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Flights from Winnipeg to Chicago

Cheap flight deals from Winnipeg to Chicago

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 Winnipeg to Chicago?

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

Cheapest flights
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  • 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
  • 15 22
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Top Airlines Flying from Winnipeg to Chicago

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

Frequently Asked Questions

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

    Airlines adjust prices for flights from Winnipeg to Chicago 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 Winnipeg (YWG) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around PHP 24,735.

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

    It takes around 2 hours 27 minutes to fly from Winnipeg (YWG) to Chicago (CHI).

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

    • The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

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

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

How to find a cheap flight from Winnipeg to Chicago

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 Winnipeg to Chicago. 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 Info | Winnipeg to Chicago

Cheapest one-way flight price PHP 5,997
Cheapest round-trip ticket price PHP 18,831
Off-season for travel March
Peak season for travel June
Flight distance 1,154.29 km
Average flight time 2 hours 27 minutes
Popular airline United Airlines

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