Cheap Flights from Chicago to Calgary

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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 AED 1,052. Find the lowest prices on one-way and round-trip tickets right here.

Calgary.AED 826 per passenger.Departing Wed, May 27, returning Sat, May 30.Round-trip flight with WestJet.Outbound direct flight with WestJet departing from Chicago O'Hare International on Wed, May 27, arriving in Calgary.Inbound direct flight with WestJet departing from Calgary on Sat, May 30, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 826, select.

Calgary.AED 919 per passenger.Departing Thu, Apr 30, returning Thu, May 7.Round-trip flight with Air Canada.Outbound indirect flight with Air Canada, departing from Chicago O'Hare International on Thu, Apr 30, arriving in Calgary.Inbound indirect flight with Air Canada, departing from Calgary on Thu, May 7, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 919, select.

Calgary.AED 936 per passenger.Departing Wed, May 27, returning Wed, Jun 3.Round-trip flight with WestJet.Outbound direct flight with WestJet departing from Chicago O'Hare International on Wed, May 27, arriving in Calgary.Inbound direct flight with WestJet departing from Calgary on Wed, Jun 3, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 936, select.

Calgary.AED 940 per passenger.Departing Thu, Apr 30, returning Thu, May 7.Round-trip flight with WestJet.Outbound direct flight with WestJet departing from Chicago O'Hare International on Thu, Apr 30, arriving in Calgary.Inbound direct flight with WestJet departing from Calgary on Thu, May 7, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 940, select.

Calgary.AED 1,052 per passenger.Departing Sat, Apr 18, returning Sat, Apr 25.Round-trip flight with United.Outbound indirect flight with United, departing from Chicago O'Hare International on Sat, Apr 18, arriving in Calgary.Inbound indirect flight with United, departing from Calgary on Sat, Apr 25, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,052, select.

Calgary.AED 1,093 per passenger.Departing Wed, May 6, returning Sun, Jul 5.Round-trip flight with Air Canada.Outbound indirect flight with Air Canada, departing from Chicago O'Hare International on Wed, May 6, arriving in Calgary.Inbound indirect flight with Air Canada, departing from Calgary on Sun, Jul 5, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,093, select.

Calgary.AED 1,098 per passenger.Departing Sat, Jun 6, returning Wed, Jun 10.Round-trip flight with WestJet.Outbound direct flight with WestJet departing from Chicago O'Hare International on Sat, Jun 6, arriving in Calgary.Inbound direct flight with WestJet departing from Calgary on Wed, Jun 10, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,098, select.

Calgary.AED 1,158 per passenger.Departing Wed, Aug 12, returning Thu, Aug 20.Round-trip flight with United.Outbound direct flight with United departing from Chicago O'Hare International on Wed, Aug 12, arriving in Calgary.Inbound direct flight with United departing from Calgary on Thu, Aug 20, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,158, select.

Calgary.AED 1,215 per passenger.Departing Wed, Jun 10, returning Thu, Jul 2.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago O'Hare International on Wed, Jun 10, arriving in Calgary.Inbound indirect flight with Delta, departing from Calgary on Thu, Jul 2, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,215, select.

Calgary.AED 1,216 per passenger.Departing Thu, Dec 10, returning Mon, Dec 14.Round-trip flight with United.Outbound indirect flight with United, departing from Chicago O'Hare International on Thu, Dec 10, arriving in Calgary.Inbound indirect flight with United, departing from Calgary on Mon, Dec 14, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,216, select.

Calgary.AED 1,216 per passenger.Departing Fri, Sep 18, returning Tue, Sep 22.Round-trip flight with United.Outbound indirect flight with United, departing from Chicago O'Hare International on Fri, Sep 18, arriving in Calgary.Inbound indirect flight with United, departing from Calgary on Tue, Sep 22, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,216, select.

Calgary.AED 1,219 per passenger.Departing Mon, Jul 13, returning Mon, Jul 20.Round-trip flight with United.Outbound indirect flight with United, departing from Chicago O'Hare International on Mon, Jul 13, arriving in Calgary.Inbound indirect flight with United, departing from Calgary on Mon, Jul 20, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,219, select.

Calgary.AED 1,222 per passenger.Departing Fri, Apr 24, returning Thu, Apr 30.Round-trip flight with WestJet.Outbound direct flight with WestJet departing from Chicago O'Hare International on Fri, Apr 24, arriving in Calgary.Inbound direct flight with WestJet departing from Calgary on Thu, Apr 30, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,222, select.

Calgary.AED 1,243 per passenger.Departing Wed, Sep 16, returning Mon, Sep 21.Round-trip flight with United.Outbound direct flight with United departing from Chicago O'Hare International on Wed, Sep 16, arriving in Calgary.Inbound direct flight with United departing from Calgary on Mon, Sep 21, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,243, select.

Calgary.AED 1,295 per passenger.Departing Tue, Aug 25, returning Sat, Sep 5.Round-trip flight with United.Outbound indirect flight with United, departing from Chicago O'Hare International on Tue, Aug 25, arriving in Calgary.Inbound indirect flight with United, departing from Calgary on Sat, Sep 5, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,295, select.

Calgary.AED 1,325 per passenger.Departing Fri, Sep 25, returning Sat, Oct 3.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Chicago O'Hare International on Fri, Sep 25, arriving in Calgary.Inbound indirect flight with Delta, departing from Calgary on Sat, Oct 3, arriving in Chicago O'Hare International.Price includes taxes and charges.From AED 1,325, 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 May.

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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.

Calgary

8km from central Calgary

ClosestCheapest

from AED 823

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Chicago to Calgary: Flight information

The things to know before you go.

Cheapest flight found	AED 826
Cheapest month to fly	May
Average flight time	3 hrs, 54 mins
Most popular airline	American Airlines
Average flights per week	183

Finding cheap flights from Chicago to Calgary: Frequently asked questions

How much are round-trip flights from Chicago to Calgary?

The best price we found for a round-trip flight from Chicago to Calgary is AED 826. 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 54 minutes is the average flight time from Chicago to Calgary.

Which airlines fly direct from Chicago to Calgary?

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

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

There are 61 flights per week flying from Chicago to Calgary, as of March 2026.

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

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

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 Wednesday, May 27, 2026.

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

Yes – the average flight time is 3 hours and 54 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 with from Chicago to Calgary?

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 27 kilometers 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 16 kilometers 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 145 kilometers 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)

The last thing you need is a long journey to your hotel if you're arriving on a late flight from Chicago to Calgary International Airport. Book one of these accommodation options near YYC instead:
Lock in the best possible rate by reserving 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

From Calgary International Airport, central Calgary is around 19 kilometers 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 AED 376. For a return flight on this route, the best price is AED 826. 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 8ºC (46ºF) to 26ºC (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 -22ºC (-8ºF) and 3ºC (37ºF).

More about Calgary

Start your Calgary trip right by choosing the perfect place to stay. Once you've booked your flight from Chicago to Calgary International Airport, browse our selection of accommodation options including:
There are so many things to see and do in this city, it can be hard to figure out where to begin. Calgary Stampede Trailblazer Centre, Calgary Tower and Peace Bridge are popular attractions which should feature on any well-planned Calgary itinerary.

Explore more of Canada

You've done Calgary, now it's time to discover other corners of Canada. Journey about 274 kilometers 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 129 kilometers north of Calgary. Discovery Canyon, Red Deer Mountain Bike Park and Old C.P.R. Bridge are key reasons to visit.