Cheap Flights from Calgary to Chicago from PHP 8,663

Frequently Asked Questions

• What are the cheapest flights from Calgary to Chicago (YYC-CHI)?

  Based on Trip.com data, Air Canada offers one-way fares as low as PHP 8,663 on Cheapest nonstop routes (e.g. YYC to ORD on Tue, Nov 3), while Air Canada offers Cheapest nonstop round-trips from PHP 14,116 departing on Mon, Nov 2 and returning on Thu, Nov 5.

• Which airlines offer direct flights from Calgary to Chicago?

  At the moment, you can catch a nonstop flight from Calgary to Chicago with the following airlines, including: WestJet Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.

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

  It takes around 3 hours 36 minutes to fly from Calgary (YYC) to Chicago (CHI).

• When is the best time to book flights from Calgary to Chicago?

  By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Calgary to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

• How many flights are there per week from Calgary to Chicago?

  Based on Trip.com data in the past 4 weeks, there is 30 flight per week flying from Calgary to Chicago. You can check the weekly schedule for popular airlines on this route below: American Airlines: S/M/T/W/T/F/S -- AA1633 (09:37)

• How can I find the best deals on flights from Calgary to Chicago?

  To find best deals on flights from Calgary to Chicago, you can use various tools on Trip.com:
  · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Tue, Nov 3, with one-way flights priced at just PHP 8,663.
  · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is United Airlines.
  · Set up price alerts to easily monitor ticket prices without having to check every day.
  · Check Trip.com flight deals and promo codes frequently.
  · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around January.
  · Get exclusive promo codes for Trip.com app users.

• When are flight tickets from Calgary (YYC) to Chicago (CHI) the cheapest?

  The cheapest months to fly from Calgary to Chicago is October, when demand for travel is lower.

• Which upcoming date is cheapest to fly from Calgary to Chicago on?

  After crunching the numbers on our October flight calendar, it's currently cheapest to fly from Calgary to Chicago on October 11, 2026 with Air Canada, with prices starting at PHP 7,809.

• Which airports can I fly into Chicago from Calgary?

  You can arrive at any of the following airports in Chicago: Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), and Chicago Rockford International Airport (RFD). Flights from Calgary International Airport to O'Hare International Airport (YYC-ORD) are by far the most popular option for this route.

• Is there any time difference between Calgary and Chicago?

  The time difference between Chicago and Calgary is 0m.

• How do I change or cancel my ticket from Calgary to Chicago?

  Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.

• What is the average cost of a one-way flight from Calgary to Chicago?

  Based on Trip.com data for flights departing in the next 30 days, the average one-way fare from Calgary to Chicago is PHP 22,037. Fares vary by travel date, airline and availability.

• What is the average cost of a round-trip flight from Calgary to Chicago?

  Based on Trip.com data for travel in the next 30 days, the average round-trip fare from Calgary to Chicago is PHP 33,250. The final price depends on the outbound and return dates, airline and fare conditions.

• How do I book flights from Calgary to Chicago on Trip.com?

  Enter Calgary and Chicago, choose your travel dates and passengers, then compare flights by price, duration and baggage. Select a fare, review the change and cancellation rules, enter traveller details and complete payment to receive your confirmation.

• Are there budget airlines on the Calgary to Chicago route?

  WestJetare the most popular budget airlines flying from Calgary to Chicago. Check baggage, seat and payment fees before comparing the final price.