$57+ 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 7/9. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — MDW
Jul 13 — Jul 201
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
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 Kentucky to Midway
Cheapest
Best
Last-minute
One-way
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 June 13, 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 June 13, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 6/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/61:23 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Sun 8/92:49 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 6/8![Allegiant Air logo]()
$171
This Southwest deal was found by Cheapflights users on 6/8. 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 8/261:15 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Wed 8/266:20 pm
MDW
- SDF
Nonstop1h 15m
Southwest
Deal found 6/8![Southwest logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
Sat 8/1511:10 am
TYS
- MDW
1 stop22h 14m
Allegiant Air
Sun 8/162:49 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 6/8![Allegiant Air logo]()
$184
This Cheapflightsfares deal was found by Cheapflights users on 6/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Thu 7/22:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 6/9![Allegiant Air logo]()
$186
This Southwest deal was found by Cheapflights users on 6/10. 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.
Tue 7/147:00 am
CVG
- MDW
2 stops7h 35m
Southwest
Wed 7/1512:45 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 6/10![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 6/12. 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.
Thu 8/67:00 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Mon 8/106:10 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 6/12![Southwest logo]()
$195
This Southwest deal was found by Cheapflights users on 6/10. 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 8/261:15 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Sat 8/297:50 am
MDW
- SDF
Nonstop1h 20m
Southwest
Deal found 6/10![Southwest logo]()
$196
This Delta deal was found by Cheapflights users on 6/10. 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.
Wed 7/12:15 pm
CVG
- MDW
1 stop5h 16m
Delta
Wed 7/89:19 am
MDW
- CVG
1 stop3h 16m
Delta
Deal found 6/10![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 6/9. 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 9/1612:45 pm
TYS
- MDW
1 stop5h 55m
Southwest
Mon 9/215:15 am
MDW
- TYS
1 stop7h 10m
Southwest
Deal found 6/9![Southwest logo]()
$198
This Southwest deal was found by Cheapflights users on 6/9. 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.
Tue 11/104:00 pm
CVG
- MDW
1 stop6h 20m
Southwest
Wed 11/111:15 pm
MDW
- CVG
2 stops7h 50m
Southwest
Deal found 6/9![Southwest logo]()
$201
This Southwest deal was found by Cheapflights users on 6/11. 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 7/147:00 am
CVG
- MDW
2 stops7h 35m
Southwest
Tue 7/145:30 pm
MDW
- CVG
1 stop4h 40m
Southwest
Deal found 6/11![Southwest logo]()
$202
This Southwest deal was found by Cheapflights users on 6/10. 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 8/263:30 pm
CVG
- MDW
1 stop6h 15m
Southwest
Sat 8/298:00 am
MDW
- CVG
Nonstop1h 25m
Southwest
Deal found 6/10![Southwest logo]()
$204
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 June 13, 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 June 13, 2026.
This Southwest deal was found by Cheapflights users on 6/10. 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 8/263:30 pm
CVG
- MDW
1 stop6h 15m
Southwest
Sat 8/298:00 am
MDW
- CVG
Nonstop1h 25m
Southwest
Deal found 6/10![Southwest logo]()
$204
This Delta deal was found by Cheapflights users on 6/11. 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.
Mon 11/237:20 am
SDF
- MDW
1 stop6h 13m
Delta
Thu 11/261:00 pm
MDW
- SDF
1 stop3h 40m
Delta
Deal found 6/11![Delta logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Wed 7/85:58 pm
LEX
- MDW
1 stop15h 20m
Allegiant Air
Fri 7/109:21 pm
MDW
- LEX
1 stop22h 29m
Allegiant Air
Deal found 6/9![Allegiant Air logo]()
$425
This Southwest deal was found by Cheapflights users on 6/10. 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.
Fri 9/45:25 pm
CVG
- MDW
1 stop5h 55m
Southwest
Mon 9/78:05 am
MDW
- CVG
Nonstop1h 20m
Southwest
Deal found 6/10![Southwest logo]()
$253
This Delta deal was found by Cheapflights users on 6/11. 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 9/36:00 am
LEX
- MDW
1 stop6h 51m
Delta
Fri 9/111:00 pm
MDW
- LEX
1 stop3h 10m
Delta
Deal found 6/11![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 6/8. 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 8/267:15 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Sun 8/306:00 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 6/8![Southwest logo]()
$253
This Delta deal was found by Cheapflights users on 6/11. 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 9/210:10 am
LEX
- MDW
1 stop6h 34m
Delta
Thu 9/106:00 am
MDW
- LEX
1 stop5h 35m
Delta
Deal found 6/11![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 6/9. 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 7/2910:10 am
BNA
- MDW
1 stop3h 25m
Southwest
Tue 8/412:45 pm
MDW
- BNA
1 stop4h 50m
Southwest
Deal found 6/9![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 6/10. 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.
Sat 10/37:35 am
LEX
- MDW
1 stop5h 59m
Delta
Mon 10/56:05 am
MDW
- LEX
1 stop4h 36m
Delta
Deal found 6/10![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 6/10. 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 7/87:10 am
TYS
- MDW
1 stop4h 50m
Southwest
Wed 7/159:00 am
MDW
- TYS
1 stop7h 00m
Southwest
Deal found 6/10![Southwest logo]()
$265
This Delta deal was found by Cheapflights users on 6/12. 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.
Fri 8/216:12 pm
TYS
- MDW
1 stop5h 24m
Delta
Mon 8/245:10 pm
MDW
- TYS
1 stop5h 42m
Delta
Deal found 6/12![Delta logo]()
$269
This Delta deal was found by Cheapflights users on 6/8. 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.
Fri 8/142:10 pm
BNA
- MDW
1 stop4h 23m
Delta
Mon 8/1712:46 pm
MDW
- BNA
1 stop4h 10m
Delta
Deal found 6/8![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 6/12. 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.
Wed 8/125:30 pm
TYS
- MDW
1 stop3h 40m
Southwest
Sun 8/165:10 am
MDW
- TYS
1 stop8h 50m
Southwest
Deal found 6/12![Southwest logo]()
$273
This Delta deal was found by Cheapflights users on 6/12. 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 8/294:50 pm
TRI
- MDW
1 stop6h 46m
Delta
Wed 9/26:05 am
MDW
- TRI
1 stop5h 56m
Delta
Deal found 6/12![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 6/7. 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.
Thu 7/98:25 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Mon 7/137:05 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 6/7![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 6/11. 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.
Sat 7/45:00 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Wed 7/87:45 am
MDW
- SDF
Nonstop1h 20m
Southwest
Deal found 6/11![Southwest logo]()
$276
This Delta deal was found by Cheapflights users on 6/8. 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.
Tue 6/307:49 am
SDF
- MDW
1 stop5h 57m
Delta
Wed 7/19:17 am
MDW
- SDF
1 stop3h 22m
Delta
Deal found 6/8![Delta logo]()
$295
This Southwest deal was found by Cheapflights users on 6/9. 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 8/135:25 pm
CVG
- MDW
1 stop5h 55m
Southwest
Sun 8/169:15 am
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 6/9![Southwest logo]()
$281
This Delta deal was found by Cheapflights users on 6/8. 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.
Fri 7/33:36 pm
TYS
- MDW
1 stop3h 55m
Delta
Sun 7/59:17 am
MDW
- TYS
1 stop4h 39m
Delta
Deal found 6/8![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 6/10. 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 7/812:45 pm
TYS
- MDW
2 stops9h 25m
Southwest
Fri 7/105:20 pm
MDW
- TYS
1 stop4h 15m
Southwest
Deal found 6/10![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 6/9. 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 7/67:00 am
CVG
- MDW
2 stops7h 35m
Southwest
Wed 7/85:30 pm
MDW
- CVG
1 stop4h 40m
Southwest
Deal found 6/9![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 6/12. 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.
Thu 9/107:30 am
TYS
- MDW
1 stop6h 00m
Delta
Sun 9/135:25 pm
MDW
- TYS
1 stop5h 22m
Delta
Deal found 6/12![Delta logo]()
$324
This Southwest deal was found by Cheapflights users on 6/8. 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 7/119:45 pm
BNA
- MDW
Nonstop1h 35m
Southwest
Tue 7/1411:50 am
MDW
- BNA
Nonstop1h 25m
Southwest
Deal found 6/8![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 6/8. 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.
Thu 7/27:15 am
TYS
- MDW
1 stop6h 31m
Delta
Sun 7/59:17 am
MDW
- TYS
1 stop4h 39m
Delta
Deal found 6/8![Delta logo]()
$344
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:30 pm
CVG
- MDW
1 stop3h 40m
Southwest
Fri 8/218:05 am
MDW
- CVG
Nonstop1h 20m
Southwest
Deal found 6/7![Southwest logo]()
$297
This Southwest deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/157:00 am
CVG
- MDW
2 stops7h 35m
Southwest
Thu 7/168:55 am
MDW
- CVG
1 stop7h 00m
Southwest
Deal found 6/7![Southwest logo]()
$298
This Delta deal was found by Cheapflights users on 6/8. 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.
Wed 7/157:35 am
LEX
- MDW
1 stop6h 03m
Delta
Sun 7/196:00 am
MDW
- LEX
1 stop5h 17m
Delta
Deal found 6/8![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 6/11. 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 8/612:40 pm
BNA
- MDW
Nonstop1h 30m
Southwest
Sun 8/97:30 am
MDW
- BNA
Nonstop1h 25m
Southwest
Deal found 6/11![Southwest logo]()
$299
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/307:35 am
LEX
- MDW
1 stop6h 03m
Delta
Mon 8/36:05 am
MDW
- LEX
1 stop5h 06m
Delta
Deal found 6/9![Delta logo]()
$379
This Southwest deal was found by Cheapflights users on 6/11. 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.
Sun 8/98:55 am
CVG
- MDW
Nonstop1h 05m
Southwest
Fri 8/148:05 am
MDW
- CVG
Nonstop1h 20m
Southwest
Deal found 6/11![Southwest logo]()
$302
Last-minute flights from Kentucky to MidwayDiscover last-minute flight deals from Kentucky to Midway. Data last updated June 13, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Midway. Data last updated June 13, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 6/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Thu 7/22:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 6/9![Allegiant Air logo]()
$186
This Mytrip deal was found by Cheapflights users on 6/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/251:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Sun 6/282:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Deal found 6/9![Allegiant Air logo]()
$227
This Delta deal was found by Cheapflights users on 6/10. 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.
Wed 7/12:15 pm
CVG
- MDW
1 stop5h 16m
Delta
Wed 7/89:19 am
MDW
- CVG
1 stop3h 16m
Delta
Deal found 6/10![Delta logo]()
$197
This Cheapflightsfares deal was found by Cheapflights users on 6/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/21:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Sun 7/52:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 6/9![Allegiant Air logo]()
$225
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/51:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Sun 7/122:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 6/11![Allegiant Air logo]()
$216
This Southwest deal was found by Cheapflights users on 6/9. 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.
Tue 7/77:40 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Thu 7/97:05 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 6/9![Southwest logo]()
$225
This Delta deal was found by Cheapflights users on 6/8. 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.
Wed 7/82:15 pm
CVG
- MDW
1 stop5h 10m
Delta
Wed 7/159:19 am
MDW
- CVG
1 stop3h 16m
Delta
Deal found 6/8![Delta logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 7/912:18 pm
CVG
- MDW
1 stop10h 45m
Frontier
Sat 7/1112:11 pm
MDW
- CVG
1 stop22h 02m
Frontier
Deal found 6/10![Frontier logo]()
$226
This Southwest deal was found by Cheapflights users on 6/10. 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.
Tue 7/147:00 am
CVG
- MDW
2 stops7h 35m
Southwest
Wed 7/1512:45 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 6/10![Southwest logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 7/161:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Sun 7/192:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 6/9![Allegiant Air logo]()
$208
This Southwest deal was found by Cheapflights users on 6/12. 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 7/189:15 am
CVG
- MDW
Nonstop1h 05m
Southwest
Tue 7/216:15 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 6/12![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 6/12. 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 7/248:00 am
CVG
- MDW
Nonstop1h 05m
Southwest
Tue 7/286:15 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 6/12![Southwest logo]()
$229
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 June 13, 2026.
Search for one-way flight options from Kentucky to Midway. Find affordable one-way fares based on user searches. Data last updated June 13, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/91:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 6/11![Allegiant Air logo]()
$57
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
Thu 7/301:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 6/12![Allegiant Air logo]()
$74
This Southwest deal was found by Cheapflights users on 6/12. 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.
Wed 7/157:40 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 6/12![Southwest logo]()
$79
This Cheapflightsfares deal was found by Cheapflights users on 6/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/211:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 6/9![Allegiant Air logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 6/8. 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.
Thu 6/251:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 6/8![Allegiant Air logo]()
$84
This Southwest deal was found by Cheapflights users on 6/8. 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 8/57:15 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 6/8![Southwest logo]()
$88
This Southwest deal was found by Cheapflights users on 6/10. 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 8/58:45 am
SDF
- MDW
Nonstop1h 15m
Southwest
Deal found 6/10![Southwest logo]()
$89
This Southwest deal was found by Cheapflights users on 6/8. 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 7/147:40 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 6/8![Southwest logo]()
$89
This Southwest deal was found by Cheapflights users on 6/10. 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 8/198:05 am
TYS
- MDW
2 stops8h 20m
Southwest
Deal found 6/10![Southwest logo]()
$96
This Southwest deal was found by Cheapflights users on 6/11. 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.
Sat 9/58:20 am
CVG
- MDW
Nonstop1h 05m
Southwest
Deal found 6/11![Southwest logo]()
$98
This Delta deal was found by Cheapflights users on 6/9. 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 8/57:55 am
SDF
- MDW
1 stop5h 44m
Delta
Deal found 6/9![Delta logo]()
$99
This Southwest deal was found by Cheapflights users on 6/12. 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.
Wed 9/97:00 am
CVG
- MDW
2 stops10h 50m
Southwest
Deal found 6/12![Southwest logo]()
$100
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 June 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $171 (Cheapflightsfares) |
One-way from | $57 (Cheapflightsfares) |
Popular in | January |
Cheapest in | November |
Average price | $356 |
Good round-trip deal | $385 or less |
Good one-way deal | $203 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 June 13, 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 8/26
3:30 pm-8:45 pm
1 stop6h 15m
Chicago Midway
Sat 8/29
8:00 am-10:25 am
Nonstop1h 25m
$204
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Fri 9/4
5:25 pm-10:20 pm
1 stop5h 55m
Chicago Midway
Mon 9/7
8:05 am-10:25 am
Nonstop1h 20m
$253
Quickest round-trip
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Wed 8/26
7:15 pm-7:25 pm
Nonstop1h 10m
Chicago Midway
Sun 8/30
6:00 pm-8:15 pm
Nonstop1h 15m
$253
NashvilleChicago
BNA - MDW
BNAMDW
Nashville Intl
Wed 7/29
10:10 am-1:35 pm
1 stop3h 25m
Chicago Midway
Tue 8/4
12:45 pm-5:35 pm
1 stop4h 50m
$257
LouisvilleChicago
SDF - MDW
SDFMDW
Louisville Intl
Mon 11/23
7:20 am-12:33 pm
1 stop6h 13m
Chicago Midway
Thu 11/26
1:00 pm-5:40 pm
1 stop3h 40m
$263
KnoxvilleChicago
TYS - MDW
TYSMDW
Knoxville McGhee Tyson
Wed 7/8
7:10 am-11:00 am
1 stop4h 50m
Chicago Midway
Wed 7/15
9:00 am-5:00 pm
1 stop7h 00m
$265
LexingtonChicago
LEX - MDW
LEXMDW
Lexington Blue Grass
Thu 9/3
6:00 am-11:51 am
1 stop6h 51m
Chicago Midway
Fri 9/11
1:00 pm-5:10 pm
1 stop3h 10m
$269
LexingtonChicago
LEX - MDW
LEXMDW
Lexington Blue Grass
Wed 9/2
10:10 am-3:44 pm
1 stop6h 34m
Chicago Midway
Thu 9/10
6:00 am-12:35 pm
1 stop5h 35m
$269
LexingtonChicago
LEX - MDW
LEXMDW
Lexington Blue Grass
Sat 10/3
7:35 am-12:34 pm
1 stop5h 59m
Chicago Midway
Mon 10/5
6:05 am-11:41 am
1 stop4h 36m
$269
KnoxvilleChicago
TYS - MDW
TYSMDW
Knoxville McGhee Tyson
Fri 8/21
6:12 pm-10:36 pm
1 stop5h 24m
Chicago Midway
Mon 8/24
5:10 pm-11:52 pm
1 stop5h 42m
$269
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
EVV-MDW
TRI-MDW
SDF-MDW
TYS-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
EVV-MDW
TRI-MDW
SDF-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 June 13, 2026.
It’s optimal to fly from Kentucky to Chicago Midway Airport at noon. By choosing this option you can save up to 11% on the cost of your flight, compared to a flight in the evening.
How much does it cost to fly round-trip from Kentucky to Chicago Midway Airport?
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 locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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
Midway flight routes
Other flight options
Popular flights
Top destinations
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 June 13, 2026.
Kentucky and Midway flights
Browse other Kentucky and Midway flight options. Last updated on June 13, 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 June 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$77 | Average$248 | FlexibilityNo cancel fee | On-time63% |