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Cheap Flights from Calgary to Chicago

Compare Calgary to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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Flight deals from Calgary to Chicago

Looking for a cheap last-minute deal or the best return flight from Calgary Airport to Chicago? If you want to travel next month, return fares start from R 5,115. Find the lowest prices on one-way and return tickets right here.
Chicago.R 2,211 per passenger.Departing Sat, 30 May.One-way flight with American Airlines.Outbound indirect flight with American Airlines, departs from Calgary on Sat, 30 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,211, select.
Chicago.R 2,245 per passenger.Departing Wed, 3 Jun.One-way flight with American Airlines.Outbound direct flight with American Airlines departs from Calgary on Wed, 3 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,245, select.
Chicago.R 2,415 per passenger.Departing Sat, 30 May.One-way flight with WestJet.Outbound direct flight with WestJet departs from Calgary on Sat, 30 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,415, select.
Chicago.R 2,468 per passenger.Departing Sat, 29 Aug.One-way flight with Air Canada.Outbound indirect flight with Air Canada, departs from Calgary on Sat, 29 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,468, select.
Chicago.R 2,473 per passenger.Departing Mon, 5 Oct.One-way flight with Air Canada.Outbound indirect flight with Air Canada, departs from Calgary on Mon, 5 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,473, select.
Chicago.R 2,477 per passenger.Departing Fri, 4 Sep.One-way flight with WestJet.Outbound direct flight with WestJet departs from Calgary on Fri, 4 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,477, select.
Chicago.R 2,488 per passenger.Departing Mon, 5 Oct.One-way flight with WestJet.Outbound direct flight with WestJet departs from Calgary on Mon, 5 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,488, select.
Chicago.R 2,563 per passenger.Departing Sat, 12 Dec.One-way flight with Delta.Outbound indirect flight with Delta, departs from Calgary on Sat, 12 Dec, arriving in Chicago Midway.Price includes taxes and charges.From R 2,563, select.
Chicago.R 2,655 per passenger.Departing Fri, 11 Dec.One-way flight with WestJet.Outbound direct flight with WestJet departs from Calgary on Fri, 11 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,655, select.
Chicago.R 2,656 per passenger.Departing Mon, 30 Nov.One-way flight with WestJet.Outbound direct flight with WestJet departs from Calgary on Mon, 30 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,656, select.
Chicago.R 2,668 per passenger.Departing Sun, 30 Aug.One-way flight with WestJet.Outbound direct flight with WestJet departs from Calgary on Sun, 30 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,668, select.
Chicago.R 2,699 per passenger.Departing Wed, 22 Jul.One-way flight with Air Canada.Outbound indirect flight with Air Canada, departs from Calgary on Wed, 22 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,699, select.
Chicago.R 2,712 per passenger.Departing Thu, 18 Feb.One-way flight with United.Outbound direct flight with United departs from Calgary on Thu, 18 Feb, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,712, select.
Chicago.R 2,734 per passenger.Departing Sat, 10 Apr.One-way flight with Air Canada.Outbound indirect flight with Air Canada, departs from Calgary on Sat, 10 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,734, select.
Chicago.R 2,803 per passenger.Departing Tue, 12 Jan.One-way flight with Delta.Outbound indirect flight with Delta, departs from Calgary on Tue, 12 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,803, select.
Chicago.R 3,043 per passenger.Departing Tue, 21 Jul.One-way flight with WestJet.Outbound direct flight with WestJet departs from Calgary on Tue, 21 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 3,043, 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.
May
from R 2,211
Jun
from R 2,245
Jul
from R 2,699
Aug
from R 2,468
Sep
from R 2,477
Oct
from R 2,473
Nov
from R 2,656
Dec
from R 2,563
Jan
from R 2,803
Feb
from R 2,712
Mar
Find prices
Apr
from R 2,734

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.

Chicago Midway

14km from central Chicago
Closest
from R 2,563
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from R 2,211
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
from R 3,487
Search flights

Calgary to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 2,211
Cheapest month to flyMay
Average flight time3 hrs, 36 mins
Most popular airlineQatar Airways
Average flights per week89

Finding cheap flights from Calgary to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Calgary to Chicago is R 3,875. 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 36 minutes is the average flight time from Calgary to Chicago.
Qatar Airways, American Airlines and Air Canada fly direct from Calgary to Chicago.
As of May 2026, there are 178 flights per week flying from Calgary to Chicago.
The cheapest month to fly from Calgary to Chicago is usually May.
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 R 3,875.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Calgary Airport to Chicago on Friday, 29 May 2026.
Yes – the average flight time is 3 hours and 36 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 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.
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.
In May, the average temperature is usually around 13°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.
Currently, WestJet offers the cheapest flight tickets to Chicago.

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

  • Around 3 hours 50 minutes is how long you can expect to be in the air on a direct flight from Calgary International Airport to Chicago.

  • Calgary International Airport is located in Calgary. Following the UTC-6 timezone, Chicago is one hour ahead of Calgary.

  • With 22 weekly flights between the two airports, Calgary International Airport (YYC) to Chicago O'Hare International Airport (ORD) is the busiest route. American Airlines operates the earliest flight at 06:29. If you'd like to get more out of your day before leaving, the last departure from YYC to ORD is with American Airlines at 13:27.

  • For hassle-free travel, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This leaves you with plenty of time to catch your YYC to Chicago flight.

  • You can expect longer lines in popular months like July. Arriving up to four hours in advance for international flights and two hours for domestic departures is a smart move.

  • Direct Calgary International Airport to Chicago tickets are available for booking. Chicago O'Hare International Airport (ORD) is where you'll be landing.

  • Top carriers that operate direct flights from Calgary International Airport to Chicago include:

  • Located around 10 kilometres from central Calgary, YYC can be reached in about 25 minutes by car. The journey on public transport takes roughly 45 minutes.

  • Booked an early flight from Calgary International Airport to Chicago? Avoid the hassle of rushing to the airport (and sneak in some extra snooze time) by choosing one of these hotels near YYC:

  • 76% of flights departing from Calgary International Airport land at their destination on time.

  • You'll find YYC at 2000 Airport Road Northeast.

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

  • R 2,211 is currently the lowest price for a one-way Calgary International Airport to Chicago flight. Return plane tickets start from R 3,875. These prices may change depending on availability and demand.

  • To find cheap flights from YYC to Chicago, book in advance. Airlines tend to offer lower prices when flights are first released.

  • The 'Whole month' search tool will show you the cheapest tickets from Calgary International Airport to Chicago across the month. It's a good way to find a bargain if your plans are flexible.

  • Locking in a cheap flight from YYC to Chicago is a breeze with Price Alerts. Simply create one of these automatic notifications and we'll let you know when a new discount appears.

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

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Chicago O'Hare International Airport (ORD) to central Chicago takes around 30 minutes to reach by car. The centre is roughly 27 kilometres away.

  • Getting there by public transport takes about 45 minutes.

  • If you're coming in on a late flight from Calgary International Airport to Chicago, nothing beats the convenience of staying near the terminal. Grab your bags from the carousel and then be showered and snoozing not long after at one of these accommodation options near ORD:

  • Reserving your ride from Chicago O'Hare International Airport about four weeks ahead of your flight from YYC to Chicago can help you lock in the best possible rate.

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

Chicago Midway International Airport (MDW)

  • Central Chicago is around 16 kilometres from Chicago Midway International Airport (MDW). Once your flight from Calgary International Airport to Chicago has hit the runway and you've navigated your way to arrivals, the drive should take about 25 minutes.

  • If you travel by public transport, the ride to the centre will take you 30 minutes or so.

  • Following your YYC to Chicago flight, unwind at a hotel near MDW. These are some comfortable options that'll help you get into relaxation mode:

  • Avoid last-minute price surges. Reserving your ride four weeks before your arrival at MDW will help you save.

  • You'll find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Step off your flight from Calgary International Airport to Chicago and go straight to your hotel or jump right into sightseeing. The centre of Chicago is around 145 kilometres from Chicago Rockford International Airport (RFD) and typically takes 1 hour 40 minutes to drive there.

  • Public transport can get you there in about 2 hours.

  • Check in to a hotel near RFD and go from landing to lounging in your room in a flash. Whether you're arriving on a late YYC to Chicago flight or just want a hassle-free arrival, these stays offer convenience when you need it most:

  • If you're hoping for a specific kind of vehicle, booking early gives you a better shot at getting what you want. Book your ride from RFD at least a few weeks ahead of your flight from Calgary International Airport to Chicago.

  • Chicago Rockford International Airport's address is 2 Airport Cir.

Best time to go to Chicago

  • July is the busiest month for flights from Calgary International Airport to Chicago. To avoid the crowds, visit Chicago in January.

  • Book a Calgary International Airport to Chicago plane ticket with a departure in July if you're eager to experience the city during its warmest month. Expect temperatures to range from 16ºC (61ºF) to 28ºC (82ºF).

  • If you want to travel in cooler conditions, look for a cheap ticket from YYC to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

  • When it comes to searching for somewhere to lay your head, you'll find the best stays in Chicago right here. Explore these options once you've locked in your flight from Calgary International Airport to Chicago:

  • There are so many things to do and see in this city it can be hard to know where to start. Art Institute of Chicago, Millennium Park and Willis Tower are major attractions which should be on any well-planned Chicago itinerary.

Explore more of the United States

  • Chicago will leave a lasting impression, but there are so many other parts of the United States waiting to be explored. About 451 kilometres southeast of Chicago, a visit to Columbus will fill your itinerary to the brim. Don't miss top attractions like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • Around 257 kilometres southeast of Chicago, Indianapolis is another essential stop in the United States. Start your sightseeing at Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

Plan the rest of your trip from Calgary to Chicago

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