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Cheap flights from Winnipeg to Kentucky from C$ 199

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 28/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SDF
14 Sep — 21 Sep1
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 15 August 2026.

Sat 3/105:44 p.m. -
1 stop4h 56m
Tue 6/1010:40 a.m. -
1 stop9h 13m
Deal found 10/8C$ 335
Fri 25/95:44 p.m. -
1 stop4h 54m
Wed 30/96:00 a.m. -
1 stop5h 51m
Deal found 10/8C$ 346
Wed 9/97:00 a.m. -
2 stops11h 00m
Wed 16/96:50 p.m. -
1 stop6h 05m
Deal found 14/8C$ 353
Fri 25/97:10 p.m. -
1 stop14h 09m
Tue 29/910:25 a.m. -
1 stop6h 02m
Deal found 11/8C$ 360
Fri 25/95:49 p.m. -
1 stop4h 54m
Tue 29/910:12 a.m. -
1 stop5h 01m
Deal found 10/8C$ 368
Fri 11/97:00 a.m. -
1 stop8h 57m
Mon 14/96:02 a.m. -
1 stop5h 50m
Deal found 10/8C$ 369
Sat 3/102:00 p.m. -
1 stop9h 14m
Tue 6/108:30 a.m. -
2 stops14h 03m
Deal found 10/8C$ 383
Fri 21/86:40 a.m. -
1 stop8h 07m
Sun 23/86:00 a.m. -
1 stop9h 08m
Deal found 13/8C$ 400
Fri 25/99:05 p.m. -
1 stop21h 05m
Wed 30/96:50 p.m. -
1 stop6h 05m
Deal found 13/8C$ 415
Thu 1/105:44 p.m. -
1 stop4h 59m
Mon 5/108:09 a.m. -
2 stops9h 45m
Deal found 10/8C$ 675
Sat 3/105:44 p.m. -
1 stop4h 06m
Sat 10/1010:37 a.m. -
2 stops13h 42m
Deal found 13/8C$ 685
Thu 1/107:10 p.m. -
2 stops24h 23m
Mon 5/107:05 a.m. -
2 stops16h 05m
Deal found 10/8C$ 688

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 15 August 2026.

Round-trip from

C$ 335

One-way from

C$ 199
Delta
  • Delta
  • 3/10-6/10
  • 2 total stops
  • 14h 09m total
  • Winnipeg to Kentucky
Search Deals
WestJet
  • WestJet
  • 28/9
  • 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 15 August 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 Winnipeg - BNA Nashville Intl

YWGBNA

Winnipeg

Sat 3/10

5:44 p.m.-10:40 p.m.

1 stop4h 56m

Nashville Intl

Tue 6/10

10:40 a.m.-7:53 p.m.

1 stop9h 13m

C$ 335

WinnipegNashville

YWG Winnipeg - BNA Nashville Intl

YWGBNA

Winnipeg

Fri 25/9

5:44 p.m.-10:38 p.m.

1 stop4h 54m

Nashville Intl

Tue 29/9

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

1 stop9h 08m

C$ 346

WinnipegNashville

YWG Winnipeg - BNA Nashville Intl

YWGBNA

Winnipeg

Fri 25/9

5:44 p.m.-10:38 p.m.

1 stop4h 54m

Nashville Intl

Wed 30/9

6:00 a.m.-11:51 a.m.

1 stop5h 51m

C$ 346

WinnipegNashville

YWG Winnipeg - BNA Nashville Intl

YWGBNA

Winnipeg

Wed 9/9

12:41 p.m.-9:53 p.m.

1 stop9h 12m

Nashville Intl

Wed 16/9

6:00 a.m.-11:51 a.m.

1 stop5h 51m

C$ 346

WinnipegNashville

YWG Winnipeg - BNA Nashville Intl

YWGBNA

Winnipeg

Fri 11/9

7:00 a.m.-3:57 p.m.

1 stop8h 57m

Nashville Intl

Mon 14/9

6:02 a.m.-11:52 a.m.

1 stop5h 50m

C$ 369

WinnipegNashville

YWG Winnipeg - BNA Nashville Intl

YWGBNA

Winnipeg

Wed 9/9

7:00 a.m.-8:33 p.m.

2 stops13h 33m

Nashville Intl

Wed 16/9

6:02 a.m.-11:52 a.m.

1 stop5h 50m

C$ 379

WinnipegNashville

YWG Winnipeg - BNA Nashville Intl

YWGBNA

Winnipeg

Thu 3/9

12:46 p.m.-10:16 p.m.

1 stop9h 30m

Nashville Intl

Sat 5/9

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

1 stop9h 08m

C$ 379

WinnipegNashville

YWG Winnipeg - BNA Nashville Intl

YWGBNA

Winnipeg

Fri 18/9

5:44 p.m.-10:38 p.m.

1 stop4h 54m

Nashville Intl

Tue 22/9

6:00 a.m.-11:51 a.m.

1 stop5h 51m

C$ 381

WinnipegLouisville

YWG Winnipeg - SDF Louisville Intl

YWGSDF

Winnipeg

Thu 1/10

5:44 p.m.-11:43 p.m.

1 stop4h 59m

Louisville Intl

Mon 5/10

8:09 a.m.-4:54 p.m.

2 stops9h 45m

C$ 675
Quickest round-trip

WinnipegLouisville

YWG Winnipeg - SDF Louisville Intl

YWGSDF

Winnipeg

Sat 3/10

5:44 p.m.-10:50 p.m.

1 stop4h 06m

Louisville Intl

Sat 10/10

6:39 p.m.-11:19 p.m.

1 stop5h 40m

C$ 685

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/8

Showing 1-10 of 28 resultsSorted by cheapest first
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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.

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$ 335, Delta can have you in Kentucky from Winnipeg in 4h 56m. 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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Fly with Cheapflights

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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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