$52+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — MDW
Sep 10 — Sep 171
Round-trip
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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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
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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 August 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 August 11, 2026.
This Southwest deal was found by Cheapflights users on 8/9. 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 9/17:15 pm -
Nonstop1h 10m
Sat 9/53:25 pm -
Nonstop1h 15m
Deal found 8/9![Southwest logo]()
$163
This Southwest deal was found by Cheapflights users on 8/10. 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.
Sat 9/52:50 pm -
1 stop6h 45m
Sun 9/68:55 am -
1 stop4h 05m
Deal found 8/10![Southwest logo]()
$164
This Southwest deal was found by Cheapflights users on 8/10. 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.
Sat 9/52:50 pm -
1 stop6h 45m
Tue 9/812:45 pm -
Nonstop1h 10m
Deal found 8/10![Southwest logo]()
$166
This Southwest deal was found by Cheapflights users on 8/7. 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 9/54:55 pm -
Nonstop1h 10m
Mon 9/78:05 am -
Nonstop1h 20m
Deal found 8/7![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 8/10. 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 9/117:10 pm -
Nonstop1h 15m
Mon 9/148:00 am -
Nonstop1h 25m
Deal found 8/10![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 8/10. 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.
Sat 9/194:55 pm -
Nonstop1h 10m
Sat 9/268:00 am -
Nonstop1h 25m
Deal found 8/10![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 8/10. 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.
Thu 10/227:50 pm -
Nonstop1h 15m
Mon 10/267:55 am -
Nonstop1h 15m
Deal found 8/10![Southwest logo]()
$183
This Southwest deal was found by Cheapflights users on 8/10. 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 9/97:00 am -
2 stops10h 50m
Fri 9/113:20 pm -
1 stop5h 20m
Deal found 8/10![Southwest logo]()
$188
This Southwest deal was found by Cheapflights users on 8/10. 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.
Mon 9/79:00 am -
Nonstop1h 15m
Thu 9/108:00 am -
Nonstop1h 25m
Deal found 8/10![Southwest logo]()
$195
This Southwest deal was found by Cheapflights users on 8/9. 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 10/137:10 pm -
Nonstop1h 15m
Sat 10/178:05 am -
Nonstop1h 15m
Deal found 8/9![Southwest logo]()
$196
This Southwest deal was found by Cheapflights users on 8/10. 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 9/224:00 pm -
2 stops6h 55m
Wed 9/239:00 am -
Nonstop1h 20m
Deal found 8/10![Southwest logo]()
$198
This Southwest deal was found by Cheapflights users on 8/10. 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.
Sat 9/54:55 pm -
Nonstop1h 20m
Sun 9/61:45 pm -
Nonstop1h 15m
Deal found 8/10![Southwest logo]()
$199
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 August 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 August 11, 2026.
This Southwest deal was found by Cheapflights users on 8/10. 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.
Sat 9/52:50 pm -
1 stop6h 45m
Tue 9/812:45 pm -
Nonstop1h 10m
Deal found 8/10![Southwest logo]()
$166
This Delta deal was found by Cheapflights users on 8/10. 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 9/154:00 pm -
1 stop3h 33m
Sat 9/199:29 am -
1 stop4h 45m
Deal found 8/10![Delta logo]()
$201
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/52:50 pm -
1 stop6h 45m
Sun 9/66:30 pm -
Nonstop1h 10m
Deal found 8/6![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 8/10. 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.
Thu 10/227:50 pm -
Nonstop1h 15m
Mon 10/267:55 am -
Nonstop1h 15m
Deal found 8/10![Southwest logo]()
$183
This Southwest deal was found by Cheapflights users on 8/10. 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 10/212:05 pm -
Nonstop1h 15m
Thu 10/227:55 am -
Nonstop1h 15m
Deal found 8/10![Southwest logo]()
$183
This Southwest deal was found by Cheapflights users on 8/10. 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.
Sat 9/52:50 pm -
1 stop6h 45m
Mon 9/78:05 am -
Nonstop1h 20m
Deal found 8/10![Southwest logo]()
$190
This Delta deal was found by Cheapflights users on 8/10. 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 9/26:00 am -
1 stop4h 59m
Sat 9/56:05 am -
1 stop5h 06m
Deal found 8/10![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 8/10. 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.
Mon 10/193:35 pm -
Nonstop1h 15m
Mon 10/196:55 pm -
Nonstop1h 10m
Deal found 8/10![Southwest logo]()
$208
This Delta deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/87:30 am -
1 stop6h 03m
Sun 1/101:00 pm -
1 stop3h 09m
Deal found 8/6![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 8/10. 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.
Fri 1/296:00 am -
1 stop4h 52m
Sun 1/315:25 pm -
1 stop5h 31m
Deal found 8/10![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 8/10. 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 9/47:10 pm -
Nonstop1h 15m
Mon 9/78:00 am -
Nonstop1h 25m
Deal found 8/10![Southwest logo]()
$220
This Delta deal was found by Cheapflights users on 8/8. 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 9/156:13 pm -
1 stop5h 31m
Tue 9/225:11 pm -
1 stop5h 44m
Deal found 8/8![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 8/7. 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 9/54:55 pm -
Nonstop1h 20m
Tue 9/81:00 pm -
Nonstop1h 15m
Deal found 8/7![Southwest logo]()
$226
This Delta deal was found by Cheapflights users on 8/10. 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 9/265:13 pm -
1 stop6h 31m
Tue 9/296:05 am -
1 stop5h 40m
Deal found 8/10![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 8/7. 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 9/54:55 pm -
Nonstop1h 20m
Sun 9/68:55 am -
1 stop4h 35m
Deal found 8/7![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/276:05 am -
1 stop4h 47m
Sat 1/306:00 am -
1 stop5h 04m
Deal found 8/6![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 8/8. 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 9/55:50 pm -
Nonstop1h 30m
Sun 9/68:10 am -
1 stop5h 35m
Deal found 8/8![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 8/9. 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 9/125:13 pm -
1 stop6h 31m
Mon 9/146:05 am -
1 stop5h 40m
Deal found 8/9![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 8/7. 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 9/155:30 pm -
1 stop3h 40m
Tue 9/221:00 pm -
2 stops6h 55m
Deal found 8/7![Southwest logo]()
$230
This Delta deal was found by Cheapflights users on 8/9. 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 9/95:13 pm -
1 stop6h 31m
Mon 9/146:05 am -
1 stop5h 40m
Deal found 8/9![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:05 am -
1 stop3h 15m
Tue 9/85:20 pm -
Nonstop1h 30m
Deal found 8/6![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 8/9. 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.
Tue 9/15:00 pm -
1 stop6h 36m
Sun 9/66:05 am -
1 stop5h 06m
Deal found 8/9![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/319:00 am -
Nonstop1h 15m
Thu 9/38:00 am -
Nonstop1h 25m
Deal found 8/6![Southwest logo]()
$235
This Delta deal was found by Cheapflights users on 8/10. 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 9/55:00 pm -
1 stop6h 36m
Sun 9/66:05 am -
1 stop5h 06m
Deal found 8/10![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 8/7. 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 9/172:15 pm -
Nonstop1h 15m
Mon 9/218:00 am -
Nonstop1h 25m
Deal found 8/7![Southwest logo]()
$235
This Delta deal was found by Cheapflights users on 8/10. 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.
Sun 9/66:00 am -
1 stop5h 10m
Tue 9/86:05 am -
1 stop4h 39m
Deal found 8/10![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 8/7. 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 9/75:40 am -
Nonstop1h 30m
Mon 9/148:45 pm -
Nonstop1h 30m
Deal found 8/7![Southwest logo]()
$235
This Delta deal was found by Cheapflights users on 8/7. 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.
Sat 8/227:15 am -
1 stop6h 24m
Sat 8/291:25 pm -
1 stop5h 01m
Deal found 8/7![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:50 pm -
1 stop5h 45m
Mon 9/78:00 am -
Nonstop1h 25m
Deal found 8/6![Southwest logo]()
$236
This Delta deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:35 am -
1 stop4h 16m
Sat 8/291:25 pm -
1 stop5h 01m
Deal found 8/6![Delta logo]()
$299
Last-minute flights from Kentucky to MidwayDiscover last-minute flight deals from Kentucky to Midway. Data last updated August 11, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Midway. Data last updated August 11, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/9. 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 9/17:15 pm -
Nonstop1h 10m
Sat 9/53:25 pm -
Nonstop1h 15m
Deal found 8/9![Southwest logo]()
$163
This Southwest deal was found by Cheapflights users on 8/10. 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.
Sat 9/52:50 pm -
1 stop6h 45m
Sun 9/68:55 am -
1 stop4h 05m
Deal found 8/10![Southwest logo]()
$164
This Southwest deal was found by Cheapflights users on 8/10. 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.
Sat 9/52:50 pm -
1 stop6h 45m
Tue 9/812:45 pm -
Nonstop1h 10m
Deal found 8/10![Southwest logo]()
$166
This Southwest deal was found by Cheapflights users on 8/7. 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 9/54:55 pm -
Nonstop1h 10m
Mon 9/78:05 am -
Nonstop1h 20m
Deal found 8/7![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 8/10. 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.
Sat 9/54:55 pm -
Nonstop1h 20m
Sun 9/61:45 pm -
Nonstop1h 15m
Deal found 8/10![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 8/7. 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 9/55:15 am -
Nonstop1h 35m
Sun 9/68:55 am -
Nonstop1h 35m
Deal found 8/7![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 8/10. 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.
Mon 9/79:00 am -
Nonstop1h 15m
Thu 9/108:00 am -
Nonstop1h 25m
Deal found 8/10![Southwest logo]()
$195
This Southwest deal was found by Cheapflights users on 8/10. 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.
Mon 9/75:40 am -
Nonstop1h 30m
Tue 9/159:00 am -
Nonstop1h 30m
Deal found 8/10![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 8/10. 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 9/97:00 am -
2 stops10h 50m
Fri 9/113:20 pm -
1 stop5h 20m
Deal found 8/10![Southwest logo]()
$188
This Southwest deal was found by Cheapflights users on 8/10. 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 9/117:10 pm -
Nonstop1h 15m
Mon 9/148:00 am -
Nonstop1h 25m
Deal found 8/10![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 8/10. 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.
Sat 9/194:55 pm -
Nonstop1h 10m
Sat 9/268:00 am -
Nonstop1h 25m
Deal found 8/10![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 8/10. 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 9/226:45 pm -
Nonstop1h 15m
Wed 9/239:00 am -
Nonstop1h 20m
Deal found 8/10![Southwest logo]()
$183
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 August 11, 2026.
Search for one-way flight options from Kentucky to Midway. Find affordable one-way fares based on user searches. Data last updated August 11, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 8/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/301:04 pm -
Nonstop1h 32m
Deal found 8/7![Allegiant Air logo]()
$52
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/163:04 pm -
Nonstop1h 37m
Deal found 8/10![Allegiant Air logo]()
$63
This Cheapflightsfares deal was found by Cheapflights users on 8/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/231:04 pm -
Nonstop1h 32m
Deal found 8/7![Allegiant Air logo]()
$67
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:55 pm -
Nonstop1h 10m
Deal found 8/6![Southwest logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Mon 8/3112:26 pm -
1 stop23h 29m
Deal found 8/10![Frontier logo]()
$82
This Delta deal was found by Cheapflights users on 8/10. 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.
Sun 9/66:10 am -
1 stop4h 07m
Deal found 8/10![Delta logo]()
$89
This Southwest deal was found by Cheapflights users on 8/9. 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.
Fri 9/117:10 pm -
Nonstop1h 15m
Deal found 8/9![Southwest logo]()
$90
This Frontier deal was found by Cheapflights users on 8/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:43 pm -
1 stop6h 08m
Deal found 8/7![Frontier logo]()
$90
This Southwest deal was found by Cheapflights users on 8/10. 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 9/97:15 pm -
Nonstop1h 10m
Deal found 8/10![Southwest logo]()
$91
This Southwest deal was found by Cheapflights users on 8/9. 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 9/98:45 am -
Nonstop1h 15m
Deal found 8/9![Southwest logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/511:34 am -
Nonstop1h 32m
Deal found 8/7![Allegiant Air logo]()
$93
This Southwest deal was found by Cheapflights users on 8/10. 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 11/41:00 pm -
1 stop6h 05m
Deal found 8/10![Southwest logo]()
$94
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 August 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $163 (Southwest) |
One-way from | $52 (Cheapflightsfares) |
Popular in | January |
Cheapest in | December |
Average price | $375 |
Good round-trip deal | $335 or less |
Good one-way deal | $184 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 August 11, 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 Cincinnati Cinci./N. Kentucky - MDW Chicago Midway
CVGMDW
Cincinnati Cinci./N. Kentucky
Sat 9/5
2:50 pm-8:35 pm
1 stop6h 45m
Chicago Midway
Tue 9/8
12:45 pm-2:55 pm
Nonstop1h 10m
$166
CincinnatiChicago
CVG Cincinnati Cinci./N. Kentucky - MDW Chicago Midway
CVGMDW
Cincinnati Cinci./N. Kentucky
Sat 9/5
2:50 pm-8:35 pm
1 stop6h 45m
Chicago Midway
Sun 9/6
6:30 pm-8:40 pm
Nonstop1h 10m
$167
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Thu 10/22
7:50 pm-8:05 pm
Nonstop1h 15m
Chicago Midway
Mon 10/26
7:55 am-10:10 am
Nonstop1h 15m
$183
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Wed 10/21
2:05 pm-2:20 pm
Nonstop1h 15m
Chicago Midway
Thu 10/22
7:55 am-10:10 am
Nonstop1h 15m
$183
CincinnatiChicago
CVG Cincinnati Cinci./N. Kentucky - MDW Chicago Midway
CVGMDW
Cincinnati Cinci./N. Kentucky
Sat 9/5
2:50 pm-8:35 pm
1 stop6h 45m
Chicago Midway
Mon 9/7
8:05 am-10:25 am
Nonstop1h 20m
$190
CincinnatiChicago
CVG Cincinnati Cinci./N. Kentucky - MDW Chicago Midway
CVGMDW
Cincinnati Cinci./N. Kentucky
Tue 9/15
4:00 pm-6:33 pm
1 stop3h 33m
Chicago Midway
Sat 9/19
9:29 am-3:14 pm
1 stop4h 45m
$201
Quickest round-trip
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Mon 10/19
3:35 pm-3:50 pm
Nonstop1h 15m
Chicago Midway
Mon 10/19
6:55 pm-9:05 pm
Nonstop1h 10m
$208
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Fri 9/4
7:10 pm-7:25 pm
Nonstop1h 15m
Chicago Midway
Mon 9/7
8:00 am-10:25 am
Nonstop1h 25m
$220
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Sat 9/5
4:55 pm-5:15 pm
Nonstop1h 20m
Chicago Midway
Tue 9/8
1:00 pm-3:15 pm
Nonstop1h 15m
$226
LouisvilleChicago
SDF Louisville Intl - MDW Chicago Midway
SDFMDW
Louisville Intl
Sat 9/5
4:55 pm-5:15 pm
Nonstop1h 20m
Chicago Midway
Sun 9/6
8:55 am-2:30 pm
1 stop4h 35m
$227
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
SDF-MDW
LEX-MDW
TYS-MDW
TRI-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
LEX-MDW
TYS-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 August 11, 2026.
It’s optimal to fly from Kentucky to Chicago Midway Airport at noon. By choosing this option you can save up to 13% on the cost of your flight, compared to a flight in the morning.
How much does it cost to fly round-trip from Kentucky to Chicago Midway Airport?
Airfare is below average for this route at the moment.
Kentucky to Chicago Midway Airport flights typically cost between $269 and $315 in September.The cheapest round-trip price found within the last 5 days was $182 on Southwest (Sep 11-Sep 14).
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
Valparaiso
Hammond
Saint Joseph
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
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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 August 11, 2026.
Kentucky and Midway flights
Browse other Kentucky and Midway flight options. Last updated on August 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 August 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$97 | Average$297 | FlexibilityNo cancel fee | On-time63% |