YYC - ORD

C$ 141 Find Cheap Flights from Calgary to Chicago

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 Chicago departing on 20/5. 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.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Calgary to Chicago.
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Cheap Flight Deals from Calgary to Chicago (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 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 Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Calgary to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
WestJet Logo
12:15 p.m. - 4:44 p.m.YYC-ORD
3h 29mdirect
WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 243WestJet
Find Deal
Tue, 3 Jun - Tue, 10 Jun
Air Canada Logo
12:45 a.m. - 8:50 a.m.YYC-ORD
7h 05m1 stop
Air Canada Logo
8:45 a.m. - 11:41 a.m.ORD-YYC
3h 56mdirect
C$ 254Air Canada
Find Deal
Sun, 4 May - Wed, 7 May
United Airlines Logo
8:30 a.m. - 1:01 p.m.YYC-ORD
3h 31mdirect
United Airlines Logo
5:02 a.m. - 1:53 p.m.ORD-YYC
9h 51m1 stop
C$ 257United Airlines
Find Deal
Thu, 22 May - Mon, 26 May
Air Canada Logo
11:55 p.m. - 8:50 a.m.YYC-ORD
7h 55m1 stop
Air Canada Logo
5:55 p.m. - 1:03 a.m.ORD-YYC
8h 08m1 stop
C$ 263Air Canada
Find Deal
Mon, 26 May - Tue, 27 May
United Airlines Logo
6:15 a.m. - 8:00 p.m.YYC-ORD
12h 45m1 stop
United Airlines Logo
5:02 a.m. - 6:21 p.m.ORD-YYC
14h 19m1 stop
C$ 265United Airlines
Find Deal
Tue, 3 Jun - Tue, 10 Jun
American Airlines Logo
6:29 a.m. - 10:54 a.m.YYC-ORD
3h 25mdirect
American Airlines Logo
8:25 p.m. - 11:29 p.m.ORD-YYC
4h 04mdirect
C$ 301American Airlines
Find Deal
Wed, 6 Aug - Wed, 13 Aug
Delta Logo
7:15 a.m. - 6:05 p.m.YYC-ORD
9h 50m1 stop
Delta Logo
1:55 p.m. - 11:03 p.m.ORD-YYC
10h 08m1 stop
C$ 308Delta
Find Deal
Wed, 6 Aug - Wed, 13 Aug
Delta Logo
7:15 a.m. - 6:05 p.m.YYC-ORD
9h 50m1 stop
Delta Logo
1:55 p.m. - 11:03 p.m.ORD-YYC
10h 08m1 stop
C$ 310Delta
Find Deal
Wed, 13 Aug - Mon, 18 Aug
WestJet Logo
12:15 p.m. - 4:44 p.m.YYC-ORD
3h 29mdirect
WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 319WestJet
Find Deal
Mon, 25 Aug - Mon, 8 Sep
American Airlines Logo
1:18 p.m. - 5:48 p.m.YYC-ORD
3h 30mdirect
American Airlines Logo
8:25 p.m. - 11:29 p.m.ORD-YYC
4h 04mdirect
C$ 335American Airlines
Find Deal
Tue, 6 May - Mon, 28 Jul

Expert advice for your flight from Calgary to Chicago

 
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 specific 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 includes two free checked bags and priority boarding for a smoother travel experience.


WestJet's EconoFlex fare includes a checked bag, seat selection, and free changes or cancellations.

Read more about WestJetby Stefanie Waldek
Air Canada

Air Canada's Preferred Economy offers up to 10 cm extra legroom for a more comfortable journey.


Air Canada offers priority check-in for higher fare classes and elite status members, saving time at the airport.

Read more about Air Canadaby Stefanie Waldek
United Airlines

United's Economy Plus offers up to 15 cm more legroom, enhancing comfort on your flight.


United offers Priority Boarding for Zone 2, ensuring overhead bin space for your carry-on.

American Airlines

American Airlines' Main Cabin Extra provides early boarding and complimentary alcoholic drinks for added value.


American Airlines' Basic Economy is budget-friendly but has restrictions like late boarding and no seat assignment.

Airports
YYC

Use the YYC Express app to pre-book security times, especially before noon for quicker access through Security D and E.

Read more about YYCby Lucas Aykroyd
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
Lucas Aykroyd

Lucas Aykroyd

Expert on YYC

Lucas Aykroyd

Lucas Aykroyd

Lucas Aykroyd is an award-winning travel writer based in Vancouver (YVR). His favorite adventures include tracking polar bears in Nunavut and rafting over a waterfall in New Zealand. Lucas has written for the in-flight magazines of Delta, SAS, and Porter Airlines. He is also a National Geographic and Toronto Star contributor.

Read more

KAYAK's insights & trends for Calgary to Chicago flights

Get data-powered insights and trends into flights from Calgary to Chicago 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?

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.
If your flying dates are flexible, you should consider flying to Chicago on a Thursday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Calgary to Chicago. For your return ticket, we recommend flying on a Wednesday and avoiding Sundays for the best 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 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 C$ 268 (return) on average. On the other hand, the most expensive months are December and October, where the average cost of round-trip tickets is C$ 657 and C$ 572 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 C$ 546, 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

C$ 141
Best time to beat the crowds but there is an average 24% increase in price.
Most popular time to fly and prices are also 36% lower on average.
Flight from Calgary to Chicago

When to book flights from Calgary to Chicago

Are your dates flexible? Find out the best times to travel from Calgary to Chicago 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 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 C$ 102 for a one-way ticket and C$ 176 for a round-trip.

  • Which airlines offer Wi-Fi service onboard planes from Calgary to Chicago?

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

  • Which aircraft models fly most regularly from Calgary to Chicago?

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

  • Which airline alliances offer flights from Calgary to Chicago?

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

  • On which days can I fly direct from Calgary to Chicago?

    There are direct flights from Calgary to Chicago 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 C$ 371 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 C$ 585 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Calgary to Chicago?

    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.

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

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

  • What is the Hacker Fare option on flights from Calgary to Chicago?

    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 with an airline and back to Calgary with another airline.

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

    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 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 C$ 301 or less one-way and C$ 431 or less round-trip.

Prefer to fly direct from Calgary to Chicago?

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

Direct departures

Calgary to Chicago O'Hare Intl

Monday

Air Canada,American Airlines,Avianca, +6 more

Air Canada,American Airlines, +7 more

Tuesday

Air Canada,American Airlines,Avianca, +6 more

Air Canada,American Airlines, +7 more

Wednesday

Air Canada,American Airlines,Avianca, +6 more

Air Canada,American Airlines, +7 more

Thursday

Air Canada,American Airlines,Avianca, +6 more

Air Canada,American Airlines, +7 more

Friday

Air Canada,American Airlines,Avianca, +6 more

Air Canada,American Airlines, +7 more

Saturday

Air Canada,American Airlines,Avianca, +6 more

Air Canada,American Airlines, +7 more

Sunday

Air Canada,American Airlines,Avianca, +6 more

Air Canada,American Airlines, +7 more

See more nonstop flights

Direct returns

Chicago O'Hare Intl to Calgary

Monday

Air Canada,American Airlines,Avianca, +6 more

Air Canada,American Airlines, +7 more

Tuesday

Air Canada,American Airlines,Avianca, +6 more

Air Canada,American Airlines, +7 more

Wednesday

Air Canada,American Airlines,Avianca, +6 more

Air Canada,American Airlines, +7 more

Thursday

Air Canada,American Airlines,Avianca, +6 more

Air Canada,American Airlines, +7 more

Friday

Air Canada,American Airlines,Avianca, +6 more

Air Canada,American Airlines, +7 more

Saturday

Air Canada,American Airlines,Avianca, +6 more

Air Canada,American Airlines, +7 more

Sunday

Air Canada,American Airlines,Avianca, +6 more

Air Canada,American Airlines, +7 more

See more nonstop flights
See more nonstop flights

Top 5 airlines serving from Calgary to Chicago

 
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 Chicago? 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 7920 reviews
7.9Entertainment
7.9Comfort
8.5Crew
8.2Boarding
7.3Food
Airline reviews

Delta flight was on time, seats were comfortable, and crew was nice.

8.0 ExcellentAnonymous, Apr 2025LAX - DEN
Read more Delta reviews

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

Delta is a cut above the others in customer service.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

I love the free WiFi!! Crew was nice. Bathroom was decent. First time flying delta in a long time and I enjoyed it. Will definitely look into booking with Delta more but I think Delta is a little more expensive than the other airlines.

third trip overseas with delta recently where the TV did not work- not acceptable for a 8 hour flight! your food really has declined crew great and I am loyal to delta

Boarding in Amsterdam is always chaotic. KLM/ Delta has not streamlined or made it efficient as it was boarding in Detroit . The food was mediocre The crew was unfriendly and more focused on getting things done quickly rather than service with a smile .

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

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.

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

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

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

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.

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

It took 30 minutes to check in with the Westjet rep. They didn’t have enough seats and she needed to make a call… I am always “randomly” selected to be checked at security. Their “randomly “ selection system may need some updating. They treat people like criminals. It is not appropriate behavior.

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

My flight was overbooked and they would not let me board. I had to book another flight and pay the full amount of that flight. I did not get any help at all from Air Canada or United Airlines.

Everything was made rather simple, so I appreciate that. All the people I dealt with from entering the airport in Jacksonville to my lonnnnnnng walk to my next gate in Chicago were excellent and very helpful.

Terrible. 3 missed flights and 24 hours delayed with lost bag and promised $100 compensation from United and absolutely nothing from them…

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.

Everything you need to know for your flight from Calgary to Chicago

Information on your arrival and departure airports

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