YYC - ORD

C$ 247 Find Cheap Flights from Calgary to Chicago – 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 Calgary to Chicago departing on 19/1. 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$ 310
Typical prices: C$ 376-C$ 599
WestJet
Sat 29/8Mon 31/8
YYC - ORD • Direct
Cheapest one-way flights
C$ 247
Typical prices: C$ 248-C$ 513
Delta
Tue 19/1
YYC - ORD • 2 stops
Advice from real travellers
AI-powered summary based on content written by travel experts. AI can make mistakes.
WestJet EconoFlex adds a checked bag, seat selection, and free changes.
American Basic Economy is cheaper, but has late boarding and no seat assignment.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from C$ 310 (round-trip)
Best reviews • 7.8 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Direct flights
You can fly direct with American Airlines, United Airlines, and WestJet. Average duration is 3h 38m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg C$ 350 (round-trip)
Shortest trip • 8h 10m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travellers who book at least 6 weeks in advance save around 15% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 15% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Calgary to Chicago (YYC-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Calgary to Chicago 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 Calgary to Chicago

Sat, 29 Aug - Mon, 31 Aug
WestJet Logo
12:00 p.m. - 4:40 p.m.
YYC
-
ORD
3h 40mdirect
WestJet Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
C$ 310WestJet
Sat, 29 Aug - Mon, 31 Aug
WestJet Logo
12:00 p.m. - 4:40 p.m.
YYC
-
ORD
3h 40mdirect
WestJet Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YYC
3h 55mdirect
C$ 313WestJet
Thu, 24 Dec - Sat, 2 Jan
United Airlines Logo
12:30 p.m. - 3:50 p.m.
YYC
-
ORD
3h 20mdirect
United Airlines Logo
9:00 a.m. - 12:54 p.m.
ORD
-
YYC
3h 54mdirect
C$ 352United Airlines
Sat, 5 Sep - Sun, 13 Sep
United Airlines Logo
8:30 a.m. - 1:05 p.m.
YYC
-
ORD
3h 35mdirect
United Airlines Logo
7:45 p.m. - 10:35 p.m.
ORD
-
YYC
3h 50mdirect
C$ 354United Airlines
Thu, 17 Sep - Sun, 20 Sep
American Airlines Logo
7:00 a.m. - 11:29 a.m.
YYC
-
ORD
3h 29mdirect
American Airlines Logo
8:30 p.m. - 11:29 p.m.
ORD
-
YYC
3h 59mdirect
C$ 354American Airlines
Fri, 28 Aug - Mon, 31 Aug
Air Canada Logo
1:00 a.m. - 10:16 a.m.
YYC
-
ORD
8h 16m
1 stop
Air Canada Logo
9:50 a.m. - 1:56 a.m.
ORD
-
YYC
17h 06m
1 stop
C$ 362Air Canada
Wed, 12 Aug - Tue, 18 Aug
Multiple Airlines Logo
6:00 a.m. - 10:46 p.m.
YYC
-
ORD
15h 46m
1 stop
Multiple Airlines Logo
2:15 p.m. - 11:00 p.m.
ORD
-
YYC
9h 45m
1 stop
C$ 364Multiple Airlines
Sat, 24 Oct - Mon, 26 Oct
Multiple Airlines Logo
12:30 p.m. - 5:05 p.m.
YYC
-
ORD
3h 35mdirect
Multiple Airlines Logo
10:15 a.m. - 4:54 p.m.
ORD
-
YYC
7h 39m
1 stop
C$ 368Multiple Airlines
Fri, 30 Oct - Mon, 2 Nov
Air Canada Logo
6:00 a.m. - 3:38 p.m.
YYC
-
ORD
8h 38m
1 stop
Air Canada Logo
10:15 a.m. - 8:59 p.m.
ORD
-
YYC
10h 44m
1 stop
C$ 380Air Canada
Sat, 24 Oct - Mon, 26 Oct
American Airlines Logo
6:44 a.m. - 3:00 p.m.
YYC
-
ORD
7h 16m
1 stop
American Airlines Logo
9:00 p.m. - 11:59 a.m.
ORD
-
YYC
15h 59m
1 stop
C$ 385American Airlines
Booking Insights

KAYAK's insights & trends for Calgary to Chicago flights

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

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

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

Flight prices are below average for this route right now.

Flights to Chicago O'Hare Intl Airport from Calgary usually cost between C$ 376 and C$ 599 in August.
The lowest price found in the past 5 days was C$ 310 on WestJet (29 Aug–31 Aug).

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

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

If your flying dates are flexible, you should consider flying to Chicago on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Calgary to Chicago. For your return ticket, we recommend flying on a Thursday and avoiding Saturdays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Calgary to Chicago O'Hare Intl Airport, 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 Calgary to Chicago O'Hare Intl Airport is November, where tickets cost C$ 354 (return) on average. On the other hand, the most expensive months are July and August, where the average cost of round-trip tickets is C$ 548 and C$ 492 respectively.

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

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$ 437 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Calgary to Chicago O'Hare Intl Airport, 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 Calgary to Chicago O'Hare Intl Airport, you should book around 6 weeks before departure, which saves you about 15% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Expert advice

Expert advice for your flight from Calgary to Chicago

 
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 WestJet, United Airlines, Air Canada 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.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

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

February

Cheapest flight

C$ 247
Best time to beat the crowds (6% less expensive on average)
Most popular time to fly and prices are also 15% lower on average.
Flight from Calgary to Chicago

When to book flights from Calgary to Chicago

Are your dates flexible? Find out the best times to travel from Calgary to Chicago 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 Calgary to Chicago flights

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

    In the last 5 days, the lowest price for a flight from Calgary to Chicago O'Hare Intl Airport was C$ 247 for a one-way ticket and C$ 310 for a round-trip.

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

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

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

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

  • Which airline alliances offer flights from Calgary to Chicago?

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Calgary to Chicago are Delta and United Airlines. With an average price for the route of C$ 391 and an overall rating of 7.8, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of C$ 539 and an overall rating of 7.4.

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

    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 Calgary to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Calgary 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 Calgary to Chicago?

    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 Chicago with an airline and back to Calgary with another airline.

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

    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 Chicago from Calgary 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 Calgary to Chicago O'Hare Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 348 or less one-way and C$ 588 or less round-trip.

Prefer to fly direct from Calgary to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Calgary to Chicago O'Hare Intl.
Find which airlines fly direct from Calgary Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.

Direct departures

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

Direct returns

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

Reviews of the top 5 airlines flying from Calgary to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Calgary to Chicago. 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 Calgary to Chicago? 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.
7.8
DeltaOverall score based on 8485 reviews
7.8Comfort
8.1Boarding
8.5Crew
7.2Food
7.8Entertainment
Airline reviews

It was as good as it could be. Flying is not a pleasant experience these days.

8.0 ExcellentMark, Jun 2026
LAX - ORD
Read more Delta reviews

It was as good as it could be. Flying is not a pleasant experience these days.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

It was beautiful easy and smooth experience. Thank you. Will definitely get Delta for my next travel.

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

long flights are never truly comfortable but the airline did their best. crew was great and the flight was safe.

The captain was amazing and kept us informed throughout that there would be some rough air. The flight also got delayed but we were able to actually leave on time, which was great.

The staff did not do a good job of getting everyone boarded quickly, so we missed our take off window and had to sit on the tarmac for 20+ min waiting for our turn. The plan was old. Pockets on the back of seats were torn and tearing off. One of the attendants was rude-she would ask a question but he walking away before you finished answering so she kept getting our drink orders wrong.

Ran out of my choice of main course in BClass. Kind of weird combo for substitute.

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

Reliable, nice crew, I fly often on that flight and I like it all.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

So far so good but food and entertainment are not available for this flight

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

lots of delays the crew were unclear about where to pick up my carry-on, which they took from me to check in on the plane.

They needed people to check a bag, they did check my bag and I had to wait 10 minutes after the flight to get it it wasn’t too bad

Despite travelling ultra basic for the first time due to such increased rates we both managed with one bag each. Even boarding last wasn’t SO bad.

Flight was early. That’s the only positive I can share. I paid for wifi on the flight and it didn’t allow me to use any streaming services so it was a waste of $20. West Jet also lost my ski equipment on my way to a ski vacation. They told me it would be delivered to the hotel as soon as it arrived at the airport. It was never delivered. I had to pick it up at the airport on my way home. I am completely disgusted with my experience on west jet

I was seated near a "stinky" person. That's not the fault of Westjet🙁😶‍🌫️

my carry-on bag was delayed and I did not receive it until the day of my return at the airport. This delay caused me significant inconvenience, as I did not have access to my personal belongings for the duration of my trip. I had expected to rely on my carry-on items, and being without them negatively impacted my travel experience.

Technology issues at the bag-check counter caused a delay, and we were unable to check out our bags, ultimately missing our flight. They offered no assistance other than telling us to book another flight out of Calgary. We arrived with plenty of time; if there hadn't been an issue with the kiosk and the length of the lines due to the technical issues, we could have made it home.

Worst check in and bag drop off experience. Staff were incredibly rude given that it’s the WestJet system that is faulty.

The staff at the airport and on the plane were wonderful I especially wanna acknowledge the staff who boarded us at the Calgary airport. The women who helped us board at the airport were incredible… they were so kind and sweet…I very happy with WestJet and I am hoping I can fly more often to Canada.

Staff was nice, helpful, and did all they could. I understand economy seats are bottom of the barrel, but we're crammed in there with others in our row.

Crew was friendly. Lost our luggage and told us it’d be in later in the evening of the day we returned. It was not. Still after 5 days have not received it.

It took 30 minutes to check in with the Westjet rep. They didn’t have enough seats and she needed to make a call… I am always “randomly” selected to be checked at security. Their “randomly “ selection system may need some updating. They treat people like criminals. It is not appropriate behavior.

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Boarding and Delays The boarding process for my American Airlines flight from Copenhagen to Philadelphia was a bit tricky. We experienced a gate change that required a long walk to a new area of the airport. Additionally, boarding was not via a jet bridge; we had to take a shuttle bus to the plane and then carry our luggage up the stairs ourselves. Furthermore, the bag drop didn't open until about 12:20 PM, which was only three hours before our scheduled departure. This meant I couldn't drop my bag off early and had to wait outside of security in order to drop off my bag and use the kiosk. The bag drop self-service kiosks also didn't open until about 12:00 PM when an American Airlines employee unlocked them so that we could print out our boarding passes and bag tags, which further created a backlog. The flight was delayed by over an hour because we had to wait for one of the tires on the plane to be changed. Flight Attendant Professionalism On a positive note, the flight attendant was very professional when handling a passenger who was sitting in the wrong seat. Even though the passenger was persistent and reluctant to move, the flight attendant calmly ensured the assigned passenger could take their seat. Kudos to the flight attendant for keeping his calm and composure, not allowing the issue to escalate, and handling it well under pressure while a line of passengers waited in the aisle to board. In-Flight Service The in-flight service was also fast, prompt, and efficient, although service had to be suspended for the last two hours of the flight due to weather and turbulence, which was outside of the crew's control. Limited Flight Options Please note that American Airlines only operates one flight per day in and out of Copenhagen. This means there are limited options available if your flight is delayed or canceled, which is something to take into consideration when booking.

This may have been the hottest cabin temperatures I have experienced on any flight prior to take off lasting for approximately 30 minutes. I am not typically one to complain but I was genuinely worried about the health of several passengers on the flight due to the extreme temperatures including a small toddler.

I will never but. through kayak again. and American Airlines. I will never fly again on. They're both thieves.

The flight was on time and crew were nice, seats were tight and there was entertainment available

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

Incompetent crew at the boarding counter. Never flying AA again.

After 3 hours of delays, they ended up cancelling my flight. And although I could purchase one-way tickets to get to my destination, they would not offer me these flights as compensation for the cancelled flight, and I didn't end up making it home until 13 hours after I was originally supposed to arrive. It made for an extremely strenuous end to an otherwise good trip.

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

Terrible. 3 missed flights and 24 hours delayed with lost bag and promised $100 compensation from United and absolutely nothing from them…

flight was delayed 6 hours for weather, then cancelled because of the crash in toronto, but none of the links to cancel or rebook my flights are working

Minimal food offered (crackers). Had to clean the seat with a wet wipe because of dried food.

They charge 5 dollars for plastic headphones for a flight of 1 hour! Seats are awful. Service is terrible.

Everything was seamless. I would have appreciated knowing there would not be any real food available for purchase in advance. Otherwise a great experience. Thank you!

I was mostly pleased. My greatest disappointment was with respect to the timely update to the estimated departure and arrival times. It was especially sad that the arrival time was not updated online once we were in flight so as to allow my wife to arrive on time to the airport. She was not happy.

I needed to catch a United flight. There wasn't enough signage or help on arrival to navigate the transfer.

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

Information on your arrival and departure airports