$424+ 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 12/22. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — SDF
Dec 11 — Dec 181
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
Last-minute
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 November 11, 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 November 11, 2026.
This Delta deal was found by Cheapflights users on 11/10. 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 12/85:45 pm -
2 stops15h 23m
Sat 12/126:35 am -
1 stop4h 56m
Deal found 11/10![Delta logo]()
$669
This United Airlines deal was found by Cheapflights users on 11/7. 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 12/183:15 pm -
1 stop7h 24m
Tue 1/58:50 am -
2 stops13h 05m
Deal found 11/7![United Airlines logo]()
$678
This United Airlines deal was found by Cheapflights users on 11/10. 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 12/159:40 am -
1 stop12h 35m
Wed 12/165:00 am -
1 stop8h 23m
Deal found 11/10![United Airlines logo]()
$680
This United Airlines deal was found by Cheapflights users on 11/10. 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 12/253:15 pm -
1 stop5h 41m
Fri 1/17:00 am -
1 stop6h 52m
Deal found 11/10![United Airlines logo]()
$703
This Air Canada deal was found by Cheapflights users on 11/7. 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.
Fri 12/183:15 pm -
1 stop7h 24m
Tue 1/53:27 pm -
1 stop6h 28m
Deal found 11/7![Air Canada logo]()
$760
This United Airlines deal was found by Cheapflights users on 11/10. 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 12/89:40 am -
2 stops8h 37m
Sat 12/1210:25 am -
2 stops11h 59m
Deal found 11/10![United Airlines logo]()
$775
This United Airlines deal was found by Cheapflights users on 11/10. 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.
Sun 11/223:15 pm -
1 stop5h 37m
Mon 11/239:02 am -
2 stops12h 55m
Deal found 11/10![United Airlines logo]()
$926
This American Airlines deal was found by Cheapflights users on 11/10. 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.
Tue 12/157:00 am -
3 stops16h 15m
Wed 12/167:22 pm -
2 stops27h 40m
Deal found 11/10![American Airlines logo]()
$1,119
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 November 11, 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 November 11, 2026.
This Delta deal was found by Cheapflights users on 11/10. 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 12/85:45 pm -
2 stops15h 23m
Sat 12/126:35 am -
1 stop4h 56m
Deal found 11/10![Delta logo]()
$669
This United Airlines deal was found by Cheapflights users on 11/7. 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 12/183:15 pm -
1 stop7h 24m
Tue 1/59:00 am -
1 stop12h 55m
Deal found 11/7![United Airlines logo]()
$678
This United Airlines deal was found by Cheapflights users on 11/7. 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 1/58:00 am -
1 stop6h 47m
Thu 1/79:00 am -
1 stop12h 55m
Deal found 11/7![United Airlines logo]()
$678
This United Airlines deal was found by Cheapflights users on 11/10. 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 12/159:40 am -
2 stops12h 52m
Wed 12/167:00 am -
1 stop6h 23m
Deal found 11/10![United Airlines logo]()
$680
This United Airlines deal was found by Cheapflights users on 11/10. 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 12/253:15 pm -
1 stop5h 41m
Fri 1/17:00 am -
1 stop6h 52m
Deal found 11/10![United Airlines logo]()
$703
Last-minute flights from Winnipeg to KentuckyDiscover last-minute flight deals from Winnipeg to Kentucky. Data last updated November 11, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Kentucky. Data last updated November 11, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 11/10. 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.
Sun 11/223:15 pm -
1 stop5h 37m
Mon 11/239:02 am -
2 stops12h 55m
Deal found 11/10![United Airlines logo]()
$926
This Delta deal was found by Cheapflights users on 11/10. 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 12/85:45 pm -
2 stops15h 23m
Sat 12/126:35 am -
1 stop4h 56m
Deal found 11/10![Delta logo]()
$669
This United Airlines deal was found by Cheapflights users on 11/10. 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 12/89:40 am -
2 stops8h 37m
Sat 12/1210:25 am -
2 stops11h 59m
Deal found 11/10![United Airlines logo]()
$775
This United Airlines deal was found by Cheapflights users on 11/10. 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 12/159:40 am -
1 stop12h 35m
Wed 12/165:00 am -
1 stop8h 23m
Deal found 11/10![United Airlines logo]()
$680
This American Airlines deal was found by Cheapflights users on 11/10. 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.
Tue 12/157:00 am -
3 stops16h 15m
Wed 12/167:22 pm -
2 stops27h 40m
Deal found 11/10![American Airlines logo]()
$1,119
This United Airlines deal was found by Cheapflights users on 11/7. 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 12/189:40 am -
2 stops12h 59m
Tue 1/57:00 am -
2 stops14h 55m
Deal found 11/7![United Airlines logo]()
$678
This Air Canada deal was found by Cheapflights users on 11/7. 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.
Fri 12/183:15 pm -
1 stop7h 24m
Tue 1/53:27 pm -
1 stop6h 28m
Deal found 11/7![Air Canada logo]()
$760
This United Airlines deal was found by Cheapflights users on 11/10. 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 12/253:15 pm -
1 stop5h 41m
Fri 1/17:00 am -
1 stop6h 52m
Deal found 11/10![United Airlines logo]()
$703
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 November 11, 2026.
Search for one-way flight options from Winnipeg to Kentucky. Find affordable one-way fares based on user searches. Data last updated November 11, 2026.
This United Airlines deal was found by Cheapflights users on 11/7. 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 12/229:40 am -
1 stop12h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![United Airlines logo]()
$424
This Kiwi.com deal was found by Cheapflights users on 11/7. 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.
Tue 12/227:00 am -
3 stops16h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![WestJet logo]()
$676
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 November 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $678 (United Airlines) |
One-way from | $424 (United Airlines) |
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 November 11, 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
Tue 12/22
9:40 am-10:30 pm
1 stop12h 50m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$424
WinnipegLouisville
YWG Winnipeg - SDF Louisville Intl
YWGSDF
Winnipeg
Tue 12/8
5:45 pm-9:08 am
2 stops15h 23m
Louisville Intl
Sat 12/12
6:35 am-11:31 am
1 stop4h 56m
$669
WinnipegLouisville
YWG Winnipeg - SDF Louisville Intl
YWGSDF
Winnipeg
Tue 12/22
7:00 am-11:23 pm
3 stops16h 23m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$676
WinnipegLouisville
YWG Winnipeg - SDF Louisville Intl
YWGSDF
Winnipeg
Fri 12/18
3:15 pm-10:39 pm
1 stop7h 24m
Louisville Intl
Tue 1/5
9:00 am-9:55 pm
1 stop12h 55m
$678
WinnipegLouisville
YWG Winnipeg - SDF Louisville Intl
YWGSDF
Winnipeg
Tue 1/5
8:00 am-2:47 pm
1 stop6h 47m
Louisville Intl
Thu 1/7
9:00 am-9:55 pm
1 stop12h 55m
$678
WinnipegLexington
YWG Winnipeg - LEX Lexington Blue Grass
YWGLEX
Winnipeg
Tue 12/15
9:40 am-10:32 pm
2 stops12h 52m
Lexington Blue Grass
Wed 12/16
7:00 am-1:23 pm
1 stop6h 23m
$680
Quickest round-trip
WinnipegLouisville
YWG Winnipeg - SDF Louisville Intl
YWGSDF
Winnipeg
Fri 12/25
3:15 pm-8:56 pm
1 stop5h 41m
Louisville Intl
Fri 1/1
7:00 am-1:52 pm
1 stop6h 52m
$703
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
YWG-LEX
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
YWG-LEX
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 November 11, 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.
Crew
7.9
Boarding
7.4
Entertainment
6.1
Overall
7.2
Food
6.2
Comfort
7.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Aug 2026
YHZ - DTW
Crew
7.9
Boarding
7.4
Entertainment
6.1
Overall
7.2
Food
6.2
Comfort
7.1
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
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Kentucky by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Winnipeg to Kentucky, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Winnipeg and Kentucky flights
Browse other Winnipeg and Kentucky flight options. Last updated on November 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 November 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$429 | Average$509 | FlexibilityNo cancel fee | On-time60% |