$226+ Cheap flights from Winnipeg (YWG) to Kentucky
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SDF
Oct 25 — Nov 11
Round-trip
1 adult, Economy
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Find cheap flights from Winnipeg to Kentucky with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Winnipeg to Kentucky
Cheapest
Best
One-way
Cheapest flights from Winnipeg to KentuckyExplore 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 September 25, 2026.
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 September 25, 2026.
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:40 pm -
1 stop4h 11m
Fri 11/136:00 am -
2 stops11h 42m
Deal found 9/22![Delta logo]()
$626
This oojo deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:00 am -
2 stops15h 13m
Sun 11/86:00 am -
2 stops11h 25m
Deal found 9/22![WestJet logo]()
$627
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/62:15 pm -
2 stops21h 48m
Fri 11/139:17 am -
2 stops12h 40m
Deal found 9/22![United Airlines logo]()
$681
This Air Canada deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:15 pm -
1 stop7h 15m
Sun 11/85:10 am -
1 stop8h 13m
Deal found 9/20![Air Canada logo]()
$908
This American Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:00 am -
3 stops15h 15m
Fri 11/136:30 am -
2 stops16h 27m
Deal found 9/22![American Airlines logo]()
$910
Best flights from Winnipeg to KentuckyDiscover carefully curated flight deals from Winnipeg to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 25, 2026.
Discover carefully curated flight deals from Winnipeg to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 25, 2026.
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/267:00 am -
2 stops11h 34m
Thu 1/282:20 pm -
2 stops9h 13m
Deal found 9/22![United Airlines logo]()
$632
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/266:35 am -
1 stop7h 42m
Thu 1/284:00 pm -
1 stop8h 34m
Deal found 9/22![Delta logo]()
$632
This Justfly.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/55:00 am -
2 stops15h 13m
Sun 11/87:00 am -
1 stop5h 48m
Deal found 9/20![WestJet logo]()
$634
One-way flights from Winnipeg to KentuckySearch for one-way flight options from Winnipeg to Kentucky. Find affordable one-way fares based on user searches. Data last updated September 25, 2026.
Search for one-way flight options from Winnipeg to Kentucky. Find affordable one-way fares based on user searches. Data last updated September 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/98:35 pm -
3 stops41h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$226
This United Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/98:40 am -
2 stops12h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![United Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/59:30 pm -
2 stops20h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$351
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:15 pm -
1 stop7h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![United Airlines logo]()
$558
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 September 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $626 (Delta) |
One-way from | $226 (Kiwi.com) |
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 7,457,451 searches. Data last updated September 25, 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
Cheapest round-trip
WinnipegLouisville
YWG Winnipeg - SDF Louisville Intl
YWGSDF
Winnipeg
Mon 11/9
8:35 pm-3:26 pm
3 stops41h 51m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$226
WinnipegLouisville
YWG Winnipeg - SDF Louisville Intl
YWGSDF
Winnipeg
Mon 11/9
8:40 am-10:24 pm
1 stop12h 44m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$349
WinnipegLouisville
YWG Winnipeg - SDF Louisville Intl
YWGSDF
Winnipeg
Thu 11/5
9:30 pm-7:19 pm
2 stops20h 49m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$351
Quickest round-trip
WinnipegLouisville
YWG Winnipeg - SDF Louisville Intl
YWGSDF
Winnipeg
Thu 11/5
2:15 pm-10:30 pm
1 stop7h 15m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$558
WinnipegLouisville
YWG Winnipeg - SDF Louisville Intl
YWGSDF
Winnipeg
Tue 1/26
7:00 am-7:34 pm
2 stops11h 34m
Louisville Intl
Thu 1/28
2:20 pm-10:33 pm
2 stops9h 13m
$632
WinnipegLouisville
YWG Winnipeg - SDF Louisville Intl
YWGSDF
Winnipeg
Tue 1/26
6:35 am-3:17 pm
1 stop7h 42m
Louisville Intl
Thu 1/28
4:00 pm-11:34 pm
1 stop8h 34m
$632
WinnipegLouisville
YWG Winnipeg - SDF Louisville Intl
YWGSDF
Winnipeg
Thu 11/5
5:00 am-9:13 pm
2 stops15h 13m
Louisville Intl
Sun 11/8
7:00 am-11:48 am
1 stop5h 48m
$634
Sorted by cheapest first
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.
YWG-SDF
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
YWG-USKY
YWG-SDF
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 September 25, 2026.
Get a feel of what it's like to fly with WestJet from Winnipeg to Kentucky by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.2
Comfort
7.1
Boarding
7.4
Entertainment
6.1
Crew
7.9
Overall
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,Aug 2026
YHZ - DTW
Food
6.2
Comfort
7.1
Boarding
7.4
Entertainment
6.1
Crew
7.9
Overall
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,Aug 2026
YHZ - DTW
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.
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Alternative routes for Winnipeg to Kentucky
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Complete your trip
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Winnipeg and Kentucky flights
Browse other Winnipeg and Kentucky flight options. Last updated on September 25, 2026.
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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 7,457,451 searches. Data last updated September 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$429 | Average$509 | FlexibilityNo cancel fee | On-time60% |