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Cheap flights from Winnipeg to Kentucky from C$ 243

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 15/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SDF
27 Apr — 4 May1
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 28 March 2026.

Wed 15/48:45 a.m.
YWG
-
BNA
2 stops11h 41m
United Airlines
Wed 22/46:00 a.m.
BNA
-
YWG
1 stop5h 52m
United Airlines
Deal found 28/3C$ 369
Wed 3/68:45 a.m.
YWG
-
BNA
2 stops14h 36m
United Airlines
Sun 7/66:00 a.m.
BNA
-
YWG
1 stop16h 33m
United Airlines
Deal found 24/3C$ 392
Wed 1/42:00 p.m.
YWG
-
BNA
2 stops19h 39m
United Airlines
Sat 11/46:35 p.m.
BNA
-
YWG
2 stops17h 17m
United Airlines
Deal found 28/3C$ 422
Sat 18/48:45 a.m.
YWG
-
BNA
2 stops11h 41m
United Airlines
Wed 22/46:00 a.m.
BNA
-
YWG
1 stop5h 52m
United Airlines
Deal found 27/3C$ 442
Sat 18/45:20 p.m.
YWG
-
BNA
1 stop5h 32m
Delta
Wed 22/46:00 a.m.
BNA
-
YWG
1 stop4h 56m
Delta
Deal found 25/3C$ 444
Fri 24/42:00 p.m.
YWG
-
BNA
2 stops19h 39m
United Airlines
Fri 1/56:00 a.m.
BNA
-
YWG
1 stop5h 52m
United Airlines
Deal found 25/3C$ 445
Sat 2/58:45 a.m.
YWG
-
BNA
1 stop13h 12m
United Airlines
Wed 6/56:00 a.m.
BNA
-
YWG
1 stop5h 52m
United Airlines
Deal found 23/3C$ 446
Sat 2/55:10 a.m.
YWG
-
BNA
2 stops9h 55m
Air Canada
Wed 6/56:00 a.m.
BNA
-
YWG
1 stop5h 52m
Air Canada
Deal found 27/3C$ 451
Mon 20/48:45 a.m.
YWG
-
BNA
1 stop13h 01m
United Airlines
Tue 21/410:40 a.m.
BNA
-
YWG
2 stops25h 12m
United Airlines
Deal found 26/3C$ 476
Sat 25/42:00 p.m.
YWG
-
BNA
1 stop5h 56m
United Airlines
Sat 2/56:00 a.m.
BNA
-
YWG
1 stop5h 52m
United Airlines
Deal found 26/3C$ 485
Tue 2/65:41 p.m.
YWG
-
SDF
1 stop5h 11m
WestJet
Fri 5/61:00 p.m.
SDF
-
YWG
2 stops12h 55m
WestJet
Deal found 27/3C$ 556
Thu 17/98:50 a.m.
YWG
-
SDF
1 stop8h 53m
Delta
Mon 21/94:00 p.m.
SDF
-
YWG
1 stop8h 27m
Delta
Deal found 25/3C$ 562

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 28 March 2026.

Round-trip from

C$ 369

One-way from

C$ 243
United Airlines
  • United Airlines
  • 2/5-6/5
  • 2 total stops
  • 13h 49m total
  • Winnipeg to Kentucky
Search Deals
United Airlines
  • United Airlines
  • 15/6
  • 2 total stops
  • 24h 06m 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 28 March 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

Wed 15/4

8:45 a.m.-8:26 p.m.

2 stops11h 41m

Nashville Intl

Wed 22/4

8:30 a.m.-11:52 a.m.

2 stops27h 22m

C$ 369

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Sat 2/5

2:00 p.m.-9:57 p.m.

1 stop7h 57m

Nashville Intl

Wed 6/5

6:00 a.m.-11:52 a.m.

1 stop5h 52m

C$ 369
Quickest round-trip

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Sat 18/4

5:20 p.m.-10:52 p.m.

1 stop5h 32m

Nashville Intl

Wed 22/4

6:00 a.m.-10:56 a.m.

1 stop4h 56m

C$ 444

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Tue 22/9

7:00 a.m.-8:06 p.m.

1 stop13h 06m

Nashville Intl

Fri 25/9

4:55 p.m.-10:24 p.m.

1 stop5h 29m

C$ 510

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Fri 17/4

5:20 p.m.-8:52 a.m.

2 stops15h 32m

Nashville Intl

Wed 22/4

6:00 a.m.-10:56 a.m.

1 stop4h 56m

C$ 549

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Mon 20/4

8:45 a.m.-9:46 p.m.

1 stop13h 01m

Nashville Intl

Fri 24/4

8:00 p.m.-11:52 a.m.

1 stop15h 52m

C$ 549

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Tue 2/6

5:41 p.m.-11:52 p.m.

1 stop5h 11m

Louisville Intl

Fri 5/6

1:00 p.m.-12:55 a.m.

2 stops12h 55m

C$ 556

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Thu 17/9

8:50 a.m.-6:43 p.m.

1 stop8h 53m

Louisville Intl

Mon 21/9

4:00 p.m.-11:27 p.m.

1 stop8h 27m

C$ 562

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Tue 2/6

8:45 a.m.-10:59 p.m.

1 stop13h 14m

Louisville Intl

Fri 5/6

5:46 p.m.-10:33 p.m.

1 stop5h 47m

C$ 563

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Sun 19/4

7:30 a.m.-11:59 p.m.

1 stop15h 29m

Louisville Intl

Thu 23/4

5:36 p.m.-3:09 p.m.

1 stop22h 33m

C$ 582

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/3

Showing 1-10 of 22 resultsSorted by cheapest first
1
2
3

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 28 March 2026.
See what other customers who have flown with United Airlines from Winnipeg to Kentucky have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,499 reviews
Check prices

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Crew

8.1

Overall

7.4

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
United Airlines
7.4
Good
9,499 reviews
United Airlines
7.4
Good
9,499 reviews
Check prices

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Crew

8.1

Overall

7.4

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

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$ 556, United Airlines can have you in Kentucky from Winnipeg in 5h 11m. Airlines will cover a distance of 1590 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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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 629,999 searches. Data last updated 28 March 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 750AverageC$ 1,224FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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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