C$ 590 Find Cheap Flights from Winnipeg to Madison – Compare and Save

There are currently no direct flights available from Winnipeg to Madison. Flights with 1 layover take between 4h 04m and 4h 48m in total, depending on the connection.

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.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about C$ 899 to C$ 1,853. That means the highest observed fare was about 2x higher than the lowest one.

One-way fares from Winnipeg to Madison are currently higher than usual. Average one-way flight prices are about C$ 750, which is 31% above the typical average for this route.

Madison Truax Field Airport (MSN) hosts 5 major car rental companies, with daily rates starting from around C$ 44 for economy cars. Top options include:
• Hertz
• Alamo
• Enterprise Rent-A-Car
• Avis
• Budget

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

Connecting flights from Winnipeg to Madison most commonly pass through:

• Chicago O'Hare Intl (ORD) – 67% of one-stop connections
• Minneapolis St Paul (MSP) – 33% of one-stop connections
Together, these airports account for 100% of one-stop bookings on this route.

Yes. Being flexible with your travel dates can save you up to 24% on the Winnipeg to Madison route. Tuesday is the cheapest departure day at C$ 560 round-trip on average, while Wednesday is the most expensive at C$ 733, a difference of C$ 173. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Flying via Minneapolis St Paul (MSP) gives the shortest average 1-stop total travel time at 4h 04m, compared with 4h 48m via Chicago O'Hare Intl (ORD).