YYC - CHI

$164 Find Cheap Flights from Calgary to Chicago - Compare and Save

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 9/25. 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, 0 bags

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Everything you should know

Cheapest round-trip
$207
Typical prices: $188-$407
WestJet
Fri 10/30Mon 11/2
YYC - ORD • Non-stop
Cheapest one-way
$164
Typical prices: $143-$217
WestJet
Fri 9/25
YYC - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United Economy Plus adds up to 6 extra inches; Air Canada Preferred Economy adds 4.
WestJet priority boarding and American early boarding add convenience on this route.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $207 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, United Airlines and WestJet. Average duration is 3h 38m
Direct flights
Direct flights
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Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $250 (round-trip)
Shortest trip • 7h 29m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 6 weeks in advance save around 24% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 32% price drop
Most popular
Good to know
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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

Fri, Oct 30 - Mon, Nov 2
WestJet Logo
9:00 am - 1:35 pm
YYC
-
ORD
3h 35mnonstop
WestJet Logo
2:20 pm - 6:15 pm
ORD
-
YYC
4h 55mnonstop
$207WestJet
Fri, Oct 30 - Mon, Nov 2
WestJet Logo
9:00 am - 1:35 pm
YYC
-
ORD
3h 35mnonstop
WestJet Logo
2:20 pm - 6:15 pm
ORD
-
YYC
4h 55mnonstop
$210WestJet
Fri, Oct 30 - Mon, Nov 2
WestJet Logo
9:00 am - 1:35 pm
YYC
-
ORD
3h 35mnonstop
WestJet Logo
2:20 pm - 6:15 pm
ORD
-
YYC
4h 55mnonstop
$220WestJet
Fri, Oct 30 - Mon, Nov 2
WestJet Logo
9:00 am - 1:35 pm
YYC
-
ORD
3h 35mnonstop
WestJet Logo
2:20 pm - 6:15 pm
ORD
-
YYC
4h 55mnonstop
$221WestJet
Fri, Sep 18 - Mon, Sep 21
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$260WestJet
Thu, Sep 24 - Sun, Sep 27
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$264WestJet
Fri, Oct 30 - Mon, Nov 2
Delta Logo
12:33 pm - 10:00 pm
YYC
-
ORD
8h 27m
1 stop
Delta Logo
2:03 pm - 11:04 pm
ORD
-
YYC
10h 01m
1 stop
$266Delta
Fri, Oct 23 - Sat, Nov 7
United Airlines Logo
12:30 pm - 5:05 pm
YYC
-
ORD
3h 35mnonstop
United Airlines Logo
2:18 pm - 9:53 pm
ORD
-
YYC
8h 35m
1 stop
$269United Airlines
Fri, Oct 30 - Mon, Nov 2
Delta Logo
7:45 am - 10:25 pm
YYC
-
MDW
13h 40m
2 stops
Delta Logo
12:28 pm - 11:04 pm
MDW
-
YYC
11h 36m
2 stops
$300Delta
Fri, Oct 30 - Mon, Nov 2
Delta Logo
7:45 am - 4:39 pm
YYC
-
MDW
7h 54m
1 stop
Delta Logo
12:28 pm - 11:04 pm
MDW
-
YYC
11h 36m
2 stops
$313Delta
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 October.

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 $224 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 Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Wednesday is the most expensive day to fly from Calgary to Chicago. For your return ticket, we recommend flying on a Friday and avoiding Thursdays 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 March, where tickets cost $62 (return) on average. On the other hand, the most expensive months are August and May, where the average cost of round-trip tickets is $143 and $108 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.

No, with an average price for the route of $273, prices are generally cheapest when you fly direct.

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 24% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Expert advice

Expert advice for your flight from Calgary to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Air Canada, WestJet, United Airlines and ORD

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.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

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.

Kaitlyn McInnis

Kaitlyn McInnis

Expert on YYC

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.

Good to know

Low seasonFebruary
Cheapest flight$164
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 9% increase in price.
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 5 days, the lowest price for a flight from Calgary to Chicago was $164 for a one-way ticket and $207 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, WestJet, Air Canada, 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 Boeing 737-800 is the aircraft model that flies most regularly on the Calgary to Chicago flight route.

  • Which airline alliances offer flights from Calgary to Chicago?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Calgary and Chicago, with SkyTeam 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, United Airlines or WestJet?

    The two airlines most popular with KAYAK users for flights from Calgary to Chicago are United Airlines and WestJet. With an average price for the route of $425 and an overall rating of 7.4, United Airlines is the most popular choice. WestJet is also a great choice for the route, with an average price of $278 and an overall rating of 7.2.

  • 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 $231 or less one-way and $393 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

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Tuesday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Wednesday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Thursday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Friday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Saturday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Sunday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

See more direct flights

Direct returns

Chicago to Calgary

Monday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Tuesday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Wednesday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Thursday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Friday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Saturday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

Sunday

American Airlines,United Airlines,WestJet

American Airlines,United Airlines, +1 more

See more direct flights

Reviews of the top 3 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.
7.4
United AirlinesOverall score based on 9940 reviews
7.7Boarding
7.3Comfort
6.6Food
7.1Entertainment
8.1Crew
Airline reviews

They were fast and I like how they used to entertainment system to play video about the safety.

10.0 ExcellentAnonymous, Apr 2026
YYC - DEN
Read more United Airlines reviews

They were fast and I like how they used to entertainment system to play video about the safety.

We Left Calgary 1/2 hour late and that made for a tight connection in Denver. After arriving everything was done to help us make our connection. That was a great effort. Thank You United

Plane 3 hours late. Missed connection. No help from gate staff. App horrible. Lost connection repeatedly. No service desk. Finally got help from young girl driving cart.

Horrible; seating was atrocious - inadequate leg room and seat width tight even for a small individual. Profits shouldn’t be everything!

I flew basic economy, so it was what I expected. Crew was nice though, and flight was quick. Would recommend for flights under 6 hours, otherwise would upgrade to something with more leg room.

Airline staff was good the checkin process was ok but the plane itself was very bad the comfort was worst it was worst and the most stiff 5 hours of my life i felt claustrophobic

Calgary desperately needs a star alliance lounge in the transborder area for United.

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

Flight was delayed but reasonable notice and communication was always there for the passengers.

I think it would have been better to get a heads up to download the app before getting on the plane as I only had wifi in the airport and didn’t realize the plane was an older one. Maybe a little more communication before hand would be lovely. The seats as always were crammed and uncomfortable and trying to convince people to spend an extra 150 so that we have an extra foot of leg room was less then ideal.

Despite travelling ultra basic for the first time due to such increased rates we both managed with one bag each. Even boarding last wasn’t SO bad.

Flight was early. That’s the only positive I can share. I paid for wifi on the flight and it didn’t allow me to use any streaming services so it was a waste of $20. West Jet also lost my ski equipment on my way to a ski vacation. They told me it would be delivered to the hotel as soon as it arrived at the airport. It was never delivered. I had to pick it up at the airport on my way home. I am completely disgusted with my experience on west jet

I was seated near a "stinky" person. That's not the fault of Westjet🙁😶‍🌫️

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.

Staff was nice, helpful, and did all they could. I understand economy seats are bottom of the barrel, but we're crammed in there with others in our row.

Crew was friendly. Lost our luggage and told us it’d be in later in the evening of the day we returned. It was not. Still after 5 days have not received it.

It took 30 minutes to check in with the Westjet rep. They didn’t have enough seats and she needed to make a call… I am always “randomly” selected to be checked at security. Their “randomly “ selection system may need some updating. They treat people like criminals. It is not appropriate behavior.

My luggage was not sent with us. Not sure if this is Envoy Air responsibility but that was a very BAD experience

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

Very efficient boarding and quick flight. Attendants don’t come by often so would often have a lot of trash at seat.

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

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

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

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

Incompetent crew at the boarding counter. Never flying AA again.

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

Information on your arrival and departure airports