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$124+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YWG
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$436
(Mytrip)

One-way from

$124
(Kiwi.com)

Popular in

February

Cheapest in

January

Average price

$743
Provider with most accurate pricing for Chicago Midway-Winnipeg flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Winnipeg flights.
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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, 3% potential price rise
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Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 17, 2025.

This Mytrip deal was found by Cheapflights users on 4/17. 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.
Sat 5/179:40 amMDW - YWG
1 stop24h 00mMultiple Airlines
Sun 5/186:55 pmYWG - MDW
1 stop13h 50mMultiple Airlines
Deal found 4/17$436
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/311:08 pmMDW - YWG
2 stops10h 17mDelta
Sat 6/76:40 amYWG - MDW
2 stops9h 41mDelta
Deal found 4/16$488
This Mytrip deal was found by Cheapflights users on 4/17. 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.
Mon 6/169:40 amMDW - YWG
2 stops13h 06mPorter Airlines
Mon 6/3011:45 amYWG - MDW
2 stops28h 39mPorter Airlines
Deal found 4/17$548
This WestJet 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/209:30 amMDW - YWG
2 stops24h 13mWestJet
Mon 7/285:38 pmYWG - MDW
1 stop24h 25mWestJet
Deal found 4/16$645

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 April 17, 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

Sat 5/17

9:40 am-9:40 am

1 stop24h 00m

Winnipeg

Sun 5/18

6:55 pm-8:45 am

1 stop13h 50m

$436

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 5/31

1:08 pm-11:25 pm

2 stops10h 17m

Winnipeg

Sat 6/7

6:40 am-4:21 pm

2 stops9h 41m

$488

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Mon 6/16

9:40 am-10:46 pm

2 stops13h 06m

Winnipeg

Mon 6/30

11:45 am-4:24 pm

2 stops28h 39m

$548

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 7/20

9:30 am-9:43 am

2 stops24h 13m

Winnipeg

Mon 7/28

5:38 pm-6:03 pm

1 stop24h 25m

$645

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 5/13

9:34 am-12:34 am

2 stops15h 00m

$124

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sun 6/1

5:50 pm-10:26 am

2 stops16h 36m

$193

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Sat 5/31

1:08 pm-11:25 pm

2 stops10h 17m

$203

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 5/23

1:55 pm-4:45 pm

1 stop26h 50m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Compare providers for flights from Midway to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Winnipeg in April.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Winnipeg flights, Cheapflights users trust eDreams the most. eDreams 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 Chicago Midway Airport-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 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Winnipeg

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

Find hourly flight availability from Midway 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 April 17, 2025.

When flying from Chicago Midway Airport to Winnipeg, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Winnipeg ranges from 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.

Temperature in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

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 April 17, 2025.
Porter Airlines
8.0
Very good
281 reviews

Crew

8.7

Entertainment

7.0

Overall

8.0

Comfort

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
281 reviews
Porter Airlines
8.0
Very good
281 reviews

Crew

8.7

Entertainment

7.0

Overall

8.0

Comfort

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,917 reviews
Porter Airlines
8.0
Very good
281 reviews

Crew

8.7

Entertainment

7.0

Overall

8.0

Comfort

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
WestJet
7.2
Good
2,809 reviews
Porter Airlines
8.0
Very good
281 reviews

Crew

8.7

Entertainment

7.0

Overall

8.0

Comfort

8.0

Food

7.6

Boarding

8.2

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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 Porter Airlines, which is currently one of the cheapest options available, starting at $193. Delta flights start at $233 while deals on WestJet start at $390 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 April is currently the most expensive (average of $506). 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.

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