YYC - ORD

$92 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 6/2. 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

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 Flight Deals 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.

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

KAYAK's recommended round-trip deals from the most popular airlines that fly from Calgary to O'Hare Intl.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
12:15 pm - 4:44 pmYYC-ORD
3h 29mnonstop
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$129WestJet
Find Deal
Sat, May 3 - Fri, May 9
12:15 pm - 4:44 pmYYC-ORD
3h 29mnonstop
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$131WestJet
Find Deal
Sat, May 10 - Tue, May 13
11:55 pm - 8:50 amYYC-ORD
7h 55m1 stop
4:00 pm - 10:58 pmORD-YYC
7h 58m1 stop
$158Air Canada
Find Deal
Thu, May 1 - Wed, May 7
12:45 am - 8:50 amYYC-ORD
7h 05m1 stop
8:40 am - 10:58 pmORD-YYC
15h 18m2 stops
$159Air Canada
Find Deal
Sat, May 10 - Tue, May 13
8:10 am - 4:48 pmYYC-ORD
7h 38m1 stop
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
Sat, May 3 - Fri, May 9
12:45 am - 8:50 amYYC-ORD
7h 05m1 stop
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
Sat, May 10 - Tue, May 13
6:29 am - 10:54 amYYC-ORD
3h 25mnonstop
8:30 pm - 11:29 pmORD-YYC
3h 59mnonstop
$182American Airlines
Find Deal
Thu, Jun 12 - Mon, Jun 16
6:29 am - 10:54 amYYC-ORD
3h 25mnonstop
8:25 pm - 11:29 pmORD-YYC
4h 04mnonstop
$186American Airlines
Find Deal
Mon, Aug 4 - Sat, Aug 16
12:43 pm - 5:10 pmYYC-ORD
3h 27mnonstop
7:10 am - 9:48 pmORD-YYC
15h 38m1 stop
$210United Airlines
Find Deal
Fri, Apr 11 - Sun, Apr 13
6:15 am - 11:02 pmYYC-ORD
15h 47m1 stop
5:00 am - 1:53 pmORD-YYC
9h 53m1 stop
$216United Airlines
Find Deal
Fri, Apr 11 - Sun, Apr 13

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
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
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.

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 free Wi-Fi across the entire airport, perfect for digital nomads needing to work on the go.

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, Air Canada, United Airlines 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

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 Thursdays 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 Mondays.

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 $194 (return) on average. On the other hand, the most expensive months are December and October, where the average cost of round-trip tickets is $475 and $414 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 $586, 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 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

May

Cheapest flight

$92
Best time to beat the crowds but there is an average 31% increase in price.
Most popular time to fly and prices are also 39% 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 $92 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, KLM, WestJet, British Airways, and Delta.

  • 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 $490 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.

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 $184 or less one-way and $149 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, American Airlines, British Airways, +6 more

Air Canada, American Airlines, +7 more

Tuesday

Air Canada, American Airlines, British Airways, +6 more

Air Canada, American Airlines, +7 more

Wednesday

Air Canada, American Airlines, British Airways, +6 more

Air Canada, American Airlines, +7 more

Thursday

Air Canada, American Airlines, British Airways, +6 more

Air Canada, American Airlines, +7 more

Friday

Air Canada, American Airlines, British Airways, +6 more

Air Canada, American Airlines, +7 more

Saturday

Air Canada, American Airlines, British Airways, +6 more

Air Canada, American Airlines, +7 more

Sunday

Air Canada, American Airlines, British Airways, +6 more

Air Canada, American Airlines, +7 more

See more direct flights

Direct returns

Chicago O'Hare Intl to Calgary

Monday

Air Canada, American Airlines, British Airways, +6 more

Air Canada, American Airlines, +7 more

Tuesday

Air Canada, American Airlines, British Airways, +6 more

Air Canada, American Airlines, +7 more

Wednesday

Air Canada, American Airlines, British Airways, +6 more

Air Canada, American Airlines, +7 more

Thursday

Air Canada, American Airlines, British Airways, +6 more

Air Canada, American Airlines, +7 more

Friday

Air Canada, American Airlines, British Airways, +6 more

Air Canada, American Airlines, +7 more

Saturday

Air Canada, American Airlines, British Airways, +6 more

Air Canada, American Airlines, +7 more

Sunday

Air Canada, American Airlines, British Airways, +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.
7.4
United AirlinesOverall score based on 8614 reviews
7.7Boarding
8.1Crew
7.3Comfort
7.0Entertainment
6.6Food
Airline reviews

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

2.0 MediocreJ.C., Mar 2025COS - ORD
Read more United Airlines reviews

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

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

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

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

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.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

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.

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.

First flight out in the morning is often the best chance of running on time. Not in this case, which unfortunately is now what passengers can expect as what is common. - If you are late for a flight, too bad for you. - If West Jet is late, too bad for you. - Bags don't make it? Too bad for you. - Flight change by 1+ days, too bad for you Prices continue to increase, while customer service nosedives. This is backwards and in any other develop country would be considered unacceptable - except for Canada. Too bad for us.

Experience was good. Was surprised they didn’t offer a complimentary meal on a 5 hour flight.

Too squished in seats. I'm 110 lbs and 5'6....can't imagine being any bigger and flying

The flight attendants were great, but not much room while sitting and it would be nice to get free movies.

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.

Not much....we did not get the complimentary beverages promised in our ticket. My partner and I did not have the window seats promised. We didnt get to sit together.....

It was great. Although when I got my luggage it was broken.

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

I liked not paying for carry on and the compensation my husband and I received from the airline for overbooking our flight. The staff was very friendly and helpful.

It was a short flight and for that reason the flight was acceptable.

Ok Did not like that the second leg of flight was moved earlier making it a rush to make it

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

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

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

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

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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