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Kentucky

$175+ Cheap flights from Winnipeg (YWG) to Kentucky

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 6/7. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SDF
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
1 adult, Economy
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Cheap flight deals from Winnipeg to Kentucky

Cheapest flights from Winnipeg to Kentucky
Explore the most affordable flight options available from Winnipeg to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 10, 2026.

This oojo deal was found by Cheapflights users on 5/10. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/86:15 am
YWG
-
BNA
1 stop11h 45m
WestJet
Mon 6/156:50 pm
BNA
-
YWG
1 stop6h 05m
WestJet
Deal found 5/10$288
This FlightHub deal was found by Cheapflights users on 5/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/216:05 pm
YWG
-
BNA
1 stop23h 55m
WestJet
Sun 7/56:50 pm
BNA
-
YWG
1 stop6h 05m
WestJet
Deal found 5/10$320
This Trip.com deal was found by Cheapflights users on 5/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/89:25 am
YWG
-
BNA
1 stop8h 35m
Multiple Airlines
Mon 6/156:50 pm
BNA
-
YWG
1 stop6h 05m
Multiple Airlines
Deal found 5/9$326
This Kiwi.com deal was found by Cheapflights users on 5/7. 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.
Fri 6/58:10 pm
YWG
-
BNA
1 stop16h 05m
Multiple Airlines
Fri 6/1212:55 pm
BNA
-
YWG
1 stop12h 00m
Multiple Airlines
Deal found 5/7$333
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:41 pm
YWG
-
SDF
1 stop5h 15m
Delta
Sat 6/134:28 pm
SDF
-
YWG
1 stop8h 01m
Delta
Deal found 5/7$378
This Kiwi.com deal was found by Cheapflights users on 5/7. 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.
Fri 6/58:45 pm
YWG
-
BNA
1 stop15h 30m
Porter Airlines
Fri 6/1212:55 pm
BNA
-
YWG
2 stops29h 08m
Porter Airlines
Deal found 5/7$378
This FlightHub deal was found by Cheapflights users on 5/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/268:30 pm
YWG
-
BNA
2 stops21h 40m
WestJet
Mon 9/286:50 pm
BNA
-
YWG
1 stop6h 05m
WestJet
Deal found 5/8$387
This oojo deal was found by Cheapflights users on 5/6. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/59:00 pm
YWG
-
SDF
2 stops13h 36m
WestJet
Sun 11/810:43 am
SDF
-
YWG
2 stops15h 12m
WestJet
Deal found 5/6$391
This FlightHub deal was found by Cheapflights users on 5/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2712:15 pm
YWG
-
BNA
2 stops29h 55m
WestJet
Sat 7/117:00 pm
BNA
-
YWG
2 stops20h 55m
WestJet
Deal found 5/9$404
This Delta deal was found by Cheapflights users on 5/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:00 am
YWG
-
SDF
1 stop9h 12m
Delta
Sun 11/84:00 pm
SDF
-
YWG
1 stop8h 34m
Delta
Deal found 5/5$405
This Justfly.com deal was found by Cheapflights users on 5/5. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2311:55 am
YWG
-
SDF
1 stop26h 53m
WestJet
Sat 5/3012:42 pm
SDF
-
YWG
2 stops10h 28m
WestJet
Deal found 5/5$430

Find flight deals from Winnipeg to Kentucky

Keep the following information in mind while searching for Winnipeg to Kentucky flight deals. Data was last updated May 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$288
(oojo)

One-way from

$175
(Trip.com)
Provider with most accurate pricing for Winnipeg-Louisville Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-Louisville Intl flights.
Search Deals
From Winnipeg to Kentucky
Search Deals
One-way flight from Winnipeg to Kentucky
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg 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 2,558,603 searches. Data last updated May 10, 2026.
Use the filters below to find and compare flights from Winnipeg to Kentucky that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Tue 6/9

5:41 pm-11:56 pm

1 stop5h 15m

Louisville Intl

Sat 6/13

4:28 pm-11:29 pm

1 stop8h 01m

$378

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Sat 5/23

6:00 am-9:18 pm

2 stops14h 18m

Louisville Intl

Sat 5/30

12:42 pm-10:10 pm

2 stops10h 28m

$391

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Thu 11/5

9:00 pm-11:36 am

2 stops13h 36m

Louisville Intl

Sun 11/8

6:36 am-8:16 pm

1 stop14h 40m

$395

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Thu 11/5

8:00 am-6:12 pm

1 stop9h 12m

Louisville Intl

Sun 11/8

4:00 pm-11:34 pm

1 stop8h 34m

$405

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Fri 8/28

10:10 am-6:10 pm

1 stop8h 00m

Nashville Intl

Wed 9/2

6:50 pm-2:25 pm

1 stop19h 35m

$441

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Sat 9/19

10:10 am-6:10 pm

1 stop8h 00m

Nashville Intl

Fri 9/25

7:00 pm-11:10 am

1 stop16h 10m

$447

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Wed 8/12

12:25 pm-6:10 pm

2 stops29h 45m

Nashville Intl

Sat 8/15

7:00 pm-9:35 am

2 stops14h 35m

$453

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Wed 9/30

4:15 pm-6:00 pm

2 stops25h 45m

Nashville Intl

Sun 10/4

6:50 pm-9:45 am

1 stop14h 55m

$459
Quickest round-trip

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Wed 9/23

7:00 am-12:24 pm

1 stop5h 24m

Nashville Intl

Fri 9/25

4:55 pm-10:24 pm

1 stop5h 29m

$471

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Mon 8/31

7:55 am-2:59 pm

1 stop7h 04m

Nashville Intl

Wed 9/2

10:05 am-4:20 pm

1 stop6h 15m

$482

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

Showing 1-10 of 25 resultsSorted by cheapest first
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Best time to book a flight from Winnipeg to Kentucky

Have a flexible travel schedule? Discover the best time to fly to Kentucky from Winnipeg with our price prediction graph.
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 Winnipeg to Kentucky
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Kentucky. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Winnipeg to Kentucky?

    Winnipeg (YWG), located 4.6 mi from the city center, is the airport you fly out of when you book flights from Winnipeg to Kentucky.

  • How long is the flight from Winnipeg to Kentucky?

    There are many flights that can get you from Winnipeg to Kentucky in 5h 15m. Fly via Delta or WestJet to get the fastest option. There are 988 mi between Winnipeg and Kentucky. This flight may include one or multiple stops.

  • Can I find deals for flights from Winnipeg to Kentucky that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Kentucky flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Kentucky?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Kentucky.

  • Can I find deals for business class flights from Winnipeg to Kentucky?

    Yes. Cheapflights offers flight deals from Winnipeg to Kentucky by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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