YYC - ORD

C$ 127 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags

Search hundreds of travel sites at once for deals on flights to Chicago

 
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.
In the last 7 days, travellers have searched 41,299,237 times on KAYAK, and here is why:

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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

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
12:50 a.m. - 10:54 a.m.YYC-ORD
9h 04m1 stop
8:50 a.m. - 11:39 a.m.ORD-YYC
3h 49mdirect
C$ 206Air Canada
Find Deal
Mon, 13 Jan - Tue, 21 Jan
12:50 a.m. - 10:54 a.m.YYC-ORD
9h 04m1 stop
2:05 p.m. - 10:09 p.m.ORD-YYC
9h 04m1 stop
C$ 221Air Canada
Find Deal
Mon, 13 Jan - Tue, 21 Jan
12:50 a.m. - 10:54 a.m.YYC-ORD
9h 04m1 stop
5:01 p.m. - 1:18 a.m.ORD-YYC
9h 17m1 stop
C$ 250Air Canada
Find Deal
Mon, 27 Jan - Wed, 19 Feb
8:00 a.m. - 9:58 p.m.YYC-ORD
12h 58m2 stops
12:15 p.m. - 8:53 p.m.ORD-YYC
9h 38m1 stop
C$ 311Delta
Find Deal
Tue, 14 Jan - Tue, 21 Jan
8:00 a.m. - 9:58 p.m.YYC-ORD
12h 58m2 stops
12:15 p.m. - 11:18 p.m.ORD-YYC
12h 03m2 stops
C$ 329Delta
Find Deal
Tue, 14 Jan - Tue, 21 Jan
12:15 p.m. - 4:44 p.m.YYC-ORD
3h 29mdirect
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 490WestJet
Find Deal
Thu, 22 May - Mon, 26 May
12:41 p.m. - 5:15 p.m.YYC-ORD
3h 34mdirect
8:53 a.m. - 11:39 a.m.ORD-YYC
3h 46mdirect
C$ 571United Airlines
Find Deal
Thu, 30 Jan - Wed, 19 Feb
6:29 a.m. - 2:25 p.m.YYC-ORD
6h 56m1 stop
1:13 p.m. - 9:57 p.m.ORD-YYC
9h 44m1 stop
C$ 680American Airlines
Find Deal
Fri, 17 Jan - Thu, 23 Jan
12:41 p.m. - 5:15 p.m.YYC-ORD
3h 34mdirect
8:50 a.m. - 11:39 a.m.ORD-YYC
3h 49mdirect
C$ 691United Airlines
Find Deal
Mon, 3 Feb - Thu, 6 Feb
6:29 a.m. - 2:25 p.m.YYC-ORD
6h 56m1 stop
11:47 a.m. - 9:57 p.m.ORD-YYC
11h 10m1 stop
C$ 710American Airlines
Find Deal
Fri, 17 Jan - Thu, 23 Jan

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, Friday 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$ 394 (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$ 691 and C$ 607 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.
Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at C$ 314 on average.

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

July

Cheapest flight

C$ 127
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly and prices are also 0% 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$ 89 for a one-way ticket and C$ 144 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, British Airways, WestJet, 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?

    Star Alliance is the only airline alliance operating flights between Calgary and Chicago.

  • 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$ 419 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$ 623 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$ 268 or less one-way and C$ 684 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,Emirates,United Airlines, +5 more

Air Canada,Emirates, +6 more

Tuesday

Air Canada,Emirates,United Airlines, +3 more

Air Canada,Emirates, +4 more

Wednesday

Air Canada,Emirates,United Airlines, +3 more

Air Canada,Emirates, +4 more

Thursday

Air Canada,Emirates,United Airlines, +5 more

Air Canada,Emirates, +6 more

Friday

Air Canada,Emirates,United Airlines, +3 more

Air Canada,Emirates, +4 more

Saturday

Air Canada,Emirates,United Airlines, +3 more

Air Canada,Emirates, +4 more

Sunday

Air Canada,Emirates,United Airlines, +5 more

Air Canada,Emirates, +6 more

See more nonstop flights

Direct returns

Chicago O'Hare Intl to Calgary

Monday

Air Canada,United Airlines,American Airlines, +4 more

Air Canada,United Airlines, +5 more

Tuesday

Air Canada,United Airlines,American Airlines, +2 more

Air Canada,United Airlines, +3 more

Wednesday

Air Canada,United Airlines,American Airlines, +2 more

Air Canada,United Airlines, +3 more

Thursday

Air Canada,United Airlines,American Airlines, +4 more

Air Canada,United Airlines, +5 more

Friday

Air Canada,United Airlines,American Airlines, +2 more

Air Canada,United Airlines, +3 more

Saturday

Air Canada,United Airlines,American Airlines, +2 more

Air Canada,United Airlines, +3 more

Sunday

Air Canada,United Airlines,American Airlines, +4 more

Air Canada,United 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.
8.6
WestJet EncoreOverall score based on 10 reviews
6.2Entertainment
9.6Boarding
7.3Food
9.2Crew
8.0Comfort
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

Pros: "Friendly staff and the support they offered to my mother who needed a wheelchair."
Cons: "I would have liked to have had WestJet internet and entertainment access. It was not offered on our flight from Toronto to Fredericton."

I think they can provide the better food/snack option for the 4 hours flight. Drinks are fine.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

Typically I give delta excellent reviews. Our flight was delayed 2hrs, I was one of the fortunate ones who were able to get to my connecting flight. Also, annoying that on the connecting flight boarding personnel make me put away a small bag into my carryon. It small enough to put in back pocket seat, why hold me and the line up to just push it into my carryon.

Everything was great. Great service, excellent communication, and early arrival

Delta flight attendants poorly managed the boarding process and overhead storage. My bag was checked last minute and no claim ticket was provided. My bag is now lost. Complete incompetence by all flight crew involved.

Inexpensive, got an exit row aisle aeat with no middle passenger, bought a great breakfast sandwich, flight comfortable & arrived ahead of schedule.

Customer service at the gate in the flight was exceptional. On time. Aircraft and seat was decent. Thanks Delta. 💗

It was terrible, if they ran flights on time it would make a big difference.

Great flight. On-time, comfortable, clean aircraft, and offered snacks pre-flight to plan for a potentially turbulent route. I wish there was Wi-Fi an all Delta Aircrafts but for a short flight this is not much of a problem.

Delta seems to be improving in many areas, except they are super bad with the food available. Bring back normal food service on long flights.

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.

Flight was great albeit the long line before the int’l immigration given the timing of the year.

They canceled our flight and left us stranded to figure it out

We appreciated the friendly, efficient, and professional flight attendants. A wider selection of hot foods would be nice.

Did not have enough time from Venice seaport at Ravenna to get to Venice airport in order to make the scheduled flights. Need to have at least 3+ hours from ship docking to airport.

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

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.

Terrible experience at the gate. Charged for carry on luggage despite them meeting the requirements for sizing.

Check in agent was good, stewardess was unfriendly and certainly did not have the care of the passengers in mind Spent the whole time on her phone

we were upgraded to business class, not sure why, so the flight exceeded our expectations. Perhaps this was because the flight Cancun to Calgary was a nightmare , not even guaranteed a seat upon checkin at the airport.

Average at best. Typical of WestJet these days. Crew far from friendly.

It was fine for a low cost trip. No entertainment and poor food offer. The sits were ok. It was on time.

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!!

I needed to catch a United flight. There wasn't enough signage or help on arrival to navigate the transfer.

Seats weren't comfortable, could have used more let room

Book cheap flights from Calgary to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Calgary to Chicago found on KAYAK in the last 72 hours.
3/3Mon
directWestJet
3h 26mYYC-ORD
C$ 127
17/3Mon
directWestJet
3h 26mYYC-ORD
C$ 133
18/2Tue
1 stopAir Canada
9h 04mYYC-ORD
C$ 140
19/2Wed
1 stopAir Canada
7h 35mYYC-ORD
C$ 147
20/3Thu
1 stopUnited Airlines
13h 13mYYC-ORD
C$ 154
8/5Thu
1 stopUnited Airlines
9h 20mYYC-ORD
C$ 169
16/2Sun
1 stopDelta
9h 54mYYC-ORD
C$ 191
13/1Mon
2 stopsDelta
13h 18mYYC-ORD
C$ 193
26/12Thu
1 stopAmerican Airlines
13h 50mYYC-ORD
C$ 257
27/12Fri
1 stopAmerican Airlines
13h 50mYYC-ORD
C$ 259

Search by stops

Search by airline

Search by price

Last minute flights from Calgary to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Calgary to Chicago that are departing in the next 10 days.
23/12Mon
multi-stopAmerican Airlines
17h 35mYYC-ORD
27/12Fri
multi-stopAmerican Airlines
15h 46mORD-YYC
C$ 431
22/12Sun
multi-stopDelta
9h 09mYYC-ORD
25/12Wed
multi-stopDelta
11h 43mORD-YYC
C$ 543
19/12Thu
directAir Canada
3h 34mYYC-ORD
7/1Tue
multi-stopAir Canada
7h 50mORD-YYC
C$ 598
22/12Sun
multi-stopUnited Airlines
8h 50mYYC-ORD
30/12Mon
directUnited Airlines
3h 54mORD-YYC
C$ 791
23/12Mon
directAir Canada
3h 34mYYC-ORD
25/12Wed
multi-stopAir Canada
11h 22mORD-YYC
C$ 793
19/12Thu
directUnited Airlines
3h 34mYYC-ORD
7/1Tue
directUnited Airlines
3h 49mORD-YYC
C$ 846
23/12Mon
multi-stop
11h 55mYYC-ORD
24/12Tue
multi-stop
10h 25mORD-YYC
C$ 963
23/12Mon
multi-stop
11h 55mYYC-ORD
26/12Thu
multi-stop
8h 29mORD-YYC
C$ 1,033
19/12Thu
multi-stopWestJet
9h 39mYYC-ORD
7/1Tue
multi-stopWestJet
11h 01mORD-YYC
C$ 1,230
19/12Thu
multi-stopWestJet
10h 09mYYC-ORD
27/12Fri
multi-stopWestJet
17h 10mORD-YYC
C$ 1,248

Search by stops

Search by airline

Search by price

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

Information on your arrival and departure airports

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