Cheap flights from Winnipeg, Canada to Chicago, IL

Travelers frequently search for route combinations, such as Winnipeg and Calgary, Edmonton, Ottawa, Halifax, Kelowna, Abbotsford, New York, Orlando, Las Vegas, Denver, Miami, Los Angeles, Atlanta, Mexico City, Bogotá, Dallas, Phoenix, Philadelphia, San Francisco, Cancún.

Travelers frequently search for route combinations, such as Chicago and New York, Seattle, Detroit, St. Louis, Toronto, Halifax, Montreal, Vancouver, Calgary, Kuwait City, Edmonton, Ottawa, Kelowna, Quebec City, Victoria, Saskatoon, Lima.

The main airport in Winnipeg is Winnipeg James Armstrong Richardson International. It is also served by Winnipeg James Armstrong Richardson International, Grand Forks International, Brandon Municipal, Thief River Falls Regional, Kenora.

The main airport in Chicago is O Hare International. It is also served by General Mitchell International, Gerald R. Ford International, Dane County Regional, General Wayne A. Downing Peoria International, Fort Wayne International, South Bend International, Quad City International, Muskegon County, Central Illinois Regional, Decatur.

A number of bus and train companies depart from Winnipeg, including Via Rail Canada.

Yes, it's possible to combine different modes of transport between Winnipeg and Chicago thanks to our Virtual Interlining technology. Making use of not only flights but also trains and buses between Winnipeg and Chicago can give rise to new adventures. Read more about how Virtual Interlining works on Kiwi.com Stories.

Virtual Interlining provides a revolutionary way of traveling. You can combine different modes of transport like flights, trains, and buses into one itinerary. And this often saves money. Thanks to the world's largest carrier database, the Kiwi.com search function enables anyone to mix and match different modes of transport easily.

Currently, you can fly between Winnipeg and Chicago with WestJet, Frontier Airlines, United Airlines, Air Canada, Flair Airlines.

If you don’t have specific dates for your trip between Winnipeg and Chicago, you can enter a date range into the departure and return fields. Most carriers on the Kiwi.com website allow you to search and book up to six months from the day of your search. Order the search results by the best, cheapest, or fastest route, or find the cheapest outbound and return combination in the pricing table.