Cheap Flights from Chicago to Winnipeg from $168

Frequently Asked Questions

• What are the cheapest flights from Chicago to Winnipeg (CHI-YWG)?

  Based on Trip.com data, Porter Airlines offers one-way fares as low as $168 on Cheapest nonstop routes (e.g. MDW to YWG on Fri, Jun 12), while WestJet offers Cheapest nonstop round-trips from $386 departing on Wed, Aug 5 and returning on Thu, Aug 13.

• Which airlines offer direct flights from Chicago to Winnipeg?

  At the moment, you can catch a nonstop flight from Chicago to Winnipeg with the following airlines, including: 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 does it take to fly from Chicago (CHI) to Winnipeg (YWG) and what is the distance?

  It takes around 2 hours 32 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 8 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 -- UA5645 (20:33)

• 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 Fri, Jun 12, with one-way flights priced at just $168.
  · 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 are flight tickets from Chicago (CHI) to Winnipeg (YWG) the cheapest?

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

• Which upcoming date is cheapest to fly from Chicago to Winnipeg on?

  After crunching the numbers on our June flight calendar, it's currently cheapest to fly from Chicago to Winnipeg on June 29, 2026 with WestJet, with prices starting at $426.

• Which airports can I fly to for Winnipeg from Chicago?

  You can land at any one of the following hubs in Winnipeg, with Chicago 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).

• Is there any time difference between Chicago and Winnipeg?

  The time difference between Winnipeg and Chicago is 0h.

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

  Tickets can only be changed or canceled 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.