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$109 Find cheap flights from Calgary to Chicago O'Hare Intl Airport

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 O'Hare Intl departing on 6/1. 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
Sat 5/25
Sat 6/1

Search hundreds of travel sites at once for deals on flights to Chicago O'Hare 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
In the last 7 days travelers have searched 45,119,101 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

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.
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
$180WestJet
Find Deal
Thu, May 16 - Fri, May 31
12:30 pm - 4:57 pmYYC-ORD
3h 27mnonstop
5:55 pm - 8:40 pmORD-YYC
3h 45mnonstop
$223WestJet
Find Deal
Thu, Jul 11 - Sun, Jul 14
12:30 pm - 5:09 pmYYC-ORD
3h 39mnonstop
1:16 pm - 8:03 pmORD-YYC
7h 47m1 stop
$293Delta
Find Deal
Thu, Sep 26 - Wed, Oct 2
6:25 am - 6:24 pmYYC-ORD
10h 59m1 stop
5:55 pm - 8:22 pmORD-YYC
3h 27mnonstop
$298Delta
Find Deal
Thu, May 16 - Fri, May 31
8:30 am - 1:00 pmYYC-ORD
3h 30mnonstop
7:57 pm - 10:43 pmORD-YYC
3h 46mnonstop
$319United Airlines
Find Deal
Wed, May 22 - Wed, May 29
3:25 pm - 12:21 amYYC-ORD
7h 56m1 stop
7:57 pm - 10:43 pmORD-YYC
3h 46mnonstop
$325United Airlines
Find Deal
Wed, May 22 - Wed, May 29
12:10 am - 8:51 amYYC-ORD
7h 41m1 stop
4:00 pm - 11:59 pmORD-YYC
8h 59m1 stop
$346Air Canada
Find Deal
Mon, Jun 3 - Tue, Jun 18
12:10 am - 9:01 amYYC-ORD
7h 51m1 stop
4:00 pm - 10:44 pmORD-YYC
7h 44m1 stop
$351Air Canada
Find Deal
Wed, Sep 4 - Wed, Sep 11
1:24 pm - 5:45 pmYYC-ORD
3h 21mnonstop
9:55 am - 12:32 pmORD-YYC
3h 37mnonstop
$422American Airlines
Find Deal
Wed, Aug 21 - Sun, Aug 25
1:24 pm - 5:45 pmYYC-ORD
3h 21mnonstop
5:19 am - 9:54 pmORD-YYC
17h 35m1 stop
$432American Airlines
Find Deal
Wed, Aug 21 - Sun, Aug 25

Flights from Calgary to O'Hare Intl - Travel Insights & Trends

Get data-powered insights and trends into flights from Calgary to O'Hare Intl 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 O'Hare Airport?

The average price of all flights from Calgary to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Chicago O'Hare Airport on a Saturday and more expensive on a Friday. On your return trip to Calgary, you should consider flying back on a Wednesday, and avoid Saturdays for better 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 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 November, where tickets cost $360 on average. On the other hand, the most expensive months are March and December, where the average cost of tickets is $576 and $547 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
To get a below average price on the flight from Calgary to Chicago O'Hare Intl Airport, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 89 days before departure.

Which airlines provide the cheapest flights from Calgary to Chicago O'Hare Airport?

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 O'Hare Airport were found on WestJet ($180) and Delta ($293). WestJet proposed the cheapest one-way flight at $109.

Which airlines fly non-stop between Calgary and Chicago O'Hare Intl Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Calgary to Chicago O'Hare Intl Airport.
There are 2 airlines that fly nonstop from Calgary to Chicago O'Hare Intl Airport. 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 O'Hare Intl Airport per day?

Each day, there are between 2 and 3 nonstop flights that take off from Calgary and land in Chicago O'Hare Intl Airport, 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. Each week, there are 18 flights. The most frequent day of departure is Saturday, when 17% of all weekly flights depart. The fewest flights depart on a Monday.

Which cabin class options are there for flights between Calgary and Chicago O'Hare Intl Airport?

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 O'Hare Airport take?

The duration of a nonstop flight to Chicago O'Hare Airport from Calgary is typically 3h 21m. The journey crosses a distance of 1,381 miles.

What’s the earliest departure time from Calgary to Chicago O'Hare Airport?

Early birds can take the earliest flight from Calgary at 8:30 am and will be landing in Chicago O'Hare Intl Airport at 1:00 pm.

What’s the latest departure time from Calgary to Chicago O'Hare Airport?

If you prefer to fly at night, the latest flight from Calgary to Chicago O'Hare Intl Airport jets off at 12:40 pm and lands at 5:10 pm.

Good to know

Low season

February

High season

August

Cheapest flight

$109
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Calgary to Chicago O'Hare Airport

When to book flights from Calgary to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Calgary to O'Hare Intl 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 O'Hare Airport 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 $109 for a one-way ticket and $180 for a round-trip.

  • Do I need a passport to fly between Calgary and Chicago O'Hare Airport?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Calgary and on arrival in Chicago O'Hare Airport.

  • Which airports will I be using when flying from Calgary to Chicago O'Hare Airport?

    Calgary and Chicago O'Hare Airport are both served by 1 main airport. You will leave Calgary from Calgary and will be arriving at Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Calgary to Chicago O'Hare Airport?

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

  • Which aircraft models fly most regularly from Calgary to Chicago O'Hare Airport?

    The Airbus A319 is the aircraft model that flies most regularly on the Calgary to Chicago O'Hare Airport flight route.

  • Which airline alliances offer flights from Calgary to Chicago O'Hare Airport?

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

  • On which days can I fly direct from Calgary to Chicago O'Hare Airport?

    There are nonstop flights from Calgary to Chicago O'Hare Airport on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Calgary to Chicago are WestJet and United Airlines. With an average price for the route of $336 and an overall rating of 7.5, WestJet is the most popular choice. United Airlines is also a great choice for the route, with an average price of $361 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Calgary to Chicago O'Hare Airport?

    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 O'Hare Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport 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 O'Hare Airport?

    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 O'Hare Airport with an airline and back to Calgary with another airline. Booking your flights between Calgary and ORD can sometimes prove cheaper using this method.

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

    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 O'Hare Airport 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 YYC to Chicago O'Hare Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $238 or less one-way and $282 or less round-trip.

Prefer to fly non-stop from Calgary to Chicago O'Hare Airport?

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

Nonstop departures

Calgary to Chicago O'Hare Intl

Monday

Air Canada, Delta, Emirates, +5 more

Air Canada, Delta, +6 more

Tuesday

Air Canada, Emirates, United Airlines, +5 more

Air Canada, Emirates, +6 more

Wednesday

Air Canada, Emirates, United Airlines, +6 more

Air Canada, Emirates, +7 more

Thursday

Air Canada, Delta, Emirates, +5 more

Air Canada, Delta, +6 more

Friday

Air Canada, Delta, Emirates, +6 more

Air Canada, Delta, +7 more

Saturday

Air Canada, Delta, Emirates, +5 more

Air Canada, Delta, +6 more

Sunday

Air Canada, Delta, Emirates, +6 more

Air Canada, Delta, +7 more

See more direct flights

Nonstop returns

Chicago O'Hare Intl to Calgary

Monday

Air Canada, Delta, Emirates, +5 more

Air Canada, Delta, +6 more

Tuesday

Air Canada, Emirates, United Airlines, +5 more

Air Canada, Emirates, +6 more

Wednesday

Air Canada, Emirates, United Airlines, +6 more

Air Canada, Emirates, +7 more

Thursday

Air Canada, Delta, Emirates, +5 more

Air Canada, Delta, +6 more

Friday

Air Canada, Delta, Emirates, +6 more

Air Canada, Delta, +7 more

Saturday

Air Canada, Delta, Emirates, +5 more

Air Canada, Delta, +6 more

Sunday

Air Canada, Delta, Emirates, +6 more

Air Canada, Delta, +7 more

See more direct flights
See more direct flights

Top 4 airlines serving from Calgary to O'Hare Intl

 
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 O'Hare Intl? 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.
7.5
WestJetOverall score based on 2991 reviews
8.2crew
7.3comfort
6.5food
7.7boarding
6.5entertainment
Airline reviews

I like WJ but I don’t like traveling anymore

6.0 GoodAnonymous, Mar 2024YYC - YWG
Read more about WestJet reviews

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.

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.

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.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Unfortunately this is not a happy ending comment. Positive: flown United before no issue Negative: it only takes one bad experience to not plan future travel with United Cancún departure was delayed by 1h20 minutes, connection in Chicago was 1h30 minutes. Flight departure time 6:08 Miraculously 7 of us ran 4 kilometres through Chicago to arrive at 6:00 to be told very rudely by the 2 unprofessional United attendants you missed your flight and that we should of arrived early. Did I mention that reason I was flying? I received a call that my brother was dying and to get home. They provided no assistance would not answer any of our questions, ignorantly walked away. Deplorable

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

If United expects people to use their own devices for entertainment they should put charging outlets in each seating area. I arrived with 14%battery power. That is not good when you arrive anywhere and need to communicate for transportation.

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

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

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

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.
6/1Sat
nonstopWestJet
3h 35mYYC-ORD
$109
5/26Sun
nonstopWestJet
3h 35mYYC-ORD
$113
5/15Wed
nonstopUnited Airlines
3h 30mYYC-ORD
$116
5/24Fri
1 stopAir Canada
7h 54mYYC-ORD
$126
5/8Wed
nonstopAir Canada
3h 30mYYC-ORD
$130
5/20Mon
1 stopUnited Airlines
6h 36mYYC-ORD
$131
5/24Fri
nonstopDelta
3h 35mYYC-ORD
$149
6/10Mon
1 stopDelta
10h 51mYYC-ORD
$155
6/5Wed
nonstopAmerican Airlines
3h 25mYYC-ORD
$161
5/24Fri
1 stopAmerican Airlines
13h 00mYYC-ORD
$176

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Last minute flights from Calgary to O'Hare Intl

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.
4/27Sat
multi-stop
15h 56mYYC-ORD
4/29Mon
multi-stop
28h 18mORD-YYC
$502
4/27Sat
multi-stop
11h 29mYYC-ORD
4/29Mon
multi-stop
28h 18mORD-YYC
$516
4/26Fri
multi-stopDelta
9h 49mYYC-ORD
4/29Mon
multi-stopDelta
6h 36mORD-YYC
$531
4/27Sat
nonstopUnited Airlines
3h 30mYYC-ORD
4/30Tue
multi-stopUnited Airlines
9h 49mORD-YYC
$569
4/27Sat
multi-stopUnited Airlines
15h 27mYYC-ORD
4/30Tue
multi-stopUnited Airlines
9h 49mORD-YYC
$574
4/27Sat
multi-stopDelta
6h 00mYYC-ORD
4/30Tue
multi-stopDelta
11h 04mORD-YYC
$575
4/26Fri
multi-stopUnited Airlines
7h 51mYYC-ORD
4/28Sun
multi-stopUnited Airlines
9h 49mORD-YYC
$591
4/27Sat
nonstopAir Canada
3h 30mYYC-ORD
4/30Tue
nonstopAir Canada
3h 46mORD-YYC
$690
4/27Sat
nonstopAir Canada
3h 30mYYC-ORD
4/30Tue
nonstopAir Canada
3h 46mORD-YYC
$710
4/26Fri
multi-stopWestJet
15h 28mYYC-ORD
4/29Mon
multi-stopWestJet
14h 44mORD-YYC
$1,715

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Calgary - Chicago O'Hare Airport Flights

Departure:

Calgary (YYC)Canada

Destination:

Chicago O'Hare Airport (ORD)United States

Return flight deals:

Chicago O'Hare Airport - Calgary

Cabin classes:

$1,979
$1,014
$2,148
$184