Calgary To Chicago Flights, Cheap Flights From Calgary (Yyc) To Chicago (Ord)

Last minute flight deals from Calgary to Chicago

Feeling spontaneous? It’s never too late to book a trip. Here’s our pick of the best last minute flights.

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Direct flights from Calgary to Chicago

Non-stop flights currently depart between April and October.



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Alternative Calgary to Chicago routes

Looking for the cheapest, fastest or easiest route from Calgary to Chicago? You could fly into the following airports instead.

Calgary to Chicago: Flight information

The things to know before you go.

Cheapest flight found


Average flight time

3 hrs 18 mins

Cheapest month to fly


Most popular airline

Air Canada

Flights per week


Time difference between Calgary and Chicago

+1 hr(GMT -5)



Warwick Allerton – Chicago


The Whitehall Hotel

COVID-19 travel restrictions are changing fast, but we're here to help you find the advice you need. Check our live page on travel restrictions to see if you can travel from Calgary to Chicago, and if you'll need to quarantine on arrival.
There are 4 airports in Chicago: Chicago O'Hare International, Chicago Midway, Chicago Rockford, and Chicago Pal-Waukee.
The best price found on for a flight from Calgary to Chicago is $328. This was found by aggregating across different carriers and is the cheapest price for the whole month.

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Compare flights from Calgary to Chicago and find the cheapest flights with is a fast and simple travel search engine that helps you to find cheap flights and great prices on flights from Calgary to Chicago. We compare hundreds of flights from all major airlines and travel agents, finding you the best deal on cheap plane tickets to Chicago from Calgary.

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When is the best time to book from Calgary to Chicago?

Book your flight from Calgary to Chicago with peace of mind during COVID-19

Check airline safety scores. From mandatory masks to social distancing, you can now see the measures major airlines are taking on their flights from Calgary to Chicago to keep you safe. Just search to see for yourself. Book smarter stays. Check out the hotels in Chicago with sparkling 5/5 cleanliness ratings, or bag a room with free cancellation. Find flexible getaways. Some airlines now have flexible ticket policies, so you won’t lose out if your flight has to be changed or cancelled. If there are any cheap flights from Calgary to Chicago with a flexible booking policy, you'll see these clearly when you search. Get insured. Choose travel cost protection that covers COVID-19, too. It's available as you book your Chicago flights with us. Get an instant quote and 24-hour support, wherever you are.

Useful information before booking your travel from Calgary to Chicago

Check the travel information panel above to get exact information about:

Distance from Calgary to ChicagoFlight time from Calgary to ChicagoWhich airlines provide the cheapest tickets from Calgary to ChicagoWhich airlines fly direct to Chicago from Calgary.

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