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Flights from Calgary to Chicago
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Flights from Calgary to Chicago Starting at NZD 147

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
        Thu, Feb 20|Calgary - Chicago|WestJet
        NZD 147NZD 227
        35% OFF
        35% OFF
        NZD 227NZD 147

        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 NZD 147 including taxes and charges.

      • YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Sun, Feb 23|Calgary - Chicago|WestJet
        NZD 152NZD 227
        33% OFF
        33% OFF
        NZD 227NZD 152

        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 NZD 152 including taxes and charges.

      • YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Sun, Feb 16|Calgary - Chicago|WestJet
        NZD 157NZD 227
        31% OFF
        31% OFF
        NZD 227NZD 157

        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 NZD 157 including taxes and charges.

      • YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Sun, Mar 9|Calgary - Chicago|WestJet
        NZD 158
        NZD 158

        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 NZD 158 including taxes and charges.

      • YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Mon, Mar 10|Calgary - Chicago|WestJet
        NZD 161
        NZD 161

        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 NZD 161 including taxes and charges.

      • YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Mon, Feb 24|Calgary - Chicago|WestJet
        NZD 168
        NZD 168

        Choose WestJet flights from Calgary to Chicago. The one-way direct flight with WestJet departs from Calgary International Airport on Mon, Feb 24, arriving at O'Hare International Airport. One-way Prices start from NZD 168 including taxes and charges.

      • YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Thu, Feb 27|Calgary - Chicago|WestJet
        NZD 176
        NZD 176

        Choose WestJet flights from Calgary to Chicago. The one-way direct flight with WestJet departs from Calgary International Airport on Thu, Feb 27, arriving at O'Hare International Airport. One-way Prices start from NZD 176 including taxes and charges.

      • YYC13:32
        3h 31m
        Nonstop
        ORD18:03
        Wed, Feb 19|Calgary - Chicago|American Airlines
        NZD 204
        NZD 204

        Choose American Airlines flights from Calgary to Chicago. The one-way direct flight with American Airlines departs from Calgary International Airport on Wed, Feb 19, arriving at O'Hare International Airport. One-way Prices start from NZD 204 including taxes and charges.

      • YYC06:19
        16h 40m
        1 stop
        ORD23:59
        Sat, Jan 11|Calgary - Chicago|United Airlines
        NZD 180
        NZD 180

        Choose United Airlines flights from Calgary to Chicago. The one-way connecting flight with United Airlines departs from Calgary International Airport on Sat, Jan 11, arriving at O'Hare International Airport. One-way Prices start from NZD 180 including taxes and charges.

      • YYC06:19
        9h 46m
        1 stop
        ORD17:05
        Sat, Jan 18|Calgary - Chicago|United Airlines
        NZD 190
        NZD 190

        Choose United Airlines flights from Calgary to Chicago. The one-way connecting flight with United Airlines departs from Calgary International Airport on Sat, Jan 18, arriving at O'Hare International Airport. One-way Prices start from NZD 190 including taxes and charges.

      • YYC01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Mon, Dec 23|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.

Find the best time to fly from Calgary to Chicago

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

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 NZD 147
United Airlines
From NZD 180
Air Canada
From NZD 191
American Airlines
From NZD 204
Delta Air Lines
From NZD 214
Flair Airlines
From NZD 273
Alaska Airlines
From NZD 336
Porter Airlines
From NZD 368
Air Transat
From NZD 398
Air North
From NZD 810

Find more flights and airlines

Alternative Routes from Calgary to Chicago

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
    Thu, Feb 20WestJet
    NZD 147
  • WestJet
    YYC
    21:45
    20h 21m
    2 transfer
    MDW
    19:06
    Calgary International Airport - Midway International Airport
    Tue, Jan 21WestJet
    NZD 194
  • WestJet
    YYC
    19:10
    23h 8m
    1 transfer
    RFD
    19:18
    Calgary International Airport - Chicago Rockford International Airport
    Thu, Dec 19WestJet
    NZD 467
  • WestJet
    YYC
    19:10
    23h 8m
    1 transfer
    RFD
    19:18
    Calgary International Airport - Chicago Rockford International Airport
    Thu, Dec 19WestJet
    NZD 467
    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 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 NZD 641.

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

    It takes around 4 hours 59 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 and Emirates.

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 from Calgary to Chicago

Cheapest nonstop flight priceNZD 147
Cheapest round-trip ticket priceNZD 212
Off-season for travelFebruary
Peak season for travelSeptember
Flight distance2,248.84 km
Average flight time4 hours 59 minutes
Popular airlineAlaska Airlines

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