$96 Flights from Chicago (CHIA) to Calgary (YYC)

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Flight deals from Chicago to Calgary Airport

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to Calgary Airport? If you want to travel next month, round-trip fares start from $287. Find the lowest prices on one-way and round-trip tickets right here.
Is this a good flight price? We'll tell you.We compare today's Chicago to Calgary Airport prices with what travelers usually pay, so you can see if now's a good time to book or if it's worth waiting.

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 May.

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$96
Cheapest month to flyMay
Average flight time3 hrs, 54 mins
Most popular airlineAmerican Airlines
Average flights per week61

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 $224. 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 54 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 61 flights per week flying from Chicago to Calgary, as of March 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 Wednesday, May 27, 2026.
Yes – the average flight time is 3 hours and 54 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.

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

  • Chicago's main base, Chicago O'Hare International Airport (ORD), is where plenty of awesome adventures begin. Explore the options for leaving from here when booking your flight from Chicago to Calgary International Airport (YYC).

  • Take off on a direct Chicago to Calgary International Airport flight and you'll be traveling for around 3 hours 50 minutes.

  • Calgary International Airport is located in Calgary. The city follows the UTC-7 timezone and is one hour behind Chicago.

  • Chicago O'Hare International Airport (ORD) to Calgary International Airport (YYC) is the most popular route. There are 22 direct flights a week to pick from. If you have plans before you fly, hop on the last flight with American Airlines at 8:25pm. Opt for the first ORD to YYC departure operated by United Airlines at 8:45am if you'd rather get a move on.

  • Arriving two hours before an international flight and one hour ahead of a domestic departure are tried-and-true travel tips. Make sure you're at the airport on time to catch your flight from Chicago to YYC.

  • If you're flying during a popular month like July, head to the airport even earlier. You'll want to arrive up to four hours before an international flight and two hours ahead of domestic departures. Security lines will be longer during peak periods like Thanksgiving and spring break.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Enjoy an uninterrupted journey from Chicago O'Hare International Airport (ORD). Direct flights from Chicago to Calgary International Airport (YYC) operate from here.

  • At ORD, there's a good selection of carriers operating direct flights from Chicago to Calgary International Airport, such as:

  • The majority of travelers prefer to book seats with United from ORD to YYC.

  • Among carriers operating on this route, American Airlines leads the way for on-time arrivals.

  • A stopover is the ideal opportunity to break up your journey and perhaps even tour another city. When browsing cheap flights from Chicago to YYC leaving from Chicago O'Hare International Airport (ORD), uncheck the 'Direct flights only' box to find out where you can stop along the way. Your journey might pause in:

    • Denver International Airport (DEN)

    • Minneapolis-Saint Paul International Airport (MSP)

    • Salt Lake City International Airport (SLC)

  • Located around 17 miles from the center of Chicago, ORD can be reached in about 30 minutes by car (depending on traffic). The journey by public transport takes roughly 45 minutes.

  • Searching for a comfortable hotel close to Chicago O'Hare International Airport? If you've booked an early flight from Chicago to Calgary International Airport, these accommodation options will put you moments from your departure lounge:

  • When it comes to Chicago O'Hare International Airport's on-time performance, 70% of flights stick to their scheduled arrival time.

  • The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Add another location to your travels or just take a moment to recharge with a stopover. If you'd like to split up your flight from Chicago to Calgary International Airport, browse these options when taking off from Chicago Midway International Airport:

    • Denver International Airport (DEN)

    • Minneapolis-Saint Paul International Airport (MSP)

    • Nashville International Airport (BNA)

  • MDW is around 10 miles from central Chicago. It'll take 25 minutes or so to get to the airport if you're driving from the city center. Public transport takes approximately 30 minutes.

  • Catching an early morning flight? You might like to check in to one of these hotels near Chicago Midway International Airport the day before your Chicago to YYC flight:

  • 76% of all departures from Chicago Midway International Airport arrive within the expected time frame.

  • You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Booking a plane ticket from Chicago to Calgary International Airport (YYC) with a stop or two can offer you more choice of departure times on top of cheaper fares. When jetting off from Chicago Rockford International Airport (RFD), here's where you can make a pit stop at on your way to YYC:

    • Los Angeles International Airport (LAX)

    • Las Vegas Harry Reid International Airport (LAS)

    • Nashville International Airport (BNA)

  • RFD is roughly 90 miles from central Chicago. Driving from the city center to the terminal takes about 1 hour 40 minutes. If you're planning to use public transport, you can expect a journey of around 2 hours.

  • Make catching an early Chicago to Calgary International Airport flight the easiest part of your journey. Book a room at one of these hotels near Chicago Rockford International Airport and get to your boarding gate feeling relaxed and unhurried:

  • Flights departing from RFD make it to their destination on schedule 71% of the time.

  • 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

  • From Calgary International Airport, central Calgary is around 12 miles away. It takes about 25 minutes to get to the city center by car.

  • If you're taking public transport, expect a journey of about 45 minutes.

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

  • The lowest price we've found for a one-way ticket from Chicago to Calgary International Airport is $96. For a return flight on this route, the best price is $224. Depending on the availability and when you book, these fares may change.

  • Book one month before you want to fly. Pricing trends show that this is the ideal window for finding cheap flights from Chicago to YYC.

  • June is when you're most likely to land a bargain on a Chicago to Calgary International Airport ticket. If you'd like to travel during a different time of year, the 'Whole month' tool will show you the lowest prices for every month.

  • Finding a cheap plane ticket from Chicago to YYC is a piece of cake with Price Alerts. Simply create one of these automatic alerts and we'll notify you as soon as there's a price drop.

  • Tailor your trip using filters. Pick your departure and arrival times, total journey duration and airlines. You can also sort your results by 'Cheapest,' 'Best' or 'Fastest' flights from Chicago to Calgary International Airport.

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

  • July is the busiest month for flights from Chicago to Calgary International Airport (YYC). Visit Calgary in January for a more laid-back experience.

  • Lock in a Chicago to YYC plane ticket departing in August if you're eager to visit the city during its warmest month. Expect temperatures in Calgary to range from 46ºF to 79ºF.

  • Look for cheap tickets from Chicago to Calgary International Airport in February if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -8ºF and 37ºF.

More about Calgary

Explore more of Canada

  • You've done Calgary, now it's time to discover other corners of Canada. Journey about 170 miles north to Edmonton to tick off its top attractions. From Rogers Place to Citadel Theatre and Muttart Conservatory, there's plenty to keep you busy.

  • If you're ready to explore another well-known destination in Canada, head for Red Deer, about 80 miles north of Calgary. Discovery Canyon, Red Deer Mountain Bike Park and Old C.P.R. Bridge are key reasons to visit.

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