YYC - ORD

$100 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 4/24. 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, 0 bags

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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$174
Overall average: $247
WestJet
Fri 1/30Mon 3/2
YYC - ORD • Non-stop
Cheapest one-way
$100
Typical prices: $125-$223
WestJet
Fri 4/24
YYC - ORD • Non-stop
Our travelers' advice
AI-generated summary based on content written by travel experts
American's Main Cabin Extra includes early boarding.
Use YYC Express for quicker security at Calgary.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
WestJet
Cheapest • from $174 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
6 weeks
in advance
Our data shows that travelers who book at least 6 weeks in advance save around 38% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
May
Cheapest • 39% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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We hope you love your trip to O'Hare Intl!
Flight Deals
Booking Insights
Expert advice
Flight Deals

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

Fri, Jan 30 - Mon, Mar 2
WestJet Logo
9:00 am - 1:35 pmYYC-ORD
3h 35mnonstop
WestJet Logo
2:20 pm - 5:15 pmORD-YYC
3h 55mnonstop
$174WestJet
Find Deal
Fri, Jan 30 - Sat, Feb 28
Multiple Airlines Logo
9:00 am - 1:35 pmYYC-ORD
3h 35mnonstop
Multiple Airlines Logo
1:52 pm - 10:46 pmORD-YYC
9h 54m1 stop
$206Multiple Airlines
Find Deal
Wed, Dec 10 - Mon, Dec 15
Multiple Airlines Logo
12:37 pm - 5:10 pmYYC-ORD
3h 33mnonstop
Multiple Airlines Logo
3:55 pm - 11:58 pmORD-YYC
9h 03m1 stop
$216Multiple Airlines
Find Deal
Sat, Jan 31 - Sat, Feb 28
Air Canada Logo
5:45 am - 2:55 pmYYC-ORD
8h 10m1 stop
Air Canada Logo
2:00 pm - 8:39 pmORD-YYC
7h 39m1 stop
$217Air Canada
Find Deal
Thu, Dec 11 - Mon, Dec 15
Delta Logo
7:35 am - 6:45 pmYYC-ORD
10h 10m1 stop
Delta Logo
8:50 am - 1:40 pmORD-YYC
5h 50m1 stop
$222Delta
Find Deal
Fri, Jan 30 - Sat, Feb 28
Air Canada Logo
5:35 am - 3:10 pmYYC-ORD
8h 35m1 stop
Air Canada Logo
2:00 pm - 8:39 pmORD-YYC
7h 39m1 stop
$224Air Canada
Find Deal
Thu, Dec 11 - Mon, Dec 15
Multiple Airlines Logo
8:55 am - 10:24 pmYYC-ORD
12h 29m1 stop
Multiple Airlines Logo
2:20 pm - 5:15 pmORD-YYC
3h 55mnonstop
$225Multiple Airlines
Find Deal
Thu, Jan 29 - Mon, Mar 2
Delta Logo
6:30 am - 5:56 pmYYC-ORD
10h 26m1 stop
Delta Logo
1:55 pm - 11:15 pmORD-YYC
10h 20m1 stop
$242Delta
Find Deal
Wed, Dec 10 - Mon, Dec 15
United Airlines Logo
12:37 pm - 5:10 pmYYC-ORD
3h 33mnonstop
United Airlines Logo
8:45 am - 11:35 amORD-YYC
3h 50mnonstop
$259United Airlines
Find Deal
Thu, Dec 11 - Mon, Dec 15
United Airlines Logo
12:37 pm - 5:10 pmYYC-ORD
3h 33mnonstop
United Airlines Logo
8:45 am - 11:35 amORD-YYC
3h 50mnonstop
$302United Airlines
Find Deal
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 Saturdays 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 $475 and $345 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 $168, 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 38% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

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

Good to know

Low seasonNovember
Cheapest flight$100
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly with an average 23% 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 $100 for a one-way ticket and $174 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?

    American Airlines, Air Canada, United Airlines, KLM, and WestJet offer inflight Wi-Fi service on the Calgary to Chicago O'Hare Airport flight route.

  • 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, and Star Alliance 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 $491 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 $219 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 $160 or less one-way and $268 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

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 direct flights

Direct returns

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 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 8998 reviews
7.3Comfort
7.1Entertainment
6.6Food
7.7Boarding
8.1Crew
Airline reviews

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

10.0 ExcellentDr. Joseph, Oct 2025STL - ORD
Read more United Airlines reviews

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Excellent all round, first time flying United. App is very helpful.

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

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Flight, food and crew were all good, friendly and very satisfactory.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Premium economy seat was decent. As always poor headphones, poor food and beverage, crew is not overly friendly

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

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

The ceiling leaked water on me. The toilets smelled very bad in the rear cabin

When I purchased the flights I included the luggage, the luggage was not added and got charged the full price anyway. Had to pay for the luggage at check in. Initial flight was delayed, we missed our 9am connection (flew with my wife), then the airline rebooks us to the next flights, putting my wife in at 1.40pm and me at 4pm, what a crazy wait time. We managed to fix it with customer service and they put me in the 1:40pm flight too, but they left my baggage behind in the 4pm flight. When arrived to my destination, of course no luggage. It was delivered to the address thankfully late at night. The experience sucked.

Very good experience. Great cabin crew. Much better than expected

Typical Canadian airline experience. Charger and tray were broken, food was poor quality, and yet you're still paying more than flights with equal to better service than elsewhere globally.

Not enough food option. And not enough advices or information about what we are gonna eat.

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.

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

Was not sent a link to check in online. Tried to check in online using website. Site didn’t work. Called support line, was told it often didn’t work. Went to counter at airport to check bags and get boarding passes. Had to stand in a lineup. They were unable to tell me how much to pay. Had to take a paper to another counter, took a long time to be told what I owed. I fondly remember the days of checking in online, getting my boarding pass digitally, paying for my luggage on line, scanning my passport at the airport to get my luggage tags, and putting my luggage on the conveyor. Easy peasy. Air Canada has really taken a step back in time, and made what was an easy check in experience to one that seemed unduly long and frustrating.

Really out of Air Canada's control due to long delay because of mechanical issues. While doing their best, disappointed by their assumption that all passengers have smart phones. Should have communicated food voucher availability at gate area. Late arrival cost me an extra $51 because public transit was not available, Otherwise, feel Air Canada did their best dealing with their challenges. Will likely continue using them in the future.

They canceled my flight, I had to rent a car, drive 14 hours. They tell to go on line for a refund, but only offer $24 for a $210 flight and you can’t get hold of anybody by phone and no help from staff at the airport.

I wish to travel with Air Canada for my next trip

They were very attentive, polite, professional and great customer service skills.

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.

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.

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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