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$73+ 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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYC
août 4 — août 111
lun. 8/4
lun. 8/11
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Calgary are usually found in May or October, booked 35 days in advance, depart on a Thursday or Friday 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 juillet 30, 2025.

Round-trip from

$156
(Trip.com)

One-way from

$73
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$337

Good round-trip deal

$218 or less

Good one-way deal

$94 or less
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. 21% potential increase in price ($83 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in July 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 juillet 30, 2025.

This Trip.com deal was found by Cheapflights users on 7/29. 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.
lun. 9/155:30 pmORD - YYC
Nonstop3h 49mWestJet
mer. 9/2412:15 pmYYC - ORD
Nonstop3h 28mWestJet
Deal found 7/29$156
This flugladen.de deal was found by Cheapflights users on 7/29. 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/153:50 pmORD - YYC
1 stop8h 32mMultiple Airlines
mer. 9/2412:15 pmYYC - ORD
Nonstop3h 28mMultiple Airlines
Deal found 7/29$158
This Mytrip deal was found by Cheapflights users on 7/29. 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.
lun. 9/156:20 pmORD - YYC
1 stop7h 52mAir Canada
mar. 9/231:10 amYYC - ORD
1 stop7h 41mAir Canada
Deal found 7/29$160
This United Airlines deal was found by Cheapflights users on 7/30. 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.
mer. 11/58:45 amORD - YYC
Nonstop3h 50mUnited Airlines
mar. 11/1112:37 pmYYC - ORD
Nonstop3h 33mUnited Airlines
Deal found 7/30$181
This American Airlines deal was found by Cheapflights users on 7/30. 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.
mer. 11/58:45 pmORD - YYC
1 stop15h 59mAmerican Airlines
mar. 11/1112:45 pmYYC - ORD
1 stop8h 35mAmerican Airlines
Deal found 7/30$206
This Delta deal was found by Cheapflights users on 7/29. 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.
sam. 9/271:43 pmMDW - YYC
1 stop7h 59mDelta
sam. 10/46:40 amYYC - MDW
1 stop9h 55mDelta
Deal found 7/29$252
This Mytrip deal was found by Cheapflights users on 7/27. 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.
mar. 9/95:20 pmMDW - YYC
1 stop15h 55mMultiple Airlines
lun. 9/156:20 amYYC - MDW
1 stop9h 04mMultiple Airlines
Deal found 7/27$308

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 juillet 30, 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

lun. 9/15

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

mer. 9/24

12:15 pm-4:43 pm

Nonstop3h 28m

$156

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

lun. 9/15

3:50 pm-11:22 pm

1 stop8h 32m

Calgary

mer. 9/24

12:15 pm-4:43 pm

Nonstop3h 28m

$158

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

lun. 9/15

6:20 pm-1:12 am

1 stop7h 52m

Calgary

mar. 9/23

1:10 am-9:51 am

1 stop7h 41m

$160

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

mer. 11/5

8:45 am-11:35 am

Nonstop3h 50m

Calgary

mar. 11/11

12:37 pm-5:10 pm

Nonstop3h 33m

$181

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

sam. 9/27

1:43 pm-8:42 pm

1 stop7h 59m

Calgary

sam. 10/4

6:40 am-5:35 pm

1 stop9h 55m

$252

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

mar. 9/9

5:20 pm-8:15 am

1 stop15h 55m

Calgary

lun. 9/15

6:20 am-4:24 pm

1 stop9h 04m

$308

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

ven. 9/26

5:30 pm-8:19 pm

Nonstop3h 49m

$73

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

lun. 9/15

8:30 pm-11:19 pm

Nonstop3h 49m

$75

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

sam. 9/27

3:35 pm-11:16 pm

1 stop8h 41m

$80

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

mar. 9/9

8:08 pm-10:53 pm

Nonstop3h 45m

$82

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 16 results
1
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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 quick snack before your flight, grab Garrett Popcorn near gate B8, a Chicago favorite.

Read more about ORDby Ramsey Qubein
YYC

Use the LINK shuttle at YYC for fast, free transfers between terminals, especially useful during peak travel times.

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 July 25, 2025.

The best time to book flights from Chicago to Calgary is 35 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 February is currently the most expensive (average of $402). 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 juillet 30, 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 44% 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. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Calgary

Explore weekly flight availability from Chicago to Calgary. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated juillet 30, 2025.

The most flights from CHI to YYC are scheduled on a Monday (17 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (7 on average).

How much does it cost to fly round-trip from Chicago to Calgary?

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 juillet 30, 2025.
Peruse reviews from past customers who have flown with Porter Airlines, Delta, and United Airlines from Chicago to Calgary to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Crew

8.7

Food

7.6

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
318 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Crew

8.7

Food

7.6

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,980 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Crew

8.7

Food

7.6

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,896 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Crew

8.7

Food

7.6

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Crew

8.7

Food

7.6

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
2,975 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Crew

8.7

Food

7.6

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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 12 inbound flights 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 $156 on this airline. Additional options worth looking into are Air Canada and United Airlines, starting at $160 and $189 round-trip. WestJet is 49% 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 $73. However, be on the lookout for offers from American Airlines and Air Canada, 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: Envoy Air (80%), Air Canada (68%), United Airlines (68%).

  • What are the cheapest flights from Chicago to Calgary?

    While on average a flight from Chicago to Calgary is generally $311, our data shows the cheapest flight currently is $67. When looking at the most popular route, (Chicago O'Hare Intl - Calgary), you can expect to pay $158 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 February is currently the most expensive (average of $402). 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 Calgary?

Book flights to Calgary if you plan to visit one of these locations
Canmore
Airdrie

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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 juillet 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$97Average$250FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$99Average$374FlexibilityNo cancel feeOn-time69%
DeltaCheapest$109Average$305FlexibilityNo cancel feeOn-timeN/A
WestJetCheapest$142Average$234FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$188Average$409FlexibilityNo cancel feeOn-time71%

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