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Cheap flights from Winnipeg to Kentucky from C$ 198

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 13/7. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SDF
31 May — 7 Jun1
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 1 May 2026.

Wed 8/78:45 a.m.
YWG
-
BNA
1 stop12h 28m
United Airlines
Sat 11/76:30 p.m.
BNA
-
YWG
2 stops17h 22m
United Airlines
Deal found 26/4C$ 364
Wed 20/510:45 a.m.
YWG
-
BNA
1 stop7h 15m
WestJet
Thu 28/56:50 p.m.
BNA
-
YWG
1 stop14h 55m
WestJet
Deal found 27/4C$ 370
Sun 14/66:05 p.m.
YWG
-
BNA
1 stop23h 55m
WestJet
Thu 18/66:50 p.m.
BNA
-
YWG
1 stop6h 05m
WestJet
Deal found 27/4C$ 374
Tue 19/52:00 p.m.
YWG
-
BNA
1 stop5h 56m
United Airlines
Thu 28/512:49 p.m.
BNA
-
YWG
1 stop9h 49m
United Airlines
Deal found 27/4C$ 375
Sat 30/57:00 a.m.
YWG
-
BNA
1 stop5h 29m
United Airlines
Wed 3/68:30 a.m.
BNA
-
YWG
2 stops14h 03m
United Airlines
Deal found 29/4C$ 379
Sat 13/66:40 a.m.
YWG
-
BNA
1 stop8h 20m
Delta
Sat 20/64:05 p.m.
BNA
-
YWG
1 stop7h 24m
Delta
Deal found 29/4C$ 385
Thu 4/65:41 p.m.
YWG
-
BNA
1 stop4h 55m
Delta
Mon 8/66:00 a.m.
BNA
-
YWG
1 stop9h 04m
Delta
Deal found 27/4C$ 386
Thu 13/86:15 a.m.
YWG
-
BNA
1 stop11h 45m
WestJet
Wed 19/86:50 p.m.
BNA
-
YWG
1 stop19h 35m
WestJet
Deal found 27/4C$ 387
Wed 20/510:45 a.m.
YWG
-
BNA
1 stop7h 15m
WestJet
Wed 27/56:50 p.m.
BNA
-
YWG
1 stop14h 55m
WestJet
Deal found 27/4C$ 401
Tue 9/67:00 a.m.
YWG
-
SDF
1 stop12h 23m
United Airlines
Sat 13/65:46 p.m.
SDF
-
YWG
1 stop5h 47m
United Airlines
Deal found 28/4C$ 445
Tue 9/66:40 a.m.
YWG
-
SDF
2 stops5h 59m
Delta
Sat 13/66:00 a.m.
SDF
-
YWG
2 stops11h 51m
Delta
Deal found 29/4C$ 454
Fri 12/66:40 a.m.
YWG
-
SDF
1 stop4h 17m
Delta
Fri 26/66:49 a.m.
SDF
-
YWG
1 stop9h 15m
Delta
Deal found 26/4C$ 460

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 1 May 2026.

Round-trip from

C$ 364

One-way from

C$ 196
United Airlines
  • United Airlines
  • 8/7-11/7
  • 3 total stops
  • 29h 50m total
  • Winnipeg to Kentucky
Search Deals
WestJet
  • WestJet
  • 13/7
  • 1 total stop
  • 7h 15m 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 1 May 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 30/5

7:00 a.m.-12:29 p.m.

1 stop5h 29m

Nashville Intl

Wed 3/6

8:30 a.m.-10:33 p.m.

2 stops14h 03m

C$ 379

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Tue 9/6

7:00 a.m.-8:23 p.m.

1 stop12h 23m

Louisville Intl

Sat 13/6

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

1 stop5h 47m

C$ 445

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Tue 9/6

6:40 a.m.-1:39 p.m.

2 stops5h 59m

Louisville Intl

Sat 13/6

6:00 a.m.-4:51 p.m.

2 stops11h 51m

C$ 454

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Fri 12/6

6:40 a.m.-11:57 a.m.

1 stop4h 17m

Louisville Intl

Fri 26/6

6:00 a.m.-4:51 p.m.

2 stops11h 51m

C$ 460

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Thu 13/8

8:15 a.m.-11:29 p.m.

2 stops15h 14m

Nashville Intl

Wed 19/8

9:47 a.m.-11:20 p.m.

2 stops13h 33m

C$ 461

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Wed 3/6

6:40 a.m.-3:14 p.m.

1 stop8h 34m

Nashville Intl

Mon 8/6

6:00 a.m.-3:04 p.m.

1 stop9h 04m

C$ 462

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Thu 11/6

5:10 a.m.-11:21 p.m.

2 stops18h 11m

Nashville Intl

Fri 12/6

7:51 p.m.-11:52 a.m.

1 stop16h 01m

C$ 521

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Thu 6/8

7:00 a.m.-5:15 p.m.

2 stops9h 15m

Louisville Intl

Mon 10/8

1:20 p.m.-11:27 p.m.

1 stop11h 07m

C$ 551

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Tue 19/5

2:00 p.m.-9:28 a.m.

3 stops19h 28m

Nashville Intl

Wed 27/5

8:30 a.m.-10:38 p.m.

2 stops14h 08m

C$ 559

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Sun 21/6

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

2 stops34h 00m

Nashville Intl

Sun 5/7

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

1 stop6h 05m

C$ 619

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/4

Showing 1-10 of 26 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 1 May 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
9,675 reviews
Check prices

Boarding

7.7

Food

6.6

Crew

8.1

Overall

7.4

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
United Airlines
7.4
Good
9,675 reviews
United Airlines
7.4
Good
9,675 reviews
Check prices

Boarding

7.7

Food

6.6

Crew

8.1

Overall

7.4

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.

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$ 454, United Airlines can have you in Kentucky from Winnipeg in 5h 15m. 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 1 May 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 738AverageC$ 1,204FlexibilityNo 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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