Cheap flights from Winnipeg to Chicago

Flights tailored to your budget

Selected dates may not give results due to COVID-19. We suggest you change the dates.
Multi-city Round trip One way
Round trip
One way
Multi-city
From
No results match your search criteria
To
No results match your search criteria
{{ weekDay }}
Dates
{{ panel.label }}
Looking for a one-way flight?

Flexible dates can save you money

Explore nearby dates to find lower fares

{{ fromDate | dateToLongNamedDate }}
?
Flexible dates
Depart {{ flexibleFromDateLabel }}
{{ option.label }}
?
Return {{ flexibleToDateLabel }}
{{ option.label }}
Passengers / Class
Number of passengers
Adults
{{ adults }}
Children
{{ children }}
Infants
{{ infants }}
Class
Economy
Available for Economy only
New Multi-city experience

Discover a new Multi-city search experience from Jetcost, designed to handle more complex itineraries. By continuing, you’ll be taken to a dedicated page powered by Kiwi.com.
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

How to estimate the price of a flight from Winnipeg to Chicago?

It depends. Prices for flights from Winnipeg to Chicago fluctuate based on several factors.

Select your dates to check current offers.

Checking fares across several nearby dates can help you see which days offer the best deals. Jetcost lets you track price changes and grab the best opportunities.

Which airports near Winnipeg or Chicago offer flights?

In many cases, using a nearby airport can improve your chances of finding direct flights or better rates.

  • Airports in Winnipeg: Only Winnipeg is currently operating.
  • Airports in Chicago: 3 options available in Chicago - Midway, O'Hare, Rockford.

Secondary airports can offer faster travel thanks to shorter lines and quicker boarding times than major ones.

Flights from Winnipeg to Chicago

Explore flights from Winnipeg to Chicago your way

On Jetcost, you can filter by round-trip or one-way, time of day, airline, number of stops, and even by agency like eDreams or Expedia. Options include Ryanair, British Airways, Easyjet, and more.

Other popular destinations

Also interested in United States? Check out: Las Vegas, Los Angeles, Miami, New York City, Orlando.

If you’re flexible with dates, try checking the days before and after to see if prices vary. Some routes are offered by multiple agencies — comparing fares can really pay off.
Frequently Asked Questions

Frequently asked questions about flights from Winnipeg to Chicago.

How much does an airline ticket from Winnipeg to Chicago cost?

Flight prices can vary a lot depending on the period and destination. At the moment, this information is not available for flights from Winnipeg to Chicago.

How far is Winnipeg from Chicago?

Winnipeg is about 721 mi from Chicago.

What are the airports in Chicago?

Chicago has 3 airports: Midway, O'Hare, Rockford.

What are the airports in Winnipeg?

Winnipeg has one airport: Winnipeg.

What are the most popular cities in United States?

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

When should I book a flight from Winnipeg to Chicago?

The best time to book a flight from Winnipeg to Chicago is 3 months in advance, while the worst time is 7 weeks in advance.

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.