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Cheap flights from Winnipeg to Kentucky from C$ 221

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 20/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SDF
10 May — 17 May1
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 10 April 2026.

Tue 2/68:45 a.m.
YWG
-
BNA
2 stops25h 02m
United Airlines
Sat 6/66:30 p.m.
BNA
-
YWG
2 stops17h 22m
United Airlines
Deal found 5/4C$ 367
Sun 17/55:41 p.m.
YWG
-
BNA
1 stop4h 55m
Delta
Thu 21/56:00 a.m.
BNA
-
YWG
1 stop8h 55m
Delta
Deal found 5/4C$ 398
Tue 5/58:45 a.m.
YWG
-
SDF
1 stop12h 46m
United Airlines
Wed 6/57:15 a.m.
SDF
-
YWG
1 stop5h 37m
United Airlines
Deal found 5/4C$ 425
Fri 22/53:50 p.m.
YWG
-
BNA
1 stop6h 46m
Delta
Tue 26/56:00 a.m.
BNA
-
YWG
1 stop8h 55m
Delta
Deal found 6/4C$ 428
Tue 2/63:50 p.m.
YWG
-
BNA
1 stop6h 46m
Delta
Sat 6/66:00 a.m.
BNA
-
YWG
1 stop8h 55m
Delta
Deal found 5/4C$ 459
Sat 23/57:20 p.m.
YWG
-
BNA
1 stop14h 14m
Air Canada
Tue 26/56:50 p.m.
BNA
-
YWG
1 stop16h 18m
Air Canada
Deal found 9/4C$ 475
Sat 20/66:40 a.m.
YWG
-
SDF
1 stop8h 06m
Delta
Tue 23/66:49 a.m.
SDF
-
YWG
1 stop9h 15m
Delta
Deal found 9/4C$ 484
Sat 11/42:00 p.m.
YWG
-
BNA
1 stop9h 24m
United Airlines
Sat 18/46:00 a.m.
BNA
-
YWG
1 stop5h 52m
United Airlines
Deal found 6/4C$ 493
Wed 3/65:10 a.m.
YWG
-
BNA
2 stops18h 11m
United Airlines
Sun 7/66:00 a.m.
BNA
-
YWG
1 stop16h 33m
United Airlines
Deal found 8/4C$ 494
Mon 8/65:10 a.m.
YWG
-
BNA
2 stops16h 29m
Air Canada
Fri 12/612:49 p.m.
BNA
-
YWG
1 stop9h 44m
Air Canada
Deal found 9/4C$ 495
Sat 20/66:15 a.m.
YWG
-
SDF
2 stops14h 00m
WestJet
Tue 23/67:05 a.m.
SDF
-
YWG
2 stops11h 10m
WestJet
Deal found 9/4C$ 600
Tue 5/56:15 a.m.
YWG
-
SDF
2 stops9h 27m
WestJet
Wed 6/56:00 a.m.
SDF
-
YWG
2 stops9h 25m
WestJet
Deal found 7/4C$ 630

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 10 April 2026.

Round-trip from

C$ 367

One-way from

C$ 221
United Airlines
  • United Airlines
  • 2/6-6/6
  • 4 total stops
  • 42h 24m total
  • Winnipeg to Kentucky
Search Deals
Delta
  • Delta
  • 20/5
  • 1 total stop
  • 4h 55m 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 10 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

Sun 17/5

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

1 stop4h 55m

Nashville Intl

Thu 21/5

6:00 a.m.-2:55 p.m.

1 stop8h 55m

C$ 398

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Tue 5/5

2:00 p.m.-11:59 p.m.

2 stops8h 59m

Louisville Intl

Wed 6/5

7:15 a.m.-11:52 a.m.

1 stop5h 37m

C$ 425

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Tue 2/6

3:50 p.m.-10:36 p.m.

1 stop6h 46m

Nashville Intl

Sat 6/6

6:00 a.m.-2:55 p.m.

1 stop8h 55m

C$ 450

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Sat 23/5

7:20 p.m.-9:34 a.m.

1 stop14h 14m

Nashville Intl

Tue 26/5

6:50 p.m.-11:08 a.m.

1 stop16h 18m

C$ 475

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Sat 20/6

6:40 a.m.-3:46 p.m.

1 stop8h 06m

Louisville Intl

Tue 23/6

6:49 a.m.-3:04 p.m.

1 stop9h 15m

C$ 484

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Tue 2/6

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

1 stop5h 29m

Nashville Intl

Sat 6/6

12:49 p.m.-10:33 p.m.

1 stop9h 44m

C$ 505

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Fri 22/5

3:50 p.m.-10:36 p.m.

1 stop6h 46m

Nashville Intl

Mon 25/5

6:00 a.m.-2:55 p.m.

1 stop8h 55m

C$ 519

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Tue 9/6

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

1 stop5h 29m

Nashville Intl

Wed 10/6

6:45 p.m.-11:08 a.m.

1 stop16h 23m

C$ 523

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Sat 23/5

8:45 a.m.-8:51 a.m.

2 stops24h 06m

Nashville Intl

Tue 26/5

6:50 p.m.-11:08 a.m.

1 stop16h 18m

C$ 546

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Sat 16/5

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

1 stop4h 55m

Nashville Intl

Tue 19/5

6:00 a.m.-2:55 p.m.

1 stop8h 55m

C$ 555

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/4

Showing 1-10 of 23 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 10 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
9,562 reviews
Check prices

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
United Airlines
7.4
Good
9,562 reviews
United Airlines
7.4
Good
9,562 reviews
Check prices

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Crew

8.1

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

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$ 398, Delta can have you in Kentucky from Winnipeg in 4h 55m. 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 10 April 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 748AverageC$ 1,221FlexibilityNo 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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