Cheap Flights from Calgary to Chicago from P7,964

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Flight deals from Calgary to Chicago

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

Chicago.P7,964 per passenger.Departing Mon, 12 May, returning Thu, 15 May.Return flight with WestJet.Outbound direct flight with WestJet departs from Calgary on Mon, 12 May, arriving in Chicago O'Hare International.Inbound direct flight with WestJet departs from Chicago O'Hare International on Thu, 15 May, arriving in Calgary.Price includes taxes and charges.From P7,964, select.

Chicago.P9,768 per passenger.Departing Sun, 20 Apr, returning Sun, 27 Apr.Return flight with WestJet.Outbound direct flight with WestJet departs from Calgary on Sun, 20 Apr, arriving in Chicago O'Hare International.Inbound direct flight with WestJet departs from Chicago O'Hare International on Sun, 27 Apr, arriving in Calgary.Price includes taxes and charges.From P9,768, select.

Chicago.P10,080 per passenger.Departing Tue, 16 Sep, returning Sat, 20 Sep.Return flight with WestJet.Outbound direct flight with WestJet departs from Calgary on Tue, 16 Sep, arriving in Chicago O'Hare International.Inbound direct flight with WestJet departs from Chicago O'Hare International on Sat, 20 Sep, arriving in Calgary.Price includes taxes and charges.From P10,080, select.

Chicago.P10,799 per passenger.Departing Wed, 20 Aug, returning Thu, 11 Sep.Return flight with WestJet.Outbound direct flight with WestJet departs from Calgary on Wed, 20 Aug, arriving in Chicago O'Hare International.Inbound direct flight with WestJet departs from Chicago O'Hare International on Thu, 11 Sep, arriving in Calgary.Price includes taxes and charges.From P10,799, select.

Chicago.P10,828 per passenger.Departing Wed, 9 Jul, returning Wed, 16 Jul.Return flight with WestJet.Outbound direct flight with WestJet departs from Calgary on Wed, 9 Jul, arriving in Chicago O'Hare International.Inbound direct flight with WestJet departs from Chicago O'Hare International on Wed, 16 Jul, arriving in Calgary.Price includes taxes and charges.From P10,828, select.

Chicago.P11,091 per passenger.Departing Sat, 31 May, returning Sun, 1 Jun.Return flight with WestJet.Outbound direct flight with WestJet departs from Calgary on Sat, 31 May, arriving in Chicago O'Hare International.Inbound direct flight with WestJet departs from Chicago O'Hare International on Sun, 1 Jun, arriving in Calgary.Price includes taxes and charges.From P11,091, select.

Chicago.P11,114 per passenger.Departing Thu, 30 Oct, returning Sun, 2 Nov.Return flight with WestJet.Outbound direct flight with WestJet departs from Calgary on Thu, 30 Oct, arriving in Chicago O'Hare International.Inbound direct flight with WestJet departs from Chicago O'Hare International on Sun, 2 Nov, arriving in Calgary.Price includes taxes and charges.From P11,114, select.

Chicago.P11,431 per passenger.Departing Fri, 21 Mar, returning Wed, 26 Mar.Return flight with United.Outbound indirect flight with United, departs from Calgary on Fri, 21 Mar, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Wed, 26 Mar, arriving in Calgary.Price includes taxes and charges.From P11,431, select.

Find the cheapest month to fly from Calgary to Chicago

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

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Direct flights from Calgary to Chicago

Alternative Calgary to Chicago routes

Looking for the cheapest, fastest or easiest route from Calgary to Chicago? You could fly into the following airports instead.

Calgary to Chicago: Flight information

The things to know before you go.

Cheapest flight found	P7,964
Cheapest month to fly	May
Average flight time	3 hrs, 28 mins
Most popular airline	Qatar Airways
Average flights per week	65

Finding cheap flights from Calgary to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.

How much are return flights from Calgary to Chicago?

The best price we found for a return flight from Calgary to Chicago is P7,964. 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 Calgary to Chicago?

3 hours and 28 minutes is the average flight time from Calgary to Chicago.

Which airlines fly direct from Calgary to Chicago?

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

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

As of February 2025, there are 65 flights per week flying from Calgary to Chicago.

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

The cheapest month to fly from Calgary to Chicago is usually February 2025.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Calgary Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from P7,964.

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

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Calgary Airport to Chicago on Monday, 12 May 2025.

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

Yes – the average flight time is 3 hours and 28 minutes.

How can I get the best flight deal from Calgary Airport to Chicago?

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 Chicago 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 Chicago?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

What’s the weather like in Chicago?

In February, the average temperature is usually around -2°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.

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

Currently, WestJet offers the cheapest flight tickets to Chicago.

Travelling from Calgary International Airport (YYC) to Chicago: what you need to know

Expect to be in the air for 3 hours 46 minutes. That's the average duration of a direct flight from Calgary International Airport to Chicago.
Calgary International Airport is located in Calgary. Based in the UTC-5 timezone, Chicago is 1 hour ahead of Calgary.
The most popular route is from Calgary International Airport (YYC) to O'Hare International Airport (ORD). Choose from 21 weekly services between these two airports. If you'd like to head off as soon as possible, the earliest flight from YYC to ORD is the 08:30 United service. If you'd rather travel later, the final departure is at 13:30 with American Airlines.
For stress-free travel, arrive at the airport two hours ahead of international flights and an hour before domestic departures. This ensures you have enough time to catch your flight from YYC to Chicago.
You can expect longer lines in popular months like July and other peak seasons. Arriving up to four hours in advance for an international flight and two hours for a domestic departure is a wise move.
You can get a direct flight from Calgary International Airport to Chicago. Start your trip at YYC and end it at O'Hare International Airport (ORD).
Pick from a variety of airlines that offer direct flights from Calgary International Airport to Chicago. Book your seat with one of these:
You can travel to United States for tourism purposes without a visa if you have a passport from Canada. But before reserving your cheap tickets from Calgary International Airport to Chicago, double-check for the newest rules and regulations. Visa rules are subject to change, and you may require some documentation if your trip is for work or other reasons.
The journey from central Calgary to YYC takes approximately 1 hour and 1 minute on public transport. If you ride-share, drive or take a cab, you'll cover the 16 kilometres in 20 minutes or so, depending on traffic conditions.
Looking for a convenient hotel near YYC? If you're boarding an early flight from Calgary International Airport to Chicago, these stays will have you sleeping moments from your departure lounge:

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

P5,510 is the lowest price we've found for a one-way ticket from Calgary International Airport to Chicago. For a return flight on this route, the best price is P7,964. Depending on when you want to go and the availability, these fares can change.
Book 9 months before flying. After crunching the numbers on our calendar, this is how far you'll want to book ahead to find cheap tickets from YYC to Chicago.
Organise your trip for May. That's the cheapest month for tickets from Calgary International Airport to Chicago. If you have flexibility with your dates, use the 'Whole month' tool to see the cheapest price across each month.
Log into your online account or use the app to create a Price Alert. We'll notify you right away if there's a cheaper deal on this route. It doesn't take long, and it'll save you from looking for cheap tickets from YYC to Chicago every day.
Tailor your travel plans with filters. Select your departure and arrival times, airlines and total journey duration. You can also sort results by 'Cheapest,' 'Fastest' or 'Best' flights from Calgary International Airport to Chicago.

Airports in Chicago

O'Hare International Airport (ORD)

O'Hare International Airport (ORD) is around 40 kilometres from central Chicago. With a cab or in your own car rental, the drive is about 35 minutes.
Travelling by public transport takes about 54 minutes.
The last thing you need is a long journey to your hotel if you're getting in late on a flight from Calgary International Airport to Chicago. Book one of these accommodation options near ORD instead:

Chicago Midway International Airport (MDW)

After your flight from Calgary International Airport to Chicago has landed, you can reach the city centre in around 21 minutes by car. Central Chicago is approximately 19 kilometres from Chicago Midway International Airport (MDW).
You can also travel by public transport, which will take around 46 minutes.
There are some great places ready to welcome you near MDW. Settle in and get cosy after your flight from YYC to Chicago at one of these well-located options:

Best time to go to Chicago

August is the busiest month to hop on a flight from Calgary International Airport to Chicago while February is the quietest. To work out the ideal time to go to Chicago, consider the pace you prefer to travel at.
Book your flight from Calgary International Airport to Chicago for July to visit the city during its warmest month. Expect temperatures to range from 15ºC to 29ºC.
January sees average temperatures of between -12ºC and 3ºC. Search for cheap flights from YYC to Chicago around that time if you like travelling in cooler conditions.

More about Chicago

After booking your flight from Calgary International Airport to Chicago, think about where you'd like to stay in this city. Make one of these options your base for exploring Chicago:
There are so many things to do and see in this city it can be hard to work out where to start. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are leading attractions which should feature on any well-planned Chicago itinerary.

Complete your Chicago trip with a car rental

We use the same magic that helped you find your cheap flight from Calgary International Airport to Chicago to track down deals on car rentals. Search for your ride in seconds and compare offers in one place. Plus you'll find all the info you need to know about car rentals in Chicago, from the most popular car type to the average daily price.