ORD - YYC

C$ 197 Find Cheap Flights from Chicago to Calgary – Compare and Save

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 24/1. 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

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Everything you should know

Cheapest round-trip
C$ 371
Typical prices: C$ 381-C$ 685
WestJet
Wed 19/8Mon 24/8
ORD - YYC • Direct
Cheapest one-way flights
C$ 197
Typical prices: C$ 188-C$ 606
United Airlines
Sun 24/1
ORD - YYC • 1 stop
Advice from real travellers
AI-powered summary based on content written by travel experts. AI can make mistakes.
WestJet Premium adds 2 free checked bags; United Economy Plus adds legroom.
Air Canada Preferred Economy and WestJet Extended Comfort add legroom for a fee.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from C$ 371 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
+1
Direct flights
You can fly direct with American Airlines, United Airlines, and WestJet. Average duration is 3h 54m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Most punctual • 73% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travellers who book at least 3 weeks in advance save around 13% compared to booking last minute.
Insights
Insights
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Insights
When to travel
Cheapest • 31% price drop
Most popular
Good to know
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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

Wed, 19 Aug - Mon, 24 Aug
WestJet Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
WestJet Logo
12:00 p.m. - 4:40 p.m.
YYC
-
ORD
3h 40mdirect
C$ 371WestJet
Tue, 1 Sep - Thu, 10 Sep
WestJet Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
WestJet Logo
12:00 p.m. - 4:40 p.m.
YYC
-
ORD
3h 40mdirect
C$ 371WestJet
Tue, 1 Sep - Wed, 9 Sep
Multiple Airlines Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
Multiple Airlines Logo
1:00 a.m. - 10:15 a.m.
YYC
-
ORD
8h 15m
1 stop
C$ 371Multiple Airlines
Wed, 19 Aug - Thu, 27 Aug
WestJet Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
WestJet Logo
12:00 p.m. - 4:40 p.m.
YYC
-
ORD
3h 40mdirect
C$ 372WestJet
Wed, 19 Aug - Fri, 28 Aug
WestJet Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
WestJet Logo
12:00 p.m. - 4:40 p.m.
YYC
-
ORD
3h 40mdirect
C$ 372WestJet
Tue, 22 Sep - Mon, 23 Nov
Multiple Airlines Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
Multiple Airlines Logo
1:45 a.m. - 10:07 a.m.
YYC
-
ORD
8h 22m
1 stop
C$ 381Multiple Airlines
Tue, 11 Aug - Fri, 28 Aug
Multiple Airlines Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
Multiple Airlines Logo
11:55 p.m. - 1:22 p.m.
YYC
-
ORD
12h 27m
1 stop
C$ 385Multiple Airlines
Mon, 17 Aug - Thu, 27 Aug
United Airlines Logo
7:46 p.m. - 10:37 p.m.
ORD
-
YYC
3h 51mdirect
United Airlines Logo
8:30 a.m. - 1:05 p.m.
YYC
-
ORD
3h 35mdirect
C$ 396United Airlines
Mon, 17 Aug - Fri, 28 Aug
United Airlines Logo
7:46 p.m. - 10:37 p.m.
ORD
-
YYC
3h 51mdirect
United Airlines Logo
8:30 a.m. - 1:05 p.m.
YYC
-
ORD
3h 35mdirect
C$ 396United Airlines
Mon, 17 Aug - Wed, 26 Aug
United Airlines Logo
7:46 p.m. - 10:37 p.m.
ORD
-
YYC
3h 51mdirect
United Airlines Logo
8:30 a.m. - 1:05 p.m.
YYC
-
ORD
3h 35mdirect
C$ 396United Airlines
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.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Calgary?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Calgary departing in September.

Flight prices are below average for this route right now.

Flights to Calgary from Chicago O'Hare Intl Airport usually cost between C$ 381 and C$ 685 in September.
The lowest price found in the past 5 days was C$ 371 on Multiple Airlines (1 Sep–9 Sep).

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 Thursday 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 Sundays.

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 January, where tickets cost C$ 323 (return) on average. On the other hand, the most expensive months are July and December, where the average cost of round-trip tickets is C$ 632 and C$ 540 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at C$ 219 on average.

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 3 weeks before departure, which saves you about 13% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Calgary

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Air Canada, WestJet, United Airlines and ORD

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.

Lucas Aykroyd

Lucas Aykroyd

Expert on YYC

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.

Good to know

Low season

November

Cheapest flight

C$ 197
Best time to beat the crowds (23% less expensive on average)
Most popular time to fly (34% 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 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Calgary was C$ 197 for a one-way ticket and C$ 371 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, WestJet, Qatar Airways, Finnair, British Airways, and Delta.

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

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago to Calgary flight route.

  • Which airline alliances offer flights from Chicago to Calgary?

    Star Alliance is the only airline alliance operating flights between Chicago and Calgary.

  • 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$ 527 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$ 499 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$ 239 or less one-way and C$ 219 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

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Tuesday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Wednesday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Thursday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Friday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Saturday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Sunday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

See more nonstop flights

Direct returns

Calgary to Chicago O'Hare Intl

Monday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Tuesday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Wednesday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Thursday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Friday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Saturday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Sunday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

See more nonstop flights

Reviews of the top airlines 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.
7.4
United AirlinesOverall score based on 10048 reviews
8.1Crew
7.3Comfort
7.1Entertainment
7.7Boarding
6.6Food
Airline reviews

The kid in the middle seat kicked me almost the whole flight, almost kicked my hot tea off my tray. The flight was delayed due to the first plane not being able to be de-iced in July! We had to get a new plane. Now I drive 3 hours back to Edmonton because direct flights from PVR were way to expensive

2.0 MediocreAnonymous, Jul 2026
ORD - YYC
Read more United Airlines reviews

The kid in the middle seat kicked me almost the whole flight, almost kicked my hot tea off my tray. The flight was delayed due to the first plane not being able to be de-iced in July! We had to get a new plane. Now I drive 3 hours back to Edmonton because direct flights from PVR were way to expensive

Not United Airlines' fault. It's ORL airport's fault.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

Flight was good but there are way to many announcements for credit cards etc.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

The pilots were late and it made us 1 hour late. The meat was tough and bok choy was also tough.

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

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.

Due to delays at SFO, my WestJet light missed its connecting WestJet flight. If they had held the plane in Calgary for 15 minutes, 2 families with children would not have been stranded in Calgary for more than 24 hours. I understand the need to be on-time, but when it is the same company, you would think they could make a phone call. Or maybe they could go to a higher altitude to make up for lost time? Instead of attempting to put us on another flight, they rescheduled us for the same connecting flight 24 hours later. We then had to scramble to find a hotel, which they state that they were not responsible for since the delay was not their fault and therefore became an additional out of pocket expense for us. The customer service is severely lacking here at this company. They also mentioned that if we purchased our tickets through a 3rd party site (Kayak) versus WestJet directly, that they couldn't help us. Seriously?? Additionally, we lost 2 days of travel and missed out on tours and taxis that were pre-booked. I will not be using WestJet again,

This airline would not refund my money and I had a physician note that I could not fly. They are crooks

No pre boarding kiosk to check in, baggage claim detected luggage didn’t leave the airport, poorly managed recovery of lost luggage, and blame lost tag from conveyor to TSA/security, very poor from TSA/security check to delivery, crucial if compensation will go thru and will likely wait for months unlike United,

Plane seating was uncomfortable, very tight fitting for someone my height, did not recline and overall un enjoyable

No communication from Kayak or West Jet. Booked extra flights, flights cancelled, no one answers calls. Will be disputing charges.

Leg room is a problem the plane was dirty and there were no movies available on the app

The personal item sizer cannot take a standard backpack, and the cabin luggage sizer cannot take a standard carry-on. Designed for people from the island of Lilliput!!. and also compels people to pay additional fees to check their bags. Making money by ticking off the passengers is a very short-sighted business strategy, especially since they have a choice of carriers

Our flight was delayed almost 3.5 hours (some of the issue seemed to be weather-related, yes) but NOTHING was offered as an conciliatory gesture for this delay. No food offering or any additional drink offering. There is no entertainment is available on any screen behind the seats. The airlines are so quick to penalize customers for slightest requests for comfort- seat changes, complicated baggage allowances, seating zones which are utterly dehumanizing (ZONE 9? after Zone 4- why? This is so clearly meant to be a message to those that do not have 'loyalty' to this airline to make a distinguishing line in the sand. There is such a lack of humanity in the way people are corralled in and spoken to. So, I don't think airlines should be all that surprised when those some dehumanizing corporate treatment is returned to them when asked. The flight on the way into Calgary was scheduled to arrived at 9:25 and we arrived at 12:45 AM. It is not okay. I would think TWICE and possibly once more before booking with them again. Their overhead bins are small and limited so they bully you into either paying for a $90 checked bag or gate check a lot of people's bags. Often on their website there is no carry-on bag allowance. Beware!

They cancelled and moved my flight with no email or text or any other notice. I discovered this only when I attempted to check in for my flight. Actual flying experience was above average.

Delayed boarding. Delayed taking off. Delayed landing. Missed our connecting flight. Our seats on this plane were not assigned until last minute, splitting up our family with kids. I sat in the last row next to the bathroom with so many people rubbing up against me to get to the bathroom the entire flight.

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

Information on your arrival and departure airports