
Southwest
Deal found 4/7![Southwest logo]()
$205
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/226:52 pm
LEX
- ORD
Nonstop1h 53m
American Airlines
Sun 5/243:44 pm
ORD
- LEX
Nonstop1h 35m
American Airlines
Deal found 4/6![American Airlines logo]()
$249
This United Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/27:50 pm
LEX
- ORD
Nonstop1h 48m
United Airlines
Sat 5/94:20 pm
ORD
- LEX
Nonstop1h 27m
United Airlines
Deal found 4/4![United Airlines logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/26:06 pm
SDF
- ORD
1 stop16h 30m
Multiple Airlines
Sat 5/97:52 pm
ORD
- SDF
2 stops36h 36m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$254
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 4/305:35 am
CVG
- ORD
2 stops8h 10m
Delta
Sat 5/21:29 pm
ORD
- CVG
2 stops9h 42m
Delta
Deal found 4/9![Delta logo]()
$221
This United Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/297:44 pm
LEX
- ORD
Nonstop1h 51m
United Airlines
Sun 5/316:45 am
ORD
- LEX
Nonstop1h 31m
United Airlines
Deal found 4/4![United Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/211:01 am
LEX
- ORD
Nonstop1h 40m
American Airlines
Tue 5/58:00 am
ORD
- LEX
Nonstop1h 31m
American Airlines
Deal found 4/7![American Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 4/305:35 am
CVG
- ORD
2 stops8h 10m
Delta
Mon 5/41:36 pm
ORD
- CVG
2 stops9h 35m
Delta
Deal found 4/9![Delta logo]()
$221
This United Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/95:30 am
LEX
- ORD
Nonstop1h 48m
United Airlines
Sun 8/96:45 am
ORD
- LEX
Nonstop1h 31m
United Airlines
Deal found 4/4![United Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 7/105:20 am
LEX
- ORD
Nonstop1h 34m
American Airlines
Tue 7/147:00 am
ORD
- LEX
1 stop4h 34m
American Airlines
Deal found 4/4![American Airlines logo]()
$259
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/88:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Tue 5/127:50 am
MDW
- CVG
2 stops8h 15m
Southwest
Deal found 4/6![Southwest logo]()
$244
This United Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 7/110:12 am
LEX
- ORD
Nonstop1h 48m
United Airlines
Sun 7/59:35 pm
ORD
- LEX
Nonstop1h 39m
United Airlines
Deal found 4/6![United Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/296:52 pm
LEX
- ORD
Nonstop1h 53m
American Airlines
Sun 5/318:59 pm
ORD
- LEX
Nonstop1h 34m
American Airlines
Deal found 4/7![American Airlines logo]()
$269
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/512:50 pm
TYS
- ORD
1 stop6h 35m
Southwest
Tue 5/122:40 pm
ORD
- TYS
1 stop4h 00m
Southwest
Deal found 4/7![Southwest logo]()
$249
This United Airlines deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 7/15:55 pm
TYS
- ORD
Nonstop2h 10m
United Airlines
Fri 7/109:35 pm
ORD
- TYS
Nonstop2h 00m
United Airlines
Deal found 4/9![United Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 5/17:19 pm
TRI
- ORD
1 stop5h 40m
Delta
Sun 5/37:10 am
ORD
- TRI
1 stop7h 12m
Delta
Deal found 4/9![Delta logo]()
$249
This American Airlines deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 4/308:24 pm
TRI
- ORD
1 stop4h 30m
American Airlines
Sun 5/35:00 am
ORD
- TRI
1 stop4h 41m
American Airlines
Deal found 4/9![American Airlines logo]()
$269
This United Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 8/286:00 am
TRI
- ORD
Nonstop2h 04m
United Airlines
Sun 8/307:27 am
ORD
- TRI
Nonstop1h 53m
United Airlines
Deal found 4/6![United Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 4/9. Clicking the “Pick Dates” 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 7/237:53 pm
TRI
- ORD
1 stop5h 00m
Delta
Sat 7/259:45 am
ORD
- TRI
1 stop5h 05m
Delta
Deal found 4/9![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/19:00 am
CVG
- MDW
Nonstop1h 15m
Southwest
Tue 5/512:50 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 4/7![Southwest logo]()
$254
Last-minute flights from Kentucky to IllinoisDiscover last-minute flight deals from Kentucky to Illinois. Data last updated April 9, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Illinois. Data last updated April 9, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Fri 4/171:10 pm
CVG
- MDW
1 stop9h 27m
Frontier
Mon 4/276:00 am
MDW
- CVG
1 stop11h 36m
Frontier
Deal found 4/6![Frontier logo]()
$181
This Frontier deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Fri 4/243:32 pm
CVG
- ORD
1 stop9h 22m
Frontier
Sun 4/265:50 am
ORD
- CVG
1 stop10h 58m
Frontier
Deal found 4/5![Frontier logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/276:06 pm
SDF
- ORD
1 stop28h 11m
Multiple Airlines
Thu 5/73:44 pm
ORD
- SDF
1 stop16h 44m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/276:06 pm
SDF
- ORD
1 stop28h 11m
Multiple Airlines
Fri 5/15:05 am
ORD
- SDF
1 stop10h 59m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/306:45 am
CVG
- MDW
1 stop17h 58m
Frontier
Fri 5/16:00 am
MDW
- CVG
1 stop11h 36m
Frontier
Deal found 4/7![Frontier logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 5/17:48 pm
SDF
- ORD
1 stop26h 29m
Multiple Airlines
Thu 5/73:44 pm
ORD
- SDF
1 stop26h 14m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/17:46 pm
CVG
- ORD
1 stop26h 26m
Multiple Airlines
Sun 5/108:39 am
ORD
- CVG
2 stops26h 02m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/16:06 pm
SDF
- ORD
1 stop16h 30m
Multiple Airlines
Sun 5/31:00 pm
ORD
- SDF
1 stop19h 28m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/17:46 pm
CVG
- MDW
1 stop23h 51m
Frontier
Tue 5/53:07 pm
MDW
- CVG
2 stops19h 53m
Frontier
Deal found 4/7![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/57:05 am
CVG
- ORD
1 stop6h 45m
Southwest
Tue 5/122:40 pm
ORD
- CVG
1 stop5h 35m
Southwest
Deal found 4/7![Southwest logo]()
$177
This Frontier deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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.
Wed 5/61:05 pm
CVG
- ORD
1 stop8h 27m
Frontier
Sat 5/99:37 pm
ORD
- CVG
1 stop12h 07m
Frontier
Deal found 4/8![Frontier logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/1510:33 am
SDF
- ORD
1 stop14h 26m
Multiple Airlines
Tue 5/191:18 pm
ORD
- SDF
1 stop21h 16m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$176
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 9, 2026.
Search for one-way flight options from Kentucky to Illinois. Find affordable one-way fares based on user searches. Data last updated April 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 4/8![Allegiant Air logo]()
$53
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/203:32 pm
CVG
- ORD
1 stop30h 45m
Frontier
Deal found 4/6![Frontier logo]()
$69
This Frontier deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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 5/211:00 am
CVG
- MDW
1 stop6h 13m
Frontier
Deal found 4/8![Frontier logo]()
$70
This Frontier deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” 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.
Thu 4/308:38 pm
CVG
- ORD
1 stop10h 30m
Frontier
Deal found 4/8![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/17:46 pm
CVG
- MDW
1 stop23h 51m
Frontier
Deal found 4/6![Frontier logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/17:46 pm
CVG
- ORD
1 stop26h 26m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$73
This Cheapflightsfares deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/211:22 pm
TYS
- MDW
Nonstop1h 35m
Allegiant Air
Deal found 4/5![Allegiant Air logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/47:46 pm
CVG
- MDW
1 stop16h 23m
Frontier
Deal found 4/5![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/47:46 pm
CVG
- ORD
1 stop13h 09m
Frontier
Deal found 4/6![Frontier logo]()
$76
This Expedia deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Wed 5/139:30 pm
CVG
- ORD
1 stop26h 43m
Frontier
Deal found 4/5![Frontier logo]()
$77
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/16:06 pm
SDF
- ORD
1 stop28h 11m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/203:38 pm
CVG
- ORD
1 stop30h 39m
Multiple Airlines
Deal found 4/7![Multiple Airlines 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 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $149 (Kiwi.com) |
One-way from | $53 (Kiwi.com) |
Popular in | January |
Cheapest in | November |
Average price | $332 |
Good round-trip deal | $107 or less |
Good one-way deal | $199 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 9, 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 5/12
7:05 am-12:50 pm
1 stop6h 45m
Chicago O'Hare Intl
Tue 5/12
2:40 pm-9:15 pm
1 stop5h 35m
$177
Quickest round-trip
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Thu 5/21
9:00 am-9:15 am
Nonstop1h 15m
Chicago Midway
Thu 5/28
7:00 pm-9:10 pm
Nonstop1h 10m
$191
LouisvilleChicago
SDF - ORD
SDFORD
Louisville Intl
Mon 4/20
6:06 pm-9:17 pm
1 stop28h 11m
Chicago O'Hare Intl
Fri 5/1
5:05 am-5:04 pm
1 stop10h 59m
$193
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Wed 5/27
9:59 am-4:12 pm
1 stop7h 13m
Chicago Midway
Thu 5/28
9:23 am-3:43 pm
1 stop5h 20m
$194
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Wed 5/6
6:02 pm-8:40 pm
1 stop3h 38m
Chicago O'Hare Intl
Thu 5/7
5:30 am-10:47 am
1 stop4h 17m
$194
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Thu 4/30
8:20 pm-8:30 pm
Nonstop1h 10m
Chicago Midway
Sat 5/2
5:25 pm-11:20 pm
1 stop4h 55m
$201
LouisvilleChicago
SDF - ORD
SDFORD
Louisville Intl
Mon 4/20
6:06 pm-10:23 am
2 stops17h 17m
Chicago O'Hare Intl
Fri 5/1
5:05 am-5:04 pm
1 stop10h 59m
$203
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Sat 5/2
5:35 am-12:43 pm
2 stops8h 08m
Chicago Midway
Wed 5/6
9:29 am-8:13 pm
2 stops9h 44m
$204
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Wed 5/6
7:05 am-2:55 pm
2 stops8h 50m
Chicago Midway
Sat 5/9
7:45 am-2:00 pm
1 stop5h 15m
$205
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Thu 4/30
5:35 am-12:45 pm
2 stops8h 10m
Chicago O'Hare Intl
Sat 5/2
1:29 pm-12:11 am
2 stops9h 42m
$221
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.
TYS-MDW
CVG-ORD
CVG-MDW
SDF-ORD
LEX-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Kentucky to Illinois
USKY-USIL
TYS-MDW
CVG-ORD
CVG-MDW
SDF-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 March is currently the most expensive (average of $180). 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 9, 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 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 4, 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.
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 9, 2026.
The most flights from USKY to USIL are scheduled on a Wednesday (45 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (27 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 9, 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.
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Comfort
8.0
Entertainment
7.5
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 9, 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 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$97 | Average$266 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$97 | Average$240 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$108 | Average$170 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$114 | Average$265 | FlexibilityNo cancel fee | On-time69% |