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$66+ 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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYC
Dec 28 — Jan 41
Sat 12/28
Sat 1/4
1 adult, Economy
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The best prices from Chicago to Calgary are usually found in September or April, booked 36 days in advance, depart on a Thursday or Wednesday and return on a Saturday

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 December 23, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$183
(Expedia)

One-way from

$66
(oojo)

Popular in

December

Cheapest in

September

Average price

$596
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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High demand for flights, 17% potential price rise
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Best time to find cheap flights, 6% potential price drop
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Average for round-trip flights in December 2024
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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 December 23, 2024.

This Air Canada deal was found by Cheapflights users on 12/22. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/244:00 pmORD - YYC
1 stop8h 18mAir Canada
Thu 12/2612:55 amYYC - ORD
1 stop8h 59mAir Canada
Deal found 12/22$382
This Delta deal was found by Cheapflights users on 12/22. 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 12/257:30 amORD - YYC
1 stop11h 43mDelta
Wed 1/17:00 amYYC - ORD
1 stop9h 09mDelta
Deal found 12/22$480
This United deal was found by Cheapflights users on 12/21. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/258:45 amORD - YYC
Nonstop3h 54mMultiple Airlines
Thu 12/2612:55 amYYC - ORD
1 stop8h 59mMultiple Airlines
Deal found 12/21$486
This Delta deal was found by Cheapflights users on 12/22. 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 12/2511:48 amMDW - YYC
1 stop10h 19mDelta
Wed 1/17:00 amYYC - MDW
1 stop9h 11mDelta
Deal found 12/22$623
This American Airlines deal was found by Cheapflights users on 12/23. 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 12/267:09 amORD - YYC
1 stop15h 41mAmerican Airlines
Mon 12/306:29 amYYC - ORD
1 stop16h 50mAmerican Airlines
Deal found 12/23$656
This United Airlines deal was found by Cheapflights users on 12/21. 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.
Wed 12/258:45 amORD - YYC
Nonstop3h 54mUnited Airlines
Fri 12/272:09 pmYYC - ORD
1 stop8h 50mUnited Airlines
Deal found 12/21$697
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Mon 12/302:20 pmMDW - YYC
1 stop22h 24mMultiple Airlines
Thu 1/23:45 pmYYC - MDW
1 stop12h 48mMultiple Airlines
Deal found 12/21$704
This WestJet deal was found by Cheapflights users on 12/22. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2611:48 amMDW - YYC
2 stops20h 48mWestJet
Thu 1/26:30 pmYYC - MDW
2 stops15h 38mWestJet
Deal found 12/22$1,099
This Travelocity deal was found by Cheapflights users on 12/21. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2510:05 amORD - YYC
2 stops12h 40mWestJet
Wed 12/2512:20 amYYC - ORD
2 stops19h 21mWestJet
Deal found 12/21$1,106
This Porter Airlines deal was found by Cheapflights users on 12/21. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/305:35 pmMDW - YYC
2 stops28h 16mPorter Airlines
Thu 1/27:10 amYYC - MDW
2 stops27h 00mPorter Airlines
Deal found 12/21$1,132

Find flights from Chicago to Calgary within your budget

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 December 23, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sun 3/23

4:45 pm-7:36 pm

Nonstop3h 51m

Calgary

Sun 3/30

11:30 am-3:56 pm

Nonstop3h 26m

$183

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 2/20

4:45 pm-7:36 pm

Nonstop3h 51m

Calgary

Mon 2/24

8:30 am-6:34 pm

1 stop9h 04m

$190

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 1/21

8:50 am-11:39 am

Nonstop3h 49m

Calgary

Mon 1/27

12:50 am-10:54 am

1 stop9h 04m

$221

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sun 1/19

7:10 am-9:41 pm

1 stop15h 31m

Calgary

Wed 1/22

6:19 am-7:31 pm

1 stop12h 12m

$240

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 1/18

11:19 am-8:53 pm

1 stop10h 34m

Calgary

Fri 1/24

6:35 am-5:47 pm

1 stop10h 12m

$249

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 1/28

11:50 am-8:53 pm

1 stop10h 03m

Calgary

Sun 2/2

6:35 am-5:29 pm

1 stop9h 54m

$249

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 2/4

8:15 am-10:25 pm

2 stops15h 10m

Calgary

Mon 2/10

12:30 am-4:16 pm

1 stop14h 46m

$304

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 4/1

7:20 am-9:50 pm

1 stop15h 30m

Calgary

Tue 4/8

1:17 pm-5:49 pm

Nonstop3h 32m

$359

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Fri 3/7

11:15 am-9:08 pm

2 stops10h 53m

Calgary

Sat 3/15

7:10 am-10:20 am

1 stop26h 10m

$641

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Fri 1/24

6:59 pm-8:53 pm

1 stop26h 54m

Calgary

Sat 1/25

12:30 am-10:12 am

1 stop8h 42m

$649

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 24 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 December.
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*3 stars
GotogatePrice Accuracy2 starsTrust Score*2 stars
MytripPrice Accuracy3 starsTrust 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.

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.

Travel insights for flights from Chicago to Calgary

Get recent, data-driven insights about flights from Chicago to Calgary including ideal travel times, pricing trends, and more.

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 December 20, 2024.

The best time to book flights from Chicago to Calgary is 36 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 March is currently the most expensive (average of $468). 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 December 23, 2024.

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 evening tend to be the most expensive. A flight at noon could potentially save you up to 29% 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. Saturday evenings 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 December 23, 2024.

The most flights from CHI to YYC are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

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 December 23, 2024.
Read reviews from past customers who have flown Porter Airlines, American Airlines and WestJet 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
9,549 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.2

Entertainment

7.1

Overall

8.0

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

Alaska Airlines
8.0
Very good
9,549 reviews
Alaska Airlines
8.0
Very good
9,549 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.2

Entertainment

7.1

Overall

8.0

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

Delta
8.0
Very good
8,588 reviews
Alaska Airlines
8.0
Very good
9,549 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.2

Entertainment

7.1

Overall

8.0

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

Porter Airlines
7.8
Good
282 reviews
Alaska Airlines
8.0
Very good
9,549 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.2

Entertainment

7.1

Overall

8.0

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

Austrian Airlines
7.6
Good
786 reviews
Alaska Airlines
8.0
Very good
9,549 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.2

Entertainment

7.1

Overall

8.0

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

Aeromexico
7.5
Good
1,913 reviews
Alaska Airlines
8.0
Very good
9,549 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.2

Entertainment

7.1

Overall

8.0

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

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 2 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 $183 on this airline. Additional options worth looking into are Air Canada and United Airlines, starting at $221 and $240 round-trip. WestJet is 48% 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 $66. 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: American Airlines (100%), Qatar Airways (100%), Envoy Air (100%).

  • What are the cheapest flights from Chicago to Calgary?

    While on average a flight from Chicago to Calgary is generally $328, our data shows the cheapest flight currently is $69. When looking at the most popular route, (Chicago O'Hare Intl - Calgary), you can expect to pay $184 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 March is currently the most expensive (average of $468). 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

Browse thousands of different options on Cheapflights for your next trip

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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 December 23, 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$107Average$370FlexibilityNo cancel feeOn-time67%
WestJetCheapest$124Average$314FlexibilityNo cancel feeOn-time60%
DeltaCheapest$154Average$367FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$187Average$407FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$205Average$452FlexibilityNo cancel feeOn-time69%
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