$300+ Cheap flights from Madison (MSN) to Winnipeg (YWG)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/5. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — YWG
Jul 9 — Jul 161
Round-trip
1 adult, Economy
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Find cheap flights from Madison to Winnipeg with Cheapflights
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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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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 June 9, 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 June 9, 2026.
This FlightHub deal was found by Cheapflights users on 6/5. 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.
Thu 10/87:55 pm
MSN
- YWG
1 stop3h 39m
WestJet
Tue 10/136:00 am
YWG
- MSN
2 stops14h 45m
WestJet
Deal found 6/5![WestJet logo]()
$700
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Sat 10/38:10 am
MSN
- YWG
1 stop4h 27m
United Airlines
Tue 10/67:00 am
YWG
- MSN
1 stop4h 53m
United Airlines
Deal found 6/8![United Airlines logo]()
$712
This oojo deal was found by Cheapflights users on 6/7. 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 7/86:13 pm
MSN
- YWG
2 stops23h 02m
WestJet
Tue 7/147:00 am
YWG
- MSN
2 stops25h 52m
WestJet
Deal found 6/7![WestJet logo]()
$732
This Delta deal was found by Cheapflights users on 6/5. 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.
Mon 7/208:52 am
MSN
- YWG
1 stop6h 15m
Delta
Mon 7/273:59 pm
YWG
- MSN
1 stop7h 01m
Delta
Deal found 6/5![Delta logo]()
$747
This oojo deal was found by Cheapflights users on 6/5. 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.
Mon 7/208:52 am
MSN
- YWG
1 stop6h 15m
WestJet
Mon 7/277:45 am
YWG
- MSN
2 stops25h 07m
WestJet
Deal found 6/5![WestJet logo]()
$764
This WestJet deal was found by Cheapflights users on 6/5. 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.
Sat 9/129:00 am
MSN
- YWG
1 stop7h 54m
WestJet
Mon 9/147:00 am
YWG
- MSN
2 stops10h 55m
WestJet
Deal found 6/5![WestJet logo]()
$803
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 June 9, 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 June 9, 2026.
This United Airlines deal was found by Cheapflights users on 6/5. 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.
Sat 9/122:50 pm
MSN
- YWG
1 stop6h 07m
United Airlines
Mon 9/147:00 am
YWG
- MSN
1 stop6h 42m
United Airlines
Deal found 6/5![United Airlines logo]()
$712
This FlightHub deal was found by Cheapflights users on 6/5. 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.
Thu 10/81:45 pm
MSN
- YWG
2 stops11h 10m
WestJet
Tue 10/139:05 pm
YWG
- MSN
2 stops22h 00m
WestJet
Deal found 6/5![WestJet logo]()
$732
This Delta deal was found by Cheapflights users on 6/5. 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.
Mon 7/208:52 am
MSN
- YWG
1 stop6h 15m
Delta
Mon 7/273:59 pm
YWG
- MSN
1 stop7h 01m
Delta
Deal found 6/5![Delta logo]()
$747
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Sat 10/38:10 am
MSN
- YWG
1 stop4h 27m
United Airlines
Tue 10/67:00 am
YWG
- MSN
1 stop4h 53m
United Airlines
Deal found 6/8![United Airlines logo]()
$712
This oojo deal was found by Cheapflights users on 6/5. 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.
Mon 7/208:52 am
MSN
- YWG
1 stop6h 15m
WestJet
Mon 7/277:45 am
YWG
- MSN
2 stops25h 07m
WestJet
Deal found 6/5![WestJet logo]()
$764
This United Airlines deal was found by Cheapflights users on 6/7. 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 7/810:48 am
MSN
- YWG
1 stop11h 50m
United Airlines
Tue 7/147:00 am
YWG
- MSN
1 stop11h 57m
United Airlines
Deal found 6/7![United Airlines logo]()
$712
This WestJet deal was found by Cheapflights users on 6/7. 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.
Wed 7/86:13 pm
MSN
- YWG
1 stop22h 38m
WestJet
Tue 7/146:00 am
YWG
- MSN
2 stops26h 52m
WestJet
Deal found 6/7![WestJet logo]()
$803
This WestJet deal was found by Cheapflights users on 6/5. 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.
Sat 9/129:00 am
MSN
- YWG
1 stop7h 54m
WestJet
Mon 9/147:00 am
YWG
- MSN
2 stops10h 55m
WestJet
Deal found 6/5![WestJet logo]()
$803
Last-minute flights from Madison to WinnipegDiscover last-minute flight deals from Madison to Winnipeg. Data last updated June 9, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Winnipeg. Data last updated June 9, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 6/7. 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 7/810:48 am
MSN
- YWG
1 stop11h 50m
United Airlines
Tue 7/147:00 am
YWG
- MSN
1 stop11h 57m
United Airlines
Deal found 6/7![United Airlines logo]()
$712
This oojo deal was found by Cheapflights users on 6/7. 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 7/86:13 pm
MSN
- YWG
2 stops23h 02m
WestJet
Tue 7/147:00 am
YWG
- MSN
2 stops25h 52m
WestJet
Deal found 6/7![WestJet logo]()
$732
This Delta deal was found by Cheapflights users on 6/5. 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.
Mon 7/208:52 am
MSN
- YWG
1 stop6h 15m
Delta
Mon 7/273:59 pm
YWG
- MSN
1 stop7h 01m
Delta
Deal found 6/5![Delta logo]()
$747
This oojo deal was found by Cheapflights users on 6/5. 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.
Mon 7/208:52 am
MSN
- YWG
1 stop6h 15m
WestJet
Mon 7/277:45 am
YWG
- MSN
2 stops25h 07m
WestJet
Deal found 6/5![WestJet logo]()
$764
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 June 9, 2026.
Search for one-way flight options from Madison to Winnipeg. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
This Air Canada deal was found by Cheapflights users on 6/6. 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.
Sun 7/512:30 pm
MSN
- YWG
1 stop10h 08m
Air Canada
Deal found 6/6![Air Canada logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 6/6. 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.
Sun 7/512:03 pm
MSN
- YWG
3 stops27h 42m
WestJet
Deal found 6/6![WestJet logo]()
$485
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 June 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $700 (FlightHub) |
One-way from | $300 (Air Canada) |
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 June 9, 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 - YWG
MSNYWG
Madison Truax Field
Sat 9/12
2:50 pm-8:57 pm
1 stop6h 07m
Winnipeg
Mon 9/14
7:00 am-1:42 pm
1 stop6h 42m
$712
Quickest round-trip
MadisonWinnipeg
MSN - YWG
MSNYWG
Madison Truax Field
Sat 10/3
8:10 am-12:37 pm
1 stop4h 27m
Winnipeg
Tue 10/6
7:00 am-11:53 am
1 stop4h 53m
$712
MadisonWinnipeg
MSN - YWG
MSNYWG
Madison Truax Field
Wed 7/8
10:48 am-10:38 pm
1 stop11h 50m
Winnipeg
Tue 7/14
7:00 am-6:57 pm
1 stop11h 57m
$712
MadisonWinnipeg
MSN - YWG
MSNYWG
Madison Truax Field
Thu 10/8
1:45 pm-12:55 am
2 stops11h 10m
Winnipeg
Tue 10/13
9:05 pm-7:05 pm
2 stops22h 00m
$732
MadisonWinnipeg
MSN - YWG
MSNYWG
Madison Truax Field
Mon 7/20
8:52 am-3:07 pm
1 stop6h 15m
Winnipeg
Mon 7/27
3:59 pm-11:00 pm
1 stop7h 01m
$747
MadisonWinnipeg
MSN - YWG
MSNYWG
Madison Truax Field
Mon 7/20
8:52 am-3:07 pm
1 stop6h 15m
Winnipeg
Mon 7/27
7:45 am-8:52 am
2 stops25h 07m
$764
MadisonWinnipeg
MSN - YWG
MSNYWG
Madison Truax Field
Wed 7/8
6:13 pm-4:51 pm
1 stop22h 38m
Winnipeg
Tue 7/14
6:00 am-8:52 am
2 stops26h 52m
$803
MadisonWinnipeg
MSN - YWG
MSNYWG
Madison Truax Field
Sat 9/12
9:00 am-4:54 pm
1 stop7h 54m
Winnipeg
Mon 9/14
7:00 am-5:55 pm
2 stops10h 55m
$803
Cheapest one-way
Quickest one-way
MadisonWinnipeg
MSN - YWG
MSNYWG
Madison Truax Field
Sun 7/5
12:30 pm-10:38 pm
1 stop10h 08m
$300
MadisonWinnipeg
MSN - YWG
MSNYWG
Madison Truax Field
Sun 7/5
12:03 pm-3:45 pm
3 stops27h 42m
$485
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.
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 June 9, 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.
Comfort
7.8
Entertainment
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Overall
7.9
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Entertainment
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Overall
7.9
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
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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Alternative routes for Madison to Winnipeg
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Complete your trip
Complete your trip to Winnipeg by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Madison to Winnipeg by cabin class
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Madison and Winnipeg flights
Browse other Madison and Winnipeg flight options. Last updated on June 9, 2026.
Other flights from Madison
Browse through other flights departing from Madison. Flights are based on user searches made on Cheapflights and were last updated on June 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Winnipeg
Explore flights to Winnipeg departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 9, 2026.
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 June 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$188 | Average$591 | FlexibilityNo cancel fee | On-timeN/A |