YYC - CHI

$109 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 11/11. 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
1 adult, Economy

KAYAK searches 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
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Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Calgary to Chicago

Wed, Nov 19 - Fri, Jan 16
Multiple Airlines Logo
5:35 am - 3:10 pmYYC-ORD
8h 35m1 stop
Multiple Airlines Logo
2:20 pm - 5:15 pmORD-YYC
3h 55mnonstop
$162Multiple Airlines
Find Deal
Mon, Jan 12 - Tue, Jan 13
Multiple Airlines Logo
6:15 am - 11:59 pmYYC-ORD
16h 44m1 stop
Multiple Airlines Logo
10:00 am - 5:04 pmORD-YYC
8h 04m1 stop
$168Multiple Airlines
Find Deal
Sun, Jan 18 - Wed, Jan 21
Air Canada Logo
5:35 am - 3:10 pmYYC-ORD
8h 35m1 stop
Air Canada Logo
3:55 pm - 12:14 amORD-YYC
9h 19m1 stop
$171Air Canada
Find Deal
Wed, Nov 19 - Fri, Jan 16
Air Canada Logo
5:35 am - 3:10 pmYYC-ORD
8h 35m1 stop
Air Canada Logo
2:00 pm - 8:39 pmORD-YYC
7h 39m1 stop
$172Air Canada
Find Deal
Wed, Oct 29 - Fri, Oct 31
United Airlines Logo
12:37 pm - 5:10 pmYYC-ORD
3h 33mnonstop
United Airlines Logo
8:45 am - 11:35 amORD-YYC
3h 50mnonstop
$177United Airlines
Find Deal
Mon, Nov 10 - Fri, Nov 14
WestJet Logo
9:00 am - 1:35 pmYYC-ORD
3h 35mnonstop
WestJet Logo
2:20 pm - 5:15 pmORD-YYC
3h 55mnonstop
$202WestJet
Find Deal
Mon, Nov 10 - Fri, Nov 14
WestJet Logo
9:00 am - 1:35 pmYYC-ORD
3h 35mnonstop
WestJet Logo
2:20 pm - 5:15 pmORD-YYC
3h 55mnonstop
$205WestJet
Find Deal
Tue, Nov 11 - Tue, Nov 18
American Airlines Logo
12:45 pm - 8:44 amYYC-ORD
18h 59m1 stop
American Airlines Logo
5:18 am - 11:44 amORD-YYC
7h 26m1 stop
$207American Airlines
Find Deal
Mon, Jan 12 - Tue, Jan 13
American Airlines Logo
1:40 pm - 6:20 pmYYC-ORD
3h 40mnonstop
American Airlines Logo
9:45 am - 12:48 pmORD-YYC
4h 03mnonstop
$208American Airlines
Find Deal
Sat, Jan 17 - Tue, Jan 20
United Airlines Logo
12:37 pm - 5:08 pmYYC-ORD
3h 31mnonstop
United Airlines Logo
2:36 pm - 9:53 pmORD-YYC
8h 17m1 stop
$210United Airlines
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
United's Economy Plus offers 6 extra inches of legroom.
Calgary Airport provides free Wi-Fi throughout.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Air Canada
Cheapest • from $171 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
YYC-ORD
Cheapest
YYC-ORD
Most popular
Insights
Insights
Insights
Insights
When to book
6 weeks
in advance
Our data shows that travelers who book at least 6 weeks in advance save around 38% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
April
Cheapest • 30% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$162
Overall average: $278
Multiple Airlines
Wed 11/19Fri 1/16
YYC - ORD • 1 stop
Cheapest non-stop
$177
Typical prices: $238-$476
United Airlines
Wed 10/29Fri 10/31
YYC - ORD • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Booking Insights

KAYAK's insights & trends for Calgary to Chicago flights

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.

How much is a round-trip flight from Calgary to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Calgary to Chicago departing in November.

What is the cheapest Calgary to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Calgary to Chicago costs $156 on the route between Calgary (YYC) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

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 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 Sunday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Calgary to Chicago. For your return ticket, we recommend flying on a Thursday and avoiding Tuesdays for the best deals.

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 round-trip 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 April, where tickets cost $191 (return) on average. On the other hand, the most expensive months are December and November, where the average cost of round-trip tickets is $463 and $397 respectively.

Can I save money by flying with a layover from Calgary to Chicago?

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 1 stop layover the cheapest option at $186 on average.

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

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, 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, you should book around 6 weeks before departure, which saves you about 38% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Expert advice

Expert advice for your flight from Calgary to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
WestJet

Bid on upgrades for Business or Premium; often cheaper than booking outright.


WestJet's priority boarding includes Premium and Extended Comfort seats for faster boarding.

Read more about WestJetby Stefanie Waldek
Air Canada

Air Canada's Preferred Economy offers up to 4 extra inches of legroom for added comfort.


Check-in four hours before your flight for priority services with higher fare classes.

Read more about Air Canadaby Stefanie Waldek
American Airlines

Main Cabin Extra offers early boarding and complimentary drinks for a small fee.


Download the American Airlines app for in-flight entertainment on your device.

United Airlines

United's Priority Boarding puts you in Zone 2, ensuring overhead bin space.


United's Economy Plus offers up to 6 extra inches of legroom for more comfort.

Airports
YYC

Calgary International Airport offers free Wi-Fi across the entire airport, making it easy for travelers to stay connected without hassle.

Read more about YYCby Kaitlyn McInnis
ORD

The CTA Blue Line train from O'Hare to downtown Chicago is fast and reliable, taking about 45 minutes and avoiding traffic delays.

Read more about ORDby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on WestJet, Air Canada, United Airlines and ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Kaitlyn McInnis

Kaitlyn McInnis

Expert on YYC

Kaitlyn McInnis

Kaitlyn McInnis

Kaitlyn is a guidebook author and travel writer splitting her time between Atlantic Canada and Istanbul, Türkiye. She has visited over fifty countries and all seven continents, so she is very familiar with many hotels, airports and airlines around the globe. But her favorite type of vacation is sunbathing by the sea with a good book in hand.

Read more

Good to know

Low seasonNovember
Cheapest flight$109
Best time to beat the crowds but there is an average 44% increase in price.
Most popular time to fly and prices are also 26% 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 $109 for a one-way ticket and $162 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, United Airlines, and WestJet offer inflight Wi-Fi service on the Calgary to Chicago flight route.

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

    The Boeing 737-700 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, and Star Alliance 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 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 $256 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $364 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 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.

KAYAK’s 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 $194 or less one-way and $311 or less round-trip.

Prefer to fly direct from Calgary to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Calgary to Chicago.
Find which airlines fly direct from Calgary Airport to Chicago, which days they fly and book direct flights.

Direct departures

Calgary to Chicago

Monday

United Airlines, WestJet, American Airlines

United Airlines, WestJet, +1 more

Tuesday

United Airlines, American Airlines

United Airlines, American Airlines

Wednesday

United Airlines, American Airlines

United Airlines, American Airlines

Thursday

United Airlines, American Airlines

United Airlines, American Airlines

Friday

United Airlines, WestJet, American Airlines

United Airlines, WestJet, +1 more

Saturday

United Airlines, American Airlines

United Airlines, American Airlines

Sunday

United Airlines, WestJet, American Airlines

United Airlines, WestJet, +1 more

See more direct flights

Direct returns

Chicago to Calgary

Monday

United Airlines, WestJet, American Airlines

United Airlines, WestJet, +1 more

Tuesday

United Airlines, American Airlines

United Airlines, American Airlines

Wednesday

United Airlines, American Airlines

United Airlines, American Airlines

Thursday

United Airlines, American Airlines

United Airlines, American Airlines

Friday

United Airlines, WestJet, American Airlines

United Airlines, WestJet, +1 more

Saturday

United Airlines, American Airlines

United Airlines, American Airlines

Sunday

United Airlines, WestJet, American Airlines

United Airlines, WestJet, +1 more

See more direct flights

Reviews of the 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.
7.9
DeltaOverall score based on 7984 reviews
7.9Comfort
8.2Boarding
8.5Crew
7.9Entertainment
7.3Food
Airline reviews

Crew blocked exits to front of ship with galley carts. Also split five person family apart on international flight without fixing.

2.0 MediocreRyan, Oct 2025FCO - JFK
Read more Delta reviews

Crew blocked exits to front of ship with galley carts. Also split five person family apart on international flight without fixing.

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

On time flight. Seat comfort could be better in the Comfort section.

My issue was with TSA agents for delta airlines. My luggage got flagged. The agent was going thru another persons first. He took 20 min to go thru hers. I asked them to bring mine closer so I could sit down . They said you can go sit it will be fine. I said I am supposed to keep my eyes on my bags at all times. The agent was meticulously unwrapping 2 gifts that the lady had and then tried to re warp it. He was trying to be kind i get it but 20 min for me to stand watching him do that was ridiculous. It was 6 am and there were a ton of travelers. Mine was flagged for some air packed tea that I bought in Turkey. My previous delta flight and 2 others before didn’t flag it. Consistency would be nice. Also on the flight the window shades were down for take off and landing - I thought that was very odd I thought they had to remain open for take off and landing.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Could have said yes to a glass of wine 🍷 instead of saying we'll come around in a couple of hours

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Flight, food and crew were all good, friendly and very satisfactory.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Premium economy seat was decent. As always poor headphones, poor food and beverage, crew is not overly friendly

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

The flight was on time and crew were nice, seats were tight and there was entertainment available

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Very good experience. Great cabin crew. Much better than expected

Typical Canadian airline experience. Charger and tray were broken, food was poor quality, and yet you're still paying more than flights with equal to better service than elsewhere globally.

Not enough food option. And not enough advices or information about what we are gonna eat.

my carry-on bag was delayed and I did not receive it until the day of my return at the airport. This delay caused me significant inconvenience, as I did not have access to my personal belongings for the duration of my trip. I had expected to rely on my carry-on items, and being without them negatively impacted my travel experience.

Technology issues at the bag-check counter caused a delay, and we were unable to check out our bags, ultimately missing our flight. They offered no assistance other than telling us to book another flight out of Calgary. We arrived with plenty of time; if there hadn't been an issue with the kiosk and the length of the lines due to the technical issues, we could have made it home.

Worst check in and bag drop off experience. Staff were incredibly rude given that it’s the WestJet system that is faulty.

The staff at the airport and on the plane were wonderful I especially wanna acknowledge the staff who boarded us at the Calgary airport. The women who helped us board at the airport were incredible… they were so kind and sweet…I very happy with WestJet and I am hoping I can fly more often to Canada.

7 hour layover was a drag. Free internet on the long leg was great.

From vancouver go calgary nd vice vetsa fligjt was delayed

It was good! Short flight and it was on time!

Was not sent a link to check in online. Tried to check in online using website. Site didn’t work. Called support line, was told it often didn’t work. Went to counter at airport to check bags and get boarding passes. Had to stand in a lineup. They were unable to tell me how much to pay. Had to take a paper to another counter, took a long time to be told what I owed. I fondly remember the days of checking in online, getting my boarding pass digitally, paying for my luggage on line, scanning my passport at the airport to get my luggage tags, and putting my luggage on the conveyor. Easy peasy. Air Canada has really taken a step back in time, and made what was an easy check in experience to one that seemed unduly long and frustrating.

Really out of Air Canada's control due to long delay because of mechanical issues. While doing their best, disappointed by their assumption that all passengers have smart phones. Should have communicated food voucher availability at gate area. Late arrival cost me an extra $51 because public transit was not available, Otherwise, feel Air Canada did their best dealing with their challenges. Will likely continue using them in the future.

They canceled my flight, I had to rent a car, drive 14 hours. They tell to go on line for a refund, but only offer $24 for a $210 flight and you can’t get hold of anybody by phone and no help from staff at the airport.

I wish to travel with Air Canada for my next trip

They were very attentive, polite, professional and great customer service skills.

Business class was not worth the extra charge. Overpriced for slightly larger seat. Nothing special. Small older plane.

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

Pros: The airplane was new and had in-flight entertainment (tablet behind seats) with new movies instead of watching on personal devices. Cons: the flight time was changed without informing us. When I booked the flight, the time was 13:30pm (also in the email confirmation). However, when I reached the airport, the time was conveniently changed to 14:55pm. When I asked at the counter, they said the flight always took off at this time. The booking was made by Air Canada, but the flight was operated by United.

The app was great, service was wonderful, everything was quick and easy

On the flight from Montreal to Calgary the flight attendant we had was excellent. Unfortunately I did not get her name but she made the flight very comfortable and enjoyable.

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

Information on your arrival and departure airports

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