Winnipeg to Chicago Flight tickets from INR 8,954

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Book flight tickets from Winnipeg to Chicago starting at INR 8,954

For as little as INR 8,954, you can take your next adventure to Chicago without breaking the bank. Choose between one-way and return tickets from Winnipeg below.

One way
Round-trip

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

Find the best time to fly from Winnipeg to Chicago

These price trend charts carefully monitor and predict how flight prices from Winnipeg to Chicago will change. Keep a close eye on them to understand when the best time to buy your tickets is.

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

Airlines Flying from Winnipeg to Chicago

We have a range of prices from different airlines providing flights from Winnipeg to Chicago. Check below for the journey which best suits your travel needs.

WestJet

From INR 8,954

Delta Air Lines

From INR 15,939

Porter Airlines

From INR 15,999

Flair Airlines

From INR 17,362

United Airlines

From INR 18,062

Air Transat

From INR 18,098

Air Canada

From INR 18,489

ANA airlines

Find more flights and airlines

Alternative Routes from Winnipeg to Chicago

Did you know that you can save money and time on an alternative route from Winnipeg to Chicago? Check out some of the different available routes below.

Cheapest
YWG
07:30
13h 19m
1 transfer
MDW
20:49
Winnipeg James Armstrong Richardson International Airport - Midway International Airport
Wed, Nov 6WestJet
INR 8,954
YWG
07:30
9h 9m
1 transfer
ORD
16:39
Winnipeg James Armstrong Richardson International Airport - O'Hare International Airport
Wed, Nov 6WestJet
INR 9,298
YWG
07:30
9h 9m
1 transfer
ORD
16:39
Winnipeg James Armstrong Richardson International Airport - O'Hare International Airport
Wed, Nov 6WestJet
INR 9,298
Find More Flights

How do I find the cheapest flights?

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 INR 38,816.
How long does it take to fly from Winnipeg (YWG) to Chicago (CHI) and what is the distance?
It takes around 2 hours 34 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 25km. It takes about 40 minutes by taxi.
- The distance from Midway International Airport to downtown is about 14km. 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

Understanding the common pitfalls when booking your flight tickets can help you save massively when it comes time to fly. We’ve listed our six essential steps to keep in mind when you’re booking flight tickets to help you find the best price.

Book Early

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

Compare prices on travel agency and airline websites.

Look Out for Deals

Check airline and travel agency websites for latest flight deals

Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

Flying during the week, early in the morning, or late at night can help save money.

Use the Trip.com App

Save up to £10 per person when booking your flights on Trip.com

Flight Information from Winnipeg to Chicago

Cheapest nonstop flight price	INR 8,953
Cheapest round-trip ticket price	INR 25,035
Off-season for travel	September
Peak season for travel	June
Flight distance	1,154.29km
Average flight time	2 hours 34 minutes
Popular airline	United Airlines