HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Winnipeg

$582+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — YWG
Aug 20 — Aug 271
Thu 8/20
Thu 8/27
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

Cheapest flights from Madison to Winnipeg
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 July 21, 2026.

This oojo deal was found by Cheapflights users on 7/16. 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
MSN
-
YWG
2 stops16h 10m
WestJet
Sat 10/37:00 am
YWG
-
MSN
2 stops14h 19m
WestJet
Deal found 7/16$582
This FlightHub deal was found by Cheapflights users on 7/20. 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.
Tue 9/16:05 am
MSN
-
YWG
1 stop5h 49m
WestJet
Wed 9/237:00 am
YWG
-
MSN
2 stops16h 01m
WestJet
Deal found 7/20$593
This oojo deal was found by Cheapflights users on 7/20. 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 8/196:05 am
MSN
-
YWG
1 stop5h 49m
WestJet
Tue 8/255:42 pm
YWG
-
MSN
1 stop5h 18m
WestJet
Deal found 7/20$602
This oojo deal was found by Cheapflights users on 7/17. 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 8/116:05 am
MSN
-
YWG
2 stops16h 05m
WestJet
Mon 8/176:05 pm
YWG
-
MSN
2 stops17h 21m
WestJet
Deal found 7/17$614
This WestJet deal was found by Cheapflights users on 7/18. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/612:10 pm
MSN
-
YWG
2 stops12h 45m
WestJet
Thu 9/105:44 pm
YWG
-
MSN
1 stop17h 36m
WestJet
Deal found 7/18$682

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 July 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$582
(oojo)
Provider with most accurate pricing for Madison Truax Field-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Winnipeg flights.
Search Deals
From Madison Truax Field to Winnipeg
Search Deals

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 2,558,603 searches. Data last updated July 21, 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

Price

Cheapest round-trip

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Fri 10/2

6:00 am-10:10 pm

2 stops16h 10m

Winnipeg

Sat 10/3

7:00 am-9:19 pm

2 stops14h 19m

$582
Quickest round-trip

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Wed 8/19

6:05 am-11:54 am

1 stop5h 49m

Winnipeg

Tue 8/25

5:42 pm-11:00 pm

1 stop5h 18m

$602

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Sun 9/6

6:05 am-10:10 pm

2 stops16h 05m

Winnipeg

Thu 9/10

3:58 pm-11:20 am

1 stop19h 22m

$682

MadisonWinnipeg

MSN - YWG

MSNYWG

Madison Truax Field

Sun 9/6

5:48 pm-10:33 pm

1 stop4h 45m

Winnipeg

Thu 9/10

7:00 am-1:42 pm

1 stop6h 42m

$733

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/16

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.
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.

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. 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 Winnipeg. Reviews last updated July 21, 2026.
Read reviews from past customers who have flown Delta from Madison to Winnipeg. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.8
Good
8,473 reviews

Comfort

7.8

Food

7.2

Overall

7.8

Crew

8.5

Boarding

8.1

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Delta
7.8
Good
8,473 reviews
Delta
7.8
Good
8,473 reviews

Comfort

7.8

Food

7.2

Overall

7.8

Crew

8.5

Boarding

8.1

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

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.

  • How long is the flight from Madison to Winnipeg?

    A quick flight from Madison to Winnipeg can take about 16h 10m. WestJet provides one of the quickest options available for as low as $582. Airlines will cover a distance of 599 mi.

  • Can I find deals for flights from Madison to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Madison to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Winnipeg.

  • Can I find deals for business class flights from Madison to Winnipeg?

    Yes. Cheapflights offers flight deals from Madison to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Madison to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.
Minneapolis to Winnipeg flights
O'Hare Intl to Winnipeg flights
Milwaukee to Winnipeg flights
Duluth to Winnipeg flights

Top airline flying from Madison to Winnipeg

Discover the top airline that operate flights from Madison to Winnipeg. 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 2,558,603 searches. Data last updated July 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$188Average$591FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.