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$90+ Cheap flights from Wisconsin 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 11/28. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — YWG
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Wisconsin to Winnipeg

Keep the following information in mind while searching for Wisconsin to Winnipeg flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$218
(oojo)

One-way from

$90
(Kiwi.com)
Provider with most accurate pricing for Milwaukee-Mitchell-Winnipeg flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Winnipeg flights.
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From Wisconsin to Winnipeg
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One-way flight from Wisconsin to Winnipeg
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Find flight deals from Wisconsin to Winnipeg

Cheapest flights from Wisconsin to Winnipeg
Explore the most affordable flight options available from Wisconsin to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This oojo deal was found by Cheapflights users on 10/30. 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 11/263:45 pmMSP - YWG
2 stops8h 56mWestJet
Fri 11/289:05 amYWG - MSP
1 stop5h 08mWestJet
Deal found 10/30$218
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Sat 12/131:24 pmORD - YWG
1 stop25h 43mMultiple Airlines
Sun 1/114:55 pmYWG - ORD
1 stop26h 48mMultiple Airlines
Deal found 10/30$218
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Thu 12/45:05 amORD - YWG
2 stops19h 36mMultiple Airlines
Sun 12/77:30 amYWG - ORD
1 stop14h 54mMultiple Airlines
Deal found 10/30$228
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Tue 12/910:00 amORD - YWG
2 stops14h 41mMultiple Airlines
Fri 12/127:30 amYWG - ORD
1 stop14h 54mMultiple Airlines
Deal found 10/29$229
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Fri 11/2811:41 amMSP - YWG
2 stops37h 00mMultiple Airlines
Fri 12/59:05 amYWG - MSP
1 stop5h 08mMultiple Airlines
Deal found 10/29$252
This oojo deal was found by Cheapflights users on 10/30. 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 11/281:55 pmMSP - YWG
2 stops10h 46mWestJet
Fri 12/59:05 amYWG - MSP
1 stop5h 08mWestJet
Deal found 10/30$265
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Wed 12/316:05 amORD - YWG
2 stops18h 36mMultiple Airlines
Wed 1/77:30 amYWG - ORD
1 stop16h 31mMultiple Airlines
Deal found 10/29$289
This oojo deal was found by Cheapflights users on 10/29. 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 11/191:55 pmMSP - YWG
1 stop9h 55mWestJet
Mon 11/246:45 amYWG - MSP
1 stop6h 20mWestJet
Deal found 10/29$296
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Wed 12/316:05 amORD - YWG
2 stops18h 36mMultiple Airlines
Thu 1/87:30 amYWG - ORD
1 stop13h 31mMultiple Airlines
Deal found 10/29$303
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/95:01 amORD - YWG
1 stop10h 06mMultiple Airlines
Mon 11/1012:55 pmYWG - ORD
2 stops22h 19mMultiple Airlines
Deal found 10/29$316
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Thu 12/2512:39 pmORD - YWG
1 stop26h 28mMultiple Airlines
Sun 4/268:30 amYWG - ORD
1 stop8h 13mMultiple Airlines
Deal found 10/29$318
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Wed 12/3111:45 amORD - YWG
2 stops47h 35mMultiple Airlines
Sun 4/268:30 amYWG - ORD
1 stop8h 13mMultiple Airlines
Deal found 10/29$327

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin 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 October 30, 2025.
Use the filters below to find and compare flights from Wisconsin to Winnipeg that are best for you.

Fly from

Wisconsin

Fly to

Winnipeg

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 12/13

1:24 pm-3:07 pm

1 stop25h 43m

Winnipeg

Sun 1/11

4:55 pm-7:43 pm

1 stop26h 48m

$218

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 3/13

2:20 pm-10:40 pm

1 stop8h 20m

Winnipeg

Mon 3/23

6:15 am-1:35 pm

1 stop7h 20m

$270

MinneapolisWinnipeg

MSP - YWG

MSPYWG

Minneapolis St Paul

Fri 3/13

1:55 pm-12:40 am

2 stops10h 45m

Winnipeg

Mon 3/23

9:05 am-3:03 pm

1 stop5h 58m

$297

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 3/9

2:20 pm-11:52 am

1 stop21h 32m

Winnipeg

Fri 3/13

6:15 am-1:35 pm

1 stop7h 20m

$297

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Mon 1/12

2:20 pm-10:41 pm

1 stop8h 21m

Winnipeg

Thu 1/15

7:50 am-1:35 pm

1 stop29h 45m

$298

MinneapolisWinnipeg

MSP - YWG

MSPYWG

Minneapolis St Paul

Fri 11/28

1:55 pm-12:41 am

2 stops10h 46m

Winnipeg

Sun 11/30

10:55 am-1:05 pm

2 stops26h 10m

$335

MinneapolisWinnipeg

MSP - YWG

MSPYWG

Minneapolis St Paul

Thu 1/15

12:15 pm-10:41 pm

2 stops10h 26m

Winnipeg

Fri 1/16

9:05 am-2:08 pm

1 stop5h 03m

$343

MinneapolisWinnipeg

MSP - YWG

MSPYWG

Minneapolis St Paul

Mon 1/19

3:45 pm-12:41 am

2 stops8h 56m

Winnipeg

Tue 1/20

9:05 am-2:08 pm

1 stop5h 03m

$343

MinneapolisWinnipeg

MSP - YWG

MSPYWG

Minneapolis St Paul

Sat 11/29

6:00 am-11:57 am

1 stop5h 57m

Winnipeg

Sat 12/6

1:30 pm-9:19 pm

1 stop7h 49m

$348

MinneapolisWinnipeg

MSP - YWG

MSPYWG

Minneapolis St Paul

Fri 11/14

6:12 am-1:23 am

1 stop19h 11m

Winnipeg

Sun 11/16

7:30 am-10:34 am

1 stop27h 04m

$349

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 45 results
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Best time to book a flight from Wisconsin to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Wisconsin 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.

Cheapflights Insights

Everything you need to know about your flight from Wisconsin to Winnipeg

What is the cheapest time of day to fly from WI to YWG?

Find hourly flight availability from Wisconsin to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

It’s optimal to fly from Wisconsin to Winnipeg in the afternoon. By choosing this option you can save up to 29% on the cost of your flight, compared to a flight in the evening.

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Winnipeg from Wisconsin?

    Winnipeg (YWG) is the airport you will fly into if you book a flight from Wisconsin to Winnipeg. It is only a 4.6 mi journey from Winnipeg (YWG) to Winnipeg’s city center.

  • How long is the flight from Wisconsin to Winnipeg?

    For as low as $432, WestJet can have you in Winnipeg from Wisconsin in 4h 49m. Airlines will cover a distance of 653 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Wisconsin to Winnipeg one-way?

    The cheapest airline one-way is WestJet, with whom users have recently found tickets for as low as $108. However, be on the lookout for offers from Air Canada and United Airlines, as they are both options that can get you from Wisconsin to Winnipeg for a low price.

  • What are the most popular routes from Wisconsin to Winnipeg?

    When deciding which route to take from Wisconsin to Winnipeg consider Minneapolis St Paul - Winnipeg, Chicago O'Hare Intl - Winnipeg or Milwaukee-Mitchell - Winnipeg as they are the most popular.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Wisconsin 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

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Alternative routes for Wisconsin to Winnipeg

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Top airline flying from Wisconsin to Winnipeg

Discover the top airline that operate flights from Wisconsin 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$282Average$611FlexibilityNo cancel feeOn-timeN/A

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