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$59+ Cheap flights from Chicago (CHI) to Calgary (YYC)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYC
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
1 adult, Economy
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Find cheap flights from Chicago to Calgary with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
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3. Compare prices and book
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Cheapflights Tip: The best prices from Chicago to Calgary are usually found in October or March, booked 22 days in advance, depart on a Thursday or Saturday and return on a Sunday

Cheap flight deals from Chicago to Calgary

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Calgary (YYC). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$145
(Flightnetwork)

One-way from

$59
(Justfly.com)

Popular in

December

Cheapest in

October

Average price

$274

Good round-trip deal

$196 or less

Good one-way deal

$115 or less
Provider with most accurate pricing for Chicago (CHI)-Calgary flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Calgary flights.
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From Chicago (CHI) to Calgary
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One-way flight from Chicago (CHI) to Calgary
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Highest demand for flights based on searches. 20% potential increase in price ($83 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Calgary.
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Price to beat on a one-way flight from Chicago (CHI) to Calgary.
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Find flight deals from Chicago to Calgary

Cheapest flights from Chicago to Calgary
Explore the most affordable flight options available from Chicago to Calgary. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 28, 2025.

This Flightnetwork deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/15:30 pmORD - YYC
Nonstop3h 49mMultiple Airlines
Mon 5/511:55 pmYYC - ORD
1 stop7h 55mMultiple Airlines
Deal found 3/27$145
This Trip.com deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/35:30 pmORD - YYC
Nonstop3h 49mWestJet
Sat 5/1012:15 pmYYC - ORD
Nonstop3h 29mWestJet
Deal found 3/27$147
This Flightnetwork deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/137:10 amORD - YYC
1 stop15h 38mAir Canada
Sat 5/2412:55 amYYC - ORD
1 stop7h 57mAir Canada
Deal found 3/27$151
This American Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/128:25 pmORD - YYC
Nonstop4h 00mAmerican Airlines
Thu 6/196:29 amYYC - ORD
Nonstop3h 25mAmerican Airlines
Deal found 3/27$180
This United Airlines deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/17:10 amORD - YYC
1 stop15h 38mUnited Airlines
Sat 5/1012:43 pmYYC - ORD
Nonstop3h 27mUnited Airlines
Deal found 3/27$189
This Delta deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/131:55 pmMDW - YYC
1 stop7h 45mDelta
Sun 5/256:30 amYYC - MDW
1 stop5h 45mDelta
Deal found 3/27$250
This Delta deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/912:15 pmORD - YYC
1 stop9h 27mDelta
Sun 4/137:40 amYYC - ORD
1 stop9h 10mDelta
Deal found 3/27$255
This Kiwi.com deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/18:03 pmMDW - YYC
1 stop19h 42mMultiple Airlines
Sun 5/412:30 amYYC - MDW
1 stop12h 04mMultiple Airlines
Deal found 3/27$270
This Mytrip deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/205:35 pmMDW - YYC
2 stops28h 38mPorter Airlines
Mon 4/287:10 amYYC - MDW
2 stops32h 30mPorter Airlines
Deal found 3/27$569

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Calgary that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 28, 2025.
Use the filters below to find and compare flights from Chicago to Calgary that are best for you.

Fly from

Chicago

Fly to

Calgary

Route

Depart

Return

Price

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 5/1

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

Mon 5/5

11:55 pm-8:50 am

1 stop7h 55m

$145

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 5/3

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

Sat 5/10

12:15 pm-4:44 pm

Nonstop3h 29m

$147

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 5/13

7:10 am-9:48 pm

1 stop15h 38m

Calgary

Sat 5/24

12:55 am-9:52 am

1 stop7h 57m

$151

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 6/12

8:25 pm-11:25 pm

Nonstop4h 00m

Calgary

Thu 6/19

6:29 am-10:54 am

Nonstop3h 25m

$180

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 5/1

5:05 am-1:53 pm

1 stop9h 48m

Calgary

Sat 5/10

12:43 pm-5:10 pm

Nonstop3h 27m

$189

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 5/13

1:55 pm-8:40 pm

1 stop7h 45m

Calgary

Sun 5/25

6:30 am-1:15 pm

1 stop5h 45m

$250

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 4/9

12:15 pm-8:42 pm

1 stop9h 27m

Calgary

Sun 4/13

7:40 am-5:50 pm

1 stop9h 10m

$255

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Thu 5/1

8:03 pm-2:45 pm

1 stop19h 42m

Calgary

Sun 5/4

12:30 am-1:34 pm

1 stop12h 04m

$270

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sun 4/20

5:35 pm-9:13 pm

2 stops28h 38m

Calgary

Mon 4/28

7:10 am-4:40 pm

2 stops32h 30m

$569

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Fri 7/11

1:05 pm-8:00 pm

1 stop7h 55m

Calgary

Sat 7/19

10:00 am-9:47 pm

1 stop10h 47m

$668

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

Showing 1-10 of 21 results
1
2
3

Compare providers for flights from Chicago to Calgary

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Calgary in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*2 stars
GotogatePrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
Trip.comPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Calgary flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Calgary flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Calgary flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Calgary flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Calgary flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

The best insider tips for Chicago to Calgary flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-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.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Calgary trip
Airlines
United Airlines

Basic Economy allows a personal item only; no carry-on bags unless flying to Canada.


Economy Plus offers extra legroom seats towards the front of the economy cabin.

Read more about United Airlinesby Harriet Baskas
Air Canada

Economy Latitude offers priority check-in and baggage handling, plus two checked bags included.


Preferred Seats offer up to four inches extra space, available for a fee in any fare class.

Read more about Air Canadaby Jessica Macdonald
Airports
ORD

For a smooth departure from ORD, consider taking the “L” train to avoid Chicago traffic delays.

Read more about ORDby Ramsey Qubein
YYC

Upon arrival at YYC, use Route 300 for a rapid transit bus into downtown Calgary.

Read more about YYCby Jenna Scatena
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United 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
Jessica Macdonald

Jessica Macdonald

Expert on Air Canada

Jessica Macdonald

Jessica Macdonald

Currently based in Scotland after living in South Africa and the United States, Jessica has been writing travel and aviation content for more than 10 years. She regularly contributes to Travel + Leisure and TripSavvy, and has had work published by Condé Nast Traveller and The Independent. She has traveled to more than 50 countries across six continents.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Jenna Scatena

Jenna Scatena

Expert on YYC

Jenna Scatena

Jenna Scatena

Journalist and Travel Writer, Jenna Scatena is an award-winning travel writer with a love for sharing stories and exploring new places, especially by Vespa. Though she's from San Francisco, she has spent a significant chunk of her vacation days over the last decade eating her way through Texas and sleeping in hotels around the world—especially in California, the Middle East, and Europe.

Read more

Best time to book a flight from Chicago to Calgary

Have a flexible travel schedule? Discover the best time to fly to Calgary from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Calgary. Price data was last updated on March 21, 2025.

The best time to book flights from Chicago to Calgary is 22 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago to Calgary?

Currently, January is the cheapest month in which you can book a flight from Chicago to Calgary (average of $300). Flying from Chicago to Calgary in June is currently the most expensive (average of $416). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to YYC?

Find hourly flight availability from Chicago to Calgary. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 28, 2025.

One of the essential ways to save on airfare from Chicago to Calgary is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 45% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Chicago to Calgary. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Calgary flight should consider departing on Friday at noon when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Calgary by month

Plan your trip to Calgary by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Calgary ranges from 0.4 - 3.7 inches per month. June is typically the wettest month, when rainfall can reach 3.7 in. January is typically the driest time to visit Calgary when rainfall is around 0.4 in.

Temperature in Calgary by month

Plan your trip to Calgary by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Calgary, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 62.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 19.4 F).

Reviews of airlines servicing Calgary

Get insights into the airlines that provide service to Calgary. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Calgary. Reviews last updated March 28, 2025.
Read reviews from past customers who have flown Alaska Airlines, Delta and Porter Airlines from Chicago to Calgary. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,798 reviews

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,798 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,896 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Porter Airlines
7.9
Good
276 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,603 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Related info for your journey

Find useful and relevant information for your journey from Chicago to Calgary. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Calgary from Chicago?

    Most people fly into Calgary (YYC) if they book a flight to Calgary from Chicago. On average, Calgary has 1 inbound flight from Chicago per day from 5 airlines. Calgary is conveniently located just 5.8 mi from Calgary’s city center.

  • What are the cheapest airlines flying from Chicago to Calgary round-trip?

    Our cheapest airline available from Chicago to Calgary is WestJet. Our recent data shows that you can find tickets from as low as $147 on this airline. Additional options worth looking into are Air Canada and American Airlines, starting at $157 and $180 round-trip. WestJet is 55% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago to Calgary one-way?

    The cheapest airline one-way is WestJet, with whom users have recently found tickets for as low as $59. However, be on the lookout for offers from Air Canada and United Airlines, as they are both options that can get you from Chicago to Calgary for a low price.

  • What are the most reliable airlines from Chicago to Calgary?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Calgary on time: Air Canada (77%), United Airlines (77%), Qatar Airways (71%).

  • What are the cheapest flights from Chicago to Calgary?

    While on average a flight from Chicago to Calgary is generally $860, our data shows the cheapest flight currently is $72. When looking at the most popular route, (Chicago O'Hare Intl - Calgary), you can expect to pay $172 for that flight.

  • Can I find deals for flights from Chicago to Calgary that include hotel bookings?

    Yes. In addition to deals on Chicago to Calgary flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Calgary?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Calgary.

  • Can I find deals for business class flights from Chicago to Calgary?

    Yes. Cheapflights offers flight deals from Chicago to Calgary by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Calgary?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Calgary (average of $300). Flying from Chicago to Calgary in June is currently the most expensive (average of $416). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Top 5 airlines flying from Chicago to Calgary

Discover the top 5 airlines that operate flights from Chicago to Calgary. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$117Average$361FlexibilityNo cancel feeOn-time67%
WestJetCheapest$133Average$270FlexibilityNo cancel feeOn-time60%
DeltaCheapest$137Average$329FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$189Average$461FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$207Average$473FlexibilityNo cancel feeOn-time69%
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