$748+ Cheap flights from Kentucky to Winnipeg (YWG)
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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — YWG
Nov 2 — Nov 91
Round-trip
1 adult, Economy
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Find cheap flights from Kentucky to Winnipeg with Cheapflights
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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
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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 Kentucky to Winnipeg
Cheapest
Best
Last-minute
Cheapest flights from Kentucky to WinnipegExplore the most affordable flight options available from Kentucky to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 3, 2026.
Explore the most affordable flight options available from Kentucky to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 3, 2026.
This Delta deal was found by Cheapflights users on 9/29. 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.
Thu 10/227:00 am -
1 stop5h 48m
Thu 10/295:40 pm -
1 stop4h 11m
Deal found 9/29![Delta logo]()
$748
This lastminute.com deal was found by Cheapflights users on 9/29. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:06 am -
2 stops10h 14m
Thu 10/299:35 pm -
2 stops18h 14m
Deal found 9/29![WestJet logo]()
$800
This Delta deal was found by Cheapflights users on 10/1. 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 11/176:42 am -
1 stop6h 13m
Tue 11/246:35 am -
1 stop4h 25m
Deal found 10/1![Delta logo]()
$812
This Air Canada deal was found by Cheapflights users on 10/3. 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.
Mon 10/265:10 am -
1 stop8h 13m
Wed 10/285:15 am -
2 stops10h 47m
Deal found 10/3![Air Canada logo]()
$871
This United Airlines deal was found by Cheapflights users on 10/3. 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 10/266:18 pm -
2 stops19h 05m
Wed 10/288:40 am -
2 stops23h 58m
Deal found 10/3![United Airlines logo]()
$952
This American Airlines deal was found by Cheapflights users on 10/1. 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 11/1710:08 am -
2 stops12h 49m
Tue 11/247:00 am -
3 stops16h 20m
Deal found 10/1![American Airlines logo]()
$1,125
This American Airlines deal was found by Cheapflights users on 10/3. 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.
Mon 10/2610:16 am -
2 stops12h 41m
Wed 10/287:00 am -
3 stops14h 05m
Deal found 10/3![American Airlines logo]()
$1,154
This Justfly.com deal was found by Cheapflights users on 9/29. 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.
Sun 10/46:00 am -
2 stops10h 25m
Sat 10/104:15 pm -
2 stops24h 44m
Deal found 9/29![WestJet logo]()
$1,227
Best flights from Kentucky to WinnipegDiscover carefully curated flight deals from Kentucky to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 3, 2026.
Discover carefully curated flight deals from Kentucky to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 3, 2026.
This Delta deal was found by Cheapflights users on 9/29. 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.
Thu 10/227:00 am -
1 stop5h 48m
Thu 10/295:40 pm -
1 stop4h 11m
Deal found 9/29![Delta logo]()
$748
This lastminute.com deal was found by Cheapflights users on 9/29. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:06 am -
2 stops10h 14m
Thu 10/299:35 pm -
2 stops18h 14m
Deal found 9/29![WestJet logo]()
$800
This Air Canada deal was found by Cheapflights users on 10/3. 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.
Mon 10/265:10 am -
1 stop8h 13m
Wed 10/282:15 pm -
1 stop7h 15m
Deal found 10/3![Air Canada logo]()
$903
This United Airlines deal was found by Cheapflights users on 10/3. 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 10/266:18 pm -
2 stops19h 05m
Wed 10/288:40 am -
2 stops23h 58m
Deal found 10/3![United Airlines logo]()
$952
This American Airlines deal was found by Cheapflights users on 10/3. 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.
Mon 10/2610:16 am -
2 stops12h 41m
Wed 10/287:00 am -
3 stops14h 05m
Deal found 10/3![American Airlines logo]()
$1,154
This Delta deal was found by Cheapflights users on 10/1. 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 11/176:42 am -
1 stop6h 13m
Tue 11/246:35 am -
1 stop4h 25m
Deal found 10/1![Delta logo]()
$812
This oojo deal was found by Cheapflights users on 10/3. 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.
Mon 10/265:57 pm -
2 stops32h 13m
Wed 10/285:00 am -
2 stops15h 13m
Deal found 10/3![WestJet logo]()
$1,563
Last-minute flights from Kentucky to WinnipegDiscover last-minute flight deals from Kentucky to Winnipeg. Data last updated October 3, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Winnipeg. Data last updated October 3, 2026 and is based on user searches.
This Justfly.com deal was found by Cheapflights users on 9/29. 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.
Sun 10/46:00 am -
2 stops10h 25m
Sat 10/104:15 pm -
2 stops24h 44m
Deal found 9/29![WestJet logo]()
$1,227
This Delta deal was found by Cheapflights users on 9/29. 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.
Thu 10/227:00 am -
1 stop5h 48m
Thu 10/295:40 pm -
1 stop4h 11m
Deal found 9/29![Delta logo]()
$748
This lastminute.com deal was found by Cheapflights users on 9/29. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2211:06 am -
2 stops10h 14m
Thu 10/299:35 pm -
2 stops18h 14m
Deal found 9/29![WestJet logo]()
$800
This Air Canada deal was found by Cheapflights users on 10/3. 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.
Mon 10/265:10 am -
1 stop8h 13m
Wed 10/285:15 am -
2 stops10h 47m
Deal found 10/3![Air Canada logo]()
$871
This United Airlines deal was found by Cheapflights users on 10/3. 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 10/266:18 pm -
2 stops19h 05m
Wed 10/288:40 am -
2 stops23h 58m
Deal found 10/3![United Airlines logo]()
$952
This American Airlines deal was found by Cheapflights users on 10/3. 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.
Mon 10/2610:16 am -
2 stops12h 41m
Wed 10/287:00 am -
3 stops14h 05m
Deal found 10/3![American Airlines logo]()
$1,154
This Delta deal was found by Cheapflights users on 10/1. 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 11/176:42 am -
1 stop6h 13m
Tue 11/246:35 am -
1 stop4h 25m
Deal found 10/1![Delta logo]()
$812
This American Airlines deal was found by Cheapflights users on 10/1. 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 11/1710:08 am -
2 stops12h 49m
Tue 11/247:00 am -
3 stops16h 20m
Deal found 10/1![American Airlines logo]()
$1,125
Find flight deals from Kentucky to Winnipeg
Keep the following information in mind while searching for Kentucky to Winnipeg flight deals. Data was last updated October 3, 2026.
Round-trip from | $748 (Delta) |
|---|
Cheapflights Fare Finder
Customize your flight search to find flights from Kentucky to Winnipeg 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 October 3, 2026.
Use the filters below to find and compare flights from Kentucky to Winnipeg that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
LouisvilleWinnipeg
SDF Louisville Intl - YWG Winnipeg
SDFYWG
Louisville Intl
Thu 10/22
7:00 am-11:48 am
1 stop5h 48m
Winnipeg
Thu 10/29
5:40 pm-10:51 pm
1 stop4h 11m
$748
LouisvilleWinnipeg
SDF Louisville Intl - YWG Winnipeg
SDFYWG
Louisville Intl
Thu 10/22
11:06 am-8:20 pm
2 stops10h 14m
Winnipeg
Thu 10/29
9:35 pm-4:49 pm
2 stops18h 14m
$800
LouisvilleWinnipeg
SDF Louisville Intl - YWG Winnipeg
SDFYWG
Louisville Intl
Tue 11/17
6:42 am-12:55 pm
1 stop6h 13m
Winnipeg
Tue 11/24
6:35 am-11:00 am
1 stop4h 25m
$812
LouisvilleWinnipeg
SDF Louisville Intl - YWG Winnipeg
SDFYWG
Louisville Intl
Mon 10/26
5:10 am-12:23 pm
1 stop8h 13m
Winnipeg
Wed 10/28
2:15 pm-10:30 pm
1 stop7h 15m
$903
LouisvilleWinnipeg
SDF Louisville Intl - YWG Winnipeg
SDFYWG
Louisville Intl
Mon 10/26
6:18 pm-12:23 pm
2 stops19h 05m
Winnipeg
Wed 10/28
8:40 am-9:38 am
2 stops23h 58m
$952
LouisvilleWinnipeg
SDF Louisville Intl - YWG Winnipeg
SDFYWG
Louisville Intl
Mon 10/26
10:16 am-9:57 pm
2 stops12h 41m
Winnipeg
Wed 10/28
7:00 am-10:05 pm
3 stops14h 05m
$1,154
LouisvilleWinnipeg
SDF Louisville Intl - YWG Winnipeg
SDFYWG
Louisville Intl
Mon 10/26
5:57 pm-1:10 am
2 stops32h 13m
Winnipeg
Wed 10/28
5:00 am-9:13 pm
2 stops15h 13m
$1,563
Sorted by cheapest first
Best time to book a flight from Kentucky to Winnipeg
Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Kentucky with our price prediction graph.
SDF-YWG
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 Kentucky to Winnipeg
USKY-YWG
SDF-YWG
No data available for this route at this time. Please check back soon.
Related info for your journey
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Book flights to Winnipeg if you plan to visit one of these locationsPortage la Prairie
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