$54+ Cheap flights from Midway (MDW) to Kentucky
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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDF
May 17 — May 241
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Midway to Kentucky with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to Kentucky
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to KentuckyExplore the most affordable flight options available from Midway to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2026.
Explore the most affordable flight options available from Midway to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:04 pm
MDW
- CVG
1 stop22h 00m
Frontier
Fri 5/812:46 pm
CVG
- MDW
1 stop10h 16m
Frontier
Deal found 4/14![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:04 pm
MDW
- CVG
1 stop22h 37m
Frontier
Fri 6/512:46 pm
CVG
- MDW
1 stop23h 18m
Frontier
Deal found 4/14![Frontier logo]()
$147
This Cheapflightsfares deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/212:47 pm
MDW
- TYS
Nonstop1h 26m
Allegiant Air
Thu 5/281:22 pm
TYS
- MDW
Nonstop1h 35m
Allegiant Air
Deal found 4/15![Allegiant Air logo]()
$152
This Southwest deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:10 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Wed 5/207:35 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Deal found 4/14![Southwest logo]()
$157
This Frontier deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:14 am
MDW
- CVG
1 stop12h 05m
Frontier
Sun 5/36:45 am
CVG
- MDW
1 stop9h 19m
Frontier
Deal found 4/12![Frontier logo]()
$160
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/139:22 am
MDW
- CVG
1 stop3h 05m
Delta
Wed 5/202:07 pm
CVG
- MDW
1 stop5h 26m
Delta
Deal found 4/15![Delta logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2412:27 pm
MDW
- TYS
2 stops32h 34m
Multiple Airlines
Thu 5/281:22 pm
TYS
- MDW
Nonstop1h 35m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$168
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/67:50 am
MDW
- CVG
2 stops8h 15m
Southwest
Wed 5/67:35 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Deal found 4/13![Southwest logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/259:30 pm
MDW
- TYS
1 stop21h 01m
Allegiant Air
Thu 5/281:22 pm
TYS
- MDW
Nonstop1h 35m
Allegiant Air
Deal found 4/15![Allegiant Air logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:04 pm
MDW
- TYS
2 stops8h 57m
Multiple Airlines
Sun 5/311:22 pm
TYS
- MDW
Nonstop1h 35m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$173
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/111:00 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Tue 5/128:35 am
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 4/13![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:00 am
MDW
- CVG
1 stop3h 40m
Southwest
Wed 5/275:50 pm
CVG
- MDW
1 stop5h 25m
Southwest
Deal found 4/14![Southwest logo]()
$177
Best flights from Midway to KentuckyDiscover carefully curated flight deals from Midway to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2026.
Discover carefully curated flight deals from Midway to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2026.
This Southwest deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:10 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Wed 5/207:35 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Deal found 4/15![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/61:24 pm
MDW
- CVG
1 stop5h 49m
Delta
Sun 5/105:48 am
CVG
- MDW
1 stop5h 12m
Delta
Deal found 4/15![Delta logo]()
$167
This Southwest deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:00 am
MDW
- CVG
1 stop6h 20m
Southwest
Wed 6/106:35 pm
CVG
- MDW
1 stop5h 35m
Southwest
Deal found 4/14![Southwest logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:21 am
MDW
- TRI
1 stop26h 52m
Multiple Airlines
Sun 5/35:12 pm
TRI
- MDW
1 stop15h 34m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$408
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/117:00 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Mon 5/188:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 4/13![Southwest logo]()
$191
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:00 am
MDW
- TRI
1 stop6h 03m
Delta
Wed 4/297:19 pm
TRI
- MDW
1 stop4h 09m
Delta
Deal found 4/15![Delta logo]()
$245
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/319:22 am
MDW
- CVG
1 stop4h 52m
Delta
Sun 6/78:10 am
CVG
- MDW
1 stop5h 26m
Delta
Deal found 4/16![Delta logo]()
$258
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:10 am
MDW
- CVG
1 stop5h 00m
Southwest
Sun 5/249:55 am
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 4/12![Southwest logo]()
$242
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/146:23 am
MDW
- CVG
1 stop5h 30m
Delta
Sun 5/178:10 am
CVG
- MDW
1 stop5h 32m
Delta
Deal found 4/15![Delta logo]()
$258
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/157:00 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Tue 5/197:35 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Deal found 4/16![Southwest logo]()
$254
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1212:53 pm
MDW
- LEX
1 stop5h 40m
Delta
Tue 5/195:55 am
LEX
- MDW
1 stop5h 05m
Delta
Deal found 4/14![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/35:00 am
MDW
- TYS
1 stop8h 05m
Southwest
Tue 5/55:50 pm
TYS
- MDW
1 stop5h 25m
Southwest
Deal found 4/12![Southwest logo]()
$259
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:53 pm
MDW
- LEX
1 stop5h 40m
Delta
Sun 5/318:04 am
LEX
- MDW
1 stop5h 38m
Delta
Deal found 4/16![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/303:40 pm
MDW
- CVG
Nonstop1h 05m
Southwest
Sun 5/318:35 am
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 4/14![Southwest logo]()
$260
This Delta deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:29 pm
MDW
- LEX
1 stop5h 30m
Delta
Wed 5/133:32 pm
LEX
- MDW
1 stop6h 37m
Delta
Deal found 4/12![Delta logo]()
$269
This Delta deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:23 am
MDW
- LEX
1 stop4h 56m
Delta
Mon 6/11:05 pm
LEX
- MDW
1 stop4h 07m
Delta
Deal found 4/12![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/141:00 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Thu 5/218:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 4/15![Southwest logo]()
$271
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:23 am
MDW
- LEX
1 stop4h 56m
Delta
Sun 5/178:04 am
LEX
- MDW
1 stop5h 38m
Delta
Deal found 4/15![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/129:25 am
MDW
- TYS
1 stop6h 45m
Southwest
Tue 5/195:50 pm
TYS
- MDW
1 stop5h 25m
Southwest
Deal found 4/12![Southwest logo]()
$284
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:00 am
MDW
- TYS
1 stop4h 17m
Delta
Wed 5/133:30 pm
TYS
- MDW
1 stop6h 39m
Delta
Deal found 4/16![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:00 am
MDW
- BNA
Nonstop1h 30m
Southwest
Wed 5/611:30 am
BNA
- MDW
2 stops5h 25m
Southwest
Deal found 4/12![Southwest logo]()
$286
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:25 pm
MDW
- LEX
1 stop5h 30m
Delta
Sun 8/167:30 am
LEX
- MDW
1 stop6h 00m
Delta
Deal found 4/15![Delta logo]()
$284
This Southwest deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:50 am
MDW
- SDF
Nonstop1h 15m
Southwest
Sat 6/67:10 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Deal found 4/15![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
MDW
- TYS
1 stop4h 17m
Delta
Sat 5/95:35 pm
TYS
- MDW
1 stop4h 34m
Delta
Deal found 4/16![Delta logo]()
$284
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/512:45 pm
MDW
- SDF
Nonstop1h 10m
Southwest
Mon 6/88:05 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Deal found 4/12![Southwest logo]()
$292
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/131:22 pm
MDW
- BNA
1 stop5h 21m
Delta
Sat 5/164:55 pm
BNA
- MDW
1 stop4h 14m
Delta
Deal found 4/13![Delta logo]()
$291
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/157:45 am
MDW
- SDF
Nonstop1h 10m
Southwest
Sat 5/164:25 pm
SDF
- MDW
1 stop5h 15m
Southwest
Deal found 4/13![Southwest logo]()
$294
This Delta deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:23 am
MDW
- TRI
1 stop5h 32m
Delta
Wed 5/273:50 pm
TRI
- MDW
1 stop6h 19m
Delta
Deal found 4/12![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/45:20 pm
MDW
- TYS
1 stop4h 10m
Southwest
Tue 6/912:45 pm
TYS
- MDW
2 stops8h 05m
Southwest
Deal found 4/15![Southwest logo]()
$298
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/22:15 pm
MDW
- TYS
1 stop3h 15m
Southwest
Mon 5/46:45 pm
TYS
- MDW
1 stop5h 45m
Southwest
Deal found 4/16![Southwest logo]()
$299
Last-minute flights from Midway to KentuckyDiscover last-minute flight deals from Midway to Kentucky. Data last updated April 17, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Kentucky. Data last updated April 17, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:14 am
MDW
- CVG
1 stop12h 05m
Frontier
Sun 5/36:45 am
CVG
- MDW
1 stop9h 19m
Frontier
Deal found 4/12![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:04 pm
MDW
- CVG
1 stop22h 00m
Frontier
Fri 5/812:46 pm
CVG
- MDW
1 stop10h 16m
Frontier
Deal found 4/14![Frontier logo]()
$140
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/67:50 am
MDW
- CVG
2 stops8h 15m
Southwest
Wed 5/67:35 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Deal found 4/13![Southwest logo]()
$172
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/111:00 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Tue 5/128:35 am
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 4/13![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:10 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Wed 5/207:35 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Deal found 4/14![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/139:22 am
MDW
- CVG
1 stop3h 05m
Delta
Wed 5/202:07 pm
CVG
- MDW
1 stop5h 26m
Delta
Deal found 4/15![Delta logo]()
$167
This Cheapflightsfares deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/212:47 pm
MDW
- TYS
Nonstop1h 26m
Allegiant Air
Thu 5/281:22 pm
TYS
- MDW
Nonstop1h 35m
Allegiant Air
Deal found 4/15![Allegiant Air logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2412:27 pm
MDW
- TYS
2 stops32h 34m
Multiple Airlines
Thu 5/281:22 pm
TYS
- MDW
Nonstop1h 35m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/259:30 pm
MDW
- TYS
1 stop21h 01m
Allegiant Air
Thu 5/281:22 pm
TYS
- MDW
Nonstop1h 35m
Allegiant Air
Deal found 4/15![Allegiant Air logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:04 pm
MDW
- CVG
1 stop22h 00m
Frontier
Wed 6/312:46 pm
CVG
- MDW
1 stop10h 16m
Frontier
Deal found 4/12![Frontier logo]()
$152
This Southwest deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:00 am
MDW
- CVG
1 stop3h 40m
Southwest
Wed 5/275:50 pm
CVG
- MDW
1 stop5h 25m
Southwest
Deal found 4/14![Southwest logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:04 pm
MDW
- CVG
1 stop22h 37m
Frontier
Fri 6/512:46 pm
CVG
- MDW
1 stop23h 18m
Frontier
Deal found 4/14![Frontier logo]()
$147
One-way flights from Midway to KentuckySearch for one-way flight options from Midway to Kentucky. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
Search for one-way flight options from Midway to Kentucky. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/242:47 pm
MDW
- TYS
Nonstop1h 26m
Allegiant Air
Deal found 4/15![Allegiant Air logo]()
$54
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:00 am
MDW
- CVG
1 stop28h 04m
Frontier
Deal found 4/13![Frontier logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1612:27 pm
MDW
- CVG
1 stop22h 22m
Frontier
Deal found 4/16![Frontier logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1312:04 pm
MDW
- CVG
1 stop22h 00m
Frontier
Deal found 4/14![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1412:19 pm
MDW
- CVG
1 stop22h 22m
Frontier
Deal found 4/14![Frontier logo]()
$78
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:10 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 4/13![Southwest logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/212:47 pm
MDW
- TYS
Nonstop1h 26m
Allegiant Air
Deal found 4/13![Allegiant Air logo]()
$80
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/211:22 pm
MDW
- CVG
1 stop4h 48m
Delta
Deal found 4/16![Delta logo]()
$84
This Trip.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:47 pm
MDW
- TYS
Nonstop1h 26m
Allegiant Air
Deal found 4/16![Allegiant Air logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1111:59 am
MDW
- CVG
1 stop22h 15m
Frontier
Deal found 4/14![Frontier logo]()
$88
This Delta deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:23 am
MDW
- CVG
1 stop5h 30m
Delta
Deal found 4/13![Delta logo]()
$89
This Orbitz deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:00 am
MDW
- CVG
1 stop4h 41m
Frontier
Deal found 4/14![Frontier logo]()
$90
Find flight deals from Midway to Kentucky
Keep the following information in mind while searching for Midway to Kentucky flight deals. Data was last updated April 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $140 (Kiwi.com) |
One-way from | $54 (Cheapflightsfares) |
Popular in | March |
Cheapest in | August |
Average price | $295 |
Good round-trip deal | $306 or less |
Good one-way deal | $172 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Kentucky 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 17, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Kentucky that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Wed 5/13
6:10 pm-8:20 pm
Nonstop1h 10m
Cincinnati Cinci./N. Kentucky
Wed 5/20
7:35 pm-7:50 pm
Nonstop1h 15m
$157
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Wed 5/6
1:24 pm-8:13 pm
1 stop5h 49m
Cincinnati Cinci./N. Kentucky
Sun 5/10
5:48 am-10:00 am
1 stop5h 12m
$167
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Wed 6/10
6:00 am-1:20 pm
1 stop6h 20m
Cincinnati Cinci./N. Kentucky
Wed 6/10
6:35 pm-11:10 pm
1 stop5h 35m
$177
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Mon 5/11
7:00 pm-9:10 pm
Nonstop1h 10m
Cincinnati Cinci./N. Kentucky
Mon 5/18
8:20 pm-8:30 pm
Nonstop1h 10m
$191
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Sat 5/23
6:10 am-12:10 pm
1 stop5h 00m
Cincinnati Cinci./N. Kentucky
Sun 5/24
9:55 am-10:05 am
Nonstop1h 10m
$242
ChicagoBlountville
MDW - TRI
MDWTRI
Chicago Midway
Tue 4/28
6:00 am-1:03 pm
1 stop6h 03m
Blountville Tri Cities TN/VA
Wed 4/29
7:19 pm-10:28 pm
1 stop4h 09m
$245
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Fri 5/15
7:00 pm-9:10 pm
Nonstop1h 10m
Cincinnati Cinci./N. Kentucky
Tue 5/19
7:35 pm-7:50 pm
Nonstop1h 15m
$254
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Sun 5/31
9:22 am-3:14 pm
1 stop4h 52m
Cincinnati Cinci./N. Kentucky
Sun 6/7
8:10 am-12:36 pm
1 stop5h 26m
$258
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Thu 5/14
6:23 am-12:53 pm
1 stop5h 30m
Cincinnati Cinci./N. Kentucky
Sun 5/17
8:10 am-12:42 pm
1 stop5h 32m
$258
ChicagoKnoxville
MDW - TYS
MDWTYS
Chicago Midway
Sun 5/3
5:00 am-2:05 pm
1 stop8h 05m
Knoxville McGhee Tyson
Tue 5/5
5:50 pm-10:15 pm
1 stop5h 25m
$259
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Midway to Kentucky
Have a flexible travel schedule? Discover the best time to fly to Kentucky from Midway with our price prediction graph.
MDW-CVG
MDW-TYS
MDW-LEX
MDW-SDF
MDW-TRI
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 Chicago Midway Airport to Kentucky
MDW-USKY
MDW-CVG
MDW-TYS
MDW-LEX
MDW-SDF
What is the cheapest time of day to fly from MDW to KY?
Find hourly flight availability from Midway to Kentucky. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 17, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 30% on flights from Chicago Midway Airport to Kentucky by exploring options for tickets in the afternoon.
What is the cheapest day to fly from Chicago Midway Airport to Kentucky?
Use this chart to determine the cheapest time to fly round-trip from Midway to Kentucky. Price data was last updated on April 11, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Kentucky flight should consider departing on Monday evenings 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.
How much does it cost to fly round-trip from Chicago Midway Airport to Kentucky?
Reviews of airlines servicing Kentucky
Get insights into the airlines that provide service to Kentucky. 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 Kentucky. Reviews last updated April 17, 2026.
Peruse reviews from past customers who have flown with Southwest from Chicago Midway Airport to Kentucky to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Boarding
8.1
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Midway to Kentucky. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Midway to Kentucky
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Kentucky by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Kentucky by cabin class
Find flights from Midway to Kentucky, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Kentucky flights
Browse other Midway and Kentucky flight options. Last updated on April 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Midway to Kentucky flights
Consider these flights traveling from Midway to Kentucky.
Top airline flying from Midway to Kentucky
Discover the top airline that operate flights from Midway to Kentucky. 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 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$124 | Average$263 | FlexibilityNo cancel fee | On-time63% |