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$174+ Cheap flights from Winnipeg (YWG) to Michigan

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 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — DTW
May 17 — May 241
Sun 5/17
Sun 5/24
1 adult, Economy
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Cheap flight deals from Winnipeg to Michigan

Cheapest flights from Winnipeg to Michigan
Explore the most affordable flight options available from Winnipeg to Michigan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/13. 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.
Mon 5/257:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Fri 5/295:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 4/13$310
This Trip.com deal was found by Cheapflights users on 4/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/237:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Thu 6/255:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 4/15$311
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 5/37:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Fri 5/85:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 4/13$313
This oojo deal was found by Cheapflights users on 4/14. 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 5/227:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Sun 5/245:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 4/14$317
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 5/277:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Fri 5/295:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 4/13$321
This Trip.com deal was found by Cheapflights users on 4/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/187:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Thu 10/225:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 4/15$330
This Trip.com deal was found by Cheapflights users on 4/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Tue 9/225:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 4/14$331
This CheapTickets deal was found by Cheapflights users on 4/16. 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 CheapTickets is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/3112:00 pm
YWG
-
ORD
1 stop28h 40m
WestJet
Sun 6/75:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 4/16$341
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 5/279:05 pm
YWG
-
ORD
2 stops34h 50m
Multiple Airlines
Fri 5/295:30 pm
ORD
-
YWG
1 stop7h 25m
Multiple Airlines
Deal found 4/13$343
This oojo deal was found by Cheapflights users on 4/15. 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.
Tue 6/237:00 am
YWG
-
ORD
1 stop9h 40m
WestJet
Tue 6/305:30 pm
ORD
-
YWG
1 stop7h 25m
WestJet
Deal found 4/15$345
This Delta deal was found by Cheapflights users on 4/13. 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.
Wed 6/1012:46 pm
YWG
-
MDW
1 stop5h 32m
Delta
Sat 6/139:54 am
MDW
-
YWG
1 stop5h 25m
Delta
Deal found 4/13$377
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 5/289:05 pm
YWG
-
MDW
2 stops14h 04m
Multiple Airlines
Mon 6/13:20 pm
MDW
-
YWG
1 stop18h 25m
Multiple Airlines
Deal found 4/13$384

Find flight deals from Winnipeg to Michigan

Keep the following information in mind while searching for Winnipeg to Michigan flight deals. Data was last updated April 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$310
(Kiwi.com)

One-way from

$174
(Kiwi.com)

Popular in

April

Cheapest in

May

Average price

$1,005
Provider with most accurate pricing for Winnipeg-Detroit (DTT) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-Detroit (DTT) flights.
Search Deals
From Winnipeg to Michigan
Search Deals
One-way flight from Winnipeg to Michigan
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($89 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease ($53 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Michigan 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 April 17, 2026.
Use the filters below to find and compare flights from Winnipeg to Michigan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Mon 9/7

8:50 am-4:48 pm

1 stop7h 58m

Chicago O'Hare Intl

Wed 9/23

6:00 am-11:34 am

1 stop5h 34m

$375

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Fri 5/1

6:30 am-1:20 pm

1 stop6h 50m

Chicago O'Hare Intl

Tue 5/5

8:35 pm-10:03 am

1 stop13h 28m

$379

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 6/23

5:42 pm-9:55 pm

1 stop4h 13m

Chicago O'Hare Intl

Tue 6/30

6:30 am-11:56 am

1 stop5h 26m

$386

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 6/14

5:42 pm-9:55 pm

1 stop4h 13m

Chicago O'Hare Intl

Mon 6/22

8:36 am-4:52 pm

1 stop8h 16m

$436

WinnipegDetroit

YWG - DTW

YWGDTW

Winnipeg

Sat 5/9

9:05 pm-4:40 pm

1 stop18h 35m

Detroit Metropolitan Wayne County

Sat 5/30

6:10 pm-9:40 pm

1 stop28h 30m

$446

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Sun 7/12

5:10 am-1:22 pm

1 stop8h 12m

Chicago O'Hare Intl

Wed 7/15

7:55 pm-10:33 pm

Nonstop2h 38m

$452

WinnipegChicago

YWG - ORD

YWGORD

Winnipeg

Tue 9/8

12:40 pm-4:48 pm

1 stop4h 08m

Chicago O'Hare Intl

Fri 9/25

8:00 am-11:27 pm

2 stops15h 27m

$479

WinnipegDetroit

YWG - DTW

YWGDTW

Winnipeg

Sat 5/9

3:50 pm-10:31 pm

1 stop5h 41m

Detroit Metropolitan Wayne County

Tue 5/12

7:01 am-10:54 am

1 stop4h 53m

$496

WinnipegChicago

YWG - MDW

YWGMDW

Winnipeg

Sat 5/30

6:40 am-1:19 pm

1 stop6h 39m

Chicago Midway

Sat 6/6

1:22 pm-11:26 pm

2 stops10h 04m

$500

WinnipegDetroit

YWG - DTW

YWGDTW

Winnipeg

Sat 5/9

8:45 am-11:59 pm

2 stops14h 14m

Detroit Metropolitan Wayne County

Tue 5/12

7:15 am-11:52 am

1 stop5h 37m

$506

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

Showing 1-10 of 58 resultsSorted by cheapest first
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Best time to book a flight from Winnipeg to Michigan

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

What is the cheapest month to book a flight from Winnipeg to Michigan?

Currently, September is the cheapest month in which you can book a flight from Winnipeg to Michigan (average of $59). Flying from Winnipeg to Michigan in February is currently the most expensive (average of $585). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Winnipeg to Michigan?

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Michigan. 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 from for flights from Winnipeg to Michigan?

    Located just 4.6 mi from the city center, Winnipeg (YWG) is the airport most travelers will use when flying to Michigan from Winnipeg.

  • How long is the flight from Winnipeg to Michigan?

    There are many flights that can get you from Winnipeg to Michigan in 6h 50m. Fly via Delta, Air Canada, or WestJet to get the fastest option. The distance from Winnipeg to Michigan is about 706 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    When deciding which route to take from Winnipeg to Michigan consider Winnipeg - Chicago O'Hare Intl, Winnipeg - Chicago Midway or Winnipeg - Detroit Metropolitan Wayne County as they are the most popular.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Winnipeg to Michigan by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Winnipeg to Michigan?

    Currently, September is the cheapest month in which you can book a flight from Winnipeg to Michigan (average of $59). Flying from Winnipeg to Michigan in February is currently the most expensive (average of $585). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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