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$118 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 6/22. 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
0 bags
Sat 6/29
Sat 7/6

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 42,686,544 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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Cheap flight deals from Calgary to O'Hare Intl (YYC-ORD)

 
These are the cheapest deals for flights from Calgary to O'Hare Intl currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. 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.

Recent one-way flight deals from Calgary to O'Hare Intl

Only flying one-way? Below are some of the best one-way flight deals from Calgary to O'Hare Intl found on KAYAK recently.

Recent last minute flight deals from Calgary to O'Hare Intl

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Calgary to O'Hare Intl.

Recent direct flight deals from Calgary to O'Hare Intl

The latest deals for direct flights from Calgary to O'Hare Intl so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Calgary to O'Hare Intl

Find recent round-trip train or bus tickets from Calgary to O'Hare Intl.

All round-trip flight deals to O'Hare Intl

The cheapest plane tickets to O'Hare Intl found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
12:30 pm - 4:57 pmYYC-ORD
3h 27mnonstop
5:55 pm - 8:40 pmORD-YYC
3h 45mnonstop
$191WestJet
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Thu, Jun 27 - Thu, Jul 4
12:30 pm - 5:09 pmYYC-ORD
3h 39mnonstop
5:55 pm - 8:45 pmORD-YYC
3h 50mnonstop
$193WestJet
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Sun, Sep 22 - Thu, Sep 26
6:50 am - 2:56 pmYYC-ORD
7h 06m1 stop
3:50 pm - 8:43 pmORD-YYC
5h 53m1 stop
$224Delta
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Sat, Oct 26 - Tue, Oct 29
6:25 am - 10:20 pmYYC-ORD
14h 55m1 stop
8:45 am - 11:39 amORD-YYC
3h 54mnonstop
$236United Airlines
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Sat, Oct 26 - Tue, Oct 29
6:45 am - 11:54 pmYYC-ORD
16h 09m2 stops
1:40 pm - 11:04 pmORD-YYC
10h 24m1 stop
$237Delta
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Tue, Aug 13 - Wed, Aug 21
6:25 am - 9:56 pmYYC-ORD
14h 31m1 stop
1:55 pm - 11:27 pmORD-YYC
10h 32m1 stop
$291Air Canada
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Fri, Jul 5 - Mon, Jul 8
12:40 pm - 5:09 pmYYC-ORD
3h 29mnonstop
5:04 am - 1:49 pmORD-YYC
9h 45m1 stop
$306United Airlines
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Wed, Jun 12 - Wed, Jun 26
12:40 pm - 5:09 pmYYC-ORD
3h 29mnonstop
8:45 am - 11:39 amORD-YYC
3h 54mnonstop
$308Air Canada
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Sat, Oct 26 - Tue, Oct 29
1:30 pm - 5:55 pmYYC-ORD
3h 25mnonstop
3:10 pm - 9:50 pmORD-YYC
7h 40m1 stop
$407American Airlines
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Mon, Jun 17 - Tue, Jun 18
1:30 pm - 5:55 pmYYC-ORD
3h 25mnonstop
9:50 am - 12:35 pmORD-YYC
3h 45mnonstop
$428American Airlines
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Wed, Jun 12 - Wed, Jun 26
12:30 pm - 4:57 pmYYC-ORD
3h 27mnonstop
$118WestJet
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Sat, Jun 22
12:30 pm - 4:57 pmYYC-ORD
3h 27mnonstop
$120WestJet
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Mon, Jul 1
8:30 am - 12:59 pmYYC-ORD
3h 29mnonstop
$124Air Canada
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Tue, Jun 4
6:45 am - 4:50 pmYYC-ORD
9h 05m1 stop
$134Delta
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Sat, Aug 24
1:00 am - 9:01 amYYC-ORD
7h 01m1 stop
$136Air Canada
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Tue, Aug 13
6:45 am - 4:57 pmYYC-ORD
9h 12m1 stop
$139Delta
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Sat, Jun 15
3:25 pm - 10:55 pmYYC-ORD
6h 30m1 stop
$140United Airlines
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Tue, Jun 4
7:15 pm - 9:45 amYYC-ORD
13h 30m1 stop
$141United Airlines
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Wed, Jul 3
1:30 pm - 5:55 pmYYC-ORD
3h 25mnonstop
$189American Airlines
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Tue, Jun 18
1:30 pm - 5:55 pmYYC-ORD
3h 25mnonstop
$209American Airlines
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Mon, Sep 30
12:30 pm - 5:05 pmYYC-ORD
3h 35mnonstop
8:26 pm - 3:04 pmORD-YYC
19h 38m1 stop
Mon, Jun 3 - Fri, Jun 14
12:30 pm - 5:05 pmYYC-ORD
3h 35mnonstop
8:26 pm - 4:47 pmORD-YYC
21h 21m3 stops
Mon, Jun 3 - Fri, Jun 14
12:30 pm - 5:05 pmYYC-ORD
3h 35mnonstop
4:20 pm - 4:47 pmORD-YYC
25h 27m2 stops
Mon, Jun 3 - Fri, Jun 14
12:30 pm - 5:05 pmYYC-ORD
3h 35mnonstop
5:55 pm - 8:22 pmORD-YYC
3h 27mnonstop
$401WestJet
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Thu, May 30 - Sun, Jun 2
7:55 am - 7:35 pmYYC-ORD
10h 40m2 stops
5:55 pm - 8:22 pmORD-YYC
3h 27mnonstop
$404Delta
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Thu, May 30 - Sun, Jun 2
12:30 pm - 5:05 pmYYC-ORD
3h 35mnonstop
5:55 pm - 8:22 pmORD-YYC
3h 27mnonstop
$448WestJet
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Mon, Jun 3 - Fri, Jun 14
12:10 am - 9:54 amYYC-ORD
8h 44m1 stop
4:00 pm - 10:47 pmORD-YYC
7h 47m1 stop
$622Air Canada
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Sun, Jun 2 - Fri, Jun 14
12:10 am - 9:54 amYYC-ORD
8h 44m1 stop
7:57 pm - 10:43 pmORD-YYC
3h 46mnonstop
$661Air Canada
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Sun, Jun 2 - Fri, Jun 14
7:00 pm - 5:18 amYYC-ORD
33h 18m2 stops
2:01 am - 10:59 amORD-YYC
33h 58m2 stops
$1,896Aeromexico
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Mon, Jun 3 - Thu, Jun 13
12:20 am - 11:58 pmYYC-ORD
22h 38m2 stops
2:01 am - 11:59 amORD-YYC
34h 58m2 stops
$2,161Aeromexico
Find Deal
Sun, Jun 2 - Thu, Jun 13
12:30 pm - 4:57 pmYYC-ORD
3h 27mnonstop
5:55 pm - 8:40 pmORD-YYC
3h 45mnonstop
$191WestJet
Find Deal
Thu, Jun 27 - Thu, Jul 4
12:30 pm - 5:09 pmYYC-ORD
3h 39mnonstop
5:55 pm - 8:45 pmORD-YYC
3h 50mnonstop
$193WestJet
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Sun, Sep 22 - Thu, Sep 26
12:40 pm - 5:09 pmYYC-ORD
3h 29mnonstop
5:55 pm - 8:40 pmORD-YYC
3h 45mnonstop
Tue, Jun 18 - Wed, Jun 19
12:40 pm - 5:09 pmYYC-ORD
3h 29mnonstop
8:45 am - 11:39 amORD-YYC
3h 54mnonstop
$308Air Canada
Find Deal
Sat, Oct 26 - Tue, Oct 29
8:30 am - 12:59 pmYYC-ORD
3h 29mnonstop
7:57 pm - 10:43 pmORD-YYC
3h 46mnonstop
$344Air Canada
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Wed, Jun 12 - Wed, Jun 19
12:41 pm - 5:08 pmYYC-ORD
3h 27mnonstop
8:45 am - 11:39 amORD-YYC
3h 54mnonstop
$407United Airlines
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Tue, Nov 5 - Sun, Nov 10
8:30 am - 12:59 pmYYC-ORD
3h 29mnonstop
7:57 pm - 10:43 pmORD-YYC
3h 46mnonstop
$415United Airlines
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Tue, Jun 18 - Tue, Jun 18
1:30 pm - 5:55 pmYYC-ORD
3h 25mnonstop
9:50 am - 12:30 pmORD-YYC
3h 40mnonstop
$426American Airlines
Find Deal
Wed, Sep 11 - Sat, Sep 14
1:30 pm - 5:55 pmYYC-ORD
3h 25mnonstop
9:50 am - 12:35 pmORD-YYC
3h 45mnonstop
$428American Airlines
Find Deal
Wed, Jun 12 - Wed, Jun 26
8:30 am - 12:59 pmYYC-ORD
3h 29mnonstop
5:55 pm - 8:40 pmORD-YYC
3h 45mnonstop
Sat, Jul 6 - Wed, Jul 10

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 flights from Calgary to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Chicago O'Hare Airport on a Saturday and more expensive on a Friday. On your return trip to Calgary, you should consider flying back on a Wednesday, and avoid Saturdays for better 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 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 January, where tickets cost $256 on average. On the other hand, the most expensive months are December and August, where the average cost of tickets is $451 and $442 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
To get a below average price on the flight from Calgary to Chicago O'Hare Intl Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 33 days before departure.

Which airlines provide the cheapest flights from Calgary to Chicago O'Hare Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the best return deals on flights connecting Calgary to Chicago O'Hare Airport were found on WestJet ($191) and Delta ($224). WestJet proposed the cheapest one-way flight at $118.

Which airlines fly most frequently between Calgary and Chicago O'Hare Airport?

United Airlines connects Calgary to Chicago O'Hare Airport with up to 2 flights per day. American Airlines also offers 1 flight per day, while WestJet follows with 1 flight per day.

Which airlines fly non-stop between Calgary and Chicago O'Hare Intl Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Calgary to Chicago O'Hare Intl Airport.
There are 3 airlines that fly nonstop from Calgary to Chicago O'Hare Intl Airport. They are: American Airlines, United Airlines and WestJet. The cheapest price of all airlines flying this route was found with WestJet at $132 for a one-way flight. On average, the best prices for this route can be found at WestJet.

How many flights are there between Calgary and Chicago O'Hare Intl Airport per day?

Each day, there are 4 nonstop flights that take off from Calgary and land in Chicago O'Hare Intl Airport, with an average flight time of 3h 29m. The most common departure time is 12:00 pm and most flights take off in the morning. Each week, there are 28 flights and there are the same amount of flights each day 4.

Which cabin class options are there for flights between Calgary and Chicago O'Hare Intl Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Calgary to Chicago O'Hare Airport take?

The duration of a nonstop flight to Chicago O'Hare Airport from Calgary is typically 3h 25m. The journey crosses a distance of 1,381 miles.

What’s the earliest departure time from Calgary to Chicago O'Hare Airport?

Early birds can take the earliest flight from Calgary at 8:30 am and will be landing in Chicago O'Hare Intl Airport at 12:59 pm.

What’s the latest departure time from Calgary to Chicago O'Hare Airport?

If you prefer to fly at night, the latest flight from Calgary to Chicago O'Hare Intl Airport jets off at 1:30 pm and lands at 5:55 pm.

Good to know

Low season

January

High season

July

Cheapest flight

$118
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly with an average 3% 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 $118 for a one-way ticket and $191 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, WestJet, Delta, United Airlines, British Airways, and KLM.

  • 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?

    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, WestJet or United Airlines?

    The two airlines most popular with KAYAK users for flights from Calgary to Chicago are WestJet and United Airlines. With an average price for the route of $301 and an overall rating of 7.5, WestJet is the most popular choice. United Airlines is also a great choice for the route, with an average price of $399 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 $211 or less one-way and $210 or less round-trip.

Prefer to fly non-stop from Calgary to Chicago O'Hare Airport?

Find which airlines fly direct from Calgary to O'Hare Intl, which days they fly and book direct flights.

Nonstop departures

Calgary to Chicago O'Hare Intl

Monday

Air Canada, American Airlines, British Airways, +5 more

Air Canada, American Airlines, +6 more

Tuesday

Air Canada, American Airlines, British Airways, +5 more

Air Canada, American Airlines, +6 more

Wednesday

Air Canada, American Airlines, Avianca, +6 more

Air Canada, American Airlines, +7 more

Thursday

Air Canada, American Airlines, British Airways, +5 more

Air Canada, American Airlines, +6 more

Friday

Air Canada, American Airlines, Avianca, +6 more

Air Canada, American Airlines, +7 more

Saturday

Air Canada, American Airlines, British Airways, +5 more

Air Canada, American Airlines, +6 more

Sunday

Air Canada, American Airlines, Avianca, +6 more

Air Canada, American Airlines, +7 more

See more direct flights

Nonstop returns

Chicago O'Hare Intl to Calgary

Monday

Air Canada, American Airlines, British Airways, +5 more

Air Canada, American Airlines, +6 more

Tuesday

Air Canada, American Airlines, British Airways, +5 more

Air Canada, American Airlines, +6 more

Wednesday

Air Canada, American Airlines, Avianca, +6 more

Air Canada, American Airlines, +7 more

Thursday

Air Canada, American Airlines, British Airways, +5 more

Air Canada, American Airlines, +6 more

Friday

Air Canada, American Airlines, Avianca, +6 more

Air Canada, American Airlines, +7 more

Saturday

Air Canada, American Airlines, British Airways, +5 more

Air Canada, American Airlines, +6 more

Sunday

Air Canada, American Airlines, Avianca, +6 more

Air Canada, American Airlines, +7 more

See more direct flights
See more direct flights

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.
7.5
WestJetOverall score based on 2866 reviews
7.3Comfort
8.1Crew
6.4Food
7.7Boarding
6.4Entertainment
Airline reviews

It was fine. I had a lot of trouble trying to buy a seat. The Westjet website charged me and then didn’t give me my seat. I ended up keeping the seat I was assigned and hope that the charges didn’t go through.. they didn’t. But this problem with the website (trying to purchase a seat at check in) has happened a few times before. But overall the flight was good.

6.0 GoodTimothy, May 2024YYC - LAX
Read more about WestJet reviews

It was fine. I had a lot of trouble trying to buy a seat. The Westjet website charged me and then didn’t give me my seat. I ended up keeping the seat I was assigned and hope that the charges didn’t go through.. they didn’t. But this problem with the website (trying to purchase a seat at check in) has happened a few times before. But overall the flight was good.

It was okay overall, but it was a 4 hours flight and the only thing we got was snacks, I really expected breakfast.

Terrible! Delayed three times, landed at some corner of airport, walked in bitter cold night, took a bus, bad experience

My wife and I had an uncomfortable experience with your WestJet ticket counter rep at the WestJet Priority Member ticket counter at YYC (Calgary) on May 15, 2024. I not knowing this individual’s exact name, however, in order to easily identify her, she was one (of only two at the time) ticket counter reps at your Priority members ticket counter check-in, upon our arrival around 12:15 p.m. She was a Caucasian woman with blonde hair, and wore spectacles, approximate age being probably somewhere in her 30’s or 40’s. Background: After arriving in to the West Jet terminal in Calgary (YYC), I asked a terminal employee where the West Jet check-in ticket counter was. He told me, “Column 16”. My wife and I continuing to walk through the terminal, we finally arrived at the Column 16 area, i.e. this woman’s ticket counter area, which we discovered later was the Priority Member ticket counter. However, I was simply going by the directions given to me by the previous employee, i.e. “Walk to column 16.” Standing in her line (my wife and I being the only people in her line at the time), I tried to get her attention, and I then gestured to her, motioning to her as if to ask her if I should then possibly leave the waiting line in order to then proceed to walk up to her ticket counter. She never really motioned me to come forward. I sort of had to figure this out on my own, as my wife and I then finally decided to walk forward to her station. From this point on, after I arrived at her ticket counter, never once did she ever look me in the eye. She was always looking at her computer screen, or down at the ground, as she and I occasionally exchanged conversation with one another in order for me to be able to acquire my boarding passes from her. Shortly after she began servicing us, she commented that her work section is for Priority members only. Fair enough. I did not realize this at the time. Wishing to be polite, I then mentioned to her that, if I should, I could then walk over to the regular West Jet check-in ticket counter in order to complete the check-in process. She remained quiet, never responding to this goodwill gesture of mine. She continued to work in order to print out my boarding passes, and then finally handed them to me, never at all the entire time looking at me. I told her, “Thank you.” Never once did she respond. My wife and I then walked away. Even my wife commented to me afterward that this woman absolutely never looked at us. I cannot say that this attendant was outright rude. However, she certainly was not at all warm, congenial, nor friendly. Additionally, … After getting on the plane, we then discovered that she had needlessly assigned us seats in the very last row of the plane, these being the seats adjacent to the restroom back wall, thus, unfortunately not at all reclinable. I think that the row number of this last row of seats was 30. [However, I am not sure.] How strangely awkward that we were assigned these uncomfortable row of seats when in fact the row immediately ahead of us, i.e. I think that was row 29, had two vacancies, which could have otherwise easily seated my wife and me. That is, my wife and I could have easily been assigned these more comfortable seats, which would be reclinable, and then row 30 could have otherwise had instead our two vacancies. After our flight departed, and the fasten seatbelt sign was turned off, my wife and I had hoped to “jump seats”, that is, to leave row 30 and instead sit in row 29 to utilize the reclinable seats. However, another couple apparently had the same idea as us. That is, these other two people, for whatever reason, decided to leave their previously assigned seats, and instead, seat themselves in row 29. Thus, my wife and I were stuck with these miserably cramped row 30 seats for the entire 3.5 hour flight. To reiterate, the WestJet rep we originally encountered, knowledgeable of the plane lay-out as it appeared on her computer screen, could have easily assigned us the more comfortable row 29 seats, instead of the non-reclinable row 30 seats.

Keep better track of bags. Not sure how they got lost. Also not sure why it took two weeks for us to get them back. Had to buy a bunch of necessities because they were packed.

Our trip was booked to be 2 hours after arriving in Calgary but it was changed until the next morning forcing us to stay overnight in Calgary with no compensation

Was the longest flight I have ever taken to Orlando. Not Westjet’s fault necessarily. There was a traffic issue in Orlando. We sat in the airplane for about 2 hrs before leaving Calgary on a 5 hour flight was just a little long to be stuck in the plane. Once we arrived in Orlando we were stuck in traffic on the ground for another 30min. I guess maybe the flight could be delayed so boarding would have been later so we wouldn’t have to have the discomfort of being on the plane so long.

I like WJ but I don’t like traveling anymore

Good flight. No I’m seat entertainment. But my phone worked just fine on the west jet app.

4 hour delay, lost our bags, staff was loud and it was an overnight flight

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Left on time. Arrived early. Turbulence coming in and gate not open due to early arrival but expected.

The CX617 from HK to BKK was delayed more than 1.5 hours.

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

Ontime boarding. Almost 1 hour take off delay. We could have boarded slightly later since the pilots were in traffic

Flight was delayed, I had to put my luggage all the way in the back! They served only a beverage no snack on the way in Air Canada, definitely not a good first impression.

I think Air Canada is the only airline I've flown where they don't give you at least a free cookie.

This was the first AC flight in a long time that we experienced no delays or frustrations. The gate attendant was extremely polite and accommodating to my husband who has Parkinson’s disease which made boarding extremely stress free. Flight departed ON TIME and was a smooth ride. If only all my AC experiences could be like this.

All but one of four were on time. One was delayed for an hour

It took 5 hour to get a crew to D Ice the plan. We had to sit on the runway for 5 hrs. in Calgary. It snows most of the winter. No proactive plan. In addition, after 3 calls to customer service they couldn't figure out how to have my wife and myself sit together on her birthday weekend. Everybody kept passing the buck. No decision from customer service, luggage drop off or check in team. The experience was a complete mess! I don't think we'll ever fly on this airline again.

When we got to the airport for our flight from Chicago to Montreal which was scheduled for 2.00 p.m. they had no record of it and booked us on a flight at 3.30 very disappointing . We also had to pay 50.00 each for a seat. All things considered ,I will never book thru Kayak again. Next time I will only book directly thru Air Canada no second party booking Sue

The wifi I paid for did not work. The seats are tight.

There were no free snacks…little pretzel bag or cookies like we had on our flight out.

Mostly crew good and the flight was safe and comfortable but service was lacking. For an overnight flight of 8hrs 50 it took some two hours to get served a drink and dinner after take off. I asked for Laurent Perrier champagne and was brought Perrier water, which I queried and asked where was the champagne. No response. The issue came up again an hour later when dinner was starting to be served and I was asked whether I wanted another drink, when I reminded I was still waiting for my first champagne! Apologies ensued but dinner service was quite slow. For breakfast I never did get served the hot course! So - no complaints and compliments on the safety of the flight but service underwhelming (and I brought them candies!)

Book cheap flights from Calgary to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Calgary to Chicago found on KAYAK in the last 72 hours.
6/22Sat
nonstopWestJet
3h 27mYYC-ORD
$118
7/1Mon
nonstopWestJet
3h 27mYYC-ORD
$120
6/4Tue
nonstopAir Canada
3h 29mYYC-ORD
$124
8/24Sat
1 stopDelta
9h 05mYYC-ORD
$134
8/13Tue
1 stopAir Canada
7h 01mYYC-ORD
$136
6/15Sat
1 stopDelta
9h 12mYYC-ORD
$139
6/4Tue
1 stopUnited Airlines
6h 30mYYC-ORD
$140
7/3Wed
1 stopUnited Airlines
13h 30mYYC-ORD
$141
6/18Tue
nonstopAmerican Airlines
3h 25mYYC-ORD
$189
9/30Mon
nonstopAmerican Airlines
3h 25mYYC-ORD
$209

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Last minute flights from Calgary to O'Hare Intl

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Calgary to Chicago that are departing in the next 10 days.
6/3Mon
nonstop
3h 35mYYC-ORD
6/14Fri
multi-stop
19h 38mORD-YYC
$302
6/3Mon
nonstop
3h 35mYYC-ORD
6/14Fri
multi-stop
21h 21mORD-YYC
$340
6/3Mon
nonstop
3h 35mYYC-ORD
6/14Fri
multi-stop
25h 27mORD-YYC
$347
5/30Thu
nonstopWestJet
3h 35mYYC-ORD
6/2Sun
nonstopWestJet
3h 27mORD-YYC
$401
5/30Thu
multi-stopDelta
10h 40mYYC-ORD
6/2Sun
nonstopDelta
3h 27mORD-YYC
$404
6/3Mon
nonstopWestJet
3h 35mYYC-ORD
6/14Fri
nonstopWestJet
3h 27mORD-YYC
$448
6/2Sun
multi-stopAir Canada
8h 44mYYC-ORD
6/14Fri
multi-stopAir Canada
7h 47mORD-YYC
$622
6/2Sun
multi-stopAir Canada
8h 44mYYC-ORD
6/14Fri
nonstopAir Canada
3h 46mORD-YYC
$661
6/3Mon
multi-stopAeromexico
33h 18mYYC-ORD
6/13Thu
multi-stopAeromexico
33h 58mORD-YYC
$1,896
6/2Sun
multi-stopAeromexico
22h 38mYYC-ORD
6/13Thu
multi-stopAeromexico
34h 58mORD-YYC
$2,161

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Calgary - Chicago O'Hare Airport Flights

Departure:

Calgary (YYC)Canada

Destination:

Chicago O'Hare Airport (ORD)United States

Return flight deals:

Chicago O'Hare Airport - Calgary

Cabin classes:

$1,860
$625
$2,148
$120