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Flights from Calgary to Chicago

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

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  • Apr

    30 6
  • 6 13
  • 13 20
  • 20 27

  • May

    27 4
  • 4 11
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
  • 8 15
  • 15 22
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Find cheap 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.
Delta Air Lines logo Delta Air Lines

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 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 Calgary (YYC) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around AED 1,255.

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

    It takes about 3 hours 30 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 25 km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14 km, 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): American Airlines, Qatar Airways, United Airlines, Air Canada, WestJet, Delta Air Lines, Emirates and British Airways.

  • What's the most popular airline for non-stop flights from Calgary (YYC) to Chicago (CHI)?

    United Airlines operates 1 non-stop flights from Calgary (YYC) to Chicago (CHI).

  • How many airports are there in Chicago (CHI)?

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.
1
Being flexible with your dates to get the cheapest Calgary to Chicago ticket.
Tap "Date" on flight search bar to scan through the calender for Calgary to Chicago airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Sun, May 4 at AED 317 for one-way flights.
2
Compare cheap Calgary to Chicago 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 Calgary to Chicago. The cheapest airline operating is WestJet.
3
Set up a Price Alert
By setting up a Price Alert for your Calgary to Chicago route, you can easily track the price of your airline tickets from without manually checking every day.
4
Don't miss cheap Calgary to Chicago 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 Calgary to Chicago to get exclusive deals for you.

Flight Info | Calgary to Chicago

Cheapest one-way flight price AED 313
Cheapest return ticket price AED 447
Off-season for travel March
Peak season for travel January
Flight distance 2,248.84 km
Average flight time 3 hours 30 minutes
Popular airline American Airlines

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