$56+ 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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — MDW
Mar 13 — Mar 201
1 adult, Economy
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Find cheap flights from Kentucky to Midway 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
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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 February 11, 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 February 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 5/211:22 pm
TYS
- MDW
Nonstop1h 35m
Allegiant Air
Thu 5/282:47 pm
MDW
- TYS
Nonstop1h 26m
Allegiant Air
Deal found 2/11![Allegiant Air logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 5/211:22 pm
TYS
- MDW
Nonstop1h 35m
Allegiant Air
Sun 5/312:47 pm
MDW
- TYS
Nonstop1h 26m
Allegiant Air
Deal found 2/11![Allegiant Air logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 5/241:22 pm
TYS
- MDW
Nonstop1h 35m
Allegiant Air
Thu 5/282:47 pm
MDW
- TYS
Nonstop1h 26m
Allegiant Air
Deal found 2/11![Allegiant Air logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 Kiwi.com 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
Sun 5/242:47 pm
MDW
- TYS
Nonstop1h 26m
Allegiant Air
Deal found 2/9![Allegiant Air logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 5/241:22 pm
TYS
- MDW
Nonstop1h 35m
Allegiant Air
Sun 5/312:47 pm
MDW
- TYS
Nonstop1h 26m
Allegiant Air
Deal found 2/11![Allegiant Air logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/281:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Sun 7/52:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 2/9![Allegiant Air logo]()
$156
This Delta deal was found by Cheapflights users on 2/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/37:13 pm
TRI
- MDW
1 stop4h 20m
Delta
Wed 3/116:00 am
MDW
- TRI
1 stop6h 00m
Delta
Deal found 2/7![Delta logo]()
$159
This Delta deal was found by Cheapflights users on 2/9. 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 5/17:15 pm
TRI
- MDW
1 stop4h 13m
Delta
Sat 5/96:30 am
MDW
- TRI
1 stop5h 23m
Delta
Deal found 2/9![Delta logo]()
$169
This Southwest deal was found by Cheapflights users on 2/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/108:55 am
SDF
- MDW
Nonstop1h 20m
Southwest
Wed 3/118:10 am
MDW
- SDF
Nonstop1h 20m
Southwest
Deal found 2/8![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 2/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/147:20 am
SDF
- MDW
Nonstop1h 20m
Southwest
Tue 3/178:10 am
MDW
- SDF
Nonstop1h 20m
Southwest
Deal found 2/8![Southwest logo]()
$178
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/48:05 am
CVG
- MDW
2 stops11h 35m
Delta
Mon 3/99:35 am
MDW
- CVG
1 stop2h 56m
Delta
Deal found 2/11![Delta logo]()
$189
This Southwest deal was found by Cheapflights users on 2/9. 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 3/56:35 am
CVG
- MDW
1 stop6h 20m
Southwest
Mon 3/94:05 pm
MDW
- CVG
1 stop5h 30m
Southwest
Deal found 2/9![Southwest logo]()
$191
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 February 11, 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 February 11, 2026.
This Delta deal was found by Cheapflights users on 2/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/67:13 pm
TRI
- MDW
1 stop4h 18m
Delta
Wed 3/116:00 am
MDW
- TRI
1 stop6h 00m
Delta
Deal found 2/7![Delta logo]()
$159
This Southwest deal was found by Cheapflights users on 2/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/108:55 am
SDF
- MDW
Nonstop1h 20m
Southwest
Wed 3/118:10 am
MDW
- SDF
Nonstop1h 20m
Southwest
Deal found 2/8![Southwest logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:15 am
BNA
- MDW
1 stop8h 11m
Multiple Airlines
Mon 3/99:51 pm
MDW
- BNA
1 stop12h 50m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$204
This Delta deal was found by Cheapflights users on 2/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/37:13 pm
TRI
- MDW
1 stop4h 20m
Delta
Mon 3/96:00 am
MDW
- TRI
1 stop6h 00m
Delta
Deal found 2/7![Delta logo]()
$159
This Delta deal was found by Cheapflights users on 2/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/37:13 pm
TRI
- MDW
1 stop4h 20m
Delta
Wed 3/116:00 am
MDW
- TRI
1 stop6h 00m
Delta
Deal found 2/7![Delta logo]()
$159
This Southwest deal was found by Cheapflights users on 2/9. 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.
Wed 3/1111:50 am
SDF
- MDW
Nonstop1h 15m
Southwest
Wed 3/116:15 pm
MDW
- SDF
Nonstop1h 15m
Southwest
Deal found 2/9![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 2/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:13 pm
TRI
- MDW
1 stop4h 18m
Delta
Tue 3/106:00 am
MDW
- TRI
1 stop6h 00m
Delta
Deal found 2/7![Delta logo]()
$159
This Southwest deal was found by Cheapflights users on 2/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/147:20 am
SDF
- MDW
Nonstop1h 20m
Southwest
Tue 3/178:10 am
MDW
- SDF
Nonstop1h 20m
Southwest
Deal found 2/8![Southwest logo]()
$178
This Delta deal was found by Cheapflights users on 2/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:13 pm
TRI
- MDW
1 stop4h 18m
Delta
Wed 3/116:00 am
MDW
- TRI
1 stop6h 00m
Delta
Deal found 2/7![Delta logo]()
$159
This Southwest deal was found by Cheapflights users on 2/9. 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 3/56:35 am
CVG
- MDW
1 stop6h 20m
Southwest
Mon 3/94:05 pm
MDW
- CVG
1 stop5h 30m
Southwest
Deal found 2/9![Southwest logo]()
$191
This Delta deal was found by Cheapflights users on 2/9. 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 5/17:15 pm
TRI
- MDW
1 stop4h 13m
Delta
Sat 5/96:30 am
MDW
- TRI
1 stop5h 23m
Delta
Deal found 2/9![Delta logo]()
$169
This Southwest deal was found by Cheapflights users on 2/7. 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.
Mon 3/94:15 pm
CVG
- MDW
1 stop5h 00m
Southwest
Mon 3/164:05 pm
MDW
- CVG
1 stop5h 30m
Southwest
Deal found 2/7![Southwest logo]()
$191
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/101:45 pm
TRI
- MDW
1 stop4h 37m
Delta
Tue 3/176:00 am
MDW
- TRI
1 stop6h 00m
Delta
Deal found 2/10![Delta logo]()
$169
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/96:50 pm
CVG
- MDW
1 stop5h 40m
Southwest
Mon 4/135:50 pm
MDW
- CVG
1 stop4h 35m
Southwest
Deal found 2/11![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/47:00 am
CVG
- MDW
Nonstop1h 25m
Southwest
Mon 3/91:25 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 2/11![Southwest logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 2/8. 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.
Mon 3/97:46 pm
EVV
- MDW
1 stop22h 27m
Multiple Airlines
Fri 3/136:15 am
MDW
- EVV
1 stop12h 51m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$325
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/48:05 am
CVG
- MDW
2 stops11h 35m
Delta
Mon 3/99:35 am
MDW
- CVG
1 stop2h 56m
Delta
Deal found 2/11![Delta logo]()
$189
This Southwest deal was found by Cheapflights users on 2/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/127:05 am
CVG
- MDW
2 stops9h 40m
Southwest
Thu 5/145:30 am
MDW
- CVG
1 stop5h 20m
Southwest
Deal found 2/8![Southwest logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/137:46 pm
EVV
- MDW
1 stop25h 59m
Multiple Airlines
Mon 3/167:25 am
MDW
- EVV
1 stop11h 41m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/96:00 am
CVG
- MDW
1 stop3h 53m
Delta
Mon 4/135:21 pm
MDW
- CVG
1 stop5h 50m
Delta
Deal found 2/11![Delta logo]()
$191
This Southwest deal was found by Cheapflights users on 2/9. 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.
Wed 5/67:15 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Thu 5/146:45 pm
MDW
- SDF
Nonstop1h 15m
Southwest
Deal found 2/9![Southwest logo]()
$196
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/177:15 pm
TRI
- MDW
1 stop4h 13m
Delta
Mon 4/205:21 pm
MDW
- TRI
1 stop4h 11m
Delta
Deal found 2/11![Delta logo]()
$194
This Southwest deal was found by Cheapflights users on 2/9. 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.
Mon 5/48:10 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Wed 5/66:20 pm
MDW
- SDF
Nonstop1h 15m
Southwest
Deal found 2/9![Southwest logo]()
$196
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/56:00 am
CVG
- MDW
2 stops7h 46m
Delta
Mon 3/96:34 pm
MDW
- CVG
1 stop3h 03m
Delta
Deal found 2/11![Delta logo]()
$196
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/76:50 am
BNA
- MDW
Nonstop1h 35m
Southwest
Tue 4/79:50 am
MDW
- BNA
Nonstop1h 25m
Southwest
Deal found 2/11![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 2/9. 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 3/117:45 am
SDF
- MDW
1 stop5h 44m
Delta
Wed 3/116:07 pm
MDW
- SDF
1 stop4h 50m
Delta
Deal found 2/9![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 2/7. 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.
Sat 3/1410:15 pm
BNA
- MDW
Nonstop1h 50m
Southwest
Wed 3/188:45 pm
MDW
- BNA
Nonstop1h 35m
Southwest
Deal found 2/7![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 2/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/255:00 am
BNA
- MDW
Nonstop1h 40m
Southwest
Wed 4/111:15 am
MDW
- BNA
Nonstop1h 30m
Southwest
Deal found 2/8![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 2/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/257:45 am
LEX
- MDW
1 stop5h 44m
Delta
Wed 4/16:07 pm
MDW
- LEX
1 stop4h 46m
Delta
Deal found 2/7![Delta logo]()
$209
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/187:10 am
BNA
- MDW
Nonstop1h 40m
Southwest
Wed 3/253:35 pm
MDW
- BNA
Nonstop1h 30m
Southwest
Deal found 2/10![Southwest logo]()
$197
Last-minute flights from Kentucky to MidwayDiscover last-minute flight deals from Kentucky to Midway. Data last updated February 11, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Midway. Data last updated February 11, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 2/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/37:13 pm
TRI
- MDW
1 stop4h 20m
Delta
Wed 3/116:00 am
MDW
- TRI
1 stop6h 00m
Delta
Deal found 2/7![Delta logo]()
$159
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/48:05 am
CVG
- MDW
2 stops11h 35m
Delta
Mon 3/99:35 am
MDW
- CVG
1 stop2h 56m
Delta
Deal found 2/11![Delta logo]()
$189
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/47:00 am
CVG
- MDW
Nonstop1h 25m
Southwest
Mon 3/91:25 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 2/11![Southwest logo]()
$194
This Southwest deal was found by Cheapflights users on 2/9. 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 3/56:35 am
CVG
- MDW
1 stop6h 20m
Southwest
Mon 3/94:05 pm
MDW
- CVG
1 stop5h 30m
Southwest
Deal found 2/9![Southwest logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/51:07 pm
CVG
- MDW
1 stop10h 22m
Frontier
Mon 3/99:51 pm
MDW
- CVG
2 stops19h 42m
Frontier
Deal found 2/10![Frontier logo]()
$193
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/101:45 pm
TRI
- MDW
1 stop4h 37m
Delta
Tue 3/176:00 am
MDW
- TRI
1 stop6h 00m
Delta
Deal found 2/10![Delta logo]()
$169
This Southwest deal was found by Cheapflights users on 2/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/108:55 am
SDF
- MDW
Nonstop1h 20m
Southwest
Wed 3/118:10 am
MDW
- SDF
Nonstop1h 20m
Southwest
Deal found 2/8![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 2/9. 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 3/117:45 am
SDF
- MDW
1 stop5h 44m
Delta
Wed 3/116:07 pm
MDW
- SDF
1 stop4h 50m
Delta
Deal found 2/9![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 2/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/147:20 am
SDF
- MDW
Nonstop1h 20m
Southwest
Tue 3/178:10 am
MDW
- SDF
Nonstop1h 20m
Southwest
Deal found 2/8![Southwest logo]()
$178
This Delta deal was found by Cheapflights users on 2/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/146:00 am
BNA
- MDW
1 stop6h 29m
Delta
Tue 3/171:10 pm
MDW
- BNA
1 stop3h 48m
Delta
Deal found 2/8![Delta logo]()
$195
This Southwest deal was found by Cheapflights users on 2/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/147:20 am
SDF
- MDW
Nonstop1h 20m
Southwest
Wed 3/1810:30 am
MDW
- SDF
2 stops10h 45m
Southwest
Deal found 2/8![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 2/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/255:00 am
BNA
- MDW
Nonstop1h 40m
Southwest
Wed 4/111:15 am
MDW
- BNA
Nonstop1h 30m
Southwest
Deal found 2/8![Southwest logo]()
$197
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 February 11, 2026.
Search for one-way flight options from Kentucky to Midway. Find affordable one-way fares based on user searches. Data last updated February 11, 2026.
This Southwest deal was found by Cheapflights users on 2/9. 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.
Sat 4/115:00 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Deal found 2/9![Southwest logo]()
$56
This Southwest deal was found by Cheapflights users on 2/9. 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.
Sat 4/114:50 pm
SDF
- MDW
Nonstop1h 20m
Southwest
Deal found 2/9![Southwest logo]()
$62
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/261:07 pm
CVG
- MDW
1 stop10h 22m
Frontier
Deal found 2/9![Frontier logo]()
$67
This Southwest deal was found by Cheapflights users on 2/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/94:25 pm
SDF
- MDW
1 stop5h 15m
Southwest
Deal found 2/8![Southwest logo]()
$72
This Southwest deal was found by Cheapflights users on 2/9. 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.
Sat 3/79:00 am
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 2/9![Southwest logo]()
$72
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/177:41 pm
CVG
- MDW
1 stop27h 38m
Frontier
Deal found 2/11![Frontier logo]()
$74
This Delta deal was found by Cheapflights users on 2/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/77:50 am
SDF
- MDW
1 stop5h 56m
Delta
Deal found 2/8![Delta logo]()
$79
This Southwest deal was found by Cheapflights users on 2/9. 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.
Wed 3/47:00 am
CVG
- MDW
Nonstop1h 25m
Southwest
Deal found 2/9![Southwest logo]()
$79
This Frontier deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/132:26 pm
CVG
- MDW
1 stop6h 43m
Frontier
Deal found 2/11![Frontier logo]()
$80
This Delta deal was found by Cheapflights users on 2/9. 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.
Sat 4/185:35 am
CVG
- MDW
2 stops8h 08m
Delta
Deal found 2/9![Delta logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/157:41 pm
CVG
- MDW
1 stop27h 38m
Frontier
Deal found 2/10![Frontier logo]()
$85
This Southwest deal was found by Cheapflights users on 2/9. 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 4/169:00 am
CVG
- MDW
Nonstop1h 15m
Southwest
Deal found 2/9![Southwest logo]()
$86
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 February 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $144 (Kiwi.com) |
One-way from | $56 (Southwest) |
Popular in | January |
Cheapest in | November |
Average price | $295 |
Good round-trip deal | $348 or less |
Good one-way deal | $190 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 February 11, 2026.
Use the filters below to find and compare flights from Kentucky to Chicago Midway Airport that are best for you.
Fly from
Kentucky
Fly to
Midway
Route
Depart
Return
Price
BlountvilleChicago
TRI - MDW
TRIMDW
Blountville Tri Cities TN/VA
Fri 3/6
7:13 pm-10:31 pm
1 stop4h 18m
Chicago Midway
Wed 3/11
6:00 am-1:00 pm
1 stop6h 00m
$159
BlountvilleChicago
TRI - MDW
TRIMDW
Blountville Tri Cities TN/VA
Tue 3/3
7:13 pm-10:33 pm
1 stop4h 20m
Chicago Midway
Mon 3/9
6:00 am-1:00 pm
1 stop6h 00m
$159
BlountvilleChicago
TRI - MDW
TRIMDW
Blountville Tri Cities TN/VA
Tue 3/3
7:13 pm-10:33 pm
1 stop4h 20m
Chicago Midway
Wed 3/11
6:00 am-1:00 pm
1 stop6h 00m
$159
BlountvilleChicago
TRI - MDW
TRIMDW
Blountville Tri Cities TN/VA
Wed 3/4
7:13 pm-10:31 pm
1 stop4h 18m
Chicago Midway
Tue 3/10
6:00 am-1:00 pm
1 stop6h 00m
$159
BlountvilleChicago
TRI - MDW
TRIMDW
Blountville Tri Cities TN/VA
Wed 3/4
7:13 pm-10:31 pm
1 stop4h 18m
Chicago Midway
Wed 3/11
6:00 am-1:00 pm
1 stop6h 00m
$159
BlountvilleChicago
TRI - MDW
TRIMDW
Blountville Tri Cities TN/VA
Fri 5/1
7:15 pm-10:28 pm
1 stop4h 13m
Chicago Midway
Sat 5/9
6:30 am-12:53 pm
1 stop5h 23m
$169
BlountvilleChicago
TRI - MDW
TRIMDW
Blountville Tri Cities TN/VA
Tue 3/10
1:45 pm-5:22 pm
1 stop4h 37m
Chicago Midway
Tue 3/17
6:00 am-1:00 pm
1 stop6h 00m
$169
LouisvilleChicago
SDF - MDW
SDFMDW
Louisville Intl
Tue 3/10
8:55 am-9:15 am
Nonstop1h 20m
Chicago Midway
Wed 3/11
8:10 am-10:30 am
Nonstop1h 20m
$177
LouisvilleChicago
SDF - MDW
SDFMDW
Louisville Intl
Wed 3/11
11:50 am-12:05 pm
Nonstop1h 15m
Chicago Midway
Wed 3/11
6:15 pm-8:30 pm
Nonstop1h 15m
$177
LouisvilleChicago
SDF - MDW
SDFMDW
Louisville Intl
Sat 3/14
7:20 am-7:40 am
Nonstop1h 20m
Chicago Midway
Tue 3/17
8:10 am-10:30 am
Nonstop1h 20m
$178
Showing 1-10 of 60 results
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
SDF-MDW
TRI-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
SDF-MDW
TRI-MDW
BNA-MDW
What is the cheapest month to book a flight from Kentucky to Chicago Midway Airport?
Currently, September is the cheapest month in which you can book a flight from Kentucky to Chicago Midway Airport (average of $77). Flying from Kentucky to Chicago Midway Airport in February is currently the most expensive (average of $338). 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 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 February 11, 2026.
It’s optimal to fly from Kentucky to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 24% 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
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 February 11, 2026.
Kentucky and Midway flights
Browse other Kentucky and Midway flight options. Last updated on February 11, 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 February 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$97 | Average$257 | FlexibilityNo cancel fee | On-time63% |