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Cheap flights from Winnipeg to Kentucky from C$ 226

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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SDF
25 May — 1 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 25 April 2026.

Thu 27/810:45 a.m.
YWG
-
BNA
1 stop7h 15m
WestJet
Sun 30/86:50 p.m.
BNA
-
YWG
1 stop6h 05m
WestJet
Deal found 21/4C$ 318
Sun 21/610:45 a.m.
YWG
-
BNA
1 stop7h 15m
WestJet
Sun 5/76:50 p.m.
BNA
-
YWG
1 stop6h 05m
WestJet
Deal found 20/4C$ 356
Wed 22/710:45 a.m.
YWG
-
BNA
1 stop7h 15m
WestJet
Sun 26/76:50 p.m.
BNA
-
YWG
2 stops19h 25m
WestJet
Deal found 23/4C$ 372
Wed 16/910:45 a.m.
YWG
-
BNA
1 stop7h 15m
WestJet
Thu 17/96:50 p.m.
BNA
-
YWG
1 stop6h 05m
WestJet
Deal found 21/4C$ 378
Tue 20/104:25 p.m.
YWG
-
BNA
1 stop25h 35m
WestJet
Sun 25/104:05 p.m.
BNA
-
YWG
1 stop19h 30m
WestJet
Deal found 24/4C$ 385
Sat 23/57:00 a.m.
YWG
-
BNA
1 stop14h 44m
United Airlines
Wed 3/66:00 a.m.
BNA
-
YWG
1 stop5h 52m
United Airlines
Deal found 24/4C$ 398
Wed 8/78:45 a.m.
YWG
-
BNA
1 stop12h 28m
United Airlines
Sat 11/71:35 p.m.
BNA
-
YWG
2 stops22h 17m
United Airlines
Deal found 22/4C$ 406
Wed 8/75:10 a.m.
YWG
-
BNA
2 stops9h 49m
Air Canada
Sat 11/78:15 a.m.
BNA
-
YWG
2 stops13h 15m
Air Canada
Deal found 24/4C$ 430
Tue 26/56:40 a.m.
YWG
-
SDF
2 stops9h 32m
Delta
Fri 29/56:05 a.m.
SDF
-
YWG
1 stop5h 49m
Delta
Deal found 20/4C$ 445
Thu 5/116:35 a.m.
YWG
-
SDF
1 stop8h 10m
Delta
Sun 8/114:00 p.m.
SDF
-
YWG
1 stop8h 34m
Delta
Deal found 22/4C$ 476
Thu 5/115:00 a.m.
YWG
-
SDF
2 stops15h 41m
WestJet
Sun 8/116:36 a.m.
SDF
-
YWG
1 stop17h 58m
WestJet
Deal found 20/4C$ 534
Thu 6/87:00 a.m.
YWG
-
SDF
2 stops11h 09m
WestJet
Mon 10/86:36 a.m.
SDF
-
YWG
1 stop17h 51m
WestJet
Deal found 23/4C$ 543

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 25 April 2026.

Round-trip from

C$ 318

One-way from

C$ 226
WestJet
  • WestJet
  • 27/8-30/8
  • 2 total stops
  • 13h 20m total
  • Winnipeg to Kentucky
Search Deals
Delta
  • Delta
  • 11/5
  • 1 total stop
  • 6h 46m 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 25 April 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
Quickest round-trip

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Wed 16/9

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

1 stop7h 15m

Nashville Intl

Thu 17/9

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

1 stop6h 05m

C$ 378

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Wed 8/7

8:45 a.m.-9:13 p.m.

1 stop12h 28m

Nashville Intl

Sat 11/7

1:35 p.m.-11:52 a.m.

2 stops22h 17m

C$ 406

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Wed 8/7

5:10 a.m.-2:59 p.m.

2 stops9h 49m

Nashville Intl

Sat 11/7

8:15 a.m.-9:30 p.m.

2 stops13h 15m

C$ 430

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Tue 26/5

6:40 a.m.-5:12 p.m.

2 stops9h 32m

Louisville Intl

Fri 29/5

6:05 a.m.-10:54 a.m.

1 stop5h 49m

C$ 445

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Sun 21/6

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

1 stop7h 15m

Nashville Intl

Sat 27/6

6:35 p.m.-10:00 a.m.

1 stop15h 25m

C$ 449

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Thu 4/6

5:41 p.m.-10:36 p.m.

1 stop4h 55m

Nashville Intl

Mon 8/6

7:57 p.m.-11:56 a.m.

2 stops15h 59m

C$ 494

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.-2:15 p.m.

2 stops19h 25m

C$ 495

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Wed 8/7

5:42 p.m.-10:26 p.m.

1 stop4h 44m

Nashville Intl

Sat 11/7

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

1 stop9h 08m

C$ 536

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Thu 6/8

7:00 a.m.-7:09 p.m.

2 stops11h 09m

Louisville Intl

Mon 10/8

6:36 a.m.-11:27 p.m.

1 stop17h 51m

C$ 543

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Tue 26/5

9:05 p.m.-10:25 a.m.

2 stops12h 20m

Louisville Intl

Fri 29/5

6:00 a.m.-5:25 p.m.

2 stops12h 25m

C$ 554

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/4

Showing 1-10 of 28 resultsSorted by cheapest first
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2
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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 25 April 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
9,650 reviews
Check prices

Comfort

7.3

Overall

7.4

Crew

8.1

Entertainment

7.1

Food

6.6

Boarding

7.7

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
9,650 reviews
United Airlines
7.4
Good
9,650 reviews
Check prices

Comfort

7.3

Overall

7.4

Crew

8.1

Entertainment

7.1

Food

6.6

Boarding

7.7

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$ 356, WestJet can have you in Kentucky from Winnipeg in 7h 15m. 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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Alternative routes for Winnipeg to Kentucky

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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 25 April 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 740AverageC$ 1,208FlexibilityNo 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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