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Cheap flights from Winnipeg to Kentucky from C$ 227

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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SDF
21 Aug — 28 Aug1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Kentucky

Enter your travel dates to find the best prices.

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 22 July 2026.

Wed 7/1010:45 a.m.
YWG
-
BNA
1 stop7h 15m
WestJet
Thu 15/106:50 p.m.
BNA
-
YWG
1 stop14h 55m
WestJet
Deal found 19/7C$ 338
Mon 24/87:45 a.m.
YWG
-
BNA
1 stop10h 15m
WestJet
Sun 30/86:50 p.m.
BNA
-
YWG
1 stop6h 05m
WestJet
Deal found 19/7C$ 354
Thu 6/87:45 a.m.
YWG
-
BNA
1 stop10h 15m
WestJet
Mon 10/86:50 p.m.
BNA
-
YWG
1 stop6h 05m
WestJet
Deal found 17/7C$ 355
Thu 20/86:15 a.m.
YWG
-
BNA
1 stop11h 45m
WestJet
Wed 26/86:50 p.m.
BNA
-
YWG
1 stop6h 05m
WestJet
Deal found 19/7C$ 384
Fri 14/87:00 a.m.
YWG
-
BNA
2 stops11h 10m
WestJet
Sun 16/86:50 p.m.
BNA
-
YWG
1 stop6h 05m
WestJet
Deal found 18/7C$ 393
Mon 31/810:45 a.m.
YWG
-
BNA
1 stop7h 15m
WestJet
Fri 4/97:00 p.m.
BNA
-
YWG
1 stop17h 15m
WestJet
Deal found 21/7C$ 427
Sat 22/88:00 a.m.
YWG
-
BNA
2 stops34h 00m
WestJet
Mon 24/86:50 p.m.
BNA
-
YWG
1 stop24h 50m
WestJet
Deal found 19/7C$ 430
Tue 20/107:00 a.m.
YWG
-
BNA
1 stop10h 37m
United Airlines
Tue 27/106:00 a.m.
BNA
-
YWG
1 stop5h 39m
United Airlines
Deal found 20/7C$ 439
Sun 6/92:00 p.m.
YWG
-
BNA
1 stop6h 06m
United Airlines
Thu 10/99:52 a.m.
BNA
-
YWG
1 stop12h 41m
United Airlines
Deal found 20/7C$ 444
Sat 19/912:41 p.m.
YWG
-
SDF
1 stop9h 09m
Delta
Wed 23/96:30 a.m.
SDF
-
YWG
1 stop6h 21m
Delta
Deal found 19/7C$ 663
Thu 5/115:00 a.m.
YWG
-
SDF
2 stops15h 14m
WestJet
Sun 8/117:00 a.m.
SDF
-
YWG
2 stops16h 50m
WestJet
Deal found 17/7C$ 714
Fri 25/96:00 a.m.
YWG
-
SDF
2 stops28h 54m
WestJet
Sun 27/97:54 p.m.
SDF
-
YWG
2 stops26h 46m
WestJet
Deal found 20/7C$ 748

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 22 July 2026.

Round-trip from

C$ 338

One-way from

C$ 227
WestJet
  • WestJet
  • 7/10-15/10
  • 2 total stops
  • 22h 10m total
  • Winnipeg to Kentucky
Search Deals
WestJet
  • WestJet
  • 12/8
  • 1 total stop
  • 11h 45m total
  • 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 629,999 searches. Data last updated 22 July 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

Sat 22/8

8:00 a.m.-6:00 p.m.

2 stops34h 00m

Nashville Intl

Mon 24/8

6:50 p.m.-7:40 p.m.

1 stop24h 50m

C$ 430

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Fri 14/8

9:05 p.m.-6:10 p.m.

1 stop21h 05m

Nashville Intl

Sun 16/8

6:50 p.m.-12:55 a.m.

1 stop6h 05m

C$ 431

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Tue 20/10

7:00 a.m.-5:37 p.m.

1 stop10h 37m

Nashville Intl

Tue 27/10

6:00 a.m.-11:39 a.m.

1 stop5h 39m

C$ 439

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Sun 6/9

12:46 p.m.-9:59 p.m.

1 stop9h 13m

Nashville Intl

Thu 10/9

6:00 a.m.-3:08 p.m.

1 stop9h 08m

C$ 444

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Sun 6/9

2:00 p.m.-8:06 p.m.

1 stop6h 06m

Nashville Intl

Thu 10/9

9:52 a.m.-10:33 p.m.

1 stop12h 41m

C$ 444

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Mon 28/9

7:00 a.m.-3:54 p.m.

1 stop8h 54m

Nashville Intl

Mon 5/10

10:29 a.m.-10:33 p.m.

1 stop12h 04m

C$ 444

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Thu 1/10

8:45 a.m.-8:40 a.m.

2 stops23h 55m

Nashville Intl

Sun 4/10

6:00 a.m.-12:37 p.m.

1 stop6h 37m

C$ 454
Quickest round-trip

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Sat 19/9

12:41 p.m.-10:50 p.m.

1 stop9h 09m

Louisville Intl

Wed 23/9

6:30 a.m.-11:51 a.m.

1 stop6h 21m

C$ 663

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Thu 5/11

5:00 a.m.-9:14 p.m.

2 stops15h 14m

Louisville Intl

Sun 8/11

7:00 a.m.-10:50 p.m.

2 stops16h 50m

C$ 714

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Fri 25/9

8:45 a.m.-10:30 p.m.

1 stop12h 45m

Louisville Intl

Sun 27/9

7:00 a.m.-12:37 p.m.

1 stop6h 37m

C$ 732

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/7

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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) is the airport you will fly out of if you book a flight from Winnipeg to Kentucky. It is only a 7.3 km journey to Winnipeg (YWG) from Winnipeg’s city centre.

  • How long is the flight from Winnipeg to Kentucky?

    For as low as C$ 444, WestJet can have you in Kentucky from Winnipeg in 9h 13m. Airlines will cover a distance of 1751 km. 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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Fly with Cheapflights

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How does Cheapflights help users find flights from Winnipeg to Kentucky?

Cheapflights makes it easy to find Winnipeg to Kentucky flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Kentucky?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Kentucky from Winnipeg.

Can Cheapflights find flights from Winnipeg to Kentucky with no change fees?

Certainly. Search results for flights to Kentucky from Winnipeg shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Winnipeg to Kentucky become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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