YYC - ORD

C$ 111 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 20/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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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Flight Deals

Cheap Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Calgary to Chicago

Sun, 26 Oct - Mon, 27 Oct
WestJet Logo
9:00 a.m. - 1:35 p.m.YYC-ORD
3h 35mdirect
WestJet Logo
2:20 p.m. - 5:15 p.m.ORD-YYC
3h 55mdirect
C$ 213WestJet
Find Deal
Wed, 22 Oct - Sat, 1 Nov
American Airlines Logo
1:29 p.m. - 5:54 p.m.YYC-ORD
3h 25mdirect
American Airlines Logo
9:49 a.m. - 12:34 p.m.ORD-YYC
3h 45mdirect
C$ 233American Airlines
Find Deal
Wed, 22 Oct - Sat, 1 Nov
Multiple Airlines Logo
12:38 p.m. - 5:10 p.m.YYC-ORD
3h 32mdirect
Multiple Airlines Logo
3:55 p.m. - 12:14 a.m.ORD-YYC
9h 19m1 stop
C$ 237Multiple Airlines
Find Deal
Sat, 22 Nov - Sat, 29 Nov
Air Canada Logo
11:40 p.m. - 9:13 a.m.YYC-ORD
8h 33m1 stop
Air Canada Logo
2:00 p.m. - 8:39 p.m.ORD-YYC
7h 39m1 stop
C$ 244Air Canada
Find Deal
Sat, 22 Nov - Sat, 29 Nov
Air Canada Logo
5:35 a.m. - 8:00 p.m.YYC-ORD
13h 25m2 stops
Air Canada Logo
10:00 a.m. - 6:54 p.m.ORD-YYC
9h 54m1 stop
C$ 248Air Canada
Find Deal
Wed, 22 Oct - Sat, 1 Nov
Multiple Airlines Logo
6:15 a.m. - 11:59 p.m.YYC-ORD
16h 44m1 stop
Multiple Airlines Logo
3:55 p.m. - 12:14 a.m.ORD-YYC
9h 19m1 stop
C$ 259Multiple Airlines
Find Deal
Sat, 22 Nov - Sat, 29 Nov
United Airlines Logo
6:15 a.m. - 11:59 p.m.YYC-ORD
16h 44m1 stop
United Airlines Logo
8:45 a.m. - 11:35 a.m.ORD-YYC
3h 50mdirect
C$ 280United Airlines
Find Deal
Tue, 28 Oct - Sat, 29 Nov
United Airlines Logo
2:13 p.m. - 8:58 p.m.YYC-ORD
5h 45m1 stop
United Airlines Logo
8:45 a.m. - 11:35 a.m.ORD-YYC
3h 50mdirect
C$ 303United Airlines
Find Deal
Mon, 20 Oct - Fri, 14 Nov
Delta Logo
7:45 a.m. - 6:41 p.m.YYC-ORD
9h 56m1 stop
Delta Logo
1:38 p.m. - 11:10 p.m.ORD-YYC
10h 32m1 stop
C$ 311Delta
Find Deal
Mon, 27 Oct - Tue, 9 Dec
Delta Logo
7:45 a.m. - 6:41 p.m.YYC-ORD
9h 56m1 stop
Delta Logo
11:00 a.m. - 11:13 p.m.ORD-YYC
13h 13m2 stops
C$ 326Delta
Find Deal

Everything you should know

Our travellers' advice
AI-generated summary based on content written by travel experts
United's Economy Plus offers extra legroom for comfort.
Use the YYC Express app to pre-book security times.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
WestJet
Cheapest • from C$ 213 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
6 weeks
in advance
Our data shows that travellers who book at least 6 weeks in advance save around 40% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
May
Cheapest • 41% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
C$ 213
Overall average: C$ 463
WestJet
Sun 26/10Mon 27/10
YYC - ORD • Direct
Cheapest one-way flights
C$ 155
Typical prices: C$ 188-361
Air Canada
Mon 20/10
YYC - ORD • 1 stop
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Booking Insights

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 Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Tuesday 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$ 229 (return) on average. On the other hand, the most expensive months are December and August, where the average cost of round-trip tickets is C$ 709 and C$ 481 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$ 440, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Calgary to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Calgary to Chicago O'Hare Intl Airport, you should book around 6 weeks before departure, which saves you about 40% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Expert advice

Expert advice for your flight from Calgary to Chicago

 
Snippets provided in this section are AI-generated based on a summarisation 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 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

Good to know

Low seasonNovember
Cheapest flightC$ 155
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly (20% more expensive 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$ 111 for a one-way ticket and C$ 153 for a round-trip.

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

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

  • 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?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Calgary and Chicago, with SkyTeam 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$ 348 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of C$ 527 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.

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$ 282 or less one-way and C$ 468 or less round-trip.

Prefer to fly direct from Calgary to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Calgary to Chicago O'Hare Intl.
Find which airlines fly direct from Calgary Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.

Direct departures

Calgary to Chicago O'Hare Intl

Monday

United Airlines,WestJet,American Airlines

United Airlines,WestJet, +1 more

Tuesday

United Airlines,American Airlines

United Airlines,American Airlines

Wednesday

United Airlines,American Airlines

United Airlines,American Airlines

Thursday

United Airlines,American Airlines

United Airlines,American Airlines

Friday

United Airlines,WestJet,American Airlines

United Airlines,WestJet, +1 more

Saturday

United Airlines,American Airlines

United Airlines,American Airlines

Sunday

United Airlines,WestJet,American Airlines

United Airlines,WestJet, +1 more

See more nonstop flights

Direct returns

Chicago O'Hare Intl to Calgary

Monday

United Airlines,WestJet,American Airlines

United Airlines,WestJet, +1 more

Tuesday

United Airlines,American Airlines

United Airlines,American Airlines

Wednesday

United Airlines,American Airlines

United Airlines,American Airlines

Thursday

United Airlines,American Airlines

United Airlines,American Airlines

Friday

United Airlines,WestJet,American Airlines

United Airlines,WestJet, +1 more

Saturday

United Airlines,American Airlines

United Airlines,American Airlines

Sunday

United Airlines,WestJet,American Airlines

United Airlines,WestJet, +1 more

See more nonstop flights

Reviews of the top 5 airlines flying 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.
7.9
DeltaOverall score based on 7969 reviews
8.5Crew
7.9Entertainment
7.3Food
8.2Boarding
7.9Comfort
Airline reviews

The crew was not very visible. This might be a good thing for people who wanted to sleep but seemed odd when compared to the Atlantic crossing where they are more present in the cabin. The Food (beef) was not good. Tough and tasteless. Would love to see more choices on a long flight like that.

8.0 ExcellentKathrin, Oct 2025SYD - LAX
Read more Delta reviews

The crew was not very visible. This might be a good thing for people who wanted to sleep but seemed odd when compared to the Atlantic crossing where they are more present in the cabin. The Food (beef) was not good. Tough and tasteless. Would love to see more choices on a long flight like that.

The flight was great. The gate location was way to far away!!!

This was our second flight using the Delta One class of service. Overall, it’s a good product but for me the POD configuration is a bit constrictive. I am an average size male at 5’ 10” height weighing 190 lbs so it’s not a size thing for me. I’d rather have extra wide seats without the POD walls to be honest.

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

Convient flight. Good experience. No complaints other than the food quality seems to have decreased.

Food tray looked like penitentiary food - little effort to make it look appealing (packaging colour and design)

Movie selection was meh. Food was great. Crew as always great. I paid for premium because that’s the only way not to feel like a sardine. That’s how economy should be imo. Sadly passengers have to pay an extra $1000 to get what they should at base price but that’s all airlines. The airline industry in general treats passengers as cargo.

Gate agent rushed to fill hot jetway with crowd so it took over 12 minutes to go from gate to plane. Just like a discount airline Pooly prepared cabin and third time that claim of rough air prevented any cabin service. Friends on a Southwest flight at similar time had service.

My only complaint on any flight is meals but your gnocchi was good. The worst is breakfast. I can’t understand why you don’t just serve something simple like yogurt, fruit and a muffin or cinnamon roll.

Cramped seating for me. Luckily it wasn’t a long flight

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

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

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

Could have said yes to a glass of wine 🍷 instead of saying we'll come around in a couple of hours

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

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

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

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

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

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

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

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

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

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

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

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

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

my carry-on bag was delayed and I did not receive it until the day of my return at the airport. This delay caused me significant inconvenience, as I did not have access to my personal belongings for the duration of my trip. I had expected to rely on my carry-on items, and being without them negatively impacted my travel experience.

Technology issues at the bag-check counter caused a delay, and we were unable to check out our bags, ultimately missing our flight. They offered no assistance other than telling us to book another flight out of Calgary. We arrived with plenty of time; if there hadn't been an issue with the kiosk and the length of the lines due to the technical issues, we could have made it home.

Worst check in and bag drop off experience. Staff were incredibly rude given that it’s the WestJet system that is faulty.

The staff at the airport and on the plane were wonderful I especially wanna acknowledge the staff who boarded us at the Calgary airport. The women who helped us board at the airport were incredible… they were so kind and sweet…I very happy with WestJet and I am hoping I can fly more often to Canada.

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

From vancouver go calgary nd vice vetsa fligjt was delayed

It was good! Short flight and it was on time!

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

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

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

I wish to travel with Air Canada for my next trip

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

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

Very bad service the way back we was on the way for r two days very bad condition and waiting for luggage till now

Pros: The airplane was new and had in-flight entertainment (tablet behind seats) with new movies instead of watching on personal devices. Cons: the flight time was changed without informing us. When I booked the flight, the time was 13:30pm (also in the email confirmation). However, when I reached the airport, the time was conveniently changed to 14:55pm. When I asked at the counter, they said the flight always took off at this time. The booking was made by Air Canada, but the flight was operated by United.

United had no (zero) record of our flight. It took over an hour of us standing in line with surly employee while others waited to get resolved. I have never experienced such poor service and poor empathy.

Or the greatest and it ended up picking us up from Chicago to Toronto not sure who was tesponsible for the 4 hr delay. United should have been properly prepared for a scheduled flight from Austin to Chicago and they were not.

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

Information on your arrival and departure airports

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