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Find cheap flights from Calgary to Chicago from $122

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 5/26. 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
Mon 6/3
Mon 6/10

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, 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
In the last 7 days travelers have searched 43,693,958 times on KAYAK, and here is why:

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Cheap flight deals from Calgary to Chicago (YYC-CHI)

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 and deals for you by selecting your travel dates.
Choose your dates
12:30 pm - 5:05 pmYYC-ORD
3h 35mnonstop
5:55 pm - 8:22 pmORD-YYC
3h 27mnonstop
$200WestJet
Find Deal
Thu, May 16 - Sat, May 18
12:30 pm - 5:05 pmYYC-ORD
3h 35mnonstop
5:55 pm - 8:22 pmORD-YYC
3h 27mnonstop
$201WestJet
Find Deal
Thu, May 16 - Sat, May 18
7:55 am - 7:10 pmYYC-ORD
10h 15m1 stop
12:20 pm - 8:46 pmORD-YYC
9h 26m1 stop
$267Delta
Find Deal
Tue, May 14 - Sat, May 18
12:30 pm - 5:05 pmYYC-ORD
3h 35mnonstop
5:55 pm - 8:22 pmORD-YYC
3h 27mnonstop
$268Delta
Find Deal
Thu, May 16 - Sat, May 18
12:10 am - 9:01 amYYC-ORD
7h 51m1 stop
2:00 pm - 10:49 pmORD-YYC
9h 49m1 stop
$271Air Canada
Find Deal
Wed, Sep 25 - Wed, Oct 2
10:00 am - 8:35 pmYYC-ORD
9h 35m1 stop
10:52 pm - 11:58 amORD-YYC
14h 06m1 stop
Tue, May 28 - Tue, Jun 4
12:30 am - 4:35 pmYYC-ORD
15h 05m2 stops
5:55 pm - 8:22 pmORD-YYC
3h 27mnonstop
Tue, May 14 - Sat, May 18
6:25 am - 10:53 pmYYC-ORD
15h 28m1 stop
7:15 am - 9:38 pmORD-YYC
15h 23m1 stop
$352United Airlines
Find Deal
Sat, Oct 26 - Tue, Oct 29
6:25 am - 11:01 pmYYC-ORD
15h 36m1 stop
5:00 am - 1:49 pmORD-YYC
9h 49m1 stop
$354United Airlines
Find Deal
Tue, May 14 - Wed, May 15
1:00 am - 9:53 amYYC-ORD
7h 53m1 stop
4:35 pm - 11:59 pmORD-YYC
8h 24m1 stop
$357Air Canada
Find Deal
Fri, Oct 25 - Tue, Oct 29

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 is the cheapest Calgary to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Calgary to Chicago.
Our data shows that the cheapest route for a one-way flight from Calgary to Chicago cost $144 and was between Calgary and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $155.

What’s the cheapest day of the week to fly from Calgary to Chicago?

The average price of all flights from Calgary to Chicago clicked on KAYAK for each day over the last 12 months.
When flying from Calgary to Chicago, you should consider leaving on a Sunday and avoid Saturdays if you are looking for the best rates. For your return to Calgary, you’ll find the best rates on Tuesdays and the most expensive ones on Saturdays.

What is the cheapest month to fly from Calgary to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Calgary to Chicago, 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 is November, where tickets cost $345 on average. On the other hand, the most expensive months are December and July, where the average cost of tickets is $564 and $495 respectively.

How far in advance should I book a flight from Calgary to Chicago?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Calgary to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Calgary to Chicago, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 83 days before departure.

Which airlines provide the cheapest flights from Calgary to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the best return deals on flights connecting Calgary to Chicago were found on WestJet ($200) and Delta ($267). WestJet proposed the cheapest one-way flight at $122.

Which airlines fly non-stop between Calgary and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Calgary to Chicago.
There are 2 airlines that fly nonstop from Calgary to Chicago. They are United Airlines and WestJet. The cheapest airline for this route is WestJet, with the best one-way deal found costing $211. On average, the best prices for this route can be found at WestJet.

How many flights are there between Calgary and Chicago per day?

Each day, there are between 2 and 3 nonstop flights that take off from Calgary and land in Chicago, with an average flight time of 3h 31m. The most common departure time is 12:00 pm and most flights take off in the morning, while the most flights land at Chicago O'Hare Intl Airport. Each week, there are 19 flights. The most frequent day of departure is Thursday, when 16% of all weekly flights depart. The fewest flights depart on a Wednesday.

Which cabin class options are there for flights between Calgary and Chicago?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Calgary to Chicago take?

A direct flight to Chicago will take on average 3h 21m to travel the 1,397 miles flying distance from Calgary.

What’s the earliest departure time from Calgary to Chicago?

Early birds can take the earliest flight from Calgary at 8:30 am and will be landing in Chicago at 12:59 pm.

What’s the latest departure time from Calgary to Chicago?

If you prefer to fly at night, the latest flight from Calgary to Chicago jets off at 1:30 pm and lands at 5:55 pm.

Good to know

Low season

March

High season

August

Cheapest flight

$122
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Calgary to Chicago O'Hare Airport

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 flights from Calgary to Chicago

  • What is the cheapest flight from Calgary to Chicago?

    In the last 3 days, the lowest price for a flight from Calgary to Chicago was $122 for a one-way ticket and $200 for a round-trip.

  • Do I need a passport to fly between Calgary and Chicago?

    A passport is required to fly from Calgary to Chicago.

  • Which airports will I be using when flying from Calgary to Chicago?

    When flying out of Calgary you will be using Calgary. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

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

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

  • 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 nonstop flights from Calgary to Chicago on a daily basis.

  • Which is the best airline for flights from Calgary to Chicago, Delta or WestJet?

    The two airlines most popular with KAYAK users for flights from Calgary to Chicago are Delta and WestJet. With an average price for the route of $367 and an overall rating of 8.0, Delta is the most popular choice. WestJet is also a great choice for the route, with an average price of $350 and an overall rating of 7.5.

  • 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 travelers 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

Top tips for finding a cheap flight from Calgary to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $207 or less one-way and $249 or less round-trip.

Prefer to fly non-stop from Calgary to Chicago?

Find which airlines fly direct from Calgary to Chicago, which days they fly and book direct flights.

Nonstop departures

Calgary to Chicago

Monday

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

Air Canada, American Airlines, +6 more

Tuesday

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

Air Canada, American Airlines, +6 more

Wednesday

Air Canada, American Airlines, Avianca, +6 more

Air Canada, American Airlines, +7 more

Thursday

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

Air Canada, American Airlines, +6 more

Friday

Air Canada, American Airlines, Avianca, +6 more

Air Canada, American Airlines, +7 more

Saturday

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

Air Canada, American Airlines, +6 more

Sunday

Air Canada, American Airlines, Avianca, +6 more

Air Canada, American Airlines, +7 more

See more direct flights

Nonstop returns

Chicago to Calgary

Monday

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

Air Canada, American Airlines, +6 more

Tuesday

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

Air Canada, American Airlines, +6 more

Wednesday

Air Canada, American Airlines, Avianca, +6 more

Air Canada, American Airlines, +7 more

Thursday

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

Air Canada, American Airlines, +6 more

Friday

Air Canada, American Airlines, Avianca, +6 more

Air Canada, American Airlines, +7 more

Saturday

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

Air Canada, American Airlines, +6 more

Sunday

Air Canada, American Airlines, Avianca, +6 more

Air Canada, American Airlines, +7 more

See more direct flights
See more direct 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 10848 reviews
7.9Comfort
8.2Boarding
7.4Food
8.6Crew
8.0Entertainment
Airline reviews

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

10.0 ExcellentAllan, May 2024SUN - SLC
Read more about Delta reviews

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

The crew were very welcoming and helpful. I just wish economy had a bit more leg room. My knees were constantly hitting the chair in front of me.

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

I like WJ but I don’t like traveling anymore

Good flight. No I’m seat entertainment. But my phone worked just fine on the west jet app.

4 hour delay, lost our bags, staff was loud and it was an overnight flight

We were late boarding, but it all worked out. So, no problem.

It was good but not comfortable seat with the long legged persons.

No problems here. WestJet does a good job, even on their short haul flights

Boarding was fine, but then we were delayed a while due to some baggage issues, then de-icing.

Tried to reserves seats and WestJet My Trip shows not available until 24 hours before the flight. When check-in was finally available and I tried to get seats again I was not able to get to select seats for me and my wife together. All in all, was not able to select seats together on Kiwi, paid extra for seats on Westjet and still did not got seats together, not pleasant for such a long flight and with my wife not very good with flying, disappointed on the way the system works with regarding to seats reservations, even with paying extra for them.

Flight full. 'Volunteers' to check hand luggage. Checked hand luggage is lost

Not the fault of WestJet but we had to wait in the plane on the tarmac in Cancun for 1 hour.

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Leg room was lacking. Legs crammed into seat in front.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

Ontime boarding. Almost 1 hour take off delay. We could have boarded slightly later since the pilots were in traffic

Flight was delayed, I had to put my luggage all the way in the back! They served only a beverage no snack on the way in Air Canada, definitely not a good first impression.

I think Air Canada is the only airline I've flown where they don't give you at least a free cookie.

This was the first AC flight in a long time that we experienced no delays or frustrations. The gate attendant was extremely polite and accommodating to my husband who has Parkinson’s disease which made boarding extremely stress free. Flight departed ON TIME and was a smooth ride. If only all my AC experiences could be like this.

All but one of four were on time. One was delayed for an hour

It took 5 hour to get a crew to D Ice the plan. We had to sit on the runway for 5 hrs. in Calgary. It snows most of the winter. No proactive plan. In addition, after 3 calls to customer service they couldn't figure out how to have my wife and myself sit together on her birthday weekend. Everybody kept passing the buck. No decision from customer service, luggage drop off or check in team. The experience was a complete mess! I don't think we'll ever fly on this airline again.

When we got to the airport for our flight from Chicago to Montreal which was scheduled for 2.00 p.m. they had no record of it and booked us on a flight at 3.30 very disappointing . We also had to pay 50.00 each for a seat. All things considered ,I will never book thru Kayak again. Next time I will only book directly thru Air Canada no second party booking Sue

The wifi I paid for did not work. The seats are tight.

There were no free snacks…little pretzel bag or cookies like we had on our flight out.

Mostly crew good and the flight was safe and comfortable but service was lacking. For an overnight flight of 8hrs 50 it took some two hours to get served a drink and dinner after take off. I asked for Laurent Perrier champagne and was brought Perrier water, which I queried and asked where was the champagne. No response. The issue came up again an hour later when dinner was starting to be served and I was asked whether I wanted another drink, when I reminded I was still waiting for my first champagne! Apologies ensued but dinner service was quite slow. For breakfast I never did get served the hot course! So - no complaints and compliments on the safety of the flight but service underwhelming (and I brought them candies!)

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.
5/26Sun
nonstopWestJet
3h 35mYYC-ORD
$122
6/1Sat
nonstopWestJet
3h 35mYYC-ORD
$123
6/4Tue
1 stopAir Canada
7h 36mYYC-ORD
$130
6/3Mon
1 stopAir Canada
7h 54mYYC-ORD
$136
6/5Wed
1 stopUnited Airlines
16h 34mYYC-ORD
$140
6/5Wed
1 stopDelta
9h 12mYYC-MDW
$144
6/5Wed
1 stopDelta
7h 54mYYC-ORD
$145
6/5Wed
nonstopAmerican Airlines
3h 25mYYC-ORD
$165
6/4Tue
nonstopUnited Airlines
3h 29mYYC-ORD
$179
6/6Thu
nonstopAmerican Airlines
3h 25mYYC-ORD
$194

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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.
5/8Wed
multi-stop
12h 33mYYC-MDW
5/16Thu
multi-stop
8h 39mMDW-YYC
$716

Search by stops

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Calgary - Chicago Flights

Departure:

Calgary (YYC)Canada

Return flight deals:

Chicago - Calgary

Cabin classes:

$1,979
$1,014
$2,148
$155