Cheap flights from Calgary to Chicago

Travelers frequently search for route combinations, such as Calgary and New York, Orlando, Las Vegas, Denver, Miami, Los Angeles, Atlanta, Mexico City, Bogotá, Dallas, Phoenix, Philadelphia, San Francisco, Cancún, Houston, San Juan, Washington, D.C., Dhaka, Fort Lauderdale, London.

Travelers frequently search for route combinations, such as Chicago and Toronto, Montreal, Vancouver, Kuwait City, Winnipeg, Edmonton, Ottawa, Kelowna, Quebec City, Victoria, Saskatoon, Lima.

The main airport in Calgary is Calgary International. It is also served by Calgary International, Red Deer Regional, Lethbridge.

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, South Bend International, Central Illinois Regional, Fort Wayne International, Quad City International, Kalamazoo/Battle Creek International, University of Illinois Willard.

A number of bus and train companies depart from Calgary, including Ebus, Red Arrow Motorcoach, Cold Shot Bus.

Yes, it's possible to combine different modes of transport between Calgary and Chicago thanks to our Virtual Interlining technology. Making use of not only flights but also trains and buses between Calgary 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 Calgary and Chicago with Air Canada, WestJet, Spirit Airlines, United Airlines, Delta Air Lines.

If you don’t have specific dates for your trip between Calgary 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.