Cheap Flights from Calgary to Chicago from CAD 148️ 2024

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Find Calgary to Chicago flights starting at CAD 148.

Book one-way or return flights from Calgary to Chicago from as little as CAD 148. Choose from the popular airlines below and book your flight today!

One way
Round-trip

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.

Find Cheapest 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.

United Airlines

From CAD 157

Delta Air Lines

From CAD 173

Flair Airlines

From CAD 174

Alaska Airlines

From CAD 178

Air Canada

From CAD 178

Lynx Air

From CAD 243

American Airlines

From CAD 309

Porter Airlines

From CAD 347

WestJet

From CAD 359

ANA airlines

Find more flights and airlines

Alternative Routes for Calgary to Chicago Flights

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

Cheapest
YYC
08:00
26h 36m
1 transfer
MDW
11:36
Calgary International Airport - Midway International Airport
Tue, Apr 30Flair Airlines
CAD 174
YYC
12:30
3h 27m
Direct
ORD
16:57
Calgary International Airport - O'Hare International Airport
Mon, Jun 17WestJet
CAD 359
YYC
23:35
20h 13m
2 transfer
RFD
20:48
Calgary International Airport - Chicago Rockford International Airport
Wed, May 29WestJet
CAD 506
YYC
23:35
20h 13m
2 transfer
RFD
20:48
Calgary International Airport - Chicago Rockford International Airport
Wed, May 29WestJet
CAD 506
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 CAD 572.
How long is the flight 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 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

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

Flight Information for Calgary to Chicago Flights

Cheapest direct flight price	CAD 147
Cheapest return ticket price	CAD 236
Cheapest month	May
Peak season for travel	October
Flight distance	2,248.84km
Average flight time	4 hours 26 minutes
Popular airline	American Airlines