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Flights from Chicago to Calgary

Cheap flight deals from Chicago to Calgary

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.

Flight Info | Chicago to Calgary

Cheapest one-way flight price AED 194
Cheapest return ticket price AED 511
Off-season for travel March
Peak season for travel June
Flight distance 2,248.84 km
Average flight time 4 hours 24 minutes
Popular airline Alaska Airlines

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

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

Cheapest flights
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  • 4 11
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
  • 8 15
  • 15 22
  • 22 29

  • Jul

    29 6
  • 6 13
  • 13 20
  • 20 27
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 Chicago (CHI) to Calgary (YYC) the cheapest?

    Airlines adjust prices for flights from Chicago to Calgary 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 do flights from Chicago (CHI) to Calgary (YYC) cost?

    According to Trip.com's data, the lowest price is around AED 1,569.

  • How long does it take to fly from Chicago (CHI) to Calgary (YYC)?

    It takes about 4 hours 24 minutes to fly from Chicago (CHI) to Calgary (YYC).

  • What are the most popular airlines that fly from Chicago (CHI) to Calgary (YYC)?

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

  • How many airports are there in Calgary (YYC)?

    There are 1 airport(s) near Calgary (YYC): Calgary International Airport.

How to find a cheap flight from Chicago to Calgary

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 Chicago to Calgary. Book your flights at the right time and save more.
1
Being flexible with your dates to get the cheapest Chicago to Calgary ticket.
Tap "Date" on flight search bar to scan through the calender for Chicago to Calgary airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Mon, May 26 at AED 195 for one-way flights.
2
Compare cheap Chicago to Calgary flight deals from over hundreds of airlines.
Our extensive search allows you to compare prices from over 500 airlines to choose the cheapest flight tickets from Chicago to Calgary. The cheapest airline operating is WestJet.
3
Set up a Price Alert
By setting up a Price Alert for your Chicago to Calgary route, you can easily track the price of your airline tickets from without manually checking every day.
4
Don't miss cheap Chicago to Calgary flight deals and promo codes.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights. If registering a free membership, you can receive more deals for your flights.
5
Book early or wait unitl the last minute.
It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.
6
Search for flights on the go.
To get the best flight booking experience on the go, download Trip.com and search for cheap flight tickets from Chicago to Calgary to get exclusive deals for you.

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