$384+ 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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — YWG
Nov 2 — Nov 91
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 3, 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 3, 2026.
This oojo deal was found by Cheapflights users on 9/30. 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 11/187:49 pm -
2 stops28h 55m
Wed 12/165:00 am -
2 stops28h 15m
Deal found 9/30![WestJet logo]()
$886
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Wed 11/185:00 am -
3 stops16h 57m
Wed 12/167:00 am -
2 stops11h 30m
Deal found 9/30![American Airlines logo]()
$1,071
This oojo deal was found by Cheapflights users on 9/28. 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 stops14h 00m
Sat 10/36:15 am -
2 stops16h 19m
Deal found 9/28![WestJet logo]()
$1,205
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 3, 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 3, 2026.
This United Airlines deal was found by Cheapflights users on 9/28. 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 1/62:49 pm -
1 stop7h 44m
Sun 1/107:00 am -
1 stop9h 58m
Deal found 9/28![United Airlines logo]()
$872
This FlightHub deal was found by Cheapflights users on 9/30. 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 11/1810:59 am -
2 stops8h 51m
Wed 12/165:24 pm -
1 stop4h 05m
Deal found 9/30![WestJet logo]()
$919
This Air Canada deal was found by Cheapflights users on 9/28. 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 1/612:30 pm -
2 stops11h 54m
Sun 1/107:00 am -
1 stop10h 51m
Deal found 9/28![Air Canada logo]()
$984
Last-minute flights from Madison to WinnipegDiscover last-minute flight deals from Madison to Winnipeg. Data last updated October 3, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Winnipeg. Data last updated October 3, 2026 and is based on user searches.
This oojo deal was found by Cheapflights users on 9/28. 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 stops14h 00m
Sat 10/36:15 am -
2 stops16h 19m
Deal found 9/28![WestJet logo]()
$1,205
This oojo deal was found by Cheapflights users on 9/30. 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 11/187:49 pm -
2 stops28h 55m
Wed 12/165:00 am -
2 stops28h 15m
Deal found 9/30![WestJet logo]()
$886
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Wed 11/185:00 am -
3 stops16h 57m
Wed 12/167:00 am -
2 stops11h 30m
Deal found 9/30![American Airlines logo]()
$1,071
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 3, 2026.
Search for one-way flight options from Madison to Winnipeg. Find affordable one-way fares based on user searches. Data last updated October 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/28. 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.
Sat 10/2410:38 am -
3 stops48h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Multiple Airlines logo]()
$384
This Delta deal was found by Cheapflights users on 9/28. 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.
Sat 10/246:00 am -
1 stop5h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Delta logo]()
$409
This oojo deal was found by Cheapflights users on 9/28. 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.
Sat 10/245:48 pm -
2 stops17h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![WestJet logo]()
$427
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 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $872 (United Airlines) |
One-way from | $384 (Kiwi.com) |
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 3, 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
MadisonWinnipeg
MSN Madison Truax Field - YWG Winnipeg
MSNYWG
Madison Truax Field
Sat 10/24
10:38 am-10:45 am
3 stops48h 07m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$384
Quickest round-trip
MadisonWinnipeg
MSN Madison Truax Field - YWG Winnipeg
MSNYWG
Madison Truax Field
Sat 10/24
6:00 am-11:48 am
1 stop5h 48m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$409
MadisonWinnipeg
MSN Madison Truax Field - YWG Winnipeg
MSNYWG
Madison Truax Field
Sat 10/24
5:48 pm-11:05 am
2 stops17h 17m
Winnipeg
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$427
MadisonWinnipeg
MSN Madison Truax Field - YWG Winnipeg
MSNYWG
Madison Truax Field
Wed 1/6
2:49 pm-10:33 pm
1 stop7h 44m
Winnipeg
Sun 1/10
7:00 am-4:58 pm
1 stop9h 58m
$872
MadisonWinnipeg
MSN Madison Truax Field - YWG Winnipeg
MSNYWG
Madison Truax Field
Wed 11/18
10:59 am-7:50 pm
2 stops8h 51m
Winnipeg
Wed 12/16
5:24 pm-9:29 pm
1 stop4h 05m
$919
MadisonWinnipeg
MSN Madison Truax Field - YWG Winnipeg
MSNYWG
Madison Truax Field
Wed 1/6
12:30 pm-12:24 am
2 stops11h 54m
Winnipeg
Sun 1/10
7:00 am-5:51 pm
1 stop10h 51m
$984
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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