MSN - YWG

$297 Find Cheap Flights from Madison to Winnipeg

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Madison to Winnipeg departing on 8/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Winnipeg

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to Winnipeg, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to Winnipeg, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$690
WestJet
Mon 8/10Tue 9/1
MSN - YWG • 1 stop
Cheapest one-way
$297
Multiple Airlines
Mon 8/10
MSN - YWG • 3 stops
Top airlines
WestJet
Cheapest • from $690 (round-trip)
Delta
Best reviews • 7.8 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Madison and Winnipeg. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Chicago (ORD)
Cheapest • Avg $431 (round-trip)
Chicago (ORD)
Shortest trip • 5h 27m (one-way)
Insights
Insights
Insights
Insights
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Winnipeg!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Madison to Winnipeg (MSN-YWG)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Madison to Winnipeg that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Madison to Winnipeg

Mon, Aug 10 - Tue, Sep 1
WestJet Logo
6:05 am - 3:08 pm
MSN
-
YWG
9h 03m
1 stop
WestJet Logo
5:42 pm - 11:00 pm
YWG
-
MSN
5h 18m
1 stop
$690WestJet
Thu, Oct 15 - Wed, Oct 21
WestJet Logo
6:15 am - 8:16 pm
MSN
-
YWG
14h 01m
1 stop
WestJet Logo
7:45 am - 4:37 pm
YWG
-
MSN
8h 52m
2 stops
$706WestJet
Sun, Aug 9 - Tue, Sep 1
Delta Logo
6:16 pm - 11:30 pm
MSN
-
YWG
5h 14m
1 stop
Delta Logo
6:40 am - 11:26 am
YWG
-
MSN
4h 46m
1 stop
$711Delta
Sat, Sep 19 - Tue, Sep 22
United Airlines Logo
6:30 am - 11:52 am
MSN
-
YWG
5h 22m
1 stop
United Airlines Logo
7:00 am - 1:42 pm
YWG
-
MSN
6h 42m
1 stop
$712United Airlines
Sun, Aug 9 - Tue, Sep 1
Delta Logo
6:16 pm - 11:30 pm
MSN
-
YWG
5h 14m
1 stop
Delta Logo
6:40 am - 12:47 pm
YWG
-
MSN
6h 07m
2 stops
$721Delta
Sat, Aug 8 - Tue, Sep 1
United Airlines Logo
5:00 am - 11:52 am
MSN
-
YWG
6h 52m
1 stop
United Airlines Logo
7:00 am - 2:59 pm
YWG
-
MSN
7h 59m
1 stop
$722United Airlines
Mon, Aug 10 - Mon, Aug 31
WestJet Logo
1:35 pm - 12:55 am
MSN
-
YWG
11h 20m
2 stops
WestJet Logo
6:00 am - 11:00 pm
YWG
-
MSN
17h 00m
2 stops
$724WestJet
Sat, Jul 18 - Fri, Jul 24
Air Canada Logo
5:45 pm - 11:15 am
MSN
-
YWG
17h 30m
2 stops
Air Canada Logo
8:45 am - 9:16 pm
YWG
-
MSN
12h 31m
1 stop
$726Air Canada
Mon, Aug 10 - Mon, Aug 31
WestJet Logo
6:05 am - 11:54 am
MSN
-
YWG
5h 49m
1 stop
WestJet Logo
7:00 am - 11:00 pm
YWG
-
MSN
16h 00m
2 stops
$731WestJet
Tue, Jul 7 - Sat, Jul 11
Air Canada Logo
5:45 pm - 10:38 pm
MSN
-
YWG
4h 53m
1 stop
Air Canada Logo
8:45 am - 9:16 pm
YWG
-
MSN
12h 31m
1 stop
$737Air Canada
Booking Insights

KAYAK's insights & trends for Madison to Winnipeg flights

Get data-powered insights and trends into flights from Madison to Winnipeg to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Madison to Winnipeg?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 5 days.

In the past 5 days, the cheapest round-trip tickets from Madison to Winnipeg were found on WestJet ($690) and Delta ($711).

Find deals

Good to know

Cheapest flight$297
Flight from Madison to Winnipeg

When to book flights from Madison to Winnipeg

Are your dates flexible? Find out the best times to travel from Madison to Winnipeg based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Madison to Winnipeg

  • What is the cheapest flight from Madison to Winnipeg?

    In the last 5 days, the lowest price for a flight from Madison to Winnipeg was $297 for a one-way ticket and $690 for a round-trip.

  • Do I need a passport to fly between Madison and Winnipeg?

    Yes, you’ll need a passport to travel to Winnipeg from Madison.

  • Which airports will I be using when flying from Madison to Winnipeg?

    Madison and Winnipeg are both served by 1 main airport. You will leave Madison from Madison Truax Field and will be arriving at Winnipeg.

  • Which aircraft models fly most regularly from Madison to Winnipeg?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Madison to Winnipeg?

    SkyTeam is the only airline alliance operating flights between Madison and Winnipeg.

  • How does KAYAK find such low prices on flights from Madison to Winnipeg?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Madison to Winnipeg.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Madison to Winnipeg?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winnipeg from Madison is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Madison to Winnipeg?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Winnipeg with an airline and back to Madison with another airline. Booking your flights between Madison and YWG can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Madison to Winnipeg?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Winnipeg from Madison up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Madison to Winnipeg

 
See real verified KAYAK customer reviews for airlines flying from Madison to Winnipeg. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Madison to Winnipeg? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.8
DeltaOverall score based on 8424 reviews
7.8Comfort
8.5Crew
8.1Boarding
7.8Entertainment
7.2Food
Airline reviews

flight was delayed 4+ hours. there was really no understanding of why? weather? the last hour of delay was post boarding. pilot seat was broken. was that the real reason? nonetheless, long day of inconveniences.

2.0 MediocreHu, Jun 2026
AUS - JFK
Read more Delta reviews

flight was delayed 4+ hours. there was really no understanding of why? weather? the last hour of delay was post boarding. pilot seat was broken. was that the real reason? nonetheless, long day of inconveniences.

Love me some Delta. One of the few airlines to recognize and support veterans. Easy boarding, flight was on time and arrived early and the flight attendants were excellent on this flight.

I thought the service was very nice and pleasant. There were no hiccups and no issues so overall a good experience.

Very good flight. Crew was great. No issues and we even arrived early.

The flights are constantly late anymore, and they won't even give you a glass of water on the plane. For years, they were able to do a service on this flight from Atlanta to Knoxville and Knoxville Atlanta now they say it's too short of a flight. You can't even get a quick drink of water.

Flight got canceled 4 times, missed my connecting flight due to delays, have to wait to go home tomorrow

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

We sat on the runway for over an hour before departure. That was unwelcome.

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

Everything you need to know for your flight from Madison to Winnipeg

Information on your arrival and departure airports

Madison (MSN)
Winnipeg (YWG)