Cheap Flights from Winnipeg to Chicago from $177

Frequently Asked Questions

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

  Based on Trip.com data, WestJet offers one-way fares as low as $177 on Cheapest nonstop routes (e.g. YWG to MDW on Wed, Sep 16), while WestJet offers Cheapest nonstop round-trips from $280 departing on Fri, Sep 11 and returning on Mon, Sep 14.

• Which airlines offer direct flights from Winnipeg to Chicago?

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

  It takes around 2 hours 28 minutes to fly from Winnipeg (YWG) to Chicago (CHI).

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

  By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Winnipeg to Chicago 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 Winnipeg to Chicago?

  Based on Trip.com data in the past 4 weeks, there is 12 flight per week flying from Winnipeg to Chicago. You can check the weekly schedule for popular airlines on this route below: United Airlines: S/M/T/W/T/F/S -- UA5639 (14:37)

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

  To find best deals on flights from Winnipeg to Chicago, 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 Wed, Sep 16, with one-way flights priced at just $177.
  · 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 Chicago travel is around July.
  · Get exclusive promo codes for Trip.com app users.

• When are flight tickets from Winnipeg (YWG) to Chicago (CHI) the cheapest?

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

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

  After crunching the numbers on our August flight calendar, it's currently cheapest to fly from Winnipeg to Chicago on August 25, 2026 with WestJet, with prices starting at $194.

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

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

• Is there any time difference between Winnipeg and Chicago?

  The time difference between Chicago and Winnipeg is 0m.

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

  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.

• What is the average cost of a one-way flight from Winnipeg to Chicago?

  Based on Trip.com data for flights departing in the next 30 days, the average one-way fare from Winnipeg to Chicago is $323. Fares vary by travel date, airline and availability.

• What is the average cost of a round-trip flight from Winnipeg to Chicago?

  Based on Trip.com data for travel in the next 30 days, the average round-trip fare from Winnipeg to Chicago is $682. The final price depends on the outbound and return dates, airline and fare conditions.

• How do I book flights from Winnipeg to Chicago on Trip.com?

  Enter Winnipeg and Chicago, choose your travel dates and passengers, then compare flights by price, duration and baggage. Select a fare, review the change and cancellation rules, enter traveler details and complete payment to receive your confirmation.

• Are there budget airlines on the Winnipeg to Chicago route?

  Porter Airlinesare the most popular budget airlines flying from Winnipeg to Chicago. Check baggage, seat and payment fees before comparing the final price.