$61 Flights from Chicago (CHIA) to Calgary (YYC)

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Flight deals from Chicago to Calgary

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to Calgary? Find the lowest prices on one-way and round-trip tickets right here.

Find the cheapest month to fly from Chicago to Calgary

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Calgary flights are currently cheapest in April.

Direct flights from Chicago to Calgary

Chicago to Calgary: Alternative routes

Compare routes from Chicago to Calgary below. You may find an airport to fly into that's cheaper, faster, or easier than Calgary.

Chicago to Calgary: Flight information

The things to know before you go.
Cheapest flight found$61
Cheapest month to flyApril
Average flight time3 hrs, 56 mins
Most popular airlineAmerican Airlines
Average flights per week59

Finding cheap flights from Chicago to Calgary: Frequently asked questions

The best price we found for a round-trip flight from Chicago to Calgary is $160. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
3 hours and 56 minutes is the average flight time from Chicago to Calgary.
American Airlines, Envoy Air and Air Canada fly direct from Chicago to Calgary.
There are 59 flights per week flying from Chicago to Calgary, as of February 2026.
The cheapest month to fly from Chicago to Calgary is usually May.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Calgary Airport on Thursday, May 7, 2026.
Yes – the average flight time is 3 hours and 56 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Calgary but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Calgary is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Calgary is WestJet.

Flying from Chicago to Calgary International Airport (YYC): What you need to know

  • Get your trip planning started by considering where you'll take off for your flight from Chicago to Calgary International Airport (YYC). O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are the two main airports in Chicago.

  • Hop on a direct Chicago to Calgary International Airport flight and you'll be traveling for an average of 3 hours 50 minutes.

  • Calgary is one hour behind Chicago. Calgary International Airport is located in Calgary, which is in the UTC-6 timezone.

  • With 22 direct weekly flights between the two airports, O'Hare International Airport (ORD) to Calgary International Airport (YYC) is the most popular route. United Airlines operates the earliest flight at 8:45am. If you prefer to make the most of your day before flying, the last departure from ORD to YYC is with American Airlines at 8:25pm.

  • For stress-free travel, turn up at the airport two hours ahead of international flights and one hour before domestic departures. This way, you can comfortably board your flight from Chicago to YYC.

  • Longer lines at check-in and security are likely if you're heading away during high season, so allow some extra breathing space. The recommendation for peak periods? Arrive up to four hours early for international flights and two hours for domestic departures.

Airports in Chicago

O'Hare International Airport (ORD)

  • You can hop on a direct flight from Chicago to Calgary International Airport (YYC) leaving from O'Hare International Airport (ORD).

  • Leading airlines that operate direct flights from Chicago to Calgary International Airport out of ORD include:

  • United Airlines sees the most traveler bookings for flights from ORD to YYC.

  • United Airlines takes the lead in punctuality. An impressive 86.89% of its services on this route complete the journey on schedule.

  • We make it a piece of cake to book cheap flights from Chicago to YYC that include a stopover. To explore all the options departing from O'Hare International Airport (ORD), deselect 'Direct flights only.' Then, select a flight with a stop long enough to tour your chosen city. Major stopovers between ORD and YYC include:

    • Denver International Airport (DEN)

    • Minneapolis-St. Paul International Airport (MSP)

    • Salt Lake City International Airport (SLC)

  • Located around 25 miles from the center of Chicago, ORD can be reached in about 35 minutes by car (depending on traffic). The journey by public transport will take roughly 55 minutes.

  • Searching for a convenient hotel near O'Hare International Airport? If you're catching an early flight from Chicago to Calgary International Airport, these accommodation options will have you sleeping moments from your departure gate:

  • When it comes to O'Hare International Airport's on-time performance, data shows 74.85% of flights stick to their scheduled arrival time.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Break up your flight from Chicago to Calgary International Airport with a stop so you can recharge or tick a new place off your list. Some top stopovers between Chicago Midway International Airport and YYC include:

    • Denver International Airport (DEN)

    • Minneapolis-St. Paul International Airport (MSP)

    • Nashville International Airport (BNA)

  • You can arrive at MDW from central Chicago in about 20 minutes by car (depending on traffic). The journey by public transport will take roughly 45 minutes to cover the 12 miles or so.

  • Get a head start on your vacation with an extra night away from home. Before your Chicago to YYC flight, kick back in one of these hotels near Chicago Midway International Airport:

  • Chicago Midway International Airport has an on-time performance rate of 77.88%. This figure provides insight into how frequently flights departing from this airport arrive at their destination on schedule.

  • MDW is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Booking a plane ticket from Chicago to Calgary International Airport (YYC) with one or more stops can offer you more departure time choices and access to lower fares. When jetting off from Chicago Rockford International Airport (RFD), here's where you can detour to on the way to YYC:

    • Los Angeles International Airport (LAX)

    • Harry Reid Airport (formerly McCarran Airport) (LAS)

    • Nashville International Airport (BNA)

  • From the center of Chicago, RFD is around 85 miles away. It takes roughly 1 hour 25 minutes to get there by car and 4 hours 15 minutes or so if you use public transport.

  • Sleep a little longer, move a little slower, and still make your Chicago to Calgary International Airport flight with time to spare. These accommodation options near Chicago Rockford International Airport make getting to the terminal a breeze if you're flying out first thing:

  • Airports have an on-time performance rating that tracks how often flights reach their destinations as expected. At RFD, that rate is 76.19%.

  • You'll find Chicago Rockford International Airport at 2 Airport Cir.

About Calgary International Airport (YYC)

Getting from Calgary International Airport (YYC) to central Calgary

  • The center of Calgary is around 6 miles from Calgary International Airport. Journey times by car rental or cab will vary depending on time of day and traffic conditions, so do a little research ahead of time.

  • If you're traveling on public transport, expect a journey time of about 1 hour.

How to find the cheapest flights from Chicago to Calgary International Airport (YYC)

  • The cheapest price we've found for a one-way ticket from Chicago to Calgary International Airport is $61. For a return flight on this route, the best price is $160. Depending on how early you book and the availability, these fares could change.

  • Score cheap flights from Chicago to YYC by booking one month ahead. Based on our research, that's the sweet spot for landing a bargain.

  • June is when you're most likely to find a good deal on a Chicago to Calgary International Airport ticket. If you need to travel at a different time of year, the 'Whole month' tool will show you the lowest prices across every month.

  • Stay on top of deals for plane tickets from Chicago to YYC by creating a Price Alert. We'll send you an email or notification on the app when a lower fare becomes available.

  • Chase down a great fare on a flight from Chicago to Calgary International Airport with the help of the filters. Choose your ideal arrival and departure times, number of stops and airlines. You can also sort your results by 'Cheapest,' 'Fastest' or 'Best.'

The best time to fly from Chicago to Calgary International Airport (YYC)

  • May is the quietest month for flights from Chicago to Calgary International Airport (YYC), while July is the busiest. Choose the best time to visit Calgary based on whether you want a laid-back vibe or a lively atmosphere.

  • Lock in a Chicago to YYC plane ticket departing in August if you want to explore the city during its warmest month. You can expect temperatures in Calgary to range from 46ºF to 79ºF.

  • Search for cheap tickets from Chicago to Calgary International Airport in December if you like traveling in cooler conditions. Temperatures are at their lowest then, ranging between 0ºF and 32ºF.

More about Calgary

Explore more of Canada

  • You've done Calgary, now it's time to discover more of Canada. Travel around 170 miles north to Edmonton to tick off its leading sights. From Rogers Place to Citadel Theatre and Muttart Conservatory, you'll have a packed itinerary ahead.

  • Around 80 miles north of Calgary, Red Deer is another favorite stop in Canada. Start your sightseeing at Michener Gardens, Discovery Canyon and Waskasoo Creek Trail.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.