Cheap flight deals from Calgary to Chicago Starting at €73

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?

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  • 2 9
  • 9 16
  • 16 23
  • 23 30

  • Apr

    30 6
  • 6 13
  • 13 20
  • 20 27

  • May

    27 4
  • 4 11
  • 11 18
  • 18 25
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Top Airlines Flying 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 logo WestJet

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 €350.

  • How long does it take to fly from Calgary (YYC) to Chicago (CHI) and what is the distance?

    It takes around 3 hours 29 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. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

  • 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, WestJet, Delta Air Lines, Emirates, Qatar Airways, American Airlines 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.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Info | Calgary to Chicago

Cheapest nonstop flight price €72
Cheapest round-trip ticket price €114
Off-season for travel March
Peak season for travel December
Flight distance 2,248.84 km
Average flight time 3 hours 29 minutes
Popular airline United Airlines

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