YYC - ORD

C$ 138 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 20/2. 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.
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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 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 Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Calgary to Chicago.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
4:45 p.m. - 7:36 p.m.ORD-YYC
3h 51mdirect
C$ 196WestJet
Find Deal
Thu, 20 Feb - Thu, 27 Feb
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
4:45 p.m. - 7:36 p.m.ORD-YYC
3h 51mdirect
C$ 217WestJet
Find Deal
Thu, 17 Apr - Sun, 20 Apr
7:20 p.m. - 9:33 a.m.YYC-ORD
13h 13m1 stop
1:05 p.m. - 9:41 p.m.ORD-YYC
9h 36m1 stop
C$ 276United Airlines
Find Deal
Mon, 17 Mar - Tue, 18 Mar
8:30 a.m. - 6:38 p.m.YYC-ORD
9h 08m1 stop
4:51 p.m. - 1:18 a.m.ORD-YYC
9h 27m1 stop
C$ 292Air Canada
Find Deal
Mon, 3 Feb - Tue, 11 Feb
12:05 a.m. - 10:10 a.m.YYC-ORD
9h 05m1 stop
6:28 p.m. - 1:18 a.m.ORD-YYC
7h 50m1 stop
C$ 302Air Canada
Find Deal
Sun, 2 Feb - Tue, 11 Feb
6:35 a.m. - 8:53 p.m.YYC-ORD
13h 18m2 stops
12:15 p.m. - 8:53 p.m.ORD-YYC
9h 38m1 stop
C$ 311Delta
Find Deal
Thu, 20 Feb - Wed, 26 Feb
6:35 a.m. - 5:29 p.m.YYC-ORD
9h 54m1 stop
12:15 p.m. - 11:15 p.m.ORD-YYC
12h 00m2 stops
C$ 312Delta
Find Deal
Mon, 3 Feb - Tue, 11 Feb
12:45 p.m. - 11:56 p.m.YYC-ORD
10h 11m1 stop
8:35 p.m. - 11:50 a.m.ORD-YYC
16h 15m1 stop
C$ 429American Airlines
Find Deal
Sat, 22 Feb - Mon, 24 Feb
1:32 p.m. - 6:03 p.m.YYC-ORD
3h 31mdirect
8:35 p.m. - 11:50 a.m.ORD-YYC
16h 15m1 stop
C$ 448American Airlines
Find Deal
Fri, 21 Feb - Mon, 24 Feb
2:09 p.m. - 12:23 a.m.YYC-ORD
9h 14m1 stop
8:47 a.m. - 11:39 a.m.ORD-YYC
3h 52mdirect
C$ 449United Airlines
Find Deal
Tue, 18 Mar - Wed, 19 Mar

Flights from Calgary to Chicago - Travel Insights & Trends

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 Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Calgary to Chicago. For your return ticket, we recommend flying on a Monday and avoiding Saturdays 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 September, where tickets cost C$ 383 (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$ 684 and C$ 605 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$ 664, 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 23 weeks before departure.

Good to know

Low season

November

High season

July

Cheapest flight

C$ 138
Best time to beat the crowds but there is an average 16% increase in price.
Most popular time to fly (2% 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$ 96 for a one-way ticket and C$ 136 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, British Airways, KLM, Air Canada, United Airlines, and Delta.

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

    The Airbus A319 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$ 418 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$ 630 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$ 384 or less one-way and C$ 522 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,British Airways, +5 more

Air Canada,American Airlines, +6 more

Tuesday

Air Canada,American Airlines,British Airways, +3 more

Air Canada,American Airlines, +4 more

Wednesday

Air Canada,American Airlines,British Airways, +3 more

Air Canada,American Airlines, +4 more

Thursday

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

Air Canada,American Airlines, +6 more

Friday

Air Canada,American Airlines,British Airways, +3 more

Air Canada,American Airlines, +4 more

Saturday

Air Canada,American Airlines,British Airways, +3 more

Air Canada,American Airlines, +4 more

Sunday

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

Air Canada,American Airlines, +6 more

See more nonstop flights

Direct returns

Chicago O'Hare Intl to Calgary

Monday

Air Canada,American Airlines,British Airways, +4 more

Air Canada,American Airlines, +5 more

Tuesday

Air Canada,American Airlines,British Airways, +2 more

Air Canada,American Airlines, +3 more

Wednesday

Air Canada,American Airlines,British Airways, +2 more

Air Canada,American Airlines, +3 more

Thursday

Air Canada,American Airlines,British Airways, +4 more

Air Canada,American Airlines, +5 more

Friday

Air Canada,American Airlines,British Airways, +2 more

Air Canada,American Airlines, +3 more

Saturday

Air Canada,American Airlines,British Airways, +2 more

Air Canada,American Airlines, +3 more

Sunday

Air Canada,American Airlines,British Airways, +4 more

Air Canada,American Airlines, +5 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.
8.9
WestJet EncoreOverall score based on 9 reviews
7.5Food
9.3Crew
6.8Entertainment
8.4Comfort
9.5Boarding
Airline reviews

Great flight, comfort, and staff. Prefer tv in back of seat but watching on phone will do

10.0 ExcellentDarren, May 2023YYZ - LAX
Read more WestJet Encore reviews

Great flight, comfort, and staff. Prefer tv in back of seat but watching on phone will do

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

Flight left early and arrived early. the whole trip was excellent.

It was terrible, I sat next to a person with a cat, I'm allergic to animal dander, my discomfort was extreme

Seats were really tight and the seat belts did not give enough slack.

Great list of movies, seat was generally comfortable, but not much shoulder room. The fresh baked cookie mostly made up for the lack of variety with the meals, which were all tomato based.

I like in St George and prefer to fly out of CDC than SGU. Hopefully, they will continue the flights out of Cedar

Broken jer bridge. Poor communication about it. Lost 2 of 4 luggage pieces

Overall, it was okay. Seat was a little cramped. Would’ve liked more substantial snacks or opportunity to buy some.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

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.

They needed people to check a bag, they did check my bag and I had to wait 10 minutes after the flight to get it it wasn’t too bad

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

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

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.

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

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

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.

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

I was mostly pleased. My greatest disappointment was with respect to the timely update to the estimated departure and arrival times. It was especially sad that the arrival time was not updated online once we were in flight so as to allow my wife to arrive on time to the airport. She was not happy.

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

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

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

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Rosemont
Schaumburg
Oak Brook
Hoffman Estates
Skokie
Glenview
Naperville
Itasca
Elk Grove Village
Des Plaines
Benton Harbor
Gurnee
North Chicago
Deerfield
New Buffalo
Joliet
Northbrook
Portage
Vernon Hills
Racine

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

Information on your arrival and departure airports

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