$274+ Cheap flights from Kentucky to Madison (MSN)
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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — MSN
Nov 9 — Nov 161
Round-trip
1 adult, Economy
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Find cheap flights from Kentucky to Madison 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 Madison
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Cheapest flights from Kentucky to MadisonExplore the most affordable flight options available from Kentucky to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 10, 2026.
Explore the most affordable flight options available from Kentucky to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 10, 2026.
This Delta deal was found by Cheapflights users on 10/6. 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.
Thu 11/127:05 am -
1 stop4h 35m
Sun 11/155:20 pm -
1 stop5h 38m
Deal found 10/6![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 10/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:11 pm -
1 stop4h 48m
Sun 11/153:11 pm -
2 stops7h 48m
Deal found 10/6![American Airlines logo]()
$324
This United Airlines deal was found by Cheapflights users on 10/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/229:04 am -
1 stop5h 33m
Sat 10/2412:39 pm -
1 stop6h 52m
Deal found 10/8![United Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/208:50 am -
1 stop5h 47m
Sat 10/244:36 pm -
1 stop6h 19m
Deal found 10/5![United Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/205:29 am -
1 stop3h 42m
Sat 10/243:28 pm -
2 stops7h 29m
Deal found 10/5![American Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 10/6. 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 10/165:59 pm -
1 stop6h 03m
Tue 10/205:22 pm -
1 stop5h 37m
Deal found 10/6![Delta logo]()
$369
This American Airlines deal was found by Cheapflights users on 10/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/812:46 pm -
1 stop6h 49m
Sun 10/115:00 am -
1 stop3h 32m
Deal found 10/7![American Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 10/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/79:00 am -
1 stop6h 08m
Sat 11/145:43 pm -
1 stop5h 11m
Deal found 10/9![United Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 10/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/214:09 pm -
2 stops8h 45m
Fri 11/277:06 pm -
1 stop3h 36m
Deal found 10/8![American Airlines logo]()
$417
This Delta deal was found by Cheapflights users on 10/6. 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.
Tue 11/247:35 am -
1 stop6h 04m
Sat 11/289:52 am -
1 stop6h 17m
Deal found 10/6![Delta logo]()
$419
This American Airlines deal was found by Cheapflights users on 10/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:39 am -
2 stops7h 16m
Wed 10/285:00 am -
1 stop3h 32m
Deal found 10/9![American Airlines logo]()
$432
This United Airlines deal was found by Cheapflights users on 10/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/205:57 pm -
1 stop6h 10m
Sun 11/295:43 pm -
1 stop3h 47m
Deal found 10/10![United Airlines logo]()
$433
Best flights from Kentucky to MadisonDiscover carefully curated flight deals from Kentucky to Madison that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 10, 2026.
Discover carefully curated flight deals from Kentucky to Madison that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 10, 2026.
This Delta deal was found by Cheapflights users on 10/8. 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 11/247:35 am -
1 stop6h 04m
Sat 11/289:52 am -
1 stop6h 17m
Deal found 10/8![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 10/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:16 am -
1 stop6h 08m
Fri 11/276:29 pm -
1 stop4h 29m
Deal found 10/8![American Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 10/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/229:04 am -
1 stop5h 33m
Sat 10/2412:39 pm -
1 stop6h 52m
Deal found 10/8![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 10/6. 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.
Thu 11/127:05 am -
1 stop4h 35m
Sun 11/155:20 pm -
1 stop5h 38m
Deal found 10/6![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 10/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:11 pm -
1 stop4h 48m
Sun 11/153:11 pm -
2 stops7h 48m
Deal found 10/6![American Airlines logo]()
$324
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/208:50 am -
1 stop5h 47m
Sat 10/244:36 pm -
1 stop6h 19m
Deal found 10/5![United Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/205:29 am -
1 stop3h 42m
Sat 10/243:28 pm -
2 stops7h 29m
Deal found 10/5![American Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 10/9. 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 10/212:36 pm -
1 stop3h 42m
Sat 10/249:27 am -
1 stop6h 24m
Deal found 10/9![Delta logo]()
$369
This United Airlines deal was found by Cheapflights users on 10/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/67:00 am -
1 stop5h 46m
Sat 1/912:27 pm -
1 stop5h 02m
Deal found 10/9![United Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 10/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/79:00 am -
1 stop6h 08m
Sat 11/145:43 pm -
1 stop5h 11m
Deal found 10/9![United Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 10/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/86:00 am -
1 stop6h 46m
Tue 1/128:15 am -
1 stop6h 14m
Deal found 10/9![United Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 10/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/205:57 pm -
1 stop6h 10m
Sun 11/295:43 pm -
1 stop3h 47m
Deal found 10/10![United Airlines logo]()
$433
This American Airlines deal was found by Cheapflights users on 10/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:50 pm -
1 stop7h 07m
Sat 10/2411:22 am -
1 stop4h 01m
Deal found 10/8![American Airlines logo]()
$545
This Delta deal was found by Cheapflights users on 10/6. 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 10/217:55 am -
1 stop5h 40m
Sun 10/251:29 pm -
1 stop6h 44m
Deal found 10/6![Delta logo]()
$588
This United Airlines deal was found by Cheapflights users on 10/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:57 pm -
1 stop6h 10m
Sun 11/85:43 pm -
1 stop3h 47m
Deal found 10/9![United Airlines logo]()
$458
This United Airlines deal was found by Cheapflights users on 10/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:57 pm -
1 stop6h 10m
Sat 11/143:52 pm -
1 stop4h 00m
Deal found 10/9![United Airlines logo]()
$458
This United Airlines deal was found by Cheapflights users on 10/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:00 am -
1 stop17h 35m
Tue 10/278:15 am -
1 stop5h 26m
Deal found 10/8![United Airlines logo]()
$543
This United Airlines deal was found by Cheapflights users on 10/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:30 pm -
1 stop6h 14m
Fri 10/236:35 pm -
1 stop4h 24m
Deal found 10/6![United Airlines logo]()
$607
This United Airlines deal was found by Cheapflights users on 10/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:00 am -
1 stop4h 54m
Sun 10/257:16 pm -
1 stop18h 25m
Deal found 10/6![United Airlines logo]()
$642
Last-minute flights from Kentucky to MadisonDiscover last-minute flight deals from Kentucky to Madison. Data last updated October 10, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Madison. Data last updated October 10, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/812:46 pm -
1 stop6h 49m
Sun 10/115:00 am -
1 stop3h 32m
Deal found 10/7![American Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 10/6. 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 10/165:59 pm -
1 stop6h 03m
Tue 10/205:22 pm -
1 stop5h 37m
Deal found 10/6![Delta logo]()
$369
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/208:50 am -
1 stop5h 47m
Sat 10/244:36 pm -
1 stop6h 19m
Deal found 10/5![United Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 10/205:29 am -
1 stop3h 42m
Sat 10/243:28 pm -
2 stops7h 29m
Deal found 10/5![American Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 10/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/229:04 am -
1 stop5h 33m
Sat 10/2412:39 pm -
1 stop6h 52m
Deal found 10/8![United Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 10/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:39 am -
2 stops7h 16m
Wed 10/285:00 am -
1 stop3h 32m
Deal found 10/9![American Airlines logo]()
$432
This United Airlines deal was found by Cheapflights users on 10/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/79:00 am -
1 stop6h 08m
Sat 11/145:43 pm -
1 stop5h 11m
Deal found 10/9![United Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 10/6. 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.
Thu 11/127:05 am -
1 stop4h 35m
Sun 11/155:20 pm -
1 stop5h 38m
Deal found 10/6![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 10/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:11 pm -
1 stop4h 48m
Sun 11/153:11 pm -
2 stops7h 48m
Deal found 10/6![American Airlines logo]()
$324
This United Airlines deal was found by Cheapflights users on 10/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/205:57 pm -
1 stop6h 10m
Sun 11/295:43 pm -
1 stop3h 47m
Deal found 10/10![United Airlines logo]()
$433
This American Airlines deal was found by Cheapflights users on 10/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/214:09 pm -
2 stops8h 45m
Fri 11/277:06 pm -
1 stop3h 36m
Deal found 10/8![American Airlines logo]()
$417
This Delta deal was found by Cheapflights users on 10/6. 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.
Tue 11/247:35 am -
1 stop6h 04m
Sat 11/289:52 am -
1 stop6h 17m
Deal found 10/6![Delta logo]()
$419
One-way flights from Kentucky to MadisonSearch for one-way flight options from Kentucky to Madison. Find affordable one-way fares based on user searches. Data last updated October 10, 2026.
Search for one-way flight options from Kentucky to Madison. Find affordable one-way fares based on user searches. Data last updated October 10, 2026.
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 11/49:00 am -
1 stop6h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![United Airlines logo]()
$274
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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 11/410:33 am -
2 stops8h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![American Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 10/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:20 pm -
1 stop5h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![American Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/19:41 pm -
3 stops37h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$421
This American Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” 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.
Sun 11/17:41 am -
2 stops8h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![American Airlines logo]()
$821
Find flight deals from Kentucky to Madison
Keep the following information in mind while searching for Kentucky to Madison flight deals. Data was last updated October 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $319 (Delta) |
One-way from | $249 (United Airlines) |
Popular in | September |
Cheapest in | December |
Average price | $430 |
Cheapflights Fare Finder
Customize your flight search to find flights from Kentucky to Madison 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 October 10, 2026.
Use the filters below to find and compare flights from Kentucky to Madison that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
LexingtonMadison
LEX Lexington Blue Grass - MSN Madison Truax Field
LEXMSN
Lexington Blue Grass
Wed 11/4
9:00 am-2:00 pm
1 stop6h 00m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$274
LexingtonMadison
LEX Lexington Blue Grass - MSN Madison Truax Field
LEXMSN
Lexington Blue Grass
Tue 11/24
7:35 am-12:39 pm
1 stop6h 04m
Madison Truax Field
Sat 11/28
9:52 am-5:09 pm
1 stop6h 17m
$319
LexingtonMadison
LEX Lexington Blue Grass - MSN Madison Truax Field
LEXMSN
Lexington Blue Grass
Sat 11/21
5:16 am-10:24 am
1 stop6h 08m
Madison Truax Field
Fri 11/27
6:29 pm-11:58 pm
1 stop4h 29m
$319
LexingtonMadison
LEX Lexington Blue Grass - MSN Madison Truax Field
LEXMSN
Lexington Blue Grass
Thu 11/12
7:05 am-10:40 am
1 stop4h 35m
Madison Truax Field
Sun 11/15
5:20 pm-11:58 pm
1 stop5h 38m
$319
LexingtonMadison
LEX Lexington Blue Grass - MSN Madison Truax Field
LEXMSN
Lexington Blue Grass
Thu 11/12
8:11 pm-11:59 pm
1 stop4h 48m
Madison Truax Field
Sun 11/15
3:11 pm-11:59 pm
2 stops7h 48m
$324
LexingtonMadison
LEX Lexington Blue Grass - MSN Madison Truax Field
LEXMSN
Lexington Blue Grass
Sun 11/1
5:00 am-11:43 am
1 stop7h 43m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$333
Quickest round-trip
LexingtonMadison
LEX Lexington Blue Grass - MSN Madison Truax Field
LEXMSN
Lexington Blue Grass
Wed 10/21
12:20 pm-5:13 pm
1 stop5h 53m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$333
LouisvilleMadison
SDF Louisville Intl - MSN Madison Truax Field
SDFMSN
Louisville Intl
Thu 10/22
9:04 am-1:37 pm
1 stop5h 33m
Madison Truax Field
Sat 10/24
12:39 pm-8:31 pm
1 stop6h 52m
$349
LexingtonMadison
LEX Lexington Blue Grass - MSN Madison Truax Field
LEXMSN
Lexington Blue Grass
Tue 10/20
8:50 am-1:37 pm
1 stop5h 47m
Madison Truax Field
Sat 10/24
4:36 pm-11:55 pm
1 stop6h 19m
$349
LexingtonMadison
LEX Lexington Blue Grass - MSN Madison Truax Field
LEXMSN
Lexington Blue Grass
Tue 10/20
5:29 am-8:11 am
1 stop3h 42m
Madison Truax Field
Sat 10/24
3:28 pm-11:57 pm
2 stops7h 29m
$354
Showing 1-10 of 23 resultsSorted by cheapest first
Best time to book a flight from Kentucky to Madison
Have a flexible travel schedule? Discover the best time to fly to Madison from Kentucky with our price prediction graph.
LEX-MSN
SDF-MSN
PAH-MSN
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 Madison
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What is the cheapest month to book a flight from Kentucky to Madison?
Currently, December is the cheapest month in which you can book a flight from Kentucky to Madison (average of $298). Flying from Kentucky to Madison in July is currently the most expensive (average of $679). 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 Kentucky to Madison?
Airfare is typical for this route at the moment.
Kentucky to Madison flights typically cost between $298 and $766 in October.The cheapest round-trip price found within the last 5 days was $349 on United Airlines (Oct 22-Oct 24).
Related info for your journey
Find useful and relevant information for your journey from Kentucky to Madison. 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 Madison?
Book flights to Madison if you plan to visit one of these locationsSun Prairie
Middleton
Fitchburg
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Alternative routes for Kentucky to Madison
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Other flights to Madison
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Top 2 airlines flying from Kentucky to Madison
Discover the top 2 airlines that operate flights from Kentucky to Madison. 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 October 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$288 | Average$348 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$318 | Average$499 | FlexibilityNo cancel fee | On-time69% |