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Cheap flights from Winnipeg to Kentucky from C$ 289

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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SDF
25 Jun — 2 Jul1
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 26 May 2026.

Wed 9/910:45 a.m.
YWG
-
BNA
1 stop7h 15m
WestJet
Sun 13/96:50 p.m.
BNA
-
YWG
1 stop19h 35m
WestJet
Deal found 23/5C$ 427
Wed 30/96:15 a.m.
YWG
-
BNA
1 stop11h 45m
WestJet
Sun 4/106:50 p.m.
BNA
-
YWG
1 stop6h 05m
WestJet
Deal found 25/5C$ 431
Sun 18/106:35 a.m.
YWG
-
BNA
1 stop8h 15m
Delta
Wed 21/106:30 p.m.
BNA
-
YWG
1 stop5h 04m
Delta
Deal found 24/5C$ 439
Sat 13/68:45 a.m.
YWG
-
BNA
2 stops23h 56m
United Airlines
Fri 19/65:00 p.m.
BNA
-
YWG
1 stop5h 38m
United Airlines
Deal found 21/5C$ 450
Sun 18/105:10 p.m.
YWG
-
BNA
1 stop16h 19m
Air Canada
Wed 21/1010:25 a.m.
BNA
-
YWG
1 stop5h 52m
Air Canada
Deal found 25/5C$ 505
Thu 5/119:00 p.m.
YWG
-
SDF
2 stops11h 54m
WestJet
Sun 8/114:00 p.m.
SDF
-
YWG
1 stop5h 16m
WestJet
Deal found 21/5C$ 522
Thu 17/96:40 a.m.
YWG
-
SDF
1 stop8h 09m
Delta
Sun 20/96:50 a.m.
SDF
-
YWG
1 stop9h 18m
Delta
Deal found 23/5C$ 537
Wed 7/106:35 a.m.
YWG
-
SDF
2 stops6h 04m
Delta
Sat 10/104:00 p.m.
SDF
-
YWG
1 stop5h 16m
Delta
Deal found 22/5C$ 540
Fri 19/67:00 a.m.
YWG
-
SDF
2 stops15h 56m
WestJet
Mon 22/62:19 p.m.
SDF
-
YWG
2 stops11h 36m
WestJet
Deal found 24/5C$ 544
Thu 5/118:00 a.m.
YWG
-
SDF
1 stop9h 12m
Delta
Sun 8/114:00 p.m.
SDF
-
YWG
1 stop8h 34m
Delta
Deal found 25/5C$ 578
Wed 3/68:45 a.m.
YWG
-
BNA
1 stop12h 28m
United Airlines
Wed 10/66:00 a.m.
BNA
-
YWG
1 stop5h 52m
United Airlines
Deal found 23/5C$ 587

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 26 May 2026.

Round-trip from

C$ 427

One-way from

C$ 289

Popular in

July

Cheapest in

January

Average price

C$ 703
WestJet
  • WestJet
  • 9/9-13/9
  • 2 total stops
  • 26h 50m total
  • Winnipeg to Kentucky
Search Deals
5/7
  • 5/7
  • 1 total stop
  • 24h 50m total
  • Winnipeg to Kentucky
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 177 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 58 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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 26 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

Wed 30/9

6:15 a.m.-6:00 p.m.

1 stop11h 45m

Nashville Intl

Sun 4/10

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

1 stop6h 05m

C$ 431

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Sat 13/6

8:45 a.m.-8:41 a.m.

2 stops23h 56m

Nashville Intl

Fri 19/6

5:00 p.m.-10:38 p.m.

1 stop5h 38m

C$ 450

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Thu 17/9

12:46 p.m.-11:59 p.m.

2 stops10h 13m

Louisville Intl

Sun 20/9

6:50 a.m.-3:08 p.m.

1 stop9h 18m

C$ 537
Quickest round-trip

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Wed 7/10

6:35 a.m.-1:39 p.m.

2 stops6h 04m

Louisville Intl

Sat 10/10

4:00 p.m.-8:16 p.m.

1 stop5h 16m

C$ 540

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Fri 19/6

7:00 a.m.-11:56 p.m.

2 stops15h 56m

Louisville Intl

Mon 22/6

2:19 p.m.-12:55 a.m.

2 stops11h 36m

C$ 544

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Thu 5/11

9:00 p.m.-9:54 a.m.

2 stops11h 54m

Louisville Intl

Sun 8/11

7:20 a.m.-12:45 a.m.

2 stops18h 25m

C$ 559

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Thu 5/11

6:35 a.m.-3:45 p.m.

1 stop8h 10m

Louisville Intl

Sun 8/11

4:00 p.m.-11:34 p.m.

1 stop8h 34m

C$ 578

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Mon 21/9

7:00 a.m.-9:37 p.m.

1 stop14h 37m

Nashville Intl

Fri 25/9

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

1 stop5h 29m

C$ 588

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Sun 21/6

10:45 a.m.-6:00 p.m.

1 stop7h 15m

Nashville Intl

Sun 5/7

6:50 p.m.-8:20 p.m.

1 stop25h 30m

C$ 596

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Sat 27/6

7:00 a.m.-11:02 p.m.

2 stops16h 02m

Nashville Intl

Sat 4/7

9:53 a.m.-10:38 p.m.

1 stop12h 45m

C$ 617

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/5

Showing 1-10 of 17 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

How much does it cost to fly round-trip from Winnipeg to Kentucky?

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 26 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
9,749 reviews
Check prices

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
United Airlines
7.4
Good
9,749 reviews
United Airlines
7.4
Good
9,749 reviews
Check prices

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

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$ 435, WestJet can have you in Kentucky from Winnipeg in 11h. 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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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 26 May 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 746AverageC$ 1,219FlexibilityNo 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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