YYC - ORD

$90 Find Cheap Flights from Calgary to Chicago O'Hare Airport

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 O'Hare Intl departing on 9/24. 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 Chicago O'Hare Intl Airport

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

Wed, Sep 3 - Tue, Sep 9
WestJet Logo
12:15 pm - 4:43 pmYYC-ORD
3h 28mnonstop
WestJet Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$133WestJet
Find Deal
Thu, Sep 4 - Tue, Sep 9
WestJet Logo
12:15 pm - 4:43 pmYYC-ORD
3h 28mnonstop
WestJet Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$153WestJet
Find Deal
Wed, Sep 24 - Thu, Oct 23
 Logo
12:15 pm - 4:43 pmYYC-ORD
3h 28mnonstop
 Logo
8:47 am - 11:38 amORD-YYC
3h 51mnonstop
Tue, Sep 2 - Tue, Sep 9
Air Canada Logo
1:10 am - 9:51 amYYC-ORD
7h 41m1 stop
Air Canada Logo
6:20 pm - 1:12 amORD-YYC
7h 52m1 stop
$165Air Canada
Find Deal
Wed, Sep 24 - Thu, Oct 23
United Airlines Logo
6:15 am - 6:26 pmYYC-ORD
11h 11m1 stop
United Airlines Logo
9:44 pm - 1:53 pmORD-YYC
17h 09m1 stop
$174United Airlines
Find Deal
Tue, Sep 23 - Thu, Oct 23
Air Canada Logo
1:10 am - 9:51 amYYC-ORD
7h 41m1 stop
Air Canada Logo
8:40 am - 3:50 pmORD-YYC
8h 10m1 stop
$178Air Canada
Find Deal
Thu, Nov 20 - Tue, Nov 25
United Airlines Logo
12:37 pm - 5:10 pmYYC-ORD
3h 33mnonstop
United Airlines Logo
8:45 am - 11:35 amORD-YYC
3h 50mnonstop
$187United Airlines
Find Deal
Wed, Sep 3 - Tue, Sep 9
 Logo
8:55 am - 9:42 pmYYC-ORD
11h 47m1 stop
 Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
Fri, Aug 29 - Thu, Sep 4
American Airlines Logo
6:29 am - 10:54 amYYC-ORD
3h 25mnonstop
American Airlines Logo
6:30 pm - 11:50 amORD-YYC
18h 20m1 stop
$210American Airlines
Find Deal
Fri, Sep 19 - Sun, Sep 21
American Airlines Logo
6:29 am - 10:54 amYYC-ORD
3h 25mnonstop
American Airlines Logo
8:30 pm - 11:19 pmORD-YYC
3h 49mnonstop
$234American Airlines
Find Deal
Expert advice

Expert advice for your flight from Calgary to O'Hare Intl

 
Snippets provided in this section are AI-generated based on a summarization 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, enhancing travel comfort.


WestJet's Wi-Fi is available for purchase; download the app for entertainment on narrowbody aircraft.

Read more about WestJetby Stefanie Waldek
United Airlines

United offers Priority Boarding for purchase, ensuring carry-on space and convenience.


United's Wi-Fi varies; check coverage map online before purchasing for reliable connectivity.

Air Canada

Air Canada offers priority boarding for Business Class and elite status passengers, enhancing travel efficiency.


Air Canada's Wi-Fi is available on select flights; check availability five days before departure.

Read more about Air Canadaby Stefanie Waldek
American Airlines

American Airlines' Main Cabin Extra offers early boarding and complimentary drinks for a small fee.


American Airlines' Wi-Fi offers 20 minutes free with an ad; T-Mobile users may get more.

Airports
YYC

Calgary Airport offers YYC Express, a free service for priority security screening, helping you save time before your flight.

Read more about YYCby Kaitlyn McInnis
ORD

Take the CTA Blue Line train from ORD to downtown Chicago in about 45 minutes, avoiding traffic delays.

Read more about ORDby Stefanie Waldek
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
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

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.

Read more
Kaitlyn McInnis

Kaitlyn McInnis

Expert on YYC

Kaitlyn McInnis

Kaitlyn McInnis

Kaitlyn is a guidebook author and travel writer splitting her time between Atlantic Canada and Istanbul, Türkiye. She has visited over fifty countries and all seven continents, so she is very familiar with many hotels, airports and airlines around the globe. But her favorite type of vacation is sunbathing by the sea with a good book in hand.

Read more
Booking Insights

KAYAK's insights & trends for Calgary to O'Hare Intl flights

Get data-powered insights and trends into flights from Calgary to O'Hare Intl 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 Calgary to Chicago O'Hare Airport?

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.

When flying from Calgary to Chicago O'Hare Airport, you should consider leaving on a Sunday and avoid Mondays if you are looking for the best rates. For your return to Calgary, you’ll find the best rates on Thursdays and the most expensive ones on Tuesdays.

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 May, where tickets cost $164 (return) on average. On the other hand, the most expensive months are December and August, where the average cost of round-trip tickets is $468 and $373 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.

No, with an average price for the route of $530, prices are generally cheapest when you fly direct.

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 35% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$90
Best time to beat the crowds but there is an average 25% increase in price.
Most popular time to fly with an average 21% increase in price.
Flight from Calgary to Chicago O'Hare Airport

When to book flights from Calgary to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Calgary to O'Hare Intl 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 O'Hare Airport flights

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

    In the last 3 days, the lowest price for a flight from Calgary to Chicago O'Hare Intl Airport was $90 for a one-way ticket and $133 for a round-trip.

  • Do I need a passport to fly between Calgary and Chicago O'Hare Airport?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Calgary and on arrival in Chicago O'Hare Airport.

  • Which airports will I be using when flying from Calgary to Chicago O'Hare Airport?

    Calgary and Chicago O'Hare Airport are both served by 1 main airport. You will leave Calgary from Calgary and will be arriving at Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Calgary to Chicago O'Hare Airport?

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

  • Which aircraft models fly most regularly from Calgary to Chicago O'Hare Airport?

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

  • Which airline alliances offer flights from Calgary to Chicago O'Hare Airport?

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

  • On which days can I fly direct from Calgary to Chicago O'Hare Airport?

    There are nonstop flights from Calgary to Chicago O'Hare Airport on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Calgary to Chicago are United Airlines and WestJet. With an average price for the route of $468 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 $220 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Calgary to Chicago O'Hare Airport?

    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 O'Hare Airport.

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

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

  • What is the Hacker Fare option on flights from Calgary to Chicago O'Hare Airport?

    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 O'Hare Airport with an airline and back to Calgary with another airline. Booking your flights between Calgary and ORD can sometimes prove cheaper using this method.

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

    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 O'Hare Airport 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 $205 or less one-way and $203 or less round-trip.

Prefer to fly direct from Calgary to Chicago O'Hare Airport?

 
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

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 direct flights

Direct returns

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 direct flights

Reviews of the top 4 airlines serving from Calgary to O'Hare Intl

 
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 O'Hare Intl? 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 8896 reviews
7.1Entertainment
7.7Boarding
6.6Food
8.1Crew
7.3Comfort
Airline reviews

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

4.0 OkayGary, Jul 2025PIA - ORD
Read more United Airlines reviews

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

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

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Very clean and comfortable cabin. Amazing Mediterranean salad for lunch before landing. Great range of films to watch. Really quiet and easy to sleep on the flight also. The initial food was a bit weird: odd fried chicken pieces in some weird white gloop, but that would be my lack of cultural knowledge on the grub. Salad more than made up for it at the other end. Staff were super attentive and helpful. Great and easy flight

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

7 hour layover was a drag. Free internet on the long leg was great.

From vancouver go calgary nd vice vetsa fligjt was delayed

It was good! Short flight and it was on time!

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.

Business class lie down seats on WestJet aren't very comfortable. Crew were excellent and overall flight was ok.

The seats very Uncomfortable, no meal and no entertainment for a 4Hours flight. Smooth Flight, Great Take off and landing. Superb crew!

Lots of overhead storage, good crew, good service, smooth landing.

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.

crew was great, wifi was very poor could not even load a youtube video

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.

Business class was not worth the extra charge. Overpriced for slightly larger seat. Nothing special. Small older plane.

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

Very bad service the way back we was on the way for r two days very bad condition and waiting for luggage till now

Pros: The airplane was new and had in-flight entertainment (tablet behind seats) with new movies instead of watching on personal devices. Cons: the flight time was changed without informing us. When I booked the flight, the time was 13:30pm (also in the email confirmation). However, when I reached the airport, the time was conveniently changed to 14:55pm. When I asked at the counter, they said the flight always took off at this time. The booking was made by Air Canada, but the flight was operated by United.

United had no (zero) record of our flight. It took over an hour of us standing in line with surly employee while others waited to get resolved. I have never experienced such poor service and poor empathy.

The app was great, service was wonderful, everything was quick and easy

On the flight from Montreal to Calgary the flight attendant we had was excellent. Unfortunately I did not get her name but she made the flight very comfortable and enjoyable.

Like- beer/wine for free Dis-like- all other aspects- customer service was horrible the entire trip. No help from Air Canada after they changed flight 6+ hours later. Also they put us on standby for no reason. Then almost 2 hours to get our bags after we arrived back at airport

Or the greatest and it ended up picking us up from Chicago to Toronto not sure who was tesponsible for the 4 hr delay. United should have been properly prepared for a scheduled flight from Austin to Chicago and they were not.

Ground personnel in better mood. Sounded agressive wrt carry on bagage sizing.

Everything you need to know for your flight from Calgary to O'Hare Intl

Information on your arrival and departure airports

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