ORD - YYC

C$ 102 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 7/11. 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, 0 bags

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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Expert advice
Flight 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

Fri, 20 Feb - Mon, 23 Feb
WestJet Logo
2:20 p.m. - 5:15 p.m.ORD-YYC
3h 55mdirect
WestJet Logo
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
C$ 235WestJet
Find Deal
Fri, 23 Jan - Fri, 30 Jan
WestJet Logo
2:20 p.m. - 5:15 p.m.ORD-YYC
3h 55mdirect
WestJet Logo
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
C$ 243WestJet
Find Deal
Sat, 13 Dec - Fri, 9 Jan
Multiple Airlines Logo
1:24 p.m. - 3:10 p.m.ORD-YYC
26h 46m2 stops
Multiple Airlines Logo
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
C$ 284Multiple Airlines
Find Deal
Sat, 13 Dec - Fri, 9 Jan
Multiple Airlines Logo
1:24 p.m. - 11:44 a.m.ORD-YYC
23h 20m1 stop
Multiple Airlines Logo
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
C$ 290Multiple Airlines
Find Deal
Wed, 10 Dec - Sat, 13 Dec
United Airlines Logo
8:45 a.m. - 11:35 a.m.ORD-YYC
3h 50mdirect
United Airlines Logo
12:37 p.m. - 5:10 p.m.YYC-ORD
3h 33mdirect
C$ 304United Airlines
Find Deal
Sat, 10 Jan - Sat, 17 Jan
United Airlines Logo
8:45 a.m. - 11:35 a.m.ORD-YYC
3h 50mdirect
United Airlines Logo
12:37 p.m. - 5:08 p.m.YYC-ORD
3h 31mdirect
C$ 316United Airlines
Find Deal
Wed, 18 Feb - Tue, 24 Feb
Air Canada Logo
3:35 p.m. - 11:44 p.m.ORD-YYC
9h 09m1 stop
Air Canada Logo
5:45 a.m. - 2:55 p.m.YYC-ORD
8h 10m1 stop
C$ 319Air Canada
Find Deal
Sat, 10 Jan - Sat, 17 Jan
Air Canada Logo
3:55 p.m. - 12:14 a.m.ORD-YYC
9h 19m1 stop
Air Canada Logo
5:45 a.m. - 2:55 p.m.YYC-ORD
8h 10m1 stop
C$ 327Air Canada
Find Deal
Tue, 2 Dec - Sun, 7 Dec
American Airlines Logo
8:45 p.m. - 11:44 a.m.ORD-YYC
15h 59m1 stop
American Airlines Logo
6:30 a.m. - 10:19 p.m.YYC-ORD
14h 49m1 stop
C$ 336American Airlines
Find Deal
Fri, 5 Dec - Mon, 8 Dec
American Airlines Logo
10:05 p.m. - 11:44 a.m.ORD-YYC
14h 39m1 stop
American Airlines Logo
6:30 a.m. - 10:18 p.m.YYC-ORD
14h 48m1 stop
C$ 338American Airlines
Find Deal

Everything you should know

Our travellers' advice
AI-generated summary based on content written by travel experts
United's Economy Plus offers 15 cm more legroom.
Expect over 30-minute waits at O'Hare security.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
WestJet
Cheapest • from C$ 235 (round-trip)
WestJet
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
4 weeks
in advance
Our data shows that travellers who book at least 4 weeks in advance save around 40% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
May
Cheapest • 27% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
C$ 235
Overall average: C$ 354
WestJet
Fri 20/2Mon 23/2
ORD - YYC • Direct
Cheapest one-way flights
C$ 102
Typical prices: C$ 134-C$ 382
WestJet
Fri 7/11
ORD - YYC • Direct
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KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Calgary!
Booking Insights

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 Wednesday 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$ 720 and C$ 449 respectively.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Calgary?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of C$ 517, prices are generally cheapest when you fly direct.

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, which saves you about 40% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Find deals
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
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
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.

Read more about United Airlinesby Stefanie Waldek
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
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 Air Canada, United Airlines, WestJet 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

Good to know

Low seasonJanuary
Cheapest flightC$ 102
Best time to beat the crowds (17% less expensive on average)
Most popular time to fly (13% 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$ 102 for a one-way ticket and C$ 235 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?

    American Airlines, Air Canada, United Airlines, KLM, and Alaska Airlines offer inflight Wi-Fi service on the Chicago to Calgary flight route.

  • 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.

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

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

  • 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$ 165 or less one-way and C$ 266 or less round-trip.

Prefer to fly direct from Chicago to Calgary?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago O'Hare Intl 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

United Airlines,WestJet,American Airlines

United Airlines,WestJet, +1 more

Tuesday

United Airlines,American Airlines

United Airlines,American Airlines

Wednesday

United Airlines,American Airlines

United Airlines,American Airlines

Thursday

United Airlines,American Airlines

United Airlines,American Airlines

Friday

United Airlines,WestJet,American Airlines

United Airlines,WestJet, +1 more

Saturday

United Airlines,American Airlines

United Airlines,American Airlines

Sunday

United Airlines,WestJet,American Airlines

United Airlines,WestJet, +1 more

See more nonstop flights

Direct returns

Calgary to Chicago O'Hare Intl

Monday

United Airlines,WestJet,American Airlines

United Airlines,WestJet, +1 more

Tuesday

United Airlines,American Airlines

United Airlines,American Airlines

Wednesday

United Airlines,American Airlines

United Airlines,American Airlines

Thursday

United Airlines,American Airlines

United Airlines,American Airlines

Friday

United Airlines,WestJet,American Airlines

United Airlines,WestJet, +1 more

Saturday

United Airlines,American Airlines

United Airlines,American Airlines

Sunday

United Airlines,WestJet,American Airlines

United Airlines,WestJet, +1 more

See more nonstop flights

Reviews of the top airline flying 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.
7.2
WestJetOverall score based on 3148 reviews
7.1Comfort
7.9Crew
7.4Boarding
6.1Entertainment
6.2Food
Airline reviews

Again, flight was late. It’s expected of this airline now i guess.

2.0 MediocreCamilo, Oct 2025YYJ - YYC
Read more WestJet reviews

Again, flight was late. It’s expected of this airline now i guess.

I rated westjet poor on food for not accepting debit to make in flight purchases. This is dumb.

Delayed 8 hours, This is the 2nd time in a month that my flight was not on time.

The snacks could have been better, and maybe some warm drinks instead of just water cause it was very very cold.

I like and appreciate the attention and patience from all west jet personal to my senior mother. Thank you!!!!

Our first flight from LAX to Winnipeg was changed but you never informed us at all. It went from a nonstop flight to a stay at Calgary. This impacted our trip negatively as we arrived much later than we planned to. Our returning flight was horrible. The flight was delayed 6 hours!! And we were NOT going to wait that long. The only way we got on our original flight was running there. However all of our suitcases were now coming on the delayed flight. It was the worst experience we ever had flying. I want my money back.

Please make more option. And be more precise on the type of food you giving. Diner and breakfast can be different

It was generally pretty good, but the check-in and boarding process were a little difficult. Check in was in terminal 2F, but there was a shuttle required to get to the gate, which added significant time. The gate was changed 30 minutes before boarding, which took us by surprise - we did not get the notice until boarding had started. The check in line moved very slowly - the agent was friendly, but did not seem very efficient/urgent given the growing line.

Delays and missed connections were very hard the crew were wonderful but 1 1/2 hours late from Abbotsford to a 4 hour wait in Calgary was too much. I am 79 years old and I didn’t get to my destination until after 1 in the morning. They could have offered a seat in the lounge or a meal. I was very disappointed in the treatment

No dogs! Can we have no dogs in the cabin? Why was there a yappy little dog behind me? Lucky I had ear plugs. Sorry for others without

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

Information on your arrival and departure airports

Chicago (ORD)
Calgary (YYC)

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