Calgary to Chicago Flight tickets from €106

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Flights from Calgary to Chicago

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Book flight tickets from Calgary to Chicago starting at €106

Whether you’re going for a one-way or round-trip to Chicago, we’ve got you covered! Check out these different flight options from Calgary below.

One way
Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Find the best time to fly from Calgary to Chicago

Price trend charts are a great way of tracking how much your flights cost in the lead up to departure and can help you choose when to book your tickets. See how prices to Chicago from Calgary have changed and are set to move below.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Airlines Flying from Calgary to Chicago

Compare prices from various providers below to understand which option best suits your travel needs, before enjoying a comfortable journey with a trusted airline from Calgary to Chicago.

WestJet

From €92

United Airlines

From €113

Delta Air Lines

From €117

Air Canada

From €120

Flair Airlines

From €127

Alaska Airlines

From €128

American Airlines

From €154

Porter Airlines

From €214

Air Transat

From €223

Air North

From €364

ANA airlines

Find more flights and airlines

Alternative Routes from Calgary to Chicago

There are various non-direct routes from Calgary to Chicago which could be cheaper and faster! Check out these alternative options to see if they could work for your trip.

Cheapest
YYC
21:30
12h 29m
2 transfer
MDW
10:59
Calgary International Airport - Midway International Airport
Tue, Oct 22WestJet
€92
YYC
21:45
19h 49m
2 transfer
ORD
18:34
Calgary International Airport - O'Hare International Airport
Mon, Dec 16WestJet
€110
YYC
21:45
19h 49m
2 transfer
ORD
18:34
Calgary International Airport - O'Hare International Airport
Mon, Dec 16WestJet
€110
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FAQ

When are flight tickets from Calgary (YYC) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Calgary to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much do flights from Calgary (YYC) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around €350.
How long does it take to fly from Calgary (YYC) to Chicago (CHI) and what is the distance?
It takes around 3 hours 32 minutes to fly from Calgary (YYC) to Chicago (CHI).
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
- The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.
What are the most popular airlines that fly from Calgary (YYC) to Chicago (CHI)?
Airlines with flights from Calgary (YYC) to Chicago (CHI): Qatar Airways, United Airlines, Air Canada, American Airlines, British Airways and Emirates.

How to find a cheap flight from Calgary to Chicago

Understanding the common pitfalls when booking your flight tickets can help you save massively when it comes time to fly. We’ve listed our six essential steps to keep in mind when you’re booking flight tickets to help you find the best price.

Book Early

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

Compare prices on travel agency and airline websites.

Look Out for Deals

Check airline and travel agency websites for latest flight deals

Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

Flying during the week, early in the morning, or late at night can help save money.

Use the Trip.com App

Save up to £10 per person when booking your flights on Trip.com

Flight Information from Calgary to Chicago

Cheapest nonstop flight price	€105
Cheapest round-trip ticket price	€179
Off-season for travel	September
Peak season for travel	July
Flight distance	2,248.84 km
Average flight time	3 hours 32 minutes
Popular airline	Alaska Airlines