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Cheap flights from Winnipeg to Kentucky from C$ 209

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 7/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SDF
17 Jun — 24 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 18 May 2026.

Thu 22/1010:45 a.m.
YWG
-
BNA
1 stop7h 15m
WestJet
Mon 26/104:05 p.m.
BNA
-
YWG
1 stop8h 40m
WestJet
Deal found 16/5C$ 364
Wed 5/87:45 a.m.
YWG
-
BNA
1 stop10h 15m
WestJet
Sun 9/86:50 p.m.
BNA
-
YWG
1 stop6h 05m
WestJet
Deal found 17/5C$ 473
Sat 6/65:10 p.m.
YWG
-
BNA
1 stop24h 50m
Multiple Airlines
Thu 25/66:50 p.m.
BNA
-
YWG
1 stop13h 50m
Multiple Airlines
Deal found 13/5C$ 478
Mon 17/86:15 a.m.
YWG
-
BNA
1 stop11h 45m
WestJet
Mon 24/86:50 p.m.
BNA
-
YWG
1 stop25h 30m
WestJet
Deal found 17/5C$ 507
Mon 27/710:45 a.m.
YWG
-
BNA
1 stop7h 15m
WestJet
Sun 9/86:50 p.m.
BNA
-
YWG
1 stop14h 55m
WestJet
Deal found 13/5C$ 514
Wed 30/912:40 p.m.
YWG
-
SDF
1 stop9h 10m
Delta
Mon 5/101:20 p.m.
SDF
-
YWG
1 stop7h 49m
Delta
Deal found 15/5C$ 518
Thu 5/116:45 a.m.
YWG
-
SDF
2 stops15h 10m
WestJet
Sun 8/1110:43 a.m.
SDF
-
YWG
2 stops15h 12m
WestJet
Deal found 16/5C$ 535
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 17/5C$ 558
Sat 27/64:55 p.m.
YWG
-
BNA
2 stops25h 05m
WestJet
Sat 11/77:00 p.m.
BNA
-
YWG
2 stops20h 55m
WestJet
Deal found 15/5C$ 568
Sat 27/65:10 a.m.
YWG
-
BNA
2 stops16h 35m
United Airlines
Sat 4/77:40 a.m.
BNA
-
YWG
1 stop14h 58m
United Airlines
Deal found 13/5C$ 584
Sat 29/85:42 p.m.
YWG
-
SDF
1 stop5h 14m
Delta
Wed 2/910:15 a.m.
SDF
-
YWG
2 stops10h 54m
Delta
Deal found 16/5C$ 599
Sat 29/87:00 a.m.
YWG
-
SDF
2 stops11h 05m
United Airlines
Wed 2/97:10 a.m.
SDF
-
YWG
2 stops10h 10m
United Airlines
Deal found 16/5C$ 602

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 18 May 2026.

Round-trip from

C$ 364

One-way from

C$ 209
WestJet
  • WestJet
  • 22/10-26/10
  • 2 total stops
  • 15h 55m total
  • Winnipeg to Kentucky
Search Deals
WestJet
  • WestJet
  • 7/6
  • 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 18 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

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Wed 30/9

12:40 p.m.-10:50 p.m.

1 stop9h 10m

Louisville Intl

Mon 5/10

1:20 p.m.-8:09 p.m.

1 stop7h 49m

C$ 518

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Thu 5/11

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

2 stops11h 54m

Louisville Intl

Sun 8/11

7:00 a.m.-12:55 a.m.

2 stops18h 55m

C$ 535

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Thu 5/11

8:00 a.m.-6:12 p.m.

1 stop9h 12m

Louisville Intl

Sun 8/11

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

1 stop8h 34m

C$ 558

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Wed 5/8

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

2 stops34h 00m

Nashville Intl

Sun 9/8

6:50 p.m.-2:15 p.m.

2 stops19h 25m

C$ 560

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Sat 6/6

7:10 p.m.-6:00 p.m.

2 stops22h 50m

Nashville Intl

Thu 25/6

6:50 p.m.-8:40 a.m.

1 stop13h 50m

C$ 583

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Sat 27/6

5:10 a.m.-9:45 p.m.

2 stops16h 35m

Nashville Intl

Sat 4/7

7:40 a.m.-10:38 p.m.

1 stop14h 58m

C$ 584

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Mon 21/9

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

1 stop14h 37m

Nashville Intl

Fri 25/9

7:25 a.m.-10:24 p.m.

1 stop14h 59m

C$ 586
Quickest round-trip

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Sat 29/8

5:42 p.m.-11:56 p.m.

1 stop5h 14m

Louisville Intl

Wed 2/9

1:20 p.m.-8:09 p.m.

1 stop7h 49m

C$ 599

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Sat 29/8

7:00 a.m.-7:05 p.m.

2 stops11h 05m

Louisville Intl

Wed 2/9

7:10 a.m.-4:20 p.m.

2 stops10h 10m

C$ 602

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Sat 27/6

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

2 stops34h 00m

Nashville Intl

Sat 11/7

7:00 p.m.-11:10 a.m.

1 stop16h 10m

C$ 619

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/5

Showing 1-10 of 21 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 18 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
9,737 reviews
Check prices

Crew

8.1

Overall

7.4

Boarding

7.7

Food

6.6

Comfort

7.3

Entertainment

7.1

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
9,737 reviews
United Airlines
7.4
Good
9,737 reviews
Check prices

Crew

8.1

Overall

7.4

Boarding

7.7

Food

6.6

Comfort

7.3

Entertainment

7.1

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$ 518, Delta can have you in Kentucky from Winnipeg in 9h 10m. 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 18 May 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 743AverageC$ 1,214FlexibilityNo 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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