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Flights from Calgary to Chicago
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Find Calgary to Chicago flights starting at CAD 119.

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

  • One way
  • Round-trip
      • Cheapest nonstop
        YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Sun, Mar 9|Calgary - Chicago|WestJet
        CAD 119CAD 151
        21% OFF
        21% OFF
        CAD 151CAD 119

        Choose WestJet flights from Calgary to Chicago. The one-way direct flight with WestJet departs from Calgary International Airport on Sun, Mar 9, arriving at O'Hare International Airport. One-way Prices start from CAD 119 including taxes and charges.

      • YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Thu, Mar 20|Calgary - Chicago|WestJet
        CAD 119CAD 151
        21% OFF
        21% OFF
        CAD 151CAD 119

        Choose WestJet flights from Calgary to Chicago. The one-way direct flight with WestJet departs from Calgary International Airport on Thu, Mar 20, arriving at O'Hare International Airport. One-way Prices start from CAD 119 including taxes and charges.

      • YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Sun, Feb 23|Calgary - Chicago|WestJet
        CAD 126CAD 151
        16% OFF
        16% OFF
        CAD 151CAD 126

        Choose WestJet flights from Calgary to Chicago. The one-way direct flight with WestJet departs from Calgary International Airport on Sun, Feb 23, arriving at O'Hare International Airport. One-way Prices start from CAD 126 including taxes and charges.

      • YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Mon, Mar 24|Calgary - Chicago|WestJet
        CAD 130
        CAD 130

        Choose WestJet flights from Calgary to Chicago. The one-way direct flight with WestJet departs from Calgary International Airport on Mon, Mar 24, arriving at O'Hare International Airport. One-way Prices start from CAD 130 including taxes and charges.

      • YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Sun, Feb 16|Calgary - Chicago|WestJet
        CAD 130
        CAD 130

        Choose WestJet flights from Calgary to Chicago. The one-way direct flight with WestJet departs from Calgary International Airport on Sun, Feb 16, arriving at O'Hare International Airport. One-way Prices start from CAD 130 including taxes and charges.

      • YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Sun, Mar 16|Calgary - Chicago|WestJet
        CAD 133
        CAD 133

        Choose WestJet flights from Calgary to Chicago. The one-way direct flight with WestJet departs from Calgary International Airport on Sun, Mar 16, arriving at O'Hare International Airport. One-way Prices start from CAD 133 including taxes and charges.

      • YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Thu, Feb 20|Calgary - Chicago|WestJet
        CAD 133
        CAD 133

        Choose WestJet flights from Calgary to Chicago. The one-way direct flight with WestJet departs from Calgary International Airport on Thu, Feb 20, arriving at O'Hare International Airport. One-way Prices start from CAD 133 including taxes and charges.

      • YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Mon, Mar 10|Calgary - Chicago|WestJet
        CAD 133
        CAD 133

        Choose WestJet flights from Calgary to Chicago. The one-way direct flight with WestJet departs from Calgary International Airport on Mon, Mar 10, arriving at O'Hare International Airport. One-way Prices start from CAD 133 including taxes and charges.

      • YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Sun, Mar 23|Calgary - Chicago|WestJet
        CAD 134
        CAD 134

        Choose WestJet flights from Calgary to Chicago. The one-way direct flight with WestJet departs from Calgary International Airport on Sun, Mar 23, arriving at O'Hare International Airport. One-way Prices start from CAD 134 including taxes and charges.

      • YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Mon, Mar 17|Calgary - Chicago|WestJet
        CAD 135
        CAD 135

        Choose WestJet flights from Calgary to Chicago. The one-way direct flight with WestJet departs from Calgary International Airport on Mon, Mar 17, arriving at O'Hare International Airport. One-way Prices start from CAD 135 including taxes and charges.

      • YYC01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Mon, Jan 13|Calgary - Chicago|WestJet
        Find More Flights
        Find More Flights

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

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

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

WestJet
From CAD 119
Air Canada
From CAD 147
United Airlines
From CAD 149
American Airlines
From CAD 169
Delta Air Lines
From CAD 178
Flair Airlines
From CAD 191
Alaska Airlines
From CAD 232
Porter Airlines
From CAD 319
Air Transat
From CAD 331
World Ticket
From CAD 519

Find more flights and airlines

Alternative Routes for Calgary to Chicago Flights

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Calgary to Chicago.

  • Cheapest
    WestJet
    YYC
    11:30
    3h 26m
    Nonstop
    ORD
    15:56
    Calgary International Airport - O'Hare International Airport
    Sun, Mar 9WestJet
    CAD 119
  • WestJet
    YYC
    21:45
    20h 21m
    2 transfer
    MDW
    19:06
    Calgary International Airport - Midway International Airport
    Tue, Jan 21WestJet
    CAD 161
  • WestJet
    YYC
    21:45
    20h 21m
    2 transfer
    MDW
    19:06
    Calgary International Airport - Midway International Airport
    Tue, Jan 21WestJet
    CAD 161
    Find More Flights

FAQ

  • 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 532.

  • How long is the flight from Calgary (YYC) to Chicago (CHI)?

    It takes about 4 hours 51 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)?

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 Information for Calgary to Chicago Flights

Cheapest direct flight priceCAD 118
Cheapest return ticket priceCAD 175
Off-season travel monthMarch
Peak season for travelApril
Flight distance2,248.84km
Average flight time4 hours 51 minutes
Popular airlineAmerican Airlines

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