YYC - ORD

C$ 151 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 47,946,175 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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

 
These are the cheapest deals for flights from Calgary to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. 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.

Recent one-way flight deals from Calgary to Chicago

Only flying one-way? Below are some of the best one-way flight deals from Calgary to Chicago found on KAYAK recently.

Recent last-minute flight deals from Calgary to Chicago

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Calgary to Chicago.

Recent direct flight deals from Calgary to Chicago

The latest deals for direct flights from Calgary to Chicago so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Calgary to Chicago

Find recent round-trip train or bus tickets from Calgary to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
12:50 a.m. - 9:55 a.m.YYC-ORD
8h 05m1 stop
9:03 a.m. - 4:52 p.m.ORD-YYC
8h 49m1 stop
C$ 274Air Canada
Find Deal
Mon, 31 Mar - Tue, 8 Apr
8:30 a.m. - 6:38 p.m.YYC-ORD
9h 08m1 stop
2:05 p.m. - 9:18 p.m.ORD-YYC
8h 13m1 stop
C$ 300Air Canada
Find Deal
Thu, 9 Jan - Sat, 18 Jan
12:50 a.m. - 10:54 a.m.YYC-ORD
9h 04m1 stop
4:00 p.m. - 1:18 a.m.ORD-YYC
10h 18m1 stop
C$ 305Air Canada
Find Deal
Thu, 23 Jan - Sun, 26 Jan
7:00 a.m. - 4:58 p.m.YYC-ORD
8h 58m1 stop
12:35 p.m. - 11:16 p.m.ORD-YYC
11h 41m2 stops
C$ 309Delta
Find Deal
Sat, 7 Dec - Tue, 10 Dec
6:35 a.m. - 8:53 p.m.YYC-ORD
13h 18m2 stops
6:55 a.m. - 8:53 p.m.ORD-YYC
14h 58m2 stops
C$ 330Delta
Find Deal
Thu, 9 Jan - Sun, 12 Jan
12:30 p.m. - 4:50 p.m.YYC-ORD
3h 20mdirect
9:00 a.m. - 11:54 a.m.ORD-YYC
3h 54mdirect
C$ 489United Airlines
Find Deal
Tue, 1 Apr - Tue, 8 Apr
12:41 p.m. - 5:15 p.m.YYC-ORD
3h 34mdirect
7:10 a.m. - 9:41 p.m.ORD-YYC
15h 31m1 stop
C$ 516United Airlines
Find Deal
Fri, 24 Jan - Sun, 26 Jan
1:20 p.m. - 5:45 p.m.YYC-ORD
3h 25mdirect
9:45 a.m. - 12:30 p.m.ORD-YYC
3h 45mdirect
C$ 530American Airlines
Find Deal
Wed, 30 Apr - Mon, 5 May
12:30 a.m. - 10:02 a.m.YYC-ORD
8h 32m1 stop
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 588WestJet
Find Deal
Tue, 29 Apr - Mon, 5 May
1:00 a.m. - 4:47 p.m.YYC-ORD
14h 47m2 stops
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 591WestJet
Find Deal
Tue, 29 Apr - Mon, 5 May
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
C$ 151WestJet
Find Deal
Mon, 3 Mar
12:15 p.m. - 4:44 p.m.YYC-ORD
3h 29mdirect
C$ 154WestJet
Find Deal
Thu, 1 May
8:30 a.m. - 6:38 p.m.YYC-ORD
9h 08m1 stop
C$ 165Air Canada
Find Deal
Sat, 18 Jan
12:50 a.m. - 8:57 a.m.YYC-ORD
7h 07m1 stop
C$ 173Air Canada
Find Deal
Fri, 17 Jan
7:00 a.m. - 9:12 p.m.YYC-ORD
13h 12m2 stops
C$ 190Delta
Find Deal
Sat, 7 Dec
7:00 a.m. - 8:28 p.m.YYC-ORD
12h 28m2 stops
C$ 191Delta
Find Deal
Tue, 17 Dec
12:45 p.m. - 7:23 a.m.YYC-ORD
17h 38m1 stop
C$ 256American Airlines
Find Deal
Tue, 3 Dec
12:41 p.m. - 5:08 p.m.YYC-ORD
3h 27mdirect
C$ 354United Airlines
Find Deal
Fri, 14 Feb
1:20 p.m. - 5:45 p.m.YYC-ORD
3h 25mdirect
C$ 355American Airlines
Find Deal
Fri, 14 Mar
12:41 p.m. - 5:09 p.m.YYC-ORD
3h 28mdirect
C$ 382United Airlines
Find Deal
Thu, 5 Dec
12:41 p.m. - 5:09 p.m.YYC-ORD
3h 28mdirect
7:28 a.m. - 8:44 p.m.ORD-YYC
14h 16m1 stop
C$ 496
Find Deal
Fri, 22 Nov - Mon, 25 Nov
2:09 p.m. - 10:51 p.m.YYC-ORD
7h 42m1 stop
7:28 a.m. - 8:44 p.m.ORD-YYC
14h 16m1 stop
C$ 625
Find Deal
Fri, 22 Nov - Mon, 25 Nov
12:41 p.m. - 5:09 p.m.YYC-ORD
3h 28mdirect
8:45 a.m. - 11:39 a.m.ORD-YYC
3h 54mdirect
C$ 781Air Canada
Find Deal
Fri, 22 Nov - Mon, 25 Nov
4:35 p.m. - 11:52 a.m.YYC-ORD
18h 17m1 stop
7:10 p.m. - 5:41 p.m.ORD-YYC
23h 31m2 stops
C$ 858
Find Deal
Fri, 22 Nov - Mon, 25 Nov
4:35 p.m. - 11:52 a.m.YYC-ORD
18h 17m1 stop
1:15 a.m. - 7:33 p.m.ORD-YYC
19h 18m2 stops
C$ 925
Find Deal
Fri, 22 Nov - Sun, 24 Nov
9:45 p.m. - 2:02 a.m.YYC-ORD
27h 17m3 stops
7:39 p.m. - 12:05 a.m.ORD-YYC
29h 26m2 stops
C$ 928
Find Deal
Fri, 22 Nov - Mon, 25 Nov
9:45 p.m. - 1:02 a.m.YYC-ORD
26h 17m3 stops
6:00 a.m. - 12:25 a.m.ORD-YYC
19h 25m1 stop
C$ 945
Find Deal
Fri, 22 Nov - Mon, 25 Nov
9:45 p.m. - 2:02 a.m.YYC-ORD
27h 17m3 stops
1:22 a.m. - 7:33 p.m.ORD-YYC
19h 11m2 stops
C$ 978
Find Deal
Fri, 22 Nov - Sun, 24 Nov
11:20 p.m. - 2:02 a.m.YYC-ORD
25h 42m3 stops
1:22 a.m. - 12:31 a.m.ORD-YYC
24h 09m3 stops
C$ 1,073
Find Deal
Fri, 22 Nov - Sun, 24 Nov
10:00 a.m. - 4:37 a.m.YYC-ORD
17h 37m2 stops
2:42 a.m. - 7:33 p.m.ORD-YYC
17h 51m2 stops
C$ 1,259
Find Deal
Fri, 22 Nov - Sun, 24 Nov
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 238WestJet
Find Deal
Mon, 21 Apr - Mon, 28 Apr
12:30 p.m. - 4:50 p.m.YYC-ORD
3h 20mdirect
9:00 a.m. - 11:54 a.m.ORD-YYC
3h 54mdirect
C$ 489United Airlines
Find Deal
Tue, 1 Apr - Tue, 8 Apr
1:20 p.m. - 5:45 p.m.YYC-ORD
3h 25mdirect
9:45 a.m. - 12:30 p.m.ORD-YYC
3h 45mdirect
C$ 530American Airlines
Find Deal
Wed, 30 Apr - Mon, 5 May
12:41 p.m. - 5:15 p.m.YYC-ORD
3h 34mdirect
8:45 a.m. - 11:34 a.m.ORD-YYC
3h 49mdirect
C$ 629United Airlines
Find Deal
Sat, 25 Jan - Mon, 27 Jan
12:41 p.m. - 5:09 p.m.YYC-ORD
3h 28mdirect
8:45 a.m. - 11:39 a.m.ORD-YYC
3h 54mdirect
C$ 685United Airlines
Find Deal
Thu, 5 Dec - Sat, 7 Dec
1:20 p.m. - 5:45 p.m.YYC-ORD
3h 25mdirect
9:45 a.m. - 12:30 p.m.ORD-YYC
3h 45mdirect
C$ 731American Airlines
Find Deal
Thu, 15 May - Fri, 30 May
12:41 p.m. - 5:10 p.m.YYC-ORD
3h 29mdirect
8:47 a.m. - 11:41 a.m.ORD-YYC
3h 54mdirect
C$ 751Air Canada
Find Deal
Fri, 7 Mar - Tue, 11 Mar
12:41 p.m. - 5:09 p.m.YYC-ORD
3h 28mdirect
8:45 a.m. - 11:39 a.m.ORD-YYC
3h 54mdirect
C$ 771United Airlines
Find Deal
Fri, 6 Dec - Wed, 25 Dec
12:41 p.m. - 5:08 p.m.YYC-ORD
3h 27mdirect
8:47 a.m. - 11:33 a.m.ORD-YYC
3h 46mdirect
C$ 846Air Canada
Find Deal
Thu, 13 Feb - Wed, 19 Feb
12:41 p.m. - 5:15 p.m.YYC-ORD
3h 34mdirect
8:45 a.m. - 11:34 a.m.ORD-YYC
3h 49mdirect
C$ 889Air Canada
Find Deal
Tue, 7 Jan - Fri, 17 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 flights from Calgary to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
When flying from Calgary to Chicago, you should consider leaving on a Wednesday and avoid Fridays 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 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 January, where tickets cost C$ 358 on average. On the other hand, the most expensive months are December and November, where the average cost of tickets is C$ 654 and C$ 605 respectively.

Can I save money by flying with a layover from Calgary to Chicago O'Hare Intl Airport?

The average 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$ 996, 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 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 18 days before departure.

Good to know

Low season

January

High season

July

Cheapest flight

C$ 151
Best time to beat the crowds (28% less expensive on average)
Most popular time to fly (5% 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$ 108 for a one-way ticket and C$ 196 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, British Airways, KLM, 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$ 406 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$ 602 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$ 369 or less one-way and C$ 668 or less round-trip.

Prefer to fly non-stop 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.

Nonstop departures

Calgary to Chicago O'Hare Intl

Monday

Air Canada,Emirates,United Airlines

Air Canada,Emirates, +1 more

Tuesday

Air Canada,Emirates,United Airlines

Air Canada,Emirates, +1 more

Wednesday

Air Canada,Emirates,United Airlines

Air Canada,Emirates, +1 more

Thursday

Air Canada,Emirates,United Airlines

Air Canada,Emirates, +1 more

Friday

Air Canada,Emirates,United Airlines

Air Canada,Emirates, +1 more

Saturday

Air Canada,Emirates,United Airlines

Air Canada,Emirates, +1 more

Sunday

Air Canada,Emirates,United Airlines

Air Canada,Emirates, +1 more

See more nonstop flights

Nonstop returns

Chicago O'Hare Intl to Calgary

Monday

Air Canada,United Airlines

Air Canada,United Airlines

Tuesday

Air Canada,United Airlines

Air Canada,United Airlines

Wednesday

Air Canada,United Airlines

Air Canada,United Airlines

Thursday

Air Canada,United Airlines

Air Canada,United Airlines

Friday

Air Canada,United Airlines

Air Canada,United Airlines

Saturday

Air Canada,United Airlines

Air Canada,United Airlines

Sunday

Air Canada,United Airlines

Air Canada,United Airlines

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
9.6Boarding
9.2Crew
8.0Comfort
6.2Entertainment
7.3Food
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 sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Crew was nice. Flight was timely. Seats could be better as well as the food considering it’s first class.

Left on time and arrived early this extending our 31 minute transfer. Bags made it also!

Good and consistent Printer in lounge did not work for me :(

Most of my discomfort was going through TSA. However, the Delta seats had inadequate leg room and I tried my very best to connect to the wi-fi and it was a cumbersome process that finally gave me the info that I needed to sign in AFTER I had completed the flight...Why make it so difficult to use? That said I really really appreciate the pilot taking a little extra time to avoid a bad storm area and both landings in Atlanta and Orlando were flawless to my delight!!!

Delayed in taking off because no flight crew. The in seat entertainment was working properly.

I love my flight attendant Faith, always smiles always helpful. She makes the flight experience wonderful thank you

My return flights were changed by the airline and my preferred seat selection with extra legroom was not transferred to the new flights

I upgraded to first class only to find out that I still had no access to the sky lounge without a sky miles card or AmEx (something that should be emphasized outside of the fine print!) Also, no food or drink service provided during the flight, so I basically paid 4x more just for “free” checked baggage and a bigger seat. Not worth it.

Very dissatisfied with the fact that I had upgraded to first class for the second part of my trip only to find out that the lounge was still not available to me, as well as not having any food or drink service on the flight due to weather, so I lost out more than what I paid for.

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.

The plane used to go to Chicago was a bit outdated and needed a refresh

My connecting gate in .Chicago was across the aisle from my arriving gate. Otherwise I would not have made my connection. So that was very fortunate.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

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.

Seat barely reclined. Boarding took forever. Flight attendants were not very friendly

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$ 151
1/5Thu
directWestJet
3h 29mYYC-ORD
C$ 154
18/1Sat
1 stopAir Canada
9h 08mYYC-ORD
C$ 165
17/1Fri
1 stopAir Canada
7h 07mYYC-ORD
C$ 173
7/12Sat
2 stopsDelta
13h 12mYYC-ORD
C$ 190
17/12Tue
2 stopsDelta
12h 28mYYC-ORD
C$ 191
3/12Tue
1 stopAmerican Airlines
17h 38mYYC-ORD
C$ 256
14/2Fri
directUnited Airlines
3h 27mYYC-ORD
C$ 354
14/3Fri
directAmerican Airlines
3h 25mYYC-ORD
C$ 355
5/12Thu
directUnited Airlines
3h 28mYYC-ORD
C$ 382

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.
22/11Fri
direct
3h 28mYYC-ORD
25/11Mon
multi-stop
14h 16mORD-YYC
C$ 496
22/11Fri
multi-stop
7h 42mYYC-ORD
25/11Mon
multi-stop
14h 16mORD-YYC
C$ 625
22/11Fri
directAir Canada
3h 28mYYC-ORD
25/11Mon
directAir Canada
3h 54mORD-YYC
C$ 781
22/11Fri
multi-stop
18h 17mYYC-ORD
25/11Mon
multi-stop
23h 31mORD-YYC
C$ 858
22/11Fri
multi-stop
18h 17mYYC-ORD
24/11Sun
multi-stop
19h 18mORD-YYC
C$ 925
22/11Fri
multi-stop
27h 17mYYC-ORD
25/11Mon
multi-stop
29h 26mORD-YYC
C$ 928
22/11Fri
multi-stop
26h 17mYYC-ORD
25/11Mon
multi-stop
19h 25mORD-YYC
C$ 945
22/11Fri
multi-stop
27h 17mYYC-ORD
24/11Sun
multi-stop
19h 11mORD-YYC
C$ 978
22/11Fri
multi-stop
25h 42mYYC-ORD
24/11Sun
multi-stop
24h 09mORD-YYC
C$ 1,073
22/11Fri
multi-stop
17h 37mYYC-ORD
24/11Sun
multi-stop
17h 51mORD-YYC
C$ 1,259

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

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.