The cheapest times to fly from MDW to YWG are
- January 1st to March 11th
- August 13th to December 9th
based on data collected exclusively by Champion Traveler across tens of millions of flights. Among all the dates above, the very cheapest time to fly from MDW to YWG is mid November. Prices can be as high as $717 for Sunday flights during mid March, or as low as $440 for Tuesday flights around mid November.
When to Fly to Winnipeg
Flying from Chicago, IL (MDW) to Winnipeg (YWG) will usually cost between $445 to $605 per person if booking more than four weeks in advance. On average the very cheapest time to fly is mid November with an average ticket price of $448. Due to high demand the most expensive time to fly is mid March, with an average price of $574. Planning your trip to low-cost times can easily save you $126 on economy flights and even more on first-class flights. Generally, any price below $495 can be considered a good price for a round-trip MDW to YWG flight.
See below for a graph of average weekly prices for the MDW to YWG route. All prices are for round-trip tickets in USD.
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Compared to other flights, the MDW to YWG flight is much cheaper than the average and costs less than the average flight leaving from Chicago. The average price per mile (for a direct flight) is $0.43, which is a bit above average.
Flight Prices by Day of the Week
Tuesday is usually the cheapest day to depart and return on this flight. Sundays are the most expensive days to fly out or take a return trip. Selecting flights on the least expensive days could save you up to $62 (12%) on this flight.
Departing prices are for round-trip flights returning on the day of departure. For example, a flight departing on Tuesday and returning a week later will cost an average of $476. Return trip prices are from the YWG to MDW flight, and often highlight the quality of our data in showing the same trend.
Departing Prices by Day
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Return Trip Prices by Day
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Nonstop Flights and Layovers
Travelers looking to fly from MDW to YWG can generally find a 1-layover flight. Because there is not usually a direct flight option the real-world direct flight time of 2 hour 17 minutes may not be realistic.
Alternative Nearby Airports
Champion Traveler tells you which airports are nearby and whether tickets might be cheaper alternative airports nearby. Sometimes it’s worth it to fly into a closer airport and then commute to your destination. Remember that there is not usually a nonstop flight from MDW to YWG while comparing.
- 136 miles (219 km) away from YWG
- Usually 29.93% less expensive than YWG
- 1-layover flights available
Flight Questions Answered
Still have questions about flying from MDW to YWG? We’ve got answers.
Which airlines fly this route?
You can find 4 major airlines flying this route most often: Delta, United, Virgin Atlantic, WestJet, and potentially more during busy seasons.
How far away is it from James Armstrong Richardson International Airport to Chicago Midway International Airport?
The distance between the two airports is roughly 722 miles or 1162 kilometers.
How long does it take to fly from MDW to YWG?
The real-world flight time for a nonstop MDW to YWG flight is about 2 hour 17 minutes.
How many flights go between Chicago, IL and Winnipeg?
It depends on the day of the week and the date, but a typical day might have around 34 available flights from MDW to YWG.
Airport Location Info
Departing Airport
Origination code | MDW |
Origination airport name | Chicago Midway International Airport |
City | Chicago, IL |
Country | the United States |
Latitude | 41.8 |
Longitude | -87.8 |
Return Airport
Destination code | YWG |
Destination airport name | James Armstrong Richardson International Airport |
City | Winnipeg |
Country | Canada |
Latitude | 49.9 |
Longitude | -97.2 |
Other Resources
Flights to YWG
Flights from YWG
Popular Flights
Flights to MDW
Flights from MDW
Please note that while we’ve worked hard to analyzed tens of millions of flights to get you this data, we do not calculate current live prices or guarantee pricing. Please see our partners using the links above for current offers.