The cheapest times to fly from YWG to ORD are

  • January 1st to March 4th (except the week of February 12th)
  • August 13th to December 16th

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 YWG to ORD is early December. Prices can be as high as $652 for Sunday flights during late March, or as low as $373 for Tuesday flights around early December.


When to Fly to Chicago

Flying from Winnipeg (YWG) to Chicago, IL (ORD) will usually cost between $373 to $485 per person if booking more than four weeks in advance. On average the very cheapest time to fly is early December with an average ticket price of $373. Due to high demand the most expensive time to fly is late March, with an average price of $514. Planning your trip to low-cost times can easily save you $141 on economy flights and even more on first-class flights. Generally, any price below $398 can be considered a good price for a round-trip YWG to ORD flight.

See below for a graph of average weekly prices for the YWG to ORD route. All prices are for round-trip tickets in USD.

YWG to ORD Flight Prices

Compared to other flights, the YWG to ORD flight is much cheaper than the average and costs less than the average flight leaving from Winnipeg. The average price per mile (for a direct flight) is $0.35, which is in the normal range for a flight.


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 $27 (6%) 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 $390. Return trip prices are from the ORD to YWG flight, and often highlight the quality of our data in showing the same trend.

Departing Prices by Day

Departure Day Prices

Return Trip Prices by Day

Return Day Prices


Nonstop Flights and Layovers

Travelers looking to fly from YWG to ORD can generally find a 0-layover flight. Because there is a direct flight option the real-world direct flight time of 2 hour 15 minutes may 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 a nonstop flight from YWG to ORD while comparing.

Destination alternative #1: Dane County Regional-Truax Field Airport (MSN) in Madison, WI

  • 108 miles (174 km) away from ORD
  • Usually 22.01% less expensive than ORD
  • 1-layover flights available

See YWG to MSN flights

Destination alternative #2: General Mitchell International Airport (MKE) in Milwaukee, WI

  • 67 miles (108 km) away from ORD
  • Usually 19.50% less expensive than ORD
  • 1-layover flights available

See YWG to MKE flights

Destination alternative #3: South Bend International Airport (SBN) in South Bend, IN

  • 84 miles (135 km) away from ORD
  • Usually 2.89% less expensive than ORD
  • 1-layover flights available

See YWG to SBN flights


Flight Questions Answered

Still have questions about flying from YWG to ORD? We’ve got answers.

Which airlines fly this route?

You can find 5 major airlines flying this route most often: Air Canada, Delta, Qantas, United, WestJet, and potentially more during busy seasons.

How far away is it from Chicago O’Hare International Airport to James Armstrong Richardson International Airport?

The distance between the two airports is roughly 707 miles or 1138 kilometers.

How long does it take to fly from YWG to ORD?

The real-world flight time for a nonstop YWG to ORD flight is about 2 hour 15 minutes.

How many flights go between Winnipeg and Chicago, IL?

It depends on the day of the week and the date, but a typical day might have around 63 available flights from YWG to ORD.


Airport Location Info


Departing Airport

Origination code YWG
Origination airport name James Armstrong Richardson International Airport
City Winnipeg
Country Canada
Latitude 49.9
Longitude -97.2

Return Airport

Destination code ORD
Destination airport name Chicago O’Hare International Airport
City Chicago, IL
Country the United States
Latitude 42
Longitude -87.9


Other Resources

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.