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$67+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYC
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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1. Tell us where you want to go
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The best prices from Chicago to Calgary are usually found in March or September, booked 36 days in advance, depart on a Thursday or Wednesday 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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$162
(Kiwi.com)

One-way from

$67
(Trip.com)

Popular in

December

Cheapest in

March

Average price

$316

Good round-trip deal

$190 or less

Good one-way deal

$100 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. 18% potential increase in price ($78 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 February 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 February 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/18. 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.
Tue 9/235:30 pmORD - YYC
Nonstop3h 49mWestJet
Sat 9/2712:15 pmYYC - ORD
Nonstop3h 28mWestJet
Deal found 2/18$153
This Mytrip deal was found by Cheapflights users on 2/18. 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.
Thu 4/104:45 pmORD - YYC
Nonstop3h 51mMultiple Airlines
Mon 4/148:30 amYYC - ORD
1 stop9h 24mMultiple Airlines
Deal found 2/18$183
This Air Canada deal was found by Cheapflights users on 2/19. 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.
Wed 3/58:53 amORD - YYC
Nonstop3h 46mAir Canada
Wed 3/1212:41 pmYYC - ORD
Nonstop3h 29mAir Canada
Deal found 2/19$195
This United Airlines deal was found by Cheapflights users on 2/18. 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.
Sat 4/121:05 pmORD - YYC
1 stop9h 43mUnited Airlines
Mon 4/1412:43 pmYYC - ORD
Nonstop3h 27mUnited Airlines
Deal found 2/18$205
This Delta deal was found by Cheapflights users on 2/19. 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 4/11:16 pmMDW - YYC
1 stop8h 26mDelta
Tue 4/86:30 amYYC - MDW
1 stop6h 47mDelta
Deal found 2/19$250
This Delta deal was found by Cheapflights users on 2/19. 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.
Mon 3/241:45 pmORD - YYC
1 stop10h 31mDelta
Sat 3/296:30 amYYC - ORD
1 stop9h 58mDelta
Deal found 2/19$250
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Sun 4/68:50 pmMDW - YYC
1 stop27h 05mMultiple Airlines
Sun 4/136:55 pmYYC - MDW
1 stop9h 25mMultiple Airlines
Deal found 2/20$282
This American Airlines deal was found by Cheapflights users on 2/19. 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 5/19:50 amORD - YYC
Nonstop3h 45mAmerican Airlines
Tue 5/61:18 pmYYC - ORD
Nonstop3h 30mAmerican Airlines
Deal found 2/19$313
This FlightHub deal was found by Cheapflights users on 2/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1111:15 amMDW - YYC
2 stops10h 58mPorter Airlines
Sun 4/134:20 pmYYC - MDW
1 stop17h 00mPorter Airlines
Deal found 2/18$535
This Trip.com deal was found by Cheapflights users on 2/19. 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 4/57:13 pmMDW - YYC
1 stop26h 29mWestJet
Sat 4/126:30 amYYC - MDW
1 stop11h 03mWestJet
Deal found 2/19$609

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 February 20, 2025.

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

Sun 5/4

12:15 pm-4:44 pm

Nonstop3h 29m

$157

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 4/10

4:45 pm-7:36 pm

Nonstop3h 51m

Calgary

Mon 4/14

8:30 am-6:54 pm

1 stop9h 24m

$183

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 3/5

8:53 am-11:39 am

Nonstop3h 46m

Calgary

Wed 3/12

12:41 pm-5:10 pm

Nonstop3h 29m

$195

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 4/12

1:05 pm-9:48 pm

1 stop9h 43m

Calgary

Mon 4/14

12:43 pm-5:10 pm

Nonstop3h 27m

$205

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Tue 4/1

1:16 pm-8:42 pm

1 stop8h 26m

Calgary

Tue 4/8

6:30 am-2:17 pm

1 stop6h 47m

$250

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 3/24

1:45 pm-11:16 pm

1 stop10h 31m

Calgary

Sat 3/29

6:30 am-5:28 pm

1 stop9h 58m

$250

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 5/2

9:50 am-12:35 pm

Nonstop3h 45m

Calgary

Wed 5/7

1:18 pm-5:48 pm

Nonstop3h 30m

$281

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sun 4/6

8:50 pm-10:55 pm

1 stop27h 05m

Calgary

Sun 4/13

6:55 pm-5:20 am

1 stop9h 25m

$282

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Fri 4/11

11:15 am-9:13 pm

2 stops10h 58m

Calgary

Sun 4/13

4:20 pm-10:20 am

1 stop17h 00m

$535

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 4/5

7:13 pm-8:42 pm

1 stop26h 29m

Calgary

Sat 4/12

6:30 am-6:33 pm

1 stop11h 03m

$609

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 20 results
1
2

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*2 stars
GotogatePrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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.

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 February 14, 2025.

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 $433). 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 February 20, 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.

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 February 20, 2025.

The most flights from CHI to YYC are scheduled on a Thursday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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 February 20, 2025.
Read reviews from past customers who have flown Delta, Porter Airlines and United 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.
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta
8.0
Very good
8,220 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Porter Airlines
7.9
Good
276 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

United Airlines
7.4
Good
8,766 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

WestJet
7.2
Good
2,801 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding 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 5 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 $162 on this airline. Additional options worth looking into are Air Canada and United Airlines, starting at $195 and $220 round-trip. WestJet is 51% 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 $67. However, be on the lookout for offers from United 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: United Airlines (90%), Air Canada (80%), American Airlines (33%).

  • What are the cheapest flights from Chicago to Calgary?

    While on average a flight from Chicago to Calgary is generally $539, our data shows the cheapest flight currently is $62. When looking at the most popular route, (Chicago O'Hare Intl - Calgary), you can expect to pay $178 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 $433). 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.

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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$121Average$364FlexibilityNo cancel feeOn-time67%
WestJetCheapest$126Average$279FlexibilityNo cancel feeOn-time60%
DeltaCheapest$145Average$338FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$188Average$459FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$209Average$482FlexibilityNo cancel feeOn-time69%
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