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Flights from Chicago to Winnipeg

Flight deals from Chicago to Winnipeg

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

  • Round-trip
  • One way

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

Find the best time to fly from Chicago to Winnipeg

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

Cheapest flights
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  • 13 20
  • 20 27

  • May

    27 4
  • 4 11
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
  • 8 15
  • 15 22
  • 22 29

  • Jul

    29 6
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Airlines Flying from Chicago to Winnipeg

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
United Airlines logo United Airlines

FAQ

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

    Airlines adjust prices for flights from Chicago to Winnipeg based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that 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 NZD 726.

  • How long does it take to fly from Chicago (CHI) to Winnipeg (YWG) and what is the distance?

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

  • 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.

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
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Information from Chicago to Winnipeg

Cheapest one-way flight price NZD 119
Cheapest round-trip ticket price NZD 550
Off-season for travel March
Peak season for travel January
Flight distance 1,154.29 km
Average flight time 2 hours 29 minutes
Popular airline Delta Air Lines

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