Cheap flights from Winnipeg to Chicago
Selected dates may not give results due to COVID-19. We suggest you change the dates.
Round trip One way
Round trip
One way
Select departure
No results match your search criteria
  • Latest searches
Select arrival
No results match your search criteria
  • Latest searches
Round trip One way
Round trip
One way
{{ weekDay }}
{{ panel.label }}
Looking for a one-way flight?
{{ fromDate | dateToDayNumber }}

{{ fromDate | dateToMonthName }}

{{ fromDate | dateToDayName }}

{{ flexibleFromDateLabel }}
{{ option.label }}
?
{{ flexibleToDateLabel }}
{{ option.label }}
Class and passengers
Class
Economy
Available for Economy only
Number of passengers
Adults
{{ adults }}
Children
{{ children }}
Infants
{{ infants }}
  • Compare with:
    Sponsored

When is the best time to book a Winnipeg - Chicago Midway flight?

Fly Scanner offers you the possibility to find flights from Winnipeg to Chicago Midway at the best price thanks to the flexible dates shopping function: compare the prices of flight tickets for dates close to those selected and save money by changing the day of departure or arrival.

Save time by comparing only direct flights

Compare the best solutions for direct flights from Winnipeg to Chicago Midway choosing among the offers of more than 300 airlines and online agencies. Save time with Fly Scanner and find your airline ticket at the best price in seconds.

Compare cheap Winnipeg - Chicago Midway flights

Fly Scanner finds the best travel solutions among the offers of hundreds of airlines, proposing even cheaper alternatives.

Direct flights and flexible dates

Fly Scanner helps you save money by also showing you travel deals for days close to your chosen dates and for airports close to Winnipeg or Chicago Midway. Moreover, if you want to avoid stopovers, with Fly Scanner you can compare only the prices of direct flights from Winnipeg to Chicago Midway by simply checking the option on the search page.

Frequently Asked Questions

Frequently asked questions about flights from Winnipeg to Chicago Midway.

How much does a Winnipeg - Chicago Midway flight cost?

The availability of airline tickets can vary greatly depending on the time of year and destination. This information is currently unavailable for flights from Winnipeg to Chicago Midway.

How far is Winnipeg from Chicago?

Winnipeg is about 1163 km from Chicago.

What are the airports in Chicago?

At Chicago there are 3 airports: Midway, O'Hare, Rockford.

What are the airports in Winnipeg?

Winnipeg has one airport: Winnipeg.

What are the most popular destinations searched for in United States?

The most searched cities in United States according to our users are: Las Vegas, Los Angeles, Miami, New York City, Orlando.

What is the cheapest month to fly from Winnipeg to Chicago?

This information is not available at the moment.

What is the most expensive month to fly from Winnipeg to Chicago?

This information is not available at the moment.

What is the best day of the week to fly from Winnipeg to Chicago?

This information is not available at the moment.
How do we get the info you see here? Please note that we offer an online comparison service and that all information and prices regarding services and/or products available on our website are provided by our third-party partners. We do our best to show you up-to-date information, but please note that we are not responsible for the completeness or accuracy of the information published, so please check all conditions carefully on the website of the partner before making a booking. Please check our Terms and Conditions for more details. Read more