$802+ 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — YWG
Oct 23 — Oct 301
Round-trip
1 adult, Economy
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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
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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 Madison to Winnipeg
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Last-minute
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 September 23, 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 September 23, 2026.
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1810:59 am -
2 stops8h 51m
Wed 12/165:00 am -
2 stops16h 24m
Deal found 9/21![WestJet logo]()
$802
This oojo deal was found by Cheapflights users on 9/18. 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.
Fri 10/26:00 am -
2 stops18h 55m
Sat 10/36:15 am -
2 stops15h 04m
Deal found 9/18![WestJet logo]()
$947
This oojo deal was found by Cheapflights users on 9/18. 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.
Tue 10/67:00 am -
2 stops13h 20m
Thu 10/89:05 pm -
2 stops23h 50m
Deal found 9/18![WestJet logo]()
$1,035
This Air Canada deal was found by Cheapflights users on 9/18. 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.
Tue 10/65:10 am -
1 stop15h 47m
Thu 10/88:45 am -
1 stop12h 22m
Deal found 9/18![Air Canada logo]()
$1,062
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 September 23, 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 September 23, 2026.
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:30 am -
1 stop5h 25m
Wed 12/165:24 pm -
1 stop4h 05m
Deal found 9/21![WestJet logo]()
$803
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.
Wed 1/66:40 am -
1 stop15h 53m
Sun 1/107:00 am -
1 stop7h 59m
Deal found 9/22![United Airlines logo]()
$851
This WestJet 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/611:00 am -
2 stops8h 50m
Sun 1/105:38 pm -
1 stop20h 17m
Deal found 9/21![WestJet logo]()
$940
Last-minute flights from Madison to WinnipegDiscover last-minute flight deals from Madison to Winnipeg. Data last updated September 23, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Winnipeg. Data last updated September 23, 2026 and is based on user searches.
This oojo deal was found by Cheapflights users on 9/18. 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.
Fri 10/26:00 am -
2 stops18h 55m
Sat 10/36:15 am -
2 stops15h 04m
Deal found 9/18![WestJet logo]()
$947
This oojo deal was found by Cheapflights users on 9/18. 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.
Tue 10/67:00 am -
2 stops13h 20m
Thu 10/89:05 pm -
2 stops23h 50m
Deal found 9/18![WestJet logo]()
$1,035
This Air Canada deal was found by Cheapflights users on 9/18. 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.
Tue 10/65:10 am -
1 stop15h 47m
Thu 10/88:45 am -
1 stop12h 22m
Deal found 9/18![Air Canada logo]()
$1,062
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.
Tue 10/65:00 am -
1 stop7h 37m
Thu 10/82:00 pm -
1 stop8h 35m
Deal found 9/21![United Airlines logo]()
$1,073
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 September 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $802 (oojo) |
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 September 23, 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
Wed 11/18
6:30 am-11:55 am
1 stop5h 25m
Winnipeg
Wed 12/16
5:24 pm-9:29 pm
1 stop4h 05m
$803
MadisonWinnipeg
MSN Madison Truax Field - YWG Winnipeg
MSNYWG
Madison Truax Field
Wed 1/6
6:40 am-10:33 pm
1 stop15h 53m
Winnipeg
Sun 1/10
7:00 am-2:59 pm
1 stop7h 59m
$851
MadisonWinnipeg
MSN Madison Truax Field - YWG Winnipeg
MSNYWG
Madison Truax Field
Wed 1/6
11:00 am-7:50 pm
2 stops8h 50m
Winnipeg
Sun 1/10
5:38 pm-1:55 pm
1 stop20h 17m
$940
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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