Cheap flight deals from Chicago to Winnipeg Starting at AED 355

We've found these cheap flights for you. You can book one-way or round-trip flight tickets.

  • Round-trip
  • One way

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to fly from Chicago to Winnipeg?

We monitor flight fares to help you find the best deals effortlessly

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  • 23 30

  • Apr

    30 6
  • 6 13
  • 13 20
  • 20 27

  • May

    27 4
  • 4 11
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
  • 8 15
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

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

    Airlines adjust prices for flights from Chicago to Winnipeg based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Chicago (CHI) to Winnipeg (YWG) cost?

    According to Trip.com's data, the lowest price is around AED 1,593.

  • How long does it take to fly from Chicago (CHI) to Winnipeg (YWG)?

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

  • What is the transportation method from the main airport to downtown in Winnipeg?

    • The distance from Winnipeg James Armstrong Richardson International Airport to downtown is about 7 km, by taxi about 20 minutes.

  • What are the most popular airlines that fly from Chicago (CHI) to Winnipeg (YWG)?

    Airlines with flights from Chicago (CHI) to Winnipeg (YWG): United Airlines, Air Canada and Air New Zealand.

  • What's the most popular airline for non-stop flights from Chicago (CHI) to Winnipeg (YWG)?

    United Airlines operates 1 non-stop flights from Chicago (CHI) to Winnipeg (YWG).

  • How many airports are there in Winnipeg (YWG)?

    There are 1 airport(s) near Winnipeg (YWG): Winnipeg James Armstrong Richardson International Airport.

How to find a cheap flight from Chicago to Winnipeg

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Winnipeg. Book your flights at the right time and save more.
1
Being flexible with your dates to get the cheapest Chicago to Winnipeg ticket.
Tap "Date" on flight search bar to scan through the calender for Chicago to Winnipeg airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Thu, Mar 27 at AED 927 for one-way flights.
2
Compare cheap Chicago to Winnipeg flight deals from over hundreds of airlines.
Our extensive search allows you to compare prices from over 500 airlines to choose the cheapest flight tickets from Chicago to Winnipeg. The cheapest airline operating is Air Canada.
3
Set up a Price Alert
By setting up a Price Alert for your Chicago to Winnipeg route, you can easily track the price of your airline tickets from without manually checking every day.
4
Don't miss cheap Chicago to Winnipeg flight deals and promo codes.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights. If registering a free membership, you can receive more deals for your flights.
5
Book early or wait unitl the last minute.
It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.
6
Search for flights on the go.
To get the best flight booking experience on the go, download Trip.com and search for cheap flight tickets from Chicago to Winnipeg to get exclusive deals for you.

Flight Info | Chicago to Winnipeg

Cheapest one-way flight price AED 355
Cheapest return ticket price AED 1,385
Off-season for travel March
Peak season for travel December
Flight distance 1,154.29 km
Average flight time 2 hours 29 minutes
Popular airline United Airlines

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