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$132+ 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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YWG
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$375
(Kiwi.com)

One-way from

$140
(Kiwi.com)

Popular in

February

Cheapest in

May

Average price

$641
From Chicago Midway to Winnipeg
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One-way flight from Chicago Midway to Winnipeg
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High demand for flights, 0% potential price rise
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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 July 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 July 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/28. 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 9/116:20 amMDW - YWG
1 stop10h 02mMultiple Airlines
Thu 9/189:00 amYWG - MDW
1 stop6h 58mMultiple Airlines
Deal found 7/28$369
This Delta deal was found by Cheapflights users on 7/28. 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.
Thu 9/119:20 amMDW - YWG
1 stop7h 30mDelta
Thu 9/186:40 amYWG - MDW
2 stops5h 48mDelta
Deal found 7/28$482
This Justfly.com deal was found by Cheapflights users on 7/28. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/149:15 amMDW - YWG
1 stop10h 55mWestJet
Fri 8/229:00 amYWG - MDW
1 stop12h 44mWestJet
Deal found 7/28$549
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/289:40 amMDW - YWG
2 stops13h 06mPorter Airlines
Mon 9/17:00 pmYWG - MDW
1 stop13h 39mPorter Airlines
Deal found 7/29$557

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 July 30, 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

Thu 9/11

6:20 am-4:22 pm

1 stop10h 02m

Winnipeg

Thu 9/18

9:00 am-3:58 pm

1 stop6h 58m

$369

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 9/11

9:20 am-4:50 pm

1 stop7h 30m

Winnipeg

Thu 9/18

6:40 am-12:28 pm

2 stops5h 48m

$482

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 8/14

9:15 am-8:10 pm

1 stop10h 55m

Winnipeg

Fri 8/22

9:00 am-9:44 pm

1 stop12h 44m

$549

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 8/28

9:40 am-10:46 pm

2 stops13h 06m

Winnipeg

Mon 9/1

7:00 pm-8:39 am

1 stop13h 39m

$557

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 9/21

6:20 am-12:30 am

2 stops18h 10m

$132

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 9/22

7:15 pm-11:27 pm

1 stop4h 12m

$193

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 9/25

9:35 am-11:41 am

2 stops26h 06m

$273

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 8/15

9:40 am-10:46 pm

2 stops13h 06m

$427

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

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.

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 July 30, 2025.
Read reviews from past customers who have flown Porter Airlines, Delta, and WestJet from Chicago Midway Airport 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.
Porter Airlines
8.0
Very good
318 reviews

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
318 reviews
Porter Airlines
8.0
Very good
318 reviews

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,980 reviews
Porter Airlines
8.0
Very good
318 reviews

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
2,975 reviews
Porter Airlines
8.0
Very good
318 reviews

Crew

8.7

Entertainment

7.0

Boarding

8.2

Food

7.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Winnipeg one-way?

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $193. WestJet flights start at $247 while deals on Porter Airlines start at $411 one-way.

  • 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 $497). 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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Portage la Prairie

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