YYC - ORD

$89 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 3/3. 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.
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Search hundreds of travel sites at once for deals on flights to Chicago O'Hare 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
In the last 7 days travelers have searched 41,299,237 times on KAYAK, and here is why:

Save 23% or moreCompare multiple travel sites with one search.

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Filter your dealsChoose cabin class, free Wi-Fi and more.

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Cheap Flight Deals from Calgary to Chicago O'Hare Airport (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 O'Hare Airport 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.

Recent round-trip flight deals from Calgary to O'Hare Intl

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Calgary to O'Hare Intl.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
$129WestJet
Find Deal
Thu, Mar 20 - Sun, Mar 30
12:50 am - 10:10 amYYC-ORD
8h 20m1 stop
6:28 pm - 1:18 amORD-YYC
7h 50m1 stop
$160Air Canada
Find Deal
Wed, Jan 8 - Sat, Jan 11
8:30 am - 6:38 pmYYC-ORD
9h 08m1 stop
3:35 pm - 11:02 pmORD-YYC
8h 27m1 stop
$169Air Canada
Find Deal
Fri, Jan 17 - Mon, Jan 20
12:15 pm - 4:44 pmYYC-ORD
3h 29mnonstop
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$184WestJet
Find Deal
Thu, Jun 12 - Sun, Jun 15
6:35 am - 5:29 pmYYC-ORD
9h 54m1 stop
5:00 pm - 11:18 pmORD-YYC
7h 18m1 stop
$216Delta
Find Deal
Thu, Jan 9 - Mon, Jan 13
6:35 am - 5:29 pmYYC-ORD
9h 54m1 stop
1:40 pm - 11:18 pmORD-YYC
10h 38m2 stops
$217Delta
Find Deal
Thu, Jan 9 - Mon, Jan 13
6:19 am - 1:18 pmYYC-ORD
5h 59m1 stop
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
$472United Airlines
Find Deal
Fri, Jan 24 - Fri, Jan 31
12:41 pm - 5:15 pmYYC-ORD
3h 34mnonstop
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
$477United Airlines
Find Deal
Fri, Jan 24 - Fri, Jan 31
6:29 am - 5:35 pmYYC-ORD
10h 06m1 stop
9:45 am - 12:42 pmORD-YYC
3h 57mnonstop
$504American Airlines
Find Deal
Sat, Mar 1 - Fri, Mar 7
6:29 am - 12:19 amYYC-ORD
16h 50m1 stop
7:09 am - 10:04 pmORD-YYC
15h 55m1 stop
$519American Airlines
Find Deal
Wed, Jan 1 - Thu, Jan 2

Flights from Calgary to O'Hare Intl - Travel Insights & Trends

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 Saturday and avoid Sundays if you are looking for the best rates. For your return to Calgary, you’ll find the best rates on Tuesdays and the most expensive ones on Sundays.

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 September, where tickets cost $276 (return) on average. On the other hand, the most expensive months are December and October, where the average cost of round-trip tickets is $484 and $425 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 2 stops layover the cheapest option at $231 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 5 weeks before departure. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low season

November

High season

July

Cheapest flight

$89
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly and prices are also 0% lower on average.
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 $89 for a one-way ticket and $129 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, Air Canada, United Airlines, British Airways, KLM, WestJet, and Delta.

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

    The Airbus A319 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?

    Star Alliance is the only airline alliance operating flights between Calgary and Chicago O'Hare Airport.

  • 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, 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 $332 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $415 and an overall rating of 7.4.

  • 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.

See more FAQs

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 $246 or less one-way and $265 or less round-trip.

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

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, Emirates, United Airlines, +5 more

Air Canada, Emirates, +6 more

Tuesday

Air Canada, Emirates, United Airlines, +3 more

Air Canada, Emirates, +4 more

Wednesday

Air Canada, Emirates, United Airlines, +3 more

Air Canada, Emirates, +4 more

Thursday

Air Canada, Emirates, United Airlines, +5 more

Air Canada, Emirates, +6 more

Friday

Air Canada, Emirates, United Airlines, +3 more

Air Canada, Emirates, +4 more

Saturday

Air Canada, Emirates, United Airlines, +3 more

Air Canada, Emirates, +4 more

Sunday

Air Canada, Emirates, United Airlines, +5 more

Air Canada, Emirates, +6 more

See more direct flights

Direct returns

Chicago O'Hare Intl to Calgary

Monday

Air Canada, United Airlines, American Airlines, +4 more

Air Canada, United Airlines, +5 more

Tuesday

Air Canada, United Airlines, American Airlines, +2 more

Air Canada, United Airlines, +3 more

Wednesday

Air Canada, United Airlines, American Airlines, +2 more

Air Canada, United Airlines, +3 more

Thursday

Air Canada, United Airlines, American Airlines, +4 more

Air Canada, United Airlines, +5 more

Friday

Air Canada, United Airlines, American Airlines, +2 more

Air Canada, United Airlines, +3 more

Saturday

Air Canada, United Airlines, American Airlines, +2 more

Air Canada, United Airlines, +3 more

Sunday

Air Canada, United Airlines, American Airlines, +4 more

Air Canada, United Airlines, +5 more

See more direct flights
See more direct flights

Top 5 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.
8.0
DeltaOverall score based on 8601 reviews
7.9Entertainment
8.0Comfort
7.3Food
8.2Boarding
8.6Crew
Airline reviews

I was with one of the last zones to board. It was kind of annoying to finally get called to board and my whole section was already on the plane. Clearly they boarded with previous zones. So by the time I got on board, there were no spaces for my luggage above my head. I had to put my luggage 4+ rows behind me, which meant that I had to wait even longer to get off the plane, since I had to wait for those rows to clear the aisle before I could retrieve my luggage and exit the plane. This also held up the plane cleaners, as they couldn't service my row until I cleared it, so they were all standing there waiting for me, while I'm standing there waiting for the other passengers to clear the aisle. Anyways, I wasn't in a rush this time, so I just waited, but I could see that being a problem in the future. Now, I could have checked my luggage, of course, but coincidentally, a friend of mine on the same flight got their luggage damaged (wheel completely knocked off) and was told by the Baggage Attendant in the airport that Delta doesn't "cover wheel damage" on luggage. This was disappointing to hear. I'm glad I didn't check mine through. If it were my luggage, I'd be highly frustrated to hear that. It makes me not want to check my luggage in the future.

8.0 ExcellentMelodii, Dec 2024ATL - MSY
Read more Delta reviews

I was with one of the last zones to board. It was kind of annoying to finally get called to board and my whole section was already on the plane. Clearly they boarded with previous zones. So by the time I got on board, there were no spaces for my luggage above my head. I had to put my luggage 4+ rows behind me, which meant that I had to wait even longer to get off the plane, since I had to wait for those rows to clear the aisle before I could retrieve my luggage and exit the plane. This also held up the plane cleaners, as they couldn't service my row until I cleared it, so they were all standing there waiting for me, while I'm standing there waiting for the other passengers to clear the aisle. Anyways, I wasn't in a rush this time, so I just waited, but I could see that being a problem in the future. Now, I could have checked my luggage, of course, but coincidentally, a friend of mine on the same flight got their luggage damaged (wheel completely knocked off) and was told by the Baggage Attendant in the airport that Delta doesn't "cover wheel damage" on luggage. This was disappointing to hear. I'm glad I didn't check mine through. If it were my luggage, I'd be highly frustrated to hear that. It makes me not want to check my luggage in the future.

I think they can provide the better food/snack option for the 4 hours flight. Drinks are fine.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

Typically I give delta excellent reviews. Our flight was delayed 2hrs, I was one of the fortunate ones who were able to get to my connecting flight. Also, annoying that on the connecting flight boarding personnel make me put away a small bag into my carryon. It small enough to put in back pocket seat, why hold me and the line up to just push it into my carryon.

Everything was great. Great service, excellent communication, and early arrival

Delta flight attendants poorly managed the boarding process and overhead storage. My bag was checked last minute and no claim ticket was provided. My bag is now lost. Complete incompetence by all flight crew involved.

Inexpensive, got an exit row aisle aeat with no middle passenger, bought a great breakfast sandwich, flight comfortable & arrived ahead of schedule.

Customer service at the gate in the flight was exceptional. On time. Aircraft and seat was decent. Thanks Delta. 💗

It was terrible, if they ran flights on time it would make a big difference.

Great flight. On-time, comfortable, clean aircraft, and offered snacks pre-flight to plan for a potentially turbulent route. I wish there was Wi-Fi an all Delta Aircrafts but for a short flight this is not much of a problem.

Did not even get on board. Was told I needed an esta agreement. Was not aware of this when I booked the fare and not told about them

Cramped seats. Audio jack for the in -flight entertainment was broken.

Flight was great albeit the long line before the int’l immigration given the timing of the year.

They canceled our flight and left us stranded to figure it out

We appreciated the friendly, efficient, and professional flight attendants. A wider selection of hot foods would be nice.

Did not have enough time from Venice seaport at Ravenna to get to Venice airport in order to make the scheduled flights. Need to have at least 3+ hours from ship docking to airport.

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

Original flight canceled and communicated poorly. A series of gate changes , delays and plane changes followed. Even after the entire flight boarded there was another plane changes followed. Food vouchers provided to my travel companion but not to me despite being on the same reservation. No in flight entertainment. The entire experience was terrible although the flight crew were great.

It was great being a direct flight from Calgary to Tokyo. No transfer to worry about.

Very old planes. Seats were not comfortable. Air was not on during the flight leading to incredibly stuffy conditions.

Traveling on two legs the food was identical and not very good

We are experiencing more delays with westjet than other companies. West jet used to be our favorite airline.

Excellent and a surprise as I had never heard of it before.

Was a short flight, not good or bad. Extremely cramped and I'm only 6feet 1inches. 295lbs.

Terrible experience at the gate. Charged for carry on luggage despite them meeting the requirements for sizing.

Check in agent was good, stewardess was unfriendly and certainly did not have the care of the passengers in mind Spent the whole time on her phone

we were upgraded to business class, not sure why, so the flight exceeded our expectations. Perhaps this was because the flight Cancun to Calgary was a nightmare , not even guaranteed a seat upon checkin at the airport.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight from Buffalo to Chicago was on an older and smaller plane. Seating was tight. Looking closely at the interior of the aircraft there were definitely signs of aging and wear.

The flight encountered a delay exceeding 4 hours. The food voucher issued was valued at $12, insufficient to cover our meal expenses. Consequently, I was unable to take my medication, leading to a drop in blood sugar levels and exacerbating my anxiety.

Airplane was cold. Flight attendants were rude. Phone charger did not work. No food available.

3hour delay In the last 3 months i had 3 flights and 2 of these had a more than 2:40 hrs delayed

My initial flight to ORD was extended without reason. We circled the airport a few time and then drove on the ground for at least 20 minutes. These kinds of delays are annoying but somewhat expected… it would be nice if the crew would make an announcement to give updates on how long we could expect to be delayed.

Fantastic. I am low vision and was impressed with how helpful and accommodating the service tam was. It was super appreciated! I was pleasantly surprised about how delicious the food was. Like, “I wish I had more even though I’m no longer hungry” delicious. 100% enjoyable trip.

The flight was uneventful. What was a problem was I was delayed getting home one entire day because the flight from Sacramento was delayed. That made getting to my connecting flight impossible. I had to stay another night at the hotel and incur that expense as a result.

Flights were on time both ways, such a big plus! Staff was very accommodating and friendly. Question the choice of snacks that, which on both flights was dairy based. Appreciated using bottled water.

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!

The seats really could do with some extra padding. The staff member who checked me in at Calgary was amazing. Friendly and lovely.

United agent at FLL excellent - due 55 min conx at ORD rerouted us on an earlier departure via DEN and got home 5 hours earlier than expected

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.

The trip from booking to execution was great! The plane from YVR to YYC had LCD panels for entertainment which was great, but the return flight from YYC to YVR did not have them. Oh well--it was a short flight. Food was a pretty minor "token" snack, but hey--it was a short flight. It could have been skipped entirely and I would have rated the flight well.

The space in exit aisle seat was great. Having the entertainment controls in the middle of the armrests is a joke. Your or the passenger next to you will unintentionally push the controls, mainly the sound bar.The placement of the controls need to be on the back of the seats or on the inside of the seats. This crazy placement may only be on the Boeing 737 series but need to be addressed.

They were so kind and helpful and they even brought an item of mine that I forgot on the plane!!

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

Seats weren't comfortable, could have used more let room

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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