Cheap Flights from Chicago to Winnipeg from £94️ (CHI-YWG)

Flights from Chicago to Winnipeg

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Flights from Chicago to Winnipeg Starting at CNY 94

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

One way
Round-trip

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

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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.

Frontier Airlines

From £94

United Airlines

From £127

Spirit Airlines

From £135

WestJet

From £144

Southwest Airlines

From £146

American Airlines

From £147

Air Canada

From £151

Porter Airlines

From £152

Delta Air Lines

From £152

Allegiant Air

From £179

ANA airlines

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Alternative Routes from Chicago to Winnipeg

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Chicago to Winnipeg.

Cheapest
MDW
07:00
7h 55m
1 transfer
YWG
14:55
Midway International Airport - Winnipeg James Armstrong Richardson International Airport
Wed, Apr 24Frontier Airlines
£94
ORD
12:34
12h 10m
1 transfer
YWG
00:44
O'Hare International Airport - Winnipeg James Armstrong Richardson International Airport
Mon, May 13Frontier Airlines
£100
RFD
19:08
29h 52m
1 transfer
YWG
01:00
Chicago Rockford International Airport - Winnipeg James Armstrong Richardson International Airport
Mon, Apr 22Allegiant Air
£179
RFD
19:08
29h 52m
1 transfer
YWG
01:00
Chicago Rockford International Airport - Winnipeg James Armstrong Richardson International Airport
Mon, Apr 22Allegiant Air
£179
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How do I find the cheapest flights?

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 cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much are flights from Chicago (CHI) to Winnipeg (YWG) cost?
According to Trip.com's data, the lowest price is around £374.
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 7km, by taxi about 20 minutes.
What's the most popular airline for direct flights from Chicago (CHI) to Winnipeg (YWG)?
United Airlines operates 1 direct flights from Chicago (CHI) to Winnipeg (YWG).
How many airports in Winnipeg (YWG)?
There are 1 airport(s) in 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.

Book Early

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Compare Flight Prices

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Look Out for Deals

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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

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Flight Information from Chicago to Winnipeg

Cheapest direct flight price	£93
Cheapest return ticket price	£301
Cheapest month	March
Peak season for travel	October
Flight distance	1,154.29km
Popular airline	Air Canada