MSN - YWG

C$ 1,219 Find Cheap Flights from Madison to Winnipeg – Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
C$ 1,219
Typical prices: C$ 735-C$ 1,037
United Airlines
Sat 6/1Wed 10/1
MSN - YWG • 1 stop
Top layover airports
Cheapest • Avg C$ 845 (round-trip)
Shortest trip • 4h 38m (one-way)
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Cheap Flights from Madison to Winnipeg (MSN-YWG)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Madison to Winnipeg

Wed, 6 Jan - Sun, 10 Jan
United Airlines Logo
8:15 a.m. - 7:28 p.m.MSN  Madison Truax Field-YWG Winnipeg
10h 13m1 stop Chicago O'Hare Intl
United Airlines Logo
8:00 a.m. - 2:11 p.m.YWG  Winnipeg-MSN Madison Truax Field
7h 11m1 stop Chicago O'Hare Intl
C$ 1,219United Airlines
3+ days ago
Wed, 6 Jan - Sun, 10 Jan
United Airlines Logo
8:15 a.m. - 7:28 p.m.MSN  Madison Truax Field-YWG Winnipeg
10h 13m1 stop Chicago O'Hare Intl
United Airlines Logo
8:00 a.m. - 2:11 p.m.YWG  Winnipeg-MSN Madison Truax Field
7h 11m1 stop Chicago O'Hare Intl
C$ 1,274United Airlines
2 days ago
Wed, 6 Jan - Sat, 9 Jan
Air Canada Logo
12:27 p.m. - 1:32 a.m.MSN  Madison Truax Field-YWG Winnipeg
12h 05m2 stops Chicago O'Hare Intl Vancouver Intl
Air Canada Logo
12:10 p.m. - 10:19 p.m.YWG  Winnipeg-MSN Madison Truax Field
11h 09m2 stops Vancouver Intl Chicago O'Hare Intl
C$ 1,294Air Canada
1 day ago
Wed, 6 Jan - Sun, 10 Jan
Air Canada Logo
6:25 a.m. - 1:32 a.m.MSN  Madison Truax Field-YWG Winnipeg
18h 07m2 stops Chicago O'Hare Intl Vancouver Intl
Air Canada Logo
12:10 p.m. - 10:19 p.m.YWG  Winnipeg-MSN Madison Truax Field
11h 09m2 stops Vancouver Intl Chicago O'Hare Intl
C$ 1,314Air Canada
3+ days ago
Wed, 6 Jan - Sun, 10 Jan
Air Canada Logo
12:27 p.m. - 1:32 a.m.MSN  Madison Truax Field-YWG Winnipeg
12h 05m2 stops Chicago O'Hare Intl Vancouver Intl
Air Canada Logo
11:05 p.m. - 8:45 p.m.YWG  Winnipeg-MSN Madison Truax Field
22h 40m2 stops Vancouver Intl Denver Intl
C$ 1,325Air Canada
3+ days ago
Wed, 6 Jan - Sun, 10 Jan
Air Canada Logo
6:25 a.m. - 7:22 p.m.MSN  Madison Truax Field-YWG Winnipeg
11h 57m2 stops Chicago O'Hare Intl Vancouver Intl
Air Canada Logo
8:00 a.m. - 10:19 p.m.YWG  Winnipeg-MSN Madison Truax Field
15h 19m1 stop Chicago O'Hare Intl
C$ 1,335Air Canada
3+ days ago
Wed, 6 Jan - Sun, 10 Jan
Air Canada Logo
6:25 a.m. - 7:22 p.m.MSN  Madison Truax Field-YWG Winnipeg
11h 57m2 stops Chicago O'Hare Intl Vancouver Intl
Air Canada Logo
8:00 a.m. - 10:19 p.m.YWG  Winnipeg-MSN Madison Truax Field
15h 19m1 stop Chicago O'Hare Intl
C$ 1,341Air Canada
3+ days ago
Wed, 6 Jan - Sat, 9 Jan
Air Canada Logo
12:27 p.m. - 1:32 a.m.MSN  Madison Truax Field-YWG Winnipeg
12h 05m2 stops Chicago O'Hare Intl Vancouver Intl
Air Canada Logo
9:40 a.m. - 8:45 p.m.YWG  Winnipeg-MSN Madison Truax Field
12h 05m1 stop Denver Intl
C$ 1,348Air Canada
1 day ago
Wed, 6 Jan - Sun, 10 Jan
Air Canada Logo
6:25 a.m. - 7:22 p.m.MSN  Madison Truax Field-YWG Winnipeg
11h 57m2 stops Chicago O'Hare Intl Vancouver Intl
Air Canada Logo
6:40 a.m. - 10:19 p.m.YWG  Winnipeg-MSN Madison Truax Field
16h 39m2 stops Vancouver Intl Chicago O'Hare Intl
C$ 1,391Air Canada
2 days ago
Wed, 6 Jan - Sun, 10 Jan
Air Canada Logo
6:25 a.m. - 7:22 p.m.MSN  Madison Truax Field-YWG Winnipeg
11h 57m2 stops Chicago O'Hare Intl Vancouver Intl
Air Canada Logo
8:00 a.m. - 10:19 p.m.YWG  Winnipeg-MSN Madison Truax Field
15h 19m1 stop Chicago O'Hare Intl
C$ 1,394Air Canada
2 days ago
Booking Insights

Price, demand, and travel trends for Madison to Winnipeg flights

Use KAYAK data on prices, travel dates, airlines, and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Madison to Winnipeg?

Round-trip flights from Madison to Winnipeg typically range from C$ 735 to C$ 1,037. The lowest price found in the past 5 days was C$ 1,219, on United Airlines.

Key details for Madison to Winnipeg flights

Cheapest flight

C$ 1,219
Round-trip 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

Your Madison to Winnipeg flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines, and booking tips.

  • How long does a flight from Madison to Winnipeg take?

    There are currently no direct flights available from Madison to Winnipeg. Flights with 1 layover take between 4h 38m and 5h 12m in total, depending on the connection.

  • Do I need a passport to fly from Madison to Winnipeg?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • Have flight prices from Madison to Winnipeg changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route varied from about C$ 1,219 to C$ 2,317. That means the highest observed fare was about 90% higher than the lowest one.

  • What car rental options are available at Winnipeg Airport (YWG)?

    Winnipeg Airport (YWG) hosts 5 major car rental companies, with daily rates averaging C$ 60 for economy cars. Top options include:

    • Thrifty
    • Dollar
    • Hertz
    • Alamo
    • Fox

  • Which airports can I use when flying from Madison to Winnipeg?

    Flights from Madison to Winnipeg usually depart from Madison Truax Field (MSN) and arrive at Winnipeg (YWG).

  • Which airports do connecting flights from Madison to Winnipeg pass through?

    Connecting flights from Madison to Winnipeg most commonly pass through:

    • Minneapolis St Paul (MSP) – 56% of one-stop connections
    • Chicago O'Hare Intl (ORD) – 44% of one-stop connections

  • Can I save money by using flexible dates for flights from Madison to Winnipeg?

    Yes. Flexible dates can save you up to 48% on flights from Madison to Winnipeg. Thursday is the cheapest departure day at C$ 602 round-trip on average, while Tuesday is the most expensive at C$ 1,138, a difference of C$ 536.

    KAYAK's flexible dates feature shows options up to three days before and after your selected dates, making it easier to compare nearby fares.

  • How much time can I save by choosing a different layover airport when travelling from Madison to Winnipeg?

    Flying via Minneapolis St Paul (MSP) gives the shortest average 1-stop total travel time at 4h 38m, compared with 5h 12m via Chicago O'Hare Intl (ORD).

  • What is the time difference between Madison and Winnipeg?

    Winnipeg is 1 hour ahead of Madison (Central Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

Your guide to booking Madison to Winnipeg flights

Get tips on when to book, when to fly, and what to know before your trip.

More options for your flight from Madison to Winnipeg

Complete your trip to Winnipeg with a hotel stay or car rental