Cheap flight deals from Calgary to Chicago

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

Round-trip
One way

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

When is the cheapest time to fly from Calgary to Chicago?

We monitor flight fares to help you find the best deals effortlessly

Cheapest flights

From price

May

27 4
4 11
11 18
18 25
Jun

25 1
1 8
8 15
15 22
22 29
Jul

29 6
6 13
13 20

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

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 Rp 5,745,256.
How long does it take to fly from Calgary (YYC) to Chicago (CHI) and what is the distance?

It takes around 3 hours 45 minutes to fly from Calgary (YYC) to Chicago (CHI).
What are the most popular airlines that fly from Calgary (YYC) to Chicago (CHI)?

Airlines with flights from Calgary (YYC) to Chicago (CHI): American Airlines, United Airlines, Qatar Airways, WestJet, Delta Air Lines, Air Canada, Emirates and British Airways.

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.

Be flexible with your travel dates to get the cheapest Calgary to Chicago ticket.

Tap "Date" in the flight search bar to browse the calendar and find airfare from Calgary to Chicago for the next six months in 2025. If you're looking to fly within the next three months, the lowest fare is Rp 1455926 for a one-way ticket on Mon, May 5.

Compare cheap Calgary to Chicago flight deals from hundreds of airlines.

Our powerful search system compares prices from over 500 airlines. So you can find the cheapest flights from Calgary to Chicago. The most affordable airline currently operating on this route is WestJet.

Set up a Price Alert to track fare drops.

Set up a Price Alert for your Calgary to Chicago route to track ticket prices effortlessly—no need to check manually every day.

Don't miss out on cheap Calgary to Chicago flight deals and promo codes.

Stay updated on the latest deals with Trip.com Deals and Promo Codes for cheap flights. Sign up for a free membership to unlock even more exclusive flight discounts.

Book early or wait unitl the last minute to fine the best fares.

It's always better to book early! Airlines typically release their lowest fares about a year before departure, so check as soon as flights become available. If you miss that window, you may still find great deals closer to your travel date.

Search for flights on the go.

For the best booking experience on the go, download Trip.com and search for cheap flights from Calgary to Chicago to access exclusive deals just for you.

Flight Info | Calgary to Chicago

Cheapest one-way flight price	Rp 1,455,926
Cheapest round-trip ticket price	Rp 2,053,525
Off-season for travel	March
Peak season for travel	January
Flight distance	2,248.84 km
Average flight time	3 hours 45 minutes
Popular airline	American Airlines