Compare all flight tickets and find cheap flights from Winnipeg to Chicago

Cheapest flight tickets

$235

Price observed over the last 3 months for a round trip.

Average price of a round trip

$253

Average flight ticket price recorded over the last 3 months for a round trip.

Flight duration

18h14

A flight from Winnipeg to Chicago takes on average 18h14.

Best time

February

According to user searches, the ideal month to go to Chicago is February.

Tips for finding a cheap flight from Winnipeg to Chicago

Check out our tips for booking your flight to Chicago (USA) from Winnipeg (Canada) at the cheapest possible price.

Usually, the cheapest month to pick up a ticket on this route is April, with an average flight ticket price of $370 (calculation over the last two years). The most touristic season corresponds to the months of March, April and October.
For the cheapest flights, it is advisable to buy your ticket at least 41 days before the departure date.

The airline offering the cheapest flight tickets is WestJet. A ticket from the airline WestJet to Chicago costs on average $253.
The airlines that offer the most flights are .

info departure city :
Winnipeg, Canada
airport :
James Armstrong Richardson International Airport (YWG)
local time :

Winnipeg is a city in the country Canada, the time zone is [[timezone]]. In Winnipeg, it is currently {fromLocalTime}, the temperature is on average 8°C, with a minimum of 3°C and a maximum of 13°C.

The city of Winnipeg has 1 airport(s): James Armstrong Richardson

destination info :
Chicago, USA
airports :
Chicago-O'Hare International Airport (ORD)
Chicago-Midway International Airport (MDW)
Chicago-Merrill C. Meigs Field Airport (CGX)
Chicago FSS (CHI)
local time :

Chicago is in the country USA, the time zone is [[timezone]]. In Chicago, it is currently {toLocalTime}, the temperature is on average 10°C, with a minimum of 4°C and a maximum of 17°C.

The city of Chicago (CHI) has 4 airport(s): Chicago-O'Hare, Chicago-Midway, Chicago-Merrill C. Meigs Field and Chicago FSS

Useful info about Chicago

What is the least touristic period to go to Chicago?

If you want to visit Chicago during the least touristic period, choose the month of February.

What is the most popular time to travel to Chicago?

In Chicago, the most popular month is March. It is during this period that the prices offered by airlines are also the highest.

When should I book my flight from Winnipeg to Chicago?

According to our data, it is recommended to book your flight 41 days before your departure. If you book your flight ticket 6 weeks before your departure, you may find a price below average. The cheapest day to book a flight from Winnipeg to Chicago is Friday.

What are the arrival and destination airports when traveling between Winnipeg and Chicago?

When you leave, you can leave from James Armstrong Richardson, and you will arrive at Chicago-Midway or Chicago-O'Hare.

How to reach Winnipeg airport from the city centre?

This information is not available at this time.

Are there other means of transportation to go from Winnipeg to Chicago?

Airplane is the only means of transportation listed on Liligo for this journey.

Are there big differences in weather between Winnipeg and Chicago?

In summer, the average temperature is 22°C in Chicago and 19°C in Winnipeg. The average rainfall in summer is 130 mm in Chicago and 92 mm in Winnipeg. In summer, it is warmer in Chicago and it rains less in Winnipeg. In winter, it is colder in Chicago and it rains more in Chicago.

Prepare your stay in Chicago

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