ORD - YYC

C$ 83 Find Cheap Flights from Chicago to Calgary

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Calgary departing on 27/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Calgary

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Calgary, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Calgary, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Chicago to Calgary (ORD-YYC)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Calgary that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Calgary

qui, 17 jul - ter, 22 jul
WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
WestJet Logo
12:15 p.m. - 4:44 p.m.YYC-ORD
3h 29mdirect
C$ 215WestJet
Find Deal
ter, 15 jul - ter, 22 jul
WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
WestJet Logo
12:15 p.m. - 4:44 p.m.YYC-ORD
3h 29mdirect
C$ 216WestJet
Find Deal
seg, 14 jul - qua, 23 jul
 Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
 Logo
11:45 p.m. - 9:09 a.m.YYC-ORD
8h 24m1 stop
C$ 235
Find Deal
seg, 22 set - seg, 29 set
Air Canada Logo
3:35 p.m. - 11:16 p.m.ORD-YYC
8h 41m1 stop
Air Canada Logo
1:10 a.m. - 9:51 a.m.YYC-ORD
7h 41m1 stop
C$ 276Air Canada
Find Deal
ter, 24 jun - seg, 30 jun
United Airlines Logo
5:02 a.m. - 6:21 p.m.ORD-YYC
14h 19m1 stop
United Airlines Logo
6:15 a.m. - 10:34 p.m.YYC-ORD
15h 19m1 stop
C$ 282United Airlines
Find Deal
seg, 11 ago - qui, 14 ago
United Airlines Logo
8:03 p.m. - 10:53 p.m.ORD-YYC
3h 50mdirect
United Airlines Logo
7:30 p.m. - 11:25 a.m.YYC-ORD
14h 55m1 stop
C$ 283United Airlines
Find Deal
ter, 22 jul - ter, 29 jul
 Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
 Logo
12:38 p.m. - 5:10 p.m.YYC-ORD
3h 32mdirect
C$ 284
Find Deal
qui, 25 set - seg, 29 set
Air Canada Logo
6:20 p.m. - 1:12 a.m.ORD-YYC
7h 52m1 stop
Air Canada Logo
1:10 a.m. - 9:51 a.m.YYC-ORD
7h 41m1 stop
C$ 286Air Canada
Find Deal
ter, 14 out - sáb, 25 out
American Airlines Logo
9:47 a.m. - 12:32 p.m.ORD-YYC
3h 45mdirect
American Airlines Logo
1:27 p.m. - 5:52 p.m.YYC-ORD
3h 25mdirect
C$ 324American Airlines
Find Deal
qui, 11 set - ter, 16 set
American Airlines Logo
8:30 p.m. - 11:19 p.m.ORD-YYC
3h 49mdirect
American Airlines Logo
6:45 a.m. - 7:15 p.m.YYC-ORD
11h 30m1 stop
C$ 345American Airlines
Find Deal
Expert advice

Expert advice for your flight from Chicago to Calgary

 
Snippets provided in this section are AI-generated based on a summarisation of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
WestJet

WestJet's Premium cabin offers priority boarding and two free checked bags.


WestJet's Extended Comfort seats offer up to 15 cm extra legroom and priority boarding.

Read more about WestJetby Stefanie Waldek
United Airlines

United offers Priority Boarding to avoid gate-checking carry-ons, placing you in Zone 2.


United's Economy Plus seats provide up to 15 cm more legroom than standard economy.

Air Canada

Air Canada offers priority check-in for higher fare classes and elite status holders.


Air Canada's Preferred Economy seats offer up to 10 cm extra legroom for a fee.

Read more about Air Canadaby Stefanie Waldek
Airports
ORD

Security lines at O'Hare can exceed 30 minutes during peak times. Arrive early to avoid delays.

Read more about ORDby Stefanie Waldek
YYC

For a quick city transfer, take bus #300 from YYC to downtown Calgary in about 40 minutes.

Read more about YYCby Lucas Aykroyd
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on WestJet, United Airlines, Air Canada and ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Lucas Aykroyd

Lucas Aykroyd

Expert on YYC

Lucas Aykroyd

Lucas Aykroyd

Lucas Aykroyd is an award-winning travel writer based in Vancouver (YVR). His favorite adventures include tracking polar bears in Nunavut and rafting over a waterfall in New Zealand. Lucas has written for the in-flight magazines of Delta, SAS, and Porter Airlines. He is also a National Geographic and Toronto Star contributor.

Read more
Useful Info

KAYAK's insights & trends for Chicago to Calgary flights

Get data-powered insights and trends into flights from Chicago to Calgary to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago to Calgary?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Calgary clicked on KAYAK for each day over the last 12 months.

When flying from Chicago to Calgary, you should consider leaving on a Monday and avoid Sundays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Fridays and the most expensive ones on Tuesdays.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Calgary?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Calgary, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Calgary is May, where tickets cost C$ 291 (return) on average. On the other hand, the most expensive months are December and July, where the average cost of round-trip tickets is C$ 785 and C$ 429 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Calgary?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Calgary, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Calgary, you should book around 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.


Good to know

Low seasonFebruary
High seasonJuly
Cheapest flightC$ 83
Best time to beat the crowds (22% less expensive on average)
Most popular time to fly (6% more expensive on average)
Flight from Chicago to Calgary

When to book flights from Chicago to Calgary

Are your dates flexible? Find out the best times to travel from Chicago to Calgary based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Calgary flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Calgary?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Calgary was C$ 61 for a one-way ticket and C$ 157 for a round-trip.

  • Which airports will I be using when flying from Chicago to Calgary?

    Chicago airport is called Chicago O'Hare Intl and the only airport in Calgary is Calgary.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Calgary?

    All the following airlines offer inflight Wi-Fi service on the Chicago to Calgary flight route: American Airlines, Air Canada, United Airlines, British Airways, KLM, WestJet, and Delta.

  • Which aircraft models fly most regularly from Chicago to Calgary?

    The Boeing 737-700 is the aircraft model that flies most regularly on the Chicago to Calgary flight route.

  • Which airline alliances offer flights from Chicago to Calgary?

    oneworld, Star Alliance, and SkyTeam are the airline alliances operating flights between Chicago and Calgary, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Calgary?

    There are direct flights from Chicago to Calgary on a daily basis.

  • Which is the best airline for flights from Chicago to Calgary, United Airlines or WestJet?

    The two airlines most popular with KAYAK users for flights from Chicago to Calgary are United Airlines and WestJet. With an average price for the route of C$ 592 and an overall rating of 7.4, United Airlines is the most popular choice. WestJet is also a great choice for the route, with an average price of C$ 300 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Chicago to Calgary?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Calgary.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Calgary?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Calgary from Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Calgary?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Calgary with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Calgary?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Calgary from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago O'Hare Intl Airport to Calgary

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 162 or less one-way and C$ 248 or less round-trip.

Prefer to fly direct from Chicago to Calgary?

Find which airlines fly direct from Chicago O'Hare Intl Airport to Calgary Airport, which days they fly and book direct flights.

Direct departures

Chicago O'Hare Intl to Calgary

Monday

Air Canada,American Airlines,Avianca, +7 more

Air Canada,American Airlines, +8 more

Tuesday

Air Canada,American Airlines,Avianca, +7 more

Air Canada,American Airlines, +8 more

Wednesday

Air Canada,American Airlines,Avianca, +7 more

Air Canada,American Airlines, +8 more

Thursday

Air Canada,American Airlines,Avianca, +7 more

Air Canada,American Airlines, +8 more

Friday

Air Canada,American Airlines,Avianca, +7 more

Air Canada,American Airlines, +8 more

Saturday

Air Canada,American Airlines,Avianca, +7 more

Air Canada,American Airlines, +8 more

Sunday

Air Canada,American Airlines,Avianca, +7 more

Air Canada,American Airlines, +8 more

See more nonstop flights

Direct returns

Calgary to Chicago O'Hare Intl

Monday

Air Canada,American Airlines,Avianca, +7 more

Air Canada,American Airlines, +8 more

Tuesday

Air Canada,American Airlines,Avianca, +7 more

Air Canada,American Airlines, +8 more

Wednesday

Air Canada,American Airlines,Avianca, +7 more

Air Canada,American Airlines, +8 more

Thursday

Air Canada,American Airlines,Avianca, +7 more

Air Canada,American Airlines, +8 more

Friday

Air Canada,American Airlines,Avianca, +7 more

Air Canada,American Airlines, +8 more

Saturday

Air Canada,American Airlines,Avianca, +7 more

Air Canada,American Airlines, +8 more

Sunday

Air Canada,American Airlines,Avianca, +7 more

Air Canada,American Airlines, +8 more

See more nonstop flights
See more nonstop flights

Top 3 airlines serving from Chicago to Calgary

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Calgary. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Calgary? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 8790 reviews
8.1Crew
6.6Food
7.3Comfort
7.0Entertainment
7.7Boarding
Airline reviews

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

4.0 OkayJ, May 2025ORD - EDI
Read more United Airlines reviews

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

They switched out gate from terminal 1 to terminal two ten minutes before boarding. So we had to make a 20 min crazy fast walk to a different terminal. Then we boarded the plane and waited for over 40 minutes until push back. Brutal

We purchased premium flex tickets for our overseas flight to London. I have food, allergies, so I knew I wouldn't be able to get a full meal. WestJet doesn't seem to provide any way for people like myself to register their allergies ahead of time. I was given one small package of crackers and cheese as my meal. I was told there were no more packages available and no other alternatives for food. The flight attendant seemed quite disinterested in providing service. That stands in stark contrast to other Westjet flights where the flight attendants have gone out of their way to provide service.

Lots of overhead storage and a good crew and service.

The flight was ahead of schedule. A half glass of juice and a cookie is pathetic! No entertainment possibilities. Not even a plug-in for phone or IPad if you wanted to watch a downloaded movie. Back to flying Air Canada!

The flight was ahead of schedule. A half glass of juice and a cookie is pathetic!

Our flight was delayed for almost 2 hours resulting in a rush to connect to our next flight

Good. Would be better if the carry on baggage was free.

Flight cancelled and Kayak switched our return flight to a red eye. Ridiculous.

Limited water service in a 6 hour flight offered at the very beginning and end of the flight.

They delayed flight because lack of staff then missed connection. Never flying with kayak or weather

WestJet claims that tickets purchased through a 3rd party (such as you kayak) they cannot make sure they mention the luggage situation. We purchased tickets that wouldn’t allowed any carry on. WHAT!? So ridiculous. We bought them and there was not one single place mentioning that. Then on our departure the WstJet attendant was a super nasty rude person. Very unprofessional, unpleasant. She should be reprimanded and given some sort of training but I believe that won’t change her nasty disposition. On our return was great, the front desk gentleman was really professional, friendly and helpful. He offered us to pay $18 usd each for our carry on backpacks as they were small (instead of $90 each at the departure, she could have mentioned but decided not to do so. Didn’t print my boarding pass with my full name as in the passport and made the flight delay because the crew needed to correct it).

Service Director cut all cabin lights and window screens defaulted to dark, but it was an afternoon flight going west. I spent hours trying to see what was reading as reading lights weren't working either. What the hell.

The food could have been better. The flight attendant was the friendliest and most helpful I have ever had.

Miserable staff as it was a late/delayed flight and crew wasn’t in the best spirits. Completely understood as neither was most of the passengers. Still unacceptable l.

It was a short flight, and no entertainment. That was not a problem for us, but there is no option for "not applicable". There was a bit of turbulence, so there was no food service.

All was good except for the seats, not very comfy.

2.5 hour delay sitting in the plane on the tarmac, you tell me how the experience was

This flight didn't happen for me because of overbooking.

Everything was simple and easy. The lady at the gate was super friendly, I wish I had her name to share. She's a little older, dark-haired. You can tell she likes her job and would be a great influence on any young people training with her.

The Entertainment system was nearly useless because videos kept stopping then jumping over segments at random but closely spaced intervals. About 75% of the plane gave up trying to watch and then the gaps and jumps became shorter, It was terrible and made it hard to know what was happening since it was not a normal buffering pause where you still get the cont6en t. Instead the video would pause then jump ahead missing short segments and dialog entirely! The economy class seats on all flights have less and less legroom. I’m tall and the upgraded seats are no better for the leg room, not worth it. I flew from Toronto to Calgary….The staff at YYZ was awesome and kind. My flight’s (prior) incoming plane from Liberia had been delayed over 3 hours and the attendant quickly and kindly transferred me to the earlier flight that got me in hours earlier. Such a great staff!! Every staff member on the plane was very-very Canadian/Kind . Great job and attitude you folks! The plane itself was new and in great condition, except the issue with the video streaming.

I did not like ANYTHING about Discover....see my previous comments regarding our trip. I will do everything possible never to fly with Discover again!!!

Everything you need to know for your flight from Chicago to Calgary

Information on your arrival and departure airports

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