Cheap Flights from Calgary to Chicago from £90️ (YYC-CHI)

Flights from Calgary to Chicago

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Flights from Calgary to Chicago Starting at £90

We've found these cheap flights for you. You can book one-way or return flight tickets.

One way
Round-trip

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

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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, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

WestJet

From £90

Flair Airlines

From £103

United Airlines

From £105

Delta Air Lines

From £105

Lynx Air

From £106

Alaska Airlines

From £115

Air Canada

From £118

American Airlines

From £186

Porter Airlines

From £203

ANA airlines

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Alternative Routes from Calgary to Chicago

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Calgary to Chicago.

Cheapest
YYC
12:30
3h 35m
Direct
ORD
17:05
Calgary International Airport - O'Hare International Airport
Sat, Jun 1WestJet
£90
YYC
08:00
26h 36m
1 transfer
MDW
11:36
Calgary International Airport - Midway International Airport
Tue, Apr 30Flair Airlines
£103
YYC
08:00
11h 56m
1 transfer
RFD
20:56
Calgary International Airport - Chicago Rockford International Airport
Thu, Apr 18Flair Airlines
£255
YYC
08:00
11h 56m
1 transfer
RFD
20:56
Calgary International Airport - Chicago Rockford International Airport
Thu, Apr 18Flair Airlines
£255
Find More Flights

How do I find the cheapest flights?

When are flight tickets from Calgary (YYC) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Calgary to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much are flights from Calgary (YYC) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around £334.
How long is the flight from Calgary (YYC) to Chicago (CHI)?
It takes about 4 hours 55 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 25km, by taxi about 40 minutes.
- The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
What are the most popular airlines that fly from Calgary (YYC) to Chicago (CHI)?
Airlines with flights from Calgary (YYC) to Chicago (CHI): United Airlines, Air Canada and Emirates.
What's the most popular airline for direct flights from Calgary (YYC) to Chicago (CHI)?
United Airlines operates 1 direct flights from Calgary (YYC) to Chicago (CHI).
How many airports in Chicago (CHI)?
There are 5 airport(s) in Chicago (CHI): Chicago Du Page County Airport, Midway International Airport, O'Hare International Airport, Chicago Palwaukee Airport and Chicago Rockford International Airport.

How to find a cheap flight from Calgary to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Calgary to Chicago. Book your flights at the right time and save more.

Book Early

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Compare Flight Prices

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Check One-way Fares

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Try Different Dates

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Use the Trip.com App

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Flight Information from Calgary to Chicago

Cheapest direct flight price	£89
Cheapest return ticket price	£167
Cheapest month	January
Peak season for travel	July
Flight distance	2,248.84km
Average flight time	4 hours 55 minutes
Popular airline	Delta Air Lines