Cheap Flight Tickets from Calgary (YYC) to Chicago (CHI)

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Latest Flight Deals from Calgary to Chicago

Book one-way or return flights from Calgary to Chicago from as little as AU$ 157. Choose from the popular airlines below and book your flight today!

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

Searching for the best last minute flight from Calgary to Chicago? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Calgary to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.

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

Airlines Flying from Calgary to Chicago

View airlines operating 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 AU$ 157

United Airlines

From AU$ 181

Flair Airlines

From AU$ 195

Alaska Airlines

From AU$ 200

Delta Air Lines

From AU$ 202

Air Canada

From AU$ 225

Lynx Air

From AU$ 273

American Airlines

From AU$ 355

Porter Airlines

From AU$ 411

ANA airlines

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Alternative Routes from Calgary to Chicago

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Calgary to Chicago.

Cheapest
YYC
12:30
3h 27m
Direct
ORD
16:57
Calgary International Airport - O'Hare International Airport
Mon, Jun 17WestJet
AU$ 157
YYC
08:00
26h 36m
1 transfer
MDW
11:36
Calgary International Airport - Midway International Airport
Tue, Apr 30Flair Airlines
AU$ 195
YYC
10:25
9h 23m
1 transfer
RFD
20:48
Calgary International Airport - Chicago Rockford International Airport
Thu, May 30WestJet
AU$ 573
YYC
10:25
9h 23m
1 transfer
RFD
20:48
Calgary International Airport - Chicago Rockford International Airport
Thu, May 30WestJet
AU$ 573
Find More Flights

How do I find the cheapest flights?

When are flight 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 lowest 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 AU$ 637.
How long is the flights from Calgary (YYC) to Chicago (CHI)?
It takes about 4 hours 26 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 time does the earliest flight from Calgary to Chicago depart?
The earliest flight departs from Calgary (YYC) at 08:30 and arrives in Chicago (ORD) at 12:59.
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

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

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Flight Information from Calgary to Chicago

Cheapest direct flight price	AU$ 157
Cheapest return ticket price	AU$ 270
Off-season for travel	January
Peak season for travel	October
Flight distance	2,248.84km
Average flight time	4 hours 26 minutes
Popular airline	United Airlines