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Kentucky

$166+ 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 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SDF
Jul 21 — Jul 281
Tue 7/21
Tue 7/28
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 June 21, 2026.

This FlightHub deal was found by Cheapflights users on 6/17. 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.
Thu 11/128:05 pm
YWG
-
BNA
1 stop19h 15m
WestJet
Mon 11/164:05 pm
BNA
-
YWG
1 stop8h 40m
WestJet
Deal found 6/17$278
This Air Canada deal was found by Cheapflights users on 6/20. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:00 am
YWG
-
BNA
2 stops9h 05m
Air Canada
Sat 11/288:15 am
BNA
-
YWG
1 stop7h 44m
Air Canada
Deal found 6/20$291
This United Airlines deal was found by Cheapflights users on 6/16. 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 10/107:00 am
YWG
-
BNA
1 stop16h 14m
United Airlines
Tue 10/136:34 pm
BNA
-
YWG
2 stops18h 03m
United Airlines
Deal found 6/16$301
This Air Canada deal was found by Cheapflights users on 6/19. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:10 pm
YWG
-
BNA
1 stop14h 03m
Air Canada
Tue 7/2110:05 am
BNA
-
YWG
1 stop6h 15m
Air Canada
Deal found 6/19$322
This oojo deal was found by Cheapflights users on 6/16. 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 8/2010:45 am
YWG
-
BNA
1 stop7h 15m
WestJet
Mon 8/246:50 pm
BNA
-
YWG
2 stops19h 25m
WestJet
Deal found 6/16$327
This oojo deal was found by Cheapflights users on 6/17. 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 7/2710:45 am
YWG
-
BNA
1 stop7h 15m
WestJet
Sat 8/17:00 pm
BNA
-
YWG
1 stop16h 10m
WestJet
Deal found 6/17$333
This FlightHub deal was found by Cheapflights users on 6/16. 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 8/210:45 am
YWG
-
BNA
1 stop7h 15m
WestJet
Thu 8/67:00 pm
BNA
-
YWG
1 stop16h 10m
WestJet
Deal found 6/16$335
This Air Canada deal was found by Cheapflights users on 6/20. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:10 pm
YWG
-
BNA
1 stop14h 03m
Air Canada
Fri 8/2110:05 am
BNA
-
YWG
1 stop6h 25m
Air Canada
Deal found 6/20$344
This FlightHub deal was found by Cheapflights users on 6/17. 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.
Tue 7/74:25 pm
YWG
-
BNA
1 stop25h 35m
WestJet
Tue 7/147:00 pm
BNA
-
YWG
1 stop16h 10m
WestJet
Deal found 6/17$370
This Air Canada deal was found by Cheapflights users on 6/20. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/207:10 pm
YWG
-
BNA
1 stop14h 03m
Air Canada
Fri 7/246:35 pm
BNA
-
YWG
1 stop15h 25m
Air Canada
Deal found 6/20$380
This United Airlines deal was found by Cheapflights users on 6/20. 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 7/198:45 am
YWG
-
SDF
2 stops23h 41m
United Airlines
Sun 7/267:15 am
SDF
-
YWG
1 stop5h 37m
United Airlines
Deal found 6/20$536
This United Airlines deal was found by Cheapflights users on 6/20. 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 10/207:00 am
YWG
-
SDF
1 stop15h 59m
United Airlines
Sat 10/243:36 pm
SDF
-
YWG
1 stop6h 21m
United Airlines
Deal found 6/20$539

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 June 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$278
(FlightHub)

One-way from

$166
(oojo)
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 June 21, 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

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Thu 8/20

12:46 pm-10:16 pm

1 stop9h 30m

Nashville Intl

Mon 8/24

6:00 am-11:54 am

1 stop5h 54m

$301

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Sat 10/10

8:45 am-11:14 pm

2 stops14h 29m

Nashville Intl

Tue 10/13

6:34 pm-12:37 pm

2 stops18h 03m

$301

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Sun 8/2

10:45 am-6:00 pm

1 stop7h 15m

Nashville Intl

Thu 8/6

7:00 pm-11:10 am

1 stop16h 10m

$335

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Sat 7/18

12:56 pm-11:02 pm

2 stops10h 06m

Nashville Intl

Tue 7/21

6:00 am-11:52 am

1 stop5h 52m

$370

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Mon 7/20

7:10 pm-9:13 am

1 stop14h 03m

Nashville Intl

Fri 7/24

6:35 pm-10:00 am

1 stop15h 25m

$380

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Tue 7/7

7:00 am-11:02 pm

2 stops16h 02m

Nashville Intl

Tue 7/14

3:08 pm-11:52 am

2 stops20h 44m

$386

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Mon 10/26

8:00 am-9:32 pm

2 stops13h 32m

Nashville Intl

Fri 10/30

9:42 am-10:39 pm

2 stops12h 57m

$389

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Mon 7/20

5:25 pm-9:13 am

1 stop15h 48m

Nashville Intl

Fri 7/24

6:30 pm-11:52 am

2 stops17h 22m

$395

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Mon 7/27

7:10 pm-3:57 pm

2 stops20h 47m

Nashville Intl

Sat 8/1

9:57 am-10:38 pm

1 stop12h 41m

$405

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Sun 7/19

8:45 am-9:26 am

2 stops23h 41m

Louisville Intl

Sun 7/26

7:15 am-11:52 am

1 stop5h 37m

$536

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

Showing 1-10 of 22 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.

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 June 21, 2026.
Get a feel of what it's like to fly with WestJet from Winnipeg 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.
WestJet
7.2
Good
3,375 reviews

Entertainment

6.1

Comfort

7.0

Overall

7.2

Food

6.2

Boarding

7.4

Crew

7.9

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.
WestJet
7.2
Good
3,375 reviews
WestJet
7.2
Good
3,375 reviews

Entertainment

6.1

Comfort

7.0

Overall

7.2

Food

6.2

Boarding

7.4

Crew

7.9

Reviews

1 / 20
10.0
Excellent

Anonymous,Oct 2024

YYZ - MCO

Friendly staff and thanks to the pilots who take care of us during the flights.

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 7h 15m. Fly via Delta, United Airlines, or WestJet to get the fastest option. There are 1088 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

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.

Top airline flying from Winnipeg to Kentucky

Discover the top airline that operate flights from Winnipeg 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 2,558,603 searches. Data last updated June 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$429Average$509FlexibilityNo cancel feeOn-time60%

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