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$79+ Cheap flights from Midway (MDW) 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YWG
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Midway to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) 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 September 11, 2025.

Round-trip from

$230
(Kiwi.com)

One-way from

$79
(Kiwi.com)

Popular in

February

Cheapest in

May

Average price

$556
From Chicago Midway to Winnipeg
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One-way flight from Chicago Midway to Winnipeg
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Highest demand for flights based on searches. 1% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midway to Winnipeg

Cheapest flights from Midway to Winnipeg
Explore the most affordable flight options available from Midway to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/245:20 pmMDW - YWG
2 stops45h 47mMultiple Airlines
Fri 10/317:30 amYWG - MDW
1 stop14h 15mMultiple Airlines
Deal found 9/9$230
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/239:26 pmMDW - YWG
1 stop18h 56mMultiple Airlines
Sat 11/89:00 pmYWG - MDW
2 stops25h 03mMultiple Airlines
Deal found 9/9$260
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 11/171:37 pmMDW - YWG
2 stops28h 29mMultiple Airlines
Sun 11/237:30 amYWG - MDW
1 stop15h 36mMultiple Airlines
Deal found 9/9$276
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/266:20 amMDW - YWG
1 stop8h 47mMultiple Airlines
Sun 11/27:30 amYWG - MDW
1 stop14h 33mMultiple Airlines
Deal found 9/11$280
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/2412:03 pmMDW - YWG
2 stops12h 27mMultiple Airlines
Sun 10/267:30 amYWG - MDW
1 stop16h 16mMultiple Airlines
Deal found 9/9$331
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/89:35 amMDW - YWG
1 stop14h 38mMultiple Airlines
Wed 10/158:15 pmYWG - MDW
2 stops27h 31mMultiple Airlines
Deal found 9/9$338
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/96:20 amMDW - YWG
1 stop10h 02mMultiple Airlines
Sun 10/123:15 pmYWG - MDW
2 stops30h 31mMultiple Airlines
Deal found 9/10$346
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/29:35 amMDW - YWG
2 stops13h 35mMultiple Airlines
Sun 10/510:45 amYWG - MDW
1 stop21h 54mMultiple Airlines
Deal found 9/9$351

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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 September 11, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Winnipeg that are best for you.

Fly from

Midway

Fly to

Winnipeg

Route

Depart

Return

Price

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 10/24

5:20 pm-3:07 pm

2 stops45h 47m

Winnipeg

Fri 10/31

7:30 am-9:45 pm

1 stop14h 15m

$230

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 10/9

6:20 am-4:22 pm

1 stop10h 02m

Winnipeg

Sun 10/12

3:15 pm-9:46 pm

2 stops30h 31m

$346

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 10/8

9:35 am-12:13 am

1 stop14h 38m

Winnipeg

Wed 10/15

6:30 am-4:24 pm

1 stop9h 54m

$370

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 2/3

5:25 pm-5:00 pm

2 stops23h 35m

Winnipeg

Wed 2/18

5:38 pm-4:25 pm

2 stops22h 47m

$435

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 2/3

5:25 pm-5:00 pm

2 stops23h 35m

Winnipeg

Thu 2/19

12:40 pm-9:56 am

2 stops21h 16m

$435

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 2/3

5:25 pm-5:00 pm

2 stops23h 35m

Winnipeg

Fri 2/20

5:38 pm-12:01 pm

2 stops18h 23m

$435

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 2/6

1:05 pm-11:33 pm

2 stops34h 28m

Winnipeg

Fri 2/20

12:40 pm-9:56 am

2 stops21h 16m

$435

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 10/2

5:20 pm-9:41 am

1 stop16h 21m

Winnipeg

Sun 10/5

9:40 am-8:39 am

1 stop22h 59m

$455

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 2/6

1:05 pm-11:33 pm

2 stops34h 28m

Winnipeg

Tue 2/17

12:40 pm-9:56 am

2 stops21h 16m

$463

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Wed 10/22

8:05 am-12:30 am

2 stops16h 25m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 18 results
1
2

Best time to book a flight from Midway to Winnipeg

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

Related info for your journey

Find useful and relevant information for your journey from Midway 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 Chicago Midway?

    Located just 4.6 mi from the city center, Winnipeg is the airport most travelers will use when flying to Winnipeg from Chicago Midway. Booking flights from Chicago Midway to Winnipeg (YWG) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 0 different airlines.

  • How long is the flight from Chicago Midway Airport to Winnipeg?

    Airlines like Delta fly from Chicago Midway Airport to Winnipeg in about 23h 35m. The time it takes to get you to your destination can typically vary by up to . The distance between Chicago Midway Airport and Winnipeg is about 722 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Winnipeg?

    Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Winnipeg (average of $358). Flying from Chicago Midway Airport to Winnipeg in December is currently the most expensive (average of $501). 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

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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