$429+ Cheap flights from Madison (MSN) 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 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — YWG
Nov 9 — Nov 161
Round-trip
1 adult, Economy
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Find cheap flights from Madison to Winnipeg 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 Madison to Winnipeg
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Best
Last-minute
One-way
Cheapest flights from Madison to WinnipegExplore the most affordable flight options available from Madison to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 10, 2026.
Explore the most affordable flight options available from Madison to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 10, 2026.
This Air Canada deal was found by Cheapflights users on 10/7. 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.
Sat 11/213:08 pm -
1 stop5h 49m
Sat 11/288:40 am -
1 stop8h 20m
Deal found 10/7![Air Canada logo]()
$900
This oojo deal was found by Cheapflights users on 10/5. 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 11/1910:59 am -
1 stop5h 43m
Thu 11/266:00 am -
2 stops27h 18m
Deal found 10/5![WestJet logo]()
$1,025
This United Airlines deal was found by Cheapflights users on 10/5. 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 11/196:25 am -
2 stops15h 49m
Thu 11/263:40 pm -
2 stops18h 21m
Deal found 10/5![United Airlines logo]()
$1,045
This Mytrip deal was found by Cheapflights users on 10/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:40 pm -
3 stops21h 40m
Thu 11/268:35 am -
3 stops29h 06m
Deal found 10/5![Multiple Airlines logo]()
$1,096
This American Airlines deal was found by Cheapflights users on 10/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:01 am -
3 stops16h 51m
Sat 11/287:00 am -
2 stops13h 01m
Deal found 10/7![American Airlines logo]()
$1,146
Best flights from Madison to WinnipegDiscover carefully curated flight deals from Madison to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 10, 2026.
Discover carefully curated flight deals from Madison to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 10, 2026.
This United Airlines deal was found by Cheapflights users on 10/9. 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.
Wed 1/612:27 pm -
1 stop7h 01m
Sun 1/108:00 am -
1 stop7h 06m
Deal found 10/9![United Airlines logo]()
$911
This Air Canada deal was found by Cheapflights users on 10/7. 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.
Sat 11/2112:43 pm -
2 stops22h 41m
Sat 11/288:40 am -
1 stop8h 20m
Deal found 10/7![Air Canada logo]()
$937
This Air Canada deal was found by Cheapflights users on 10/9. 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.
Wed 1/612:27 pm -
2 stops13h 05m
Sun 1/109:40 am -
1 stop11h 05m
Deal found 10/9![Air Canada logo]()
$1,013
Last-minute flights from Madison to WinnipegDiscover last-minute flight deals from Madison to Winnipeg. Data last updated October 10, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Winnipeg. Data last updated October 10, 2026 and is based on user searches.
This oojo deal was found by Cheapflights users on 10/5. 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 11/1910:59 am -
1 stop5h 43m
Thu 11/266:00 am -
2 stops27h 18m
Deal found 10/5![WestJet logo]()
$1,025
This United Airlines deal was found by Cheapflights users on 10/5. 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 11/196:25 am -
2 stops15h 49m
Thu 11/263:40 pm -
2 stops18h 21m
Deal found 10/5![United Airlines logo]()
$1,045
This Mytrip deal was found by Cheapflights users on 10/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:40 pm -
3 stops21h 40m
Thu 11/268:35 am -
3 stops29h 06m
Deal found 10/5![Multiple Airlines logo]()
$1,096
This Air Canada deal was found by Cheapflights users on 10/7. 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.
Sat 11/213:08 pm -
1 stop5h 49m
Sat 11/288:40 am -
1 stop8h 20m
Deal found 10/7![Air Canada logo]()
$900
This American Airlines deal was found by Cheapflights users on 10/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:01 am -
3 stops16h 51m
Sat 11/287:00 am -
2 stops13h 01m
Deal found 10/7![American Airlines logo]()
$1,146
One-way flights from Madison to WinnipegSearch for one-way flight options from Madison to Winnipeg. Find affordable one-way fares based on user searches. Data last updated October 10, 2026.
Search for one-way flight options from Madison to Winnipeg. Find affordable one-way fares based on user searches. Data last updated October 10, 2026.
This Delta deal was found by Cheapflights users on 10/9. 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.
Mon 11/2310:59 am -
1 stop6h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Delta logo]()
$429
Find flight deals from Madison to Winnipeg
Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $900 (Air Canada) |
One-way from | $429 (Delta) |
Cheapflights Fare Finder
Customize your flight search to find flights from Madison 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 10, 2026.
Use the filters below to find and compare flights from Madison to Winnipeg that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
MadisonWinnipeg
MSN Madison Truax Field - YWG Winnipeg
MSNYWG
Madison Truax Field
Mon 11/23
10:59 am-5:42 pm
1 stop6h 43m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$429
MadisonWinnipeg
MSN Madison Truax Field - YWG Winnipeg
MSNYWG
Madison Truax Field
Wed 1/6
12:27 pm-7:28 pm
1 stop7h 01m
Winnipeg
Sun 1/10
8:00 am-3:06 pm
1 stop7h 06m
$911
MadisonWinnipeg
MSN Madison Truax Field - YWG Winnipeg
MSNYWG
Madison Truax Field
Sat 11/21
12:43 pm-11:24 am
2 stops22h 41m
Winnipeg
Sat 11/28
8:40 am-5:00 pm
1 stop8h 20m
$937
MadisonWinnipeg
MSN Madison Truax Field - YWG Winnipeg
MSNYWG
Madison Truax Field
Wed 1/6
12:27 pm-1:32 am
2 stops13h 05m
Winnipeg
Sun 1/10
9:40 am-8:45 pm
1 stop11h 05m
$1,013
Sorted by cheapest first
- Most accurate provider: When it comes to deals on Madison-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-Winnipeg flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Madison-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Madison-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Madison to Winnipeg
Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Madison with our price prediction graph.
MSN-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.
Related info for your journey
Find useful and relevant information for your journey from Madison to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Winnipeg?
Book flights to Winnipeg if you plan to visit one of these locationsPortage la Prairie
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