$274+ Cheap flights from Madison (MSN) to Kentucky
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SDF
Oct 24 — Oct 311
Round-trip
1 adult, Economy
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Find cheap flights from Madison to Kentucky with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Madison to Kentucky
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Cheapest flights from Madison to KentuckyExplore the most affordable flight options available from Madison to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 24, 2026.
Explore the most affordable flight options available from Madison to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 24, 2026.
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:00 am -
1 stop3h 34m
Thu 10/295:10 am -
1 stop5h 51m
Deal found 9/22![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:29 pm -
1 stop6h 37m
Fri 10/307:45 am -
1 stop5h 50m
Deal found 9/22![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:00 am -
1 stop4h 44m
Sat 10/319:17 am -
2 stops10h 18m
Deal found 9/19![American Airlines logo]()
$324
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1311:16 am -
1 stop4h 57m
Sun 11/156:27 am -
1 stop5h 19m
Deal found 9/19![American Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/95:00 am -
1 stop3h 28m
Mon 10/128:50 am -
1 stop5h 47m
Deal found 9/20![United Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/199:25 am -
2 stops7h 00m
Mon 11/236:30 am -
1 stop6h 10m
Deal found 9/19![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:35 pm -
1 stop4h 24m
Sat 10/107:00 am -
1 stop5h 54m
Deal found 9/21![United Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:00 am -
1 stop4h 44m
Sat 10/106:58 pm -
1 stop5h 14m
Deal found 9/22![American Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/208:17 am -
1 stop5h 15m
Tue 10/275:30 am -
1 stop6h 19m
Deal found 9/21![United Airlines logo]()
$394
This American Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:00 am -
1 stop4h 44m
Sat 10/246:21 am -
2 stops9h 34m
Deal found 9/22![American Airlines logo]()
$395
This American Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:00 am -
1 stop3h 32m
Thu 10/296:29 am -
1 stop5h 23m
Deal found 9/23![American Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/63:11 pm -
2 stops7h 48m
Sun 11/88:11 pm -
1 stop4h 48m
Deal found 9/19![American Airlines logo]()
$404
Best flights from Madison to KentuckyDiscover carefully curated flight deals from Madison to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 24, 2026.
Discover carefully curated flight deals from Madison to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 24, 2026.
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:00 am -
1 stop3h 34m
Thu 10/295:10 am -
1 stop5h 51m
Deal found 9/22![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:20 pm -
1 stop5h 38m
Mon 11/167:35 am -
1 stop6h 04m
Deal found 9/22![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:00 am -
1 stop4h 44m
Sat 10/316:21 am -
1 stop7h 23m
Deal found 9/19![American Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:30 am -
1 stop5h 19m
Mon 11/237:05 am -
1 stop4h 35m
Deal found 9/22![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1311:16 am -
1 stop4h 57m
Sun 11/156:27 am -
1 stop5h 19m
Deal found 9/19![American Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:35 pm -
1 stop4h 24m
Sat 10/107:00 am -
1 stop5h 54m
Deal found 9/21![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:29 pm -
1 stop6h 37m
Fri 10/307:45 am -
1 stop5h 50m
Deal found 9/19![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/199:25 am -
2 stops7h 00m
Mon 11/231:30 pm -
2 stops7h 41m
Deal found 9/19![American Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/208:17 am -
1 stop5h 15m
Tue 10/275:30 am -
1 stop6h 19m
Deal found 9/21![United Airlines logo]()
$394
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/63:11 pm -
2 stops7h 48m
Sun 11/88:11 pm -
1 stop4h 48m
Deal found 9/19![American Airlines logo]()
$404
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:35 pm -
1 stop4h 24m
Sat 10/246:16 pm -
1 stop3h 44m
Deal found 9/20![United Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/108:22 am -
1 stop3h 58m
Sat 1/162:08 pm -
1 stop4h 43m
Deal found 9/20![United Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/95:30 am -
1 stop5h 26m
Wed 11/115:40 pm -
1 stop4h 33m
Deal found 9/22![Delta logo]()
$457
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/69:53 am -
2 stops7h 34m
Sat 10/1010:08 am -
1 stop5h 47m
Deal found 9/21![American Airlines logo]()
$432
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/277:19 pm -
1 stop3h 37m
Sat 1/308:45 am -
1 stop4h 02m
Deal found 9/19![United Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:49 am -
1 stop5h 26m
Mon 10/129:04 am -
1 stop5h 33m
Deal found 9/23![United Airlines logo]()
$499
This United Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:17 am -
1 stop5h 15m
Mon 10/125:00 am -
1 stop17h 35m
Deal found 9/23![United Airlines logo]()
$528
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:17 am -
1 stop5h 15m
Fri 10/92:23 pm -
2 stops24h 41m
Deal found 9/20![United Airlines logo]()
$733
Last-minute flights from Madison to KentuckyDiscover last-minute flight deals from Madison to Kentucky. Data last updated September 24, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Kentucky. Data last updated September 24, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:00 am -
1 stop3h 28m
Sat 9/266:10 pm -
1 stop3h 50m
Deal found 9/20![United Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:35 pm -
1 stop4h 24m
Sat 10/107:00 am -
1 stop5h 54m
Deal found 9/21![United Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/75:00 am -
1 stop4h 44m
Sat 10/106:58 pm -
1 stop5h 14m
Deal found 9/22![American Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/95:00 am -
1 stop3h 28m
Mon 10/128:50 am -
1 stop5h 47m
Deal found 9/20![United Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:29 pm -
1 stop6h 37m
Fri 10/307:45 am -
1 stop5h 50m
Deal found 9/22![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/208:17 am -
1 stop5h 15m
Tue 10/275:30 am -
1 stop6h 19m
Deal found 9/21![United Airlines logo]()
$394
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/204:10 pm -
1 stop6h 49m
Sat 10/241:25 pm -
1 stop7h 50m
Deal found 9/22![United Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:00 am -
1 stop4h 44m
Sat 10/246:21 am -
2 stops9h 34m
Deal found 9/22![American Airlines logo]()
$395
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:00 am -
1 stop3h 34m
Thu 10/295:10 am -
1 stop5h 51m
Deal found 9/22![United Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:00 am -
1 stop3h 32m
Thu 10/296:29 am -
1 stop5h 23m
Deal found 9/23![American Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:00 am -
1 stop4h 44m
Sat 10/319:17 am -
2 stops10h 18m
Deal found 9/19![American Airlines logo]()
$324
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/303:00 pm -
1 stop4h 52m
Sun 11/15:57 pm -
1 stop6h 10m
Deal found 9/21![United Airlines logo]()
$424
One-way flights from Madison to KentuckySearch for one-way flight options from Madison to Kentucky. Find affordable one-way fares based on user searches. Data last updated September 24, 2026.
Search for one-way flight options from Madison to Kentucky. Find affordable one-way fares based on user searches. Data last updated September 24, 2026.
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/194:21 pm -
1 stop6h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![American Airlines logo]()
$274
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:00 am -
2 stops7h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![American Airlines logo]()
$279
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:00 am -
1 stop4h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![United Airlines logo]()
$384
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:30 am -
3 stops56h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$386
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:00 am -
1 stop3h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![United Airlines logo]()
$388
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/164:10 pm -
1 stop6h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![United Airlines logo]()
$390
This United Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2912:39 pm -
1 stop6h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![United Airlines logo]()
$397
This American Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2912:56 pm -
2 stops9h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![American Airlines logo]()
$402
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:45 pm -
3 stops22h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![United Airlines logo]()
$490
This United Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:10 am -
3 stops14h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![United Airlines logo]()
$668
Find flight deals from Madison to Kentucky
Keep the following information in mind while searching for Madison to Kentucky flight deals. Data was last updated September 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $319 (United Airlines) |
One-way from | $274 (United Airlines) |
Popular in | June |
Cheapest in | October |
Average price | $746 |
Cheapflights Fare Finder
Customize your flight search to find flights from Madison to Kentucky that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 24, 2026.
Use the filters below to find and compare flights from Madison to Kentucky that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MadisonLexington
MSN Madison Truax Field - LEX Lexington Blue Grass
MSNLEX
Madison Truax Field
Tue 10/20
6:35 pm-11:55 pm
1 stop4h 20m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$274
MadisonLexington
MSN Madison Truax Field - LEX Lexington Blue Grass
MSNLEX
Madison Truax Field
Fri 11/6
12:24 pm-7:41 pm
1 stop6h 17m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$274
MadisonLouisville
MSN Madison Truax Field - SDF Louisville Intl
MSNSDF
Madison Truax Field
Thu 10/22
5:00 am-9:34 am
1 stop3h 34m
Louisville Intl
Thu 10/29
5:10 am-10:01 am
1 stop5h 51m
$319
MadisonLexington
MSN Madison Truax Field - LEX Lexington Blue Grass
MSNLEX
Madison Truax Field
Fri 11/13
5:20 pm-11:58 pm
1 stop5h 38m
Lexington Blue Grass
Mon 11/16
7:35 am-12:39 pm
1 stop6h 04m
$319
MadisonLexington
MSN Madison Truax Field - LEX Lexington Blue Grass
MSNLEX
Madison Truax Field
Wed 10/28
5:00 am-10:44 am
1 stop4h 44m
Lexington Blue Grass
Sat 10/31
6:21 am-12:44 pm
1 stop7h 23m
$319
MadisonLexington
MSN Madison Truax Field - LEX Lexington Blue Grass
MSNLEX
Madison Truax Field
Thu 11/19
5:30 am-11:49 am
1 stop5h 19m
Lexington Blue Grass
Mon 11/23
7:05 am-10:40 am
1 stop4h 35m
$319
MadisonLexington
MSN Madison Truax Field - LEX Lexington Blue Grass
MSNLEX
Madison Truax Field
Fri 10/16
1:29 pm-9:06 pm
1 stop6h 37m
Lexington Blue Grass
Fri 10/30
7:45 am-12:35 pm
1 stop5h 50m
$319
MadisonLouisville
MSN Madison Truax Field - SDF Louisville Intl
MSNSDF
Madison Truax Field
Fri 11/13
11:16 am-5:13 pm
1 stop4h 57m
Louisville Intl
Sun 11/15
6:27 am-10:46 am
1 stop5h 19m
$334
MadisonLouisville
MSN Madison Truax Field - SDF Louisville Intl
MSNSDF
Madison Truax Field
Tue 10/6
6:35 pm-11:59 pm
1 stop4h 24m
Louisville Intl
Sat 10/10
7:00 am-11:54 am
1 stop5h 54m
$349
MadisonLexington
MSN Madison Truax Field - LEX Lexington Blue Grass
MSNLEX
Madison Truax Field
Thu 11/19
9:25 am-5:25 pm
2 stops7h 00m
Lexington Blue Grass
Mon 11/23
1:30 pm-8:11 pm
2 stops7h 41m
$359
Showing 1-10 of 27 resultsSorted by cheapest first
Best time to book a flight from Madison to Kentucky
Have a flexible travel schedule? Discover the best time to fly to Kentucky from Madison with our price prediction graph.
MSN-LEX
MSN-SDF
MSN-PAH
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 Madison to Kentucky
MSN-USKY
MSN-LEX
MSN-SDF
MSN-PAH
What is the cheapest month to book a flight from Madison to Kentucky?
Currently, August is the cheapest month in which you can book a flight from Madison to Kentucky (average of $298). Flying from Madison to Kentucky in June is currently the most expensive (average of $736). 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.
How much does it cost to fly round-trip from Madison to Kentucky?
Airfare is below average for this route at the moment.
Madison to Kentucky flights typically cost between $514 and $656 in October.The cheapest round-trip price found within the last 5 days was $319 on United Airlines (Oct 22-Oct 29).
Reviews of airlines servicing Kentucky
Get insights into the airlines that provide service to Kentucky. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kentucky. Reviews last updated September 24, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican Airlines from Madison to Kentucky by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.8
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Overall
7.8
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Overall
7.8
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Overall
7.8
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Related info for your journey
Find useful and relevant information for your journey from Madison to Kentucky. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Madison to Kentucky
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Kentucky by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Madison to Kentucky by cabin class
Find flights from Madison to Kentucky, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Madison and Kentucky flights
Browse other Madison and Kentucky flight options. Last updated on September 24, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Madison to Kentucky flights
Consider these flights traveling from Madison to Kentucky.
Top 3 airlines flying from Madison to Kentucky
Discover the top 3 airlines that operate flights from Madison to Kentucky. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$235 | Average$476 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$283 | Average$438 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$288 | Average$407 | FlexibilityNo cancel fee | On-time71% |