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Cheap flights from Winnipeg to Kentucky from C$ 240

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
11 Jun — 18 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 12 May 2026.

Mon 8/66:15 a.m.
YWG
-
BNA
1 stop11h 45m
WestJet
Mon 15/66:50 p.m.
BNA
-
YWG
1 stop6h 05m
WestJet
Deal found 10/5C$ 395
Sun 21/66:05 p.m.
YWG
-
BNA
1 stop23h 55m
WestJet
Sun 5/76:50 p.m.
BNA
-
YWG
1 stop6h 05m
WestJet
Deal found 11/5C$ 419
Mon 8/69:25 a.m.
YWG
-
BNA
1 stop8h 35m
Multiple Airlines
Mon 15/66:50 p.m.
BNA
-
YWG
1 stop6h 05m
Multiple Airlines
Deal found 9/5C$ 447
Fri 5/68:10 p.m.
YWG
-
BNA
1 stop16h 05m
Multiple Airlines
Fri 12/612:55 p.m.
BNA
-
YWG
1 stop12h 00m
Multiple Airlines
Deal found 7/5C$ 456
Thu 10/96:15 a.m.
YWG
-
BNA
1 stop11h 45m
WestJet
Mon 14/96:50 p.m.
BNA
-
YWG
1 stop25h 30m
WestJet
Deal found 11/5C$ 480
Sat 6/65:10 p.m.
YWG
-
BNA
1 stop24h 50m
Multiple Airlines
Sat 27/612:55 p.m.
BNA
-
YWG
1 stop19h 45m
Multiple Airlines
Deal found 12/5C$ 510
Mon 31/87:40 p.m.
YWG
-
BNA
1 stop13h 33m
Air Canada
Wed 2/910:05 a.m.
BNA
-
YWG
1 stop6h 15m
Air Canada
Deal found 11/5C$ 514
Sat 29/87:00 a.m.
YWG
-
SDF
1 stop5h 11m
United Airlines
Wed 2/911:00 a.m.
SDF
-
YWG
1 stop12h 33m
United Airlines
Deal found 11/5C$ 518
Thu 5/119:00 p.m.
YWG
-
SDF
2 stops13h 36m
WestJet
Sun 8/117:00 a.m.
SDF
-
YWG
2 stops18h 55m
WestJet
Deal found 11/5C$ 534
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 12/5C$ 601
Sat 29/85:42 p.m.
YWG
-
SDF
1 stop21h 10m
WestJet
Wed 2/96:00 a.m.
SDF
-
YWG
2 stops12h 15m
WestJet
Deal found 10/5C$ 612

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 12 May 2026.

Round-trip from

C$ 395

One-way from

C$ 240
WestJet
  • WestJet
  • 8/6-15/6
  • 2 total stops
  • 17h 50m 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 12 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

Sat 29/8

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

2 stops11h 05m

Louisville Intl

Wed 2/9

11:00 a.m.-10:33 p.m.

1 stop12h 33m

C$ 518

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Thu 5/11

9:00 p.m.-11:36 a.m.

2 stops13h 36m

Louisville Intl

Sun 8/11

6:36 a.m.-8:16 p.m.

1 stop14h 40m

C$ 541

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Mon 8/6

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

1 stop8h 00m

Nashville Intl

Mon 15/6

6:50 p.m.-9:45 a.m.

1 stop14h 55m

C$ 558

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Fri 5/6

4:15 p.m.-12:15 p.m.

2 stops20h 00m

Nashville Intl

Wed 24/6

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

1 stop13h 50m

C$ 577

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Fri 28/8

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

1 stop8h 00m

Nashville Intl

Wed 2/9

6:50 p.m.-2:25 p.m.

1 stop19h 35m

C$ 604

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Sat 29/8

3:58 p.m.-11:55 a.m.

1 stop18h 57m

Louisville Intl

Wed 2/9

7:00 a.m.-8:20 p.m.

2 stops14h 20m

C$ 612

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Wed 12/8

12:25 p.m.-6:10 p.m.

2 stops29h 45m

Nashville Intl

Sat 15/8

7:00 p.m.-9:35 a.m.

2 stops14h 35m

C$ 621

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Fri 28/8

7:00 a.m.-9:43 a.m.

2 stops26h 43m

Nashville Intl

Wed 2/9

6:00 a.m.-10:33 p.m.

2 stops16h 33m

C$ 653
Quickest round-trip

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Mon 31/8

7:55 a.m.-2:59 p.m.

1 stop7h 04m

Nashville Intl

Wed 2/9

10:05 a.m.-4:20 p.m.

1 stop6h 15m

C$ 660

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Mon 31/8

8:15 a.m.-6:47 p.m.

2 stops10h 32m

Nashville Intl

Wed 2/9

6:00 a.m.-4:20 p.m.

2 stops10h 20m

C$ 678

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/5

Showing 1-10 of 28 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 12 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
9,701 reviews
Check prices

Crew

8.1

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Overall

7.4

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
9,701 reviews
United Airlines
7.4
Good
9,701 reviews
Check prices

Crew

8.1

Boarding

7.7

Entertainment

7.1

Food

6.6

Comfort

7.3

Overall

7.4

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$ 518, United Airlines can have you in Kentucky from Winnipeg in 11h 05m. 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 12 May 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 741AverageC$ 1,210FlexibilityNo 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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