App
Customer Support
PKR
Find Bookings
Trip.com
>
Cheap Flights
>
United States
>
Illinois
>
Chicago
>
Flights from Calgary to Chicago
Worldwide Coverage
Worldwide Coverage
Flights to over 5,000 cities
One-stop Service Guarantee
One-stop Service Guarantee
Price guaranteed upon confirmed payment, booking guaranteed once tickets issued
Secure Payment
Secure Payment
Convenient & reliable booking and payment system

Flights from Calgary to Chicago Starting at Rs 23,693

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
        Rs 23,693Rs 37,153
        36% OFF
        36% OFF
        Rs 37,153Rs 23,693

        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 Rs 23,693 including taxes and charges.

      • YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Sun, Feb 23|Calgary - Chicago|WestJet
        Rs 24,419Rs 37,153
        34% OFF
        34% OFF
        Rs 37,153Rs 24,419

        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 Rs 24,419 including taxes and charges.

      • YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Sun, Feb 16|Calgary - Chicago|WestJet
        Rs 25,183Rs 37,153
        32% OFF
        32% OFF
        Rs 37,153Rs 25,183

        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 Rs 25,183 including taxes and charges.

      • YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Mon, Mar 10|Calgary - Chicago|WestJet
        Rs 25,871
        Rs 25,871

        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 Rs 25,871 including taxes and charges.

      • YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Mon, Feb 24|Calgary - Chicago|WestJet
        Rs 27,018
        Rs 27,018

        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 Rs 27,018 including taxes and charges.

      • YYC11:30
        3h 26m
        Nonstop
        ORD15:56
        Thu, Feb 27|Calgary - Chicago|WestJet
        Rs 28,202
        Rs 28,202

        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 Rs 28,202 including taxes and charges.

      • YYC13:32
        3h 31m
        Nonstop
        ORD18:03
        Wed, Feb 19|Calgary - Chicago|American Airlines
        Rs 32,788
        Rs 32,788

        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 Rs 32,788 including taxes and charges.

      • YYC13:32
        3h 31m
        Nonstop
        ORD18:03
        Wed, Mar 5|Calgary - Chicago|American Airlines
        Rs 33,438
        Rs 33,438

        Choose American Airlines flights from Calgary to Chicago. The one-way direct flight with American Airlines departs from Calgary International Airport on Wed, Mar 5, arriving at O'Hare International Airport. One-way Prices start from Rs 33,438 including taxes and charges.

      • YYC06:19
        16h 40m
        1 stop
        ORD23:59
        Sat, Jan 11|Calgary - Chicago|United Airlines
        Rs 28,852
        Rs 28,852

        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 Rs 28,852 including taxes and charges.

      • YYC06:19
        9h 46m
        1 stop
        ORD17:05
        Sat, Jan 18|Calgary - Chicago|United Airlines
        Rs 30,457
        Rs 30,457

        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 Rs 30,457 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

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.

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 Rs 23,693
United Airlines
From Rs 28,852
Air Canada
From Rs 30,648
American Airlines
From Rs 32,788
Delta Air Lines
From Rs 34,431
Flair Airlines
From Rs 43,794
Alaska Airlines
From Rs 54,035
Porter Airlines
From Rs 59,118
Air Transat
From Rs 63,971
Air North
From Rs 130,159

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
    Rs 23,693
  • WestJet
    YYC
    21:45
    20h 21m
    2 transfer
    MDW
    19:06
    Calgary International Airport - Midway International Airport
    Tue, Jan 21WestJet
    Rs 31,107
  • WestJet
    YYC
    19:10
    23h 8m
    1 transfer
    RFD
    19:18
    Calgary International Airport - Chicago Rockford International Airport
    Thu, Dec 19WestJet
    Rs 75,015
  • WestJet
    YYC
    19:10
    23h 8m
    1 transfer
    RFD
    19:18
    Calgary International Airport - Chicago Rockford International Airport
    Thu, Dec 19WestJet
    Rs 75,015
    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 Rs 103,141.

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

    It takes around 4 hours 57 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 priceRs 23,693
Cheapest round-trip ticket priceRs 34,087
Off-season for travelFebruary
Peak season for travelSeptember
Flight distance2,248.84 km
Average flight time4 hours 57 minutes
Popular airlineAlaska Airlines

Contact Us

About

Other Services

Payment Methods
Our Partners
Copyright © 2024 Trip.com Travel Singapore Pte. Ltd. All rights reserved
Site Operator: Trip.com Travel Singapore Pte. Ltd.