$68+ Cheap flights from Kentucky to Midway (MDW)
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 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — MDW
Apr 24 — May 11
Round-trip
1 adult, Economy
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Find cheap flights from Kentucky to Midway with Cheapflights
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Cheapest flights from Kentucky to MidwayExplore the most affordable flight options available from Kentucky to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 25, 2026.
Explore the most affordable flight options available from Kentucky to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 25, 2026.
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/148:35 am
CVG
- MDW
Nonstop1h 10m
Southwest
Mon 4/277:00 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 3/19![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 6/27:35 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Wed 6/36:10 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 3/23![Southwest logo]()
$176
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/213:30 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Tue 4/287:40 am
MDW
- SDF
Nonstop1h 10m
Southwest
Deal found 3/24![Southwest logo]()
$177
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/188:00 am
CVG
- MDW
1 stop9h 00m
Frontier
Sun 4/196:00 am
MDW
- CVG
1 stop10h 48m
Frontier
Deal found 3/20![Frontier logo]()
$180
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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.
Mon 4/1312:19 pm
CVG
- MDW
1 stop11h 00m
Frontier
Fri 4/179:14 am
MDW
- CVG
1 stop13h 06m
Frontier
Deal found 3/23![Frontier logo]()
$181
This Frontier deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/1811:00 am
CVG
- MDW
1 stop6h 00m
Frontier
Mon 4/206:00 am
MDW
- CVG
1 stop11h 36m
Frontier
Deal found 3/21![Frontier logo]()
$182
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:35 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Wed 4/158:00 am
MDW
- CVG
1 stop3h 40m
Southwest
Deal found 3/24![Southwest logo]()
$185
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/227:35 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Wed 4/298:00 am
MDW
- CVG
1 stop3h 40m
Southwest
Deal found 3/23![Southwest logo]()
$186
This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/185:00 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Sat 4/253:40 pm
MDW
- CVG
Nonstop1h 05m
Southwest
Deal found 3/20![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2112:50 pm
TYS
- MDW
2 stops7h 55m
Southwest
Tue 4/2812:50 pm
MDW
- TYS
2 stops7h 00m
Southwest
Deal found 3/24![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:35 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Mon 5/187:00 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 3/24![Southwest logo]()
$193
This Trip.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/2312:19 pm
BNA
- MDW
1 stop10h 03m
Frontier
Sat 4/259:14 am
MDW
- BNA
1 stop7h 44m
Frontier
Deal found 3/23![Frontier logo]()
$195
Best flights from Kentucky to MidwayDiscover carefully curated flight deals from Kentucky to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 25, 2026.
Discover carefully curated flight deals from Kentucky to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 25, 2026.
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/225:50 pm
CVG
- MDW
1 stop5h 25m
Southwest
Wed 4/298:00 am
MDW
- CVG
1 stop3h 40m
Southwest
Deal found 3/23![Southwest logo]()
$195
This Delta deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/97:51 am
TYS
- MDW
1 stop5h 51m
Delta
Sun 5/109:22 am
MDW
- TYS
1 stop3h 58m
Delta
Deal found 3/24![Delta logo]()
$241
This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 5/98:45 am
CVG
- MDW
Nonstop1h 10m
Southwest
Mon 5/113:50 pm
MDW
- CVG
1 stop5h 00m
Southwest
Deal found 3/20![Southwest logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/199:31 am
LEX
- MDW
2 stops35h 00m
Multiple Airlines
Thu 4/239:16 am
MDW
- LEX
1 stop22h 26m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$459
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/147:05 am
CVG
- MDW
2 stops9h 40m
Southwest
Mon 4/272:10 pm
MDW
- CVG
2 stops8h 15m
Southwest
Deal found 3/19![Southwest logo]()
$210
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/217:19 pm
TRI
- MDW
1 stop4h 09m
Delta
Tue 4/286:00 am
MDW
- TRI
1 stop6h 03m
Delta
Deal found 3/22![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/207:15 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Sat 5/237:50 am
MDW
- SDF
Nonstop1h 15m
Southwest
Deal found 3/24![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 7/223:50 pm
TRI
- MDW
1 stop6h 55m
Delta
Sat 7/256:00 am
MDW
- TRI
1 stop5h 06m
Delta
Deal found 3/20![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/2112:40 pm
BNA
- MDW
1 stop3h 05m
Southwest
Tue 4/283:00 pm
MDW
- BNA
Nonstop1h 30m
Southwest
Deal found 3/22![Southwest logo]()
$220
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/107:17 pm
TRI
- MDW
1 stop4h 14m
Delta
Mon 4/136:00 am
MDW
- TRI
1 stop6h 03m
Delta
Deal found 3/22![Delta logo]()
$264
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 5/16:45 pm
TYS
- MDW
1 stop5h 45m
Southwest
Sat 5/22:15 pm
MDW
- TYS
1 stop3h 15m
Southwest
Deal found 3/23![Southwest logo]()
$231
This Delta deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/217:19 am
LEX
- MDW
1 stop5h 48m
Delta
Tue 4/285:21 pm
MDW
- LEX
1 stop5h 33m
Delta
Deal found 3/22![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/158:10 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Tue 5/1912:50 pm
MDW
- SDF
Nonstop1h 15m
Southwest
Deal found 3/22![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 5/27:50 am
TYS
- MDW
1 stop5h 53m
Delta
Tue 5/56:00 am
MDW
- TYS
1 stop4h 17m
Delta
Deal found 3/21![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/306:45 pm
TYS
- MDW
1 stop5h 45m
Southwest
Sun 5/36:00 am
MDW
- TYS
1 stop8h 15m
Southwest
Deal found 3/22![Southwest logo]()
$242
This Delta deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:05 am
BNA
- MDW
1 stop6h 38m
Delta
Mon 4/206:00 am
MDW
- BNA
1 stop4h 13m
Delta
Deal found 3/24![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 6/63:25 pm
BNA
- MDW
Nonstop1h 35m
Southwest
Wed 6/107:45 am
MDW
- BNA
1 stop3h 30m
Southwest
Deal found 3/23![Southwest logo]()
$242
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/94:50 pm
SDF
- MDW
Nonstop1h 20m
Southwest
Sat 5/167:50 am
MDW
- SDF
Nonstop1h 15m
Southwest
Deal found 3/24![Southwest logo]()
$244
This Delta deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 6/95:55 pm
LEX
- MDW
1 stop4h 50m
Delta
Sat 6/136:00 am
MDW
- LEX
1 stop5h 37m
Delta
Deal found 3/20![Delta logo]()
$302
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/173:50 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Tue 5/197:40 am
MDW
- SDF
Nonstop1h 10m
Southwest
Deal found 3/24![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/236:45 pm
TYS
- MDW
1 stop5h 45m
Southwest
Sun 4/266:00 am
MDW
- TYS
1 stop8h 15m
Southwest
Deal found 3/22![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 5/163:32 pm
LEX
- MDW
1 stop6h 37m
Delta
Mon 5/185:10 pm
MDW
- LEX
1 stop5h 49m
Delta
Deal found 3/20![Delta logo]()
$344
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:25 pm
BNA
- MDW
Nonstop1h 35m
Southwest
Fri 5/89:35 pm
MDW
- BNA
Nonstop1h 25m
Southwest
Deal found 3/24![Southwest logo]()
$260
This Delta deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/247:19 pm
TRI
- MDW
1 stop4h 09m
Delta
Sun 4/266:00 am
MDW
- TRI
1 stop6h 05m
Delta
Deal found 3/24![Delta logo]()
$354
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 6/412:35 pm
TYS
- MDW
1 stop8h 35m
Southwest
Sat 6/62:10 pm
MDW
- TYS
2 stops6h 10m
Southwest
Deal found 3/23![Southwest logo]()
$262
This Delta deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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
- MDW
1 stop4h 09m
Delta
Sun 5/36:00 am
MDW
- TRI
1 stop6h 05m
Delta
Deal found 3/20![Delta logo]()
$394
This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 5/26:40 am
TYS
- MDW
2 stops8h 40m
Southwest
Tue 5/510:15 am
MDW
- TYS
2 stops8h 25m
Southwest
Deal found 3/20![Southwest logo]()
$270
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 4/217:15 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Tue 4/286:20 pm
MDW
- SDF
Nonstop1h 15m
Southwest
Deal found 3/22![Southwest logo]()
$271
This Delta deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/175:56 pm
LEX
- MDW
1 stop5h 19m
Delta
Tue 7/215:10 pm
MDW
- LEX
1 stop5h 45m
Delta
Deal found 3/24![Delta logo]()
$417
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 5/611:55 am
BNA
- MDW
Nonstop1h 35m
Southwest
Wed 5/138:00 am
MDW
- BNA
Nonstop1h 30m
Southwest
Deal found 3/22![Southwest logo]()
$271
Last-minute flights from Kentucky to MidwayDiscover last-minute flight deals from Kentucky to Midway. Data last updated March 25, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Midway. Data last updated March 25, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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.
Mon 4/1312:19 pm
CVG
- MDW
1 stop11h 00m
Frontier
Fri 4/179:14 am
MDW
- CVG
1 stop13h 06m
Frontier
Deal found 3/23![Frontier logo]()
$181
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/148:35 am
CVG
- MDW
Nonstop1h 10m
Southwest
Mon 4/277:00 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 3/19![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:35 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Wed 4/158:00 am
MDW
- CVG
1 stop3h 40m
Southwest
Deal found 3/24![Southwest logo]()
$185
This Delta deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:59 am
CVG
- MDW
1 stop3h 48m
Delta
Tue 4/141:24 pm
MDW
- CVG
1 stop3h 47m
Delta
Deal found 3/24![Delta logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:13 am
BNA
- MDW
1 stop20h 46m
Frontier
Sat 4/256:00 am
MDW
- BNA
2 stops10h 58m
Frontier
Deal found 3/25![Frontier logo]()
$197
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/188:00 am
CVG
- MDW
1 stop9h 00m
Frontier
Sun 4/196:00 am
MDW
- CVG
1 stop10h 48m
Frontier
Deal found 3/20![Frontier logo]()
$180
This Frontier deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/1811:00 am
CVG
- MDW
1 stop6h 00m
Frontier
Mon 4/206:00 am
MDW
- CVG
1 stop11h 36m
Frontier
Deal found 3/21![Frontier logo]()
$182
This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/185:00 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Sat 4/253:40 pm
MDW
- CVG
Nonstop1h 05m
Southwest
Deal found 3/20![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/213:30 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Tue 4/287:40 am
MDW
- SDF
Nonstop1h 10m
Southwest
Deal found 3/24![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2112:50 pm
TYS
- MDW
2 stops7h 55m
Southwest
Tue 4/2812:50 pm
MDW
- TYS
2 stops7h 00m
Southwest
Deal found 3/24![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/227:35 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Wed 4/298:00 am
MDW
- CVG
1 stop3h 40m
Southwest
Deal found 3/23![Southwest logo]()
$186
This Trip.com deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/2312:19 pm
BNA
- MDW
1 stop10h 03m
Frontier
Sat 4/259:14 am
MDW
- BNA
1 stop7h 44m
Frontier
Deal found 3/23![Frontier logo]()
$195
One-way flights from Kentucky to MidwaySearch for one-way flight options from Kentucky to Midway. Find affordable one-way fares based on user searches. Data last updated March 25, 2026.
Search for one-way flight options from Kentucky to Midway. Find affordable one-way fares based on user searches. Data last updated March 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/121:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 3/24![Allegiant Air logo]()
$68
This Kiwi.com deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/247:46 pm
CVG
- MDW
1 stop27h 28m
Frontier
Deal found 3/24![Frontier logo]()
$71
This Booking.com deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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.
Sun 8/21:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 3/21![Allegiant Air logo]()
$72
This Kiwi.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/207:46 pm
CVG
- MDW
1 stop27h 28m
Frontier
Deal found 3/20![Frontier logo]()
$72
This Super.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1012:19 pm
CVG
- MDW
1 stop8h 48m
Frontier
Deal found 3/20![Frontier logo]()
$75
This Kiwi.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/177:46 pm
CVG
- MDW
1 stop27h 28m
Frontier
Deal found 3/20![Frontier logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” 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 6/111:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 3/22![Allegiant Air logo]()
$83
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/158:35 am
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 3/24![Southwest logo]()
$88
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/53:30 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Deal found 3/24![Southwest logo]()
$89
This Frontier deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:00 am
CVG
- MDW
1 stop9h 00m
Frontier
Deal found 3/24![Frontier logo]()
$90
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” 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 4/225:50 pm
TYS
- MDW
1 stop5h 25m
Southwest
Deal found 3/23![Southwest logo]()
$91
This Kiwi.com deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:38 pm
CVG
- MDW
1 stop25h 53m
Frontier
Deal found 3/24![Frontier logo]()
$93
Find flight deals from Kentucky to Midway
Keep the following information in mind while searching for Kentucky to Midway flight deals. Data was last updated March 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $174 (Southwest) |
One-way from | $68 (Kiwi.com) |
Popular in | January |
Cheapest in | November |
Average price | $286 |
Good round-trip deal | $374 or less |
Good one-way deal | $196 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Kentucky to Midway 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 March 25, 2026.
Use the filters below to find and compare flights from Kentucky to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Wed 4/22
5:50 pm-10:15 pm
1 stop5h 25m
Chicago Midway
Wed 4/29
8:00 am-12:40 pm
1 stop3h 40m
$195
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Sat 5/9
8:45 am-8:55 am
Nonstop1h 10m
Chicago Midway
Mon 5/11
3:50 pm-9:50 pm
1 stop5h 00m
$201
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Tue 4/14
7:05 am-3:45 pm
2 stops9h 40m
Chicago Midway
Mon 4/27
2:10 pm-11:25 pm
2 stops8h 15m
$210
LouisvilleChicago
SDF - MDW
SDFMDW
Louisville Intl
Wed 5/20
7:15 pm-7:30 pm
Nonstop1h 15m
Chicago Midway
Sat 5/23
7:50 am-10:05 am
Nonstop1h 15m
$211
NashvilleChicago
BNA - MDW
BNAMDW
Nashville Intl
Tue 4/21
12:40 pm-3:45 pm
1 stop3h 05m
Chicago Midway
Tue 4/28
3:00 pm-4:30 pm
Nonstop1h 30m
$220
KnoxvilleChicago
TYS - MDW
TYSMDW
Knoxville McGhee Tyson
Fri 5/1
6:45 pm-11:30 pm
1 stop5h 45m
Chicago Midway
Sat 5/2
2:15 pm-6:30 pm
1 stop3h 15m
$231
LouisvilleChicago
SDF - MDW
SDFMDW
Louisville Intl
Fri 5/15
8:10 pm-8:25 pm
Nonstop1h 15m
Chicago Midway
Tue 5/19
12:50 pm-3:05 pm
Nonstop1h 15m
$232
KnoxvilleChicago
TYS - MDW
TYSMDW
Knoxville McGhee Tyson
Sat 5/9
7:51 am-12:42 pm
1 stop5h 51m
Chicago Midway
Sun 5/10
9:22 am-2:20 pm
1 stop3h 58m
$241
KnoxvilleChicago
TYS - MDW
TYSMDW
Knoxville McGhee Tyson
Thu 4/30
6:45 pm-11:30 pm
1 stop5h 45m
Chicago Midway
Sun 5/3
6:00 am-3:15 pm
1 stop8h 15m
$242
NashvilleChicago
BNA - MDW
BNAMDW
Nashville Intl
Sat 6/6
3:25 pm-5:00 pm
Nonstop1h 35m
Chicago Midway
Wed 6/10
7:45 am-11:15 am
1 stop3h 30m
$242
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Kentucky to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Kentucky with our price prediction graph.
CVG-MDW
TYS-MDW
SDF-MDW
BNA-MDW
EVV-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Kentucky to Chicago Midway Airport
USKY-MDW
CVG-MDW
TYS-MDW
SDF-MDW
BNA-MDW
What is the cheapest time of day to fly from KY to MDW?
Find hourly flight availability from Kentucky to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 25, 2026.
It’s optimal to fly from Kentucky to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 15% on the cost of your flight, compared to a flight in the morning.
Related info for your journey
Find useful and relevant information for your journey from Kentucky to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes
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Alternative routes for Kentucky to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Kentucky to Midway by cabin class
Find flights from Kentucky to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on March 25, 2026.
Kentucky and Midway flights
Browse other Kentucky and Midway flight options. Last updated on March 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Kentucky to Midway flights
Consider these flights traveling from Kentucky to Midway.
Top airline flying from Kentucky to Midway
Discover the top airline that operate flights from Kentucky to Midway. 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 March 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$97 | Average$247 | FlexibilityNo cancel fee | On-time63% |