Cheap flights from Chicago to Calgary

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Flight deals from Chicago to Calgary

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

Calgary.P9,100 per passenger.Departing Fri, 24 Apr, returning Sun, 26 Apr.Return flight with WestJet.Outbound direct flight with WestJet departs from Chicago O'Hare International on Fri, 24 Apr, arriving in Calgary.Inbound direct flight with WestJet departs from Calgary on Sun, 26 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From P9,100, select.

Calgary.P9,376 per passenger.Departing Sat, 2 May, returning Sun, 10 May.Return flight with WestJet.Outbound direct flight with WestJet departs from Chicago O'Hare International on Sat, 2 May, arriving in Calgary.Inbound direct flight with WestJet departs from Calgary on Sun, 10 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From P9,376, select.

Calgary.P9,927 per passenger.Departing Fri, 9 Jan, returning Fri, 16 Jan.Return flight with WestJet.Outbound direct flight with WestJet departs from Chicago O'Hare International on Fri, 9 Jan, arriving in Calgary.Inbound direct flight with WestJet departs from Calgary on Fri, 16 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From P9,927, select.

Calgary.P10,179 per passenger.Departing Mon, 27 Apr, returning Mon, 4 May.Return flight with WestJet.Outbound direct flight with WestJet departs from Chicago O'Hare International on Mon, 27 Apr, arriving in Calgary.Inbound direct flight with WestJet departs from Calgary on Mon, 4 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From P10,179, select.

Calgary.P11,440 per passenger.Departing Fri, 20 Feb, returning Fri, 27 Feb.Return flight with WestJet.Outbound direct flight with WestJet departs from Chicago O'Hare International on Fri, 20 Feb, arriving in Calgary.Inbound direct flight with WestJet departs from Calgary on Fri, 27 Feb, arriving in Chicago O'Hare International.Price includes taxes and charges.From P11,440, select.

Calgary.P11,817 per passenger.Departing Thu, 11 Jun, returning Tue, 16 Jun.Return flight with WestJet.Outbound direct flight with WestJet departs from Chicago O'Hare International on Thu, 11 Jun, arriving in Calgary.Inbound direct flight with WestJet departs from Calgary on Tue, 16 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From P11,817, select.

Calgary.P11,817 per passenger.Departing Mon, 16 Mar, returning Fri, 20 Mar.Return flight with WestJet.Outbound direct flight with WestJet departs from Chicago O'Hare International on Mon, 16 Mar, arriving in Calgary.Inbound direct flight with WestJet departs from Calgary on Fri, 20 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From P11,817, select.

Calgary.P13,833 per passenger.Departing Sat, 29 Nov, returning Fri, 5 Dec.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 29 Nov, arriving in Calgary.Inbound direct flight with United departs from Calgary on Fri, 5 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From P13,833, select.

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.

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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	P9,100
Cheapest month to fly	April
Average flight time	3 hrs, 57 mins
Most popular airline	American Airlines
Average flights per week	63

Finding cheap flights from Chicago to Calgary: Frequently asked questions

How much are return flights from Chicago to Calgary?

The best price we found for a return flight from Chicago to Calgary is P9,100. 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.

How long does it take to fly from Chicago to Calgary?

3 hours and 57 minutes is the average flight time from Chicago to Calgary.

Which airlines fly direct from Chicago to Calgary?

American Airlines, Envoy Air and Qatar Airways fly direct from Chicago to Calgary.

How many flights are there a week from Chicago to Calgary?

As of November 2025, there are 63 flights per week flying from Chicago to Calgary.

When is the cheapest time to fly from Chicago to Calgary?

The cheapest month to fly from Chicago to Calgary is usually April.

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

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Calgary Airport on Friday, 24 April 2026.

Can I get a direct flight from Chicago to Calgary Airport?

Yes – the average flight time is 3 hours and 57 minutes.

How can I find the best flight deal to Calgary?

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.

When is the best time to book flights to Calgary?

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.

Which is the cheapest airline to fly from Chicago to Calgary with?

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 travelling 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 traveller 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 40 kilometres from the centre 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 19 kilometres or so.
Get a head start on your holiday 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 centre of Chicago, RFD is around 137 kilometres 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)

If you're coming in on a late flight from Chicago to Calgary International Airport, nothing tops the convenience of staying near the terminal. Collect your bags from the carousel and then be showered and relaxing soon after at one of these hotels near YYC:
Follow your own route with a Calgary International Airport rental car. Book your wheels from Routes Car Rentals, Thrifty or Avis and see more of Calgary and beyond.
For the best deal, reserve your vehicle around four weeks ahead of your Chicago to Calgary International Airport flight.
YYC is located at 2000 Airport Road Northeast.

Getting from Calgary International Airport (YYC) to central Calgary

The centre of Calgary is around 10 kilometres from Calgary International Airport. Journey times by car hire or cab will vary depending on time of day and traffic conditions, so do a little research ahead of time.
If you're travelling 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 P3,733. For a return flight on this route, the best price is P9,100. 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 8ºC (46ºF) to 26ºC (79ºF).
Search for cheap tickets from Chicago to Calgary International Airport in December if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between -18ºC (0ºF) and 0ºC (32ºF).

More about Calgary

After booking your flight from Chicago to Calgary International Airport, find a hotel that keeps you close to what you want to see. Make one of these options your base for exploring Calgary:
Stampede park and Calgary Stampede Trailblazer Centre are a couple of leading attractions to add to your Calgary travel itinerary. Keep the momentum going by heading to Calgary Tower.

Explore more of Canada

You've done Calgary, now it's time to discover more of Canada. Travel around 274 kilometres 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 129 kilometres north of Calgary, Red Deer is another favourite stop in Canada. Start your sightseeing at Michener Gardens, Discovery Canyon and Waskasoo Creek Trail.