Find flights
When to book
Airlines
FAQs

Cheap flights from Winnipeg to Kentucky from C$ 278

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 31/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SDF
6 Jun — 13 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 7 May 2026.

Sun 16/86:15 a.m.
YWG
-
BNA
1 stop11h 45m
WestJet
Wed 19/86:50 p.m.
BNA
-
YWG
1 stop25h 30m
WestJet
Deal found 3/5C$ 382
Tue 2/63:50 p.m.
YWG
-
BNA
1 stop6h 46m
Delta
Tue 9/66:00 a.m.
BNA
-
YWG
1 stop9h 04m
Delta
Deal found 3/5C$ 431
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 7/5C$ 464
Wed 23/98:50 a.m.
YWG
-
BNA
1 stop8h 42m
Delta
Fri 25/96:30 p.m.
BNA
-
YWG
1 stop4h 57m
Delta
Deal found 3/5C$ 481
Tue 9/66:40 a.m.
YWG
-
SDF
2 stops5h 59m
Delta
Sat 13/66:00 a.m.
SDF
-
YWG
2 stops11h 51m
Delta
Deal found 2/5C$ 488
Tue 2/63:50 p.m.
YWG
-
BNA
1 stop6h 46m
Delta
Tue 16/66:00 a.m.
BNA
-
YWG
1 stop9h 04m
Delta
Deal found 3/5C$ 494
Mon 18/53:50 p.m.
YWG
-
SDF
1 stop7h 02m
KLM
Sun 24/56:05 a.m.
SDF
-
YWG
1 stop5h 49m
KLM
Deal found 4/5C$ 511
Mon 18/511:55 a.m.
YWG
-
SDF
2 stops9h 41m
Delta
Sun 24/56:05 a.m.
SDF
-
YWG
1 stop5h 49m
Delta
Deal found 4/5C$ 518
Mon 1/66:15 a.m.
YWG
-
BNA
1 stop11h 45m
Multiple Airlines
Fri 12/612:55 p.m.
BNA
-
YWG
1 stop12h 00m
Multiple Airlines
Deal found 4/5C$ 521
Thu 5/119:00 p.m.
YWG
-
SDF
2 stops13h 36m
WestJet
Sun 8/1110:43 a.m.
SDF
-
YWG
2 stops15h 12m
WestJet
Deal found 4/5C$ 532
Wed 8/710:45 a.m.
YWG
-
BNA
1 stop7h 15m
WestJet
Wed 15/77:00 p.m.
BNA
-
YWG
2 stops14h 35m
WestJet
Deal found 4/5C$ 545
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 5/5C$ 552

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 7 May 2026.

Round-trip from

C$ 382

One-way from

C$ 278
WestJet
  • WestJet
  • 16/8-19/8
  • 2 total stops
  • 37h 15m total
  • Winnipeg to Kentucky
Search Deals
WestJet
  • WestJet
  • 31/5
  • 1 total stop
  • 23h 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 7 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

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Sun 16/8

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

2 stops34h 00m

Nashville Intl

Wed 19/8

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

2 stops19h 25m

C$ 434
Quickest round-trip

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Wed 23/9

8:50 a.m.-5:32 p.m.

1 stop8h 42m

Nashville Intl

Fri 25/9

6:30 p.m.-11:27 p.m.

1 stop4h 57m

C$ 481

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Tue 9/6

5:41 p.m.-11:56 p.m.

1 stop5h 15m

Louisville Intl

Sat 13/6

6:00 a.m.-4:51 p.m.

2 stops11h 51m

C$ 488

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Tue 2/6

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

1 stop6h 46m

Nashville Intl

Tue 16/6

6:00 a.m.-3:04 p.m.

1 stop9h 04m

C$ 494

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Mon 18/5

11:55 a.m.-10:36 p.m.

2 stops9h 41m

Louisville Intl

Sun 24/5

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

1 stop5h 49m

C$ 518

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Sat 23/5

6:00 a.m.-9:18 p.m.

2 stops14h 18m

Louisville Intl

Sat 30/5

12:42 p.m.-10:10 p.m.

2 stops10h 28m

C$ 533

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Tue 2/6

8:45 a.m.-9:47 a.m.

2 stops25h 02m

Nashville Intl

Tue 16/6

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

1 stop14h 58m

C$ 567

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Tue 2/6

6:40 a.m.-5:31 p.m.

2 stops10h 51m

Nashville Intl

Tue 9/6

6:00 a.m.-3:04 p.m.

1 stop9h 04m

C$ 574

WinnipegLouisville

YWG - SDF

YWGSDF

Winnipeg

Tue 9/6

6:40 a.m.-7:11 p.m.

1 stop11h 31m

Louisville Intl

Sat 13/6

12:38 p.m.-11:29 p.m.

1 stop11h 51m

C$ 603

WinnipegNashville

YWG - BNA

YWGBNA

Winnipeg

Wed 30/9

4:15 p.m.-6:00 p.m.

2 stops25h 45m

Nashville Intl

Sun 4/10

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

1 stop14h 55m

C$ 626

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/5

Showing 1-10 of 22 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 7 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
9,690 reviews
Check prices

Boarding

7.7

Food

6.6

Crew

8.1

Comfort

7.3

Entertainment

7.1

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
9,690 reviews
United Airlines
7.4
Good
9,690 reviews
Check prices

Boarding

7.7

Food

6.6

Crew

8.1

Comfort

7.3

Entertainment

7.1

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$ 481, WestJet can have you in Kentucky from Winnipeg in 8h 42m. 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Winnipeg to Kentucky

See prices for flight routes from nearby airports that may be better suited for you.
Winnipeg to Las Vegas flights
Winnipeg to Minneapolis flights
Winnipeg to O'Hare Intl flights
Winnipeg to LaGuardia flights
Winnipeg to Newark flights
Winnipeg to John F Kennedy Intl flights
Winnipeg to Los Angeles flights
Winnipeg to San Francisco flights
Winnipeg to Dulles Intl flights
Winnipeg to Baltimore flights
Winnipeg to Denver flights
Winnipeg to Ontario flights
Winnipeg to Orlando flights
Winnipeg to Atlanta flights
Winnipeg to Sky Harbor Intl flights
Winnipeg to Austin flights
Winnipeg to Fort Lauderdale flights
Winnipeg to Hobby flights
Winnipeg to Sacramento flights
Winnipeg to Reagan-National flights
Winnipeg to Miami flights
Winnipeg to Dallas/Fort Worth flights
Winnipeg to George Bush Intcntl flights
Winnipeg to San Diego flights
Winnipeg to Seattle flights
Winnipeg to Boston flights
Winnipeg to Kahului flights
Winnipeg to Nashville flights
Winnipeg to Philadelphia flights
Winnipeg to Santa Ana flights
Winnipeg to Portland flights
Winnipeg to Fort Myers flights
Winnipeg to Honolulu flights
Winnipeg to Tampa flights
Winnipeg to Charlotte flights
Winnipeg to Love Field flights
Winnipeg to Kansas City flights
Winnipeg to Norfolk flights
Winnipeg to Anchorage flights
Winnipeg to Buffalo flights
Winnipeg to Salt Lake City flights
Winnipeg to Palm Springs flights
Winnipeg to Detroit flights
Winnipeg to Tulsa flights
Winnipeg to Colorado Springs flights
Winnipeg to Albany flights
Winnipeg to Indianapolis flights
Winnipeg to Louisville flights
Winnipeg to Tucson flights

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 7 May 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 737AverageC$ 1,204FlexibilityNo 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!

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.