US$111️ Cheap Flights from Calgary to Chicago (2024)

Flights from Calgary to Chicago

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Find cheap one-way flights from Calgary to Chicago starting at CNY 111.

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

One way
Round-trip

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

When is the cheapest time to book flights from Calgary to Chicago?

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

Cheapest airlines flights 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 US$111

Flair Airlines

From US$127

United Airlines

From US$131

Delta Air Lines

From US$131

Lynx Air

From US$132

Alaska Airlines

From US$143

Air Canada

From US$147

American Airlines

From US$231

Porter Airlines

From US$253

ANA airlines

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Find cheap flights from Calgary to Chicago by different airports

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
US$111
YYC
08:00
26h 36m
1 transfer
MDW
11:36
Calgary International Airport - Midway International Airport
Tue, Apr 30Flair Airlines
US$127
YYC
08:00
11h 56m
1 transfer
RFD
20:56
Calgary International Airport - Chicago Rockford International Airport
Thu, Apr 25Flair Airlines
US$336
YYC
08:00
11h 56m
1 transfer
RFD
20:56
Calgary International Airport - Chicago Rockford International Airport
Thu, Apr 25Flair Airlines
US$336
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Frequently Asked Questions

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 $415.
How long does it take to fly from Calgary (YYC) to Chicago (CHI) and what is the distance?
It takes around 4 hours 53 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. It takes about 40 minutes by taxi.
- The distance from Midway International Airport to downtown is about 14km. 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): United Airlines, Air Canada and Emirates.

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

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

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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

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Calgary to Chicago Flight Information

Cheapest nonstop flight price	$111
Cheapest round-trip ticket price	$208
Off-season for travel	January
Peak season for travel	July
Flight distance	2,248.84km
Average flight time	4 hours 53 minutes
Popular airline	Delta Air Lines