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$108+ Cheap flights from Calgary (YYC) to Chicago (CHI)

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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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1. Tell us where you want to go
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The best prices from Calgary to Chicago are usually found in September or February, booked 84 days in advance, depart on a Wednesday or Sunday and return on a Thursday

Cheap flight deals from Calgary to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Calgary (YYC) to Chicago (CHI). 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 November 21, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

December

Cheapest in

September

Round-trip from

$215
(Air Canada)

One-way from

$108
(Justfly.com)
Provider with most accurate pricing for Calgary-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Calgary-Chicago (CHI) flights.
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High demand for flights, 17% potential price rise
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Best time to find cheap flights, 20% potential price drop
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From Calgary to Chicago (CHI)
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One-way flight from Calgary to Chicago (CHI)
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Find flight deals from Calgary to Chicago

Cheapest flights from Calgary to Chicago
Explore the most affordable flight options available from Calgary to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 21, 2024.

This Delta deal was found by Cheapflights users on 11/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/77:00 amYYC - ORD
1 stop8h 58mDelta
Tue 12/1012:35 pmORD - YYC
2 stops11h 41mDelta
Deal found 11/20$221
This Air Canada deal was found by Cheapflights users on 11/20. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/48:30 amYYC - ORD
1 stop9h 06mAir Canada
Sat 12/712:52 pmORD - YYC
1 stop11h 26mAir Canada
Deal found 11/20$250
This Delta deal was found by Cheapflights users on 11/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/77:00 amYYC - MDW
1 stop10h 32mDelta
Tue 12/109:30 amMDW - YYC
2 stops12h 08mDelta
Deal found 11/20$255
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/176:55 pmYYC - ORD
1 stop9h 47mMultiple Airlines
Thu 12/198:34 pmORD - YYC
1 stop27h 21mMultiple Airlines
Deal found 11/19$296
This United Airlines deal was found by Cheapflights users on 11/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2112:41 pmYYC - ORD
Nonstop3h 28mUnited Airlines
Fri 11/298:45 amORD - YYC
Nonstop3h 54mUnited Airlines
Deal found 11/19$313
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/39:45 pmYYC - MDW
2 stops12h 57mMultiple Airlines
Mon 12/912:05 pmMDW - YYC
1 stop12h 20mMultiple Airlines
Deal found 11/19$444
This American Airlines deal was found by Cheapflights users on 11/19. 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.
Fri 11/296:29 amYYC - ORD
1 stop11h 51mAmerican Airlines
Sun 12/17:00 amORD - YYC
1 stop15h 51mAmerican Airlines
Deal found 11/19$486
This Alaska Airlines deal was found by Cheapflights users on 11/20. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/511:30 amYYC - ORD
1 stop28h 24mAlaska Airlines
Mon 12/96:32 amORD - YYC
1 stop29h 08mAlaska Airlines
Deal found 11/20$528
This WestJet deal was found by Cheapflights users on 11/20. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/49:20 amYYC - ORD
2 stops12h 23mWestJet
Sat 12/76:20 amORD - YYC
2 stops13h 11mWestJet
Deal found 11/20$554
This WestJet deal was found by Cheapflights users on 11/19. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/39:45 pmYYC - MDW
2 stops11h 05mWestJet
Mon 12/97:14 pmMDW - YYC
2 stops24h 54mWestJet
Deal found 11/19$557
This FlightHub deal was found by Cheapflights users on 11/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/177:10 amYYC - MDW
1 stop27h 00mPorter Airlines
Thu 12/195:35 pmMDW - YYC
1 stop22h 53mPorter Airlines
Deal found 11/19$573

Find flights from Calgary to Chicago within your budget

Customize your flight search to find flights from Calgary to Chicago 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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 1/9

8:30 am-6:38 pm

1 stop9h 08m

Chicago O'Hare Intl

Mon 1/13

4:00 pm-11:18 pm

1 stop8h 18m

$215

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 12/7

7:00 am-4:58 pm

1 stop8h 58m

Chicago O'Hare Intl

Tue 12/10

12:35 pm-11:16 pm

2 stops11h 41m

$221

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 1/8

6:35 am-6:14 pm

2 stops10h 39m

Chicago Midway

Sun 1/12

9:34 am-8:53 pm

2 stops12h 19m

$221

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 4/30

7:00 am-10:21 pm

2 stops14h 21m

Chicago O'Hare Intl

Mon 5/5

5:30 pm-8:19 pm

Nonstop3h 49m

$253

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 1/23

12:30 am-11:54 am

1 stop10h 24m

Chicago Midway

Sun 1/26

12:43 pm-10:55 pm

1 stop11h 12m

$271

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 4/1

12:30 pm-4:50 pm

Nonstop3h 20m

Chicago O'Hare Intl

Tue 4/8

9:00 am-11:54 am

Nonstop3h 54m

$350

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 1/9

6:29 am-2:25 pm

1 stop6h 56m

Chicago O'Hare Intl

Sun 1/12

9:10 am-9:57 pm

1 stop13h 47m

$365

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 4/21

11:30 am-3:56 pm

Nonstop3h 26m

Chicago O'Hare Intl

Mon 4/28

6:00 am-6:40 pm

2 stops13h 40m

$387

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 4/30

6:55 pm-1:03 pm

2 stops17h 08m

Chicago O'Hare Intl

Mon 5/5

3:21 pm-10:37 am

2 stops20h 16m

$457

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 1/9

6:35 am-12:46 pm

1 stop5h 11m

Chicago Midway

Mon 1/13

1:26 pm-8:53 pm

1 stop8h 27m

$499

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

Showing 1-10 of 22 results
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Compare providers for flights from Calgary to Chicago

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 Calgary to Chicago in November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
SmartFaresPrice Accuracy2 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 Calgary-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Calgary-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Calgary-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Calgary-Chicago 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 Calgary-Chicago 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 Calgary to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Calgary 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 Calgary to Chicago

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

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

Use this chart to determine the optimal time to book a round-trip flight from Calgary to Chicago. Price data was last updated on November 15, 2024.

To ensure you get the cheapest price possible for a flight from Calgary to Chicago, you should look to book at least 84 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, September is the cheapest month in which you can book a flight from Calgary to Chicago (average of $232). Flying from Calgary to Chicago in June is currently the most expensive (average of $308). 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 YYC to CHI?

Find hourly flight availability from Calgary to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 21, 2024.

Unlike at noon, when flights are generally more expensive, you can save up to 44% on flights from Calgary to Chicago by exploring options for tickets in the afternoon.

Weekly flight availability from Calgary to Chicago

Explore weekly flight availability from Calgary to Chicago. 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 November 21, 2024.

The most flights from YYC to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Chicago by month

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

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

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

If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated November 21, 2024.
Read reviews from past customers who have flown Air Canada, United Airlines and American Airlines from Calgary to Chicago. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,458 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.2

Boarding

8.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

Alaska Airlines
8.0
Very good
9,458 reviews
Alaska Airlines
8.0
Very good
9,458 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.2

Boarding

8.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

Delta
8.0
Very good
8,759 reviews
Alaska Airlines
8.0
Very good
9,458 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.2

Boarding

8.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

Porter Airlines
7.8
Good
286 reviews
Alaska Airlines
8.0
Very good
9,458 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.2

Boarding

8.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

United Airlines
7.4
Good
9,173 reviews
Alaska Airlines
8.0
Very good
9,458 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.2

Boarding

8.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

WestJet
7.3
Good
2,810 reviews
Alaska Airlines
8.0
Very good
9,458 reviews

Entertainment

7.1

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.2

Boarding

8.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

Related info for your journey

Find useful and relevant information for your journey from Calgary to Chicago. 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 from for flights from Calgary to Chicago?

    Most people fly from Calgary (YYC) if they book a flight from Calgary to Chicago. On average, Calgary has 3 outbound flights to Chicago per day from 4 airlines. Calgary is conveniently located just 5.8 mi from Calgary’s city center.

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

    Our cheapest airline available from Calgary to Chicago is Air Canada. Our recent data shows that you can find tickets from as low as $215 on this airline. Additional options worth looking into are Delta and United Airlines, starting at $221 and $350 round-trip. Air Canada is currently priced 41% below the average price you’ll pay for this route.

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

    To fly one-way, consider booking your trip with WestJet, which is currently one of the cheapest options available, starting at $108. Air Canada flights start at $118 while deals on Delta start at $136 one-way.

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

    Before booking your flight to Chicago from Calgary, check out the most reliable airlines to get you to your destination on time: Air Canada (92%), United Airlines (92%), WestJet( 92%).

  • What are the cheapest flights from Calgary to Chicago?

    Looking for the cheapest flight from Calgary to Chicago? While on average our users pay $416, our data indicates the cheapest price to be $110. The most popular route (Calgary - Chicago O'Hare Intl), is priced around $199.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Calgary to Chicago 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 Calgary to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Calgary to Chicago (average of $232). Flying from Calgary to Chicago in June is currently the most expensive (average of $308). 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 4 airlines flying from Calgary to Chicago

Discover the top 4 airlines that operate flights from Calgary to Chicago. 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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$186Average$307FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$213Average$412FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$219Average$443FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$226Average$403FlexibilityNo cancel feeOn-time69%
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