Cheap Flights Chicago to Winnipeg from CAD 226

Flight FAQs

• Which airlines offer the cheapest flights from Chicago (CHI) to Winnipeg (YWG)?

  Based on Trip.com data, Porter Airlines offers one-way fares as low as CAD 226 on Cheapest nonstop routes (e.g. MDW to YWG on Sun, Aug 2), while WestJet offers Cheapest nonstop round-trips from CAD 593 departing on Thu, Sep 3 and returning on Sun, Sep 6.

• Which airlines offer direct flights from Chicago to Winnipeg?

  At the moment, you can catch a direct flight from Chicago to Winnipeg with the following airlines, including: Flair Airlines American Airlines United Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.

• How long is the flight from Chicago (CHI) to Winnipeg (YWG)?

  It takes about 2 hours 29 minutes to fly from Chicago (CHI) to Winnipeg (YWG).

• When is the best time to book flights from Chicago to Winnipeg?

  By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Chicago to Winnipeg is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

• How many flights are there per week from Chicago to Winnipeg?

  Based on Trip.com data in the past 4 weeks, there is 13 flight per week flying from Chicago to Winnipeg. You can check the weekly schedule for popular airlines on this route below: United Airlines: S/M/T/W/T/F/S -- UA5475 (09:48)

• How can I find the best deals on flights from Chicago to Winnipeg?

  To find best deals on flights from Chicago to Winnipeg, you can use various tools on Trip.com:
  · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Sun, Aug 2, with one-way flights priced at just CAD 226.
  · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is United Airlines.
  · Set up price alerts to easily monitor ticket prices without having to check every day.
  · Check Trip.com flight deals and promo codes frequently.
  · Avoid peak season unless you book very early. It seems the peak season for Winnipeg travel is around July.
  · Get exclusive promo codes for Trip.com app users.

• When is the best time to book a flight from Chicago to Winnipeg to get the best price?

  The cheapest months to fly from Chicago to Winnipeg is October, when demand for travel is lower.

• Which upcoming date is the cheapest for flights from Chicago to Winnipeg?

  After crunching the numbers on our July flight calendar, it's currently cheapest to fly from Chicago to Winnipeg on July 21, 2026 with Porter Airlines, with prices starting at CAD 230.

• Which airports can I fly through when travelling to Winnipeg from Chicago?

  You can land at any one of the following hubs in Winnipeg, with O'Hare International Airport to Winnipeg James Armstrong Richardson International Airport (ORD-YWG) is by far the most common option on this route: Winnipeg James Armstrong Richardson International Airport (YWG).

• What is the time difference between Chicago and Winnipeg?

  The time difference between Winnipeg and Chicago is 0h.

• How can I change or cancel my flight ticket from Chicago to Winnipeg?

  Tickets can only be changed or cancelled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.