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$114+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
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Cheapflights Tip: The best prices from Calgary to Chicago are usually found in April or February, booked 66 days in advance, depart on a Sunday or Wednesday and return on a Thursday

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 October 23, 2025.

This American Airlines deal was found by Cheapflights users on 10/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/251:29 pmYYC - ORD
Nonstop3h 25mAmerican Airlines
Tue 10/289:49 amORD - YYC
Nonstop3h 45mAmerican Airlines
Deal found 10/22$182
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Fri 12/129:00 amYYC - ORD
Nonstop3h 35mWestJet
Mon 12/152:20 pmORD - YYC
Nonstop3h 55mWestJet
Deal found 10/21$183
This Trip.com deal was found by Cheapflights users on 10/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/59:00 amYYC - ORD
Nonstop3h 35mWestJet
Mon 12/82:20 pmORD - YYC
Nonstop3h 55mWestJet
Deal found 10/21$190
This United Airlines deal was found by Cheapflights users on 10/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2512:38 pmYYC - ORD
Nonstop3h 32mUnited Airlines
Tue 10/283:55 pmORD - YYC
1 stop6h 58mUnited Airlines
Deal found 10/22$192
This Air Canada deal was found by Cheapflights users on 10/22. 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.
Sat 12/65:45 amYYC - ORD
1 stop8h 10mAir Canada
Sat 12/132:00 pmORD - YYC
1 stop7h 39mAir Canada
Deal found 10/22$198
This Air Canada deal was found by Cheapflights users on 10/21. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/185:35 amYYC - ORD
1 stop8h 35mAir Canada
Tue 11/2510:00 amORD - YYC
1 stop9h 54mAir Canada
Deal found 10/21$204
This United Airlines deal was found by Cheapflights users on 10/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2512:38 pmYYC - ORD
Nonstop3h 32mUnited Airlines
Sun 10/268:45 amORD - YYC
Nonstop3h 50mUnited Airlines
Deal found 10/20$210
This Air Canada deal was found by Cheapflights users on 10/20. 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.
Fri 10/241:10 amYYC - ORD
1 stop7h 41mAir Canada
Sat 10/253:35 pmORD - YYC
1 stop8h 41mAir Canada
Deal found 10/20$212
This American Airlines deal was found by Cheapflights users on 10/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/251:29 pmYYC - ORD
Nonstop3h 25mAmerican Airlines
Sun 10/269:45 pmORD - YYC
1 stop15h 14mAmerican Airlines
Deal found 10/20$216
This Mytrip deal was found by Cheapflights users on 10/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/241:10 amYYC - ORD
2 stops17h 56mMultiple Airlines
Sun 10/262:20 pmORD - YYC
Nonstop3h 55mMultiple Airlines
Deal found 10/20$217
This United Airlines deal was found by Cheapflights users on 10/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2512:38 pmYYC - ORD
Nonstop3h 32mUnited Airlines
Sat 11/18:45 amORD - YYC
Nonstop3h 50mUnited Airlines
Deal found 10/23$220
This Delta deal was found by Cheapflights users on 10/22. 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.
Sat 12/66:35 amYYC - MDW
1 stop5h 33mDelta
Sat 12/131:50 pmMDW - YYC
1 stop8h 07mDelta
Deal found 10/22$222

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 October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$183
(Kiwi.com)

One-way from

$114
(United Airlines)

Popular in

December

Cheapest in

April

Average price

$323

Good round-trip deal

$218 or less

Good one-way deal

$194 or less
Provider with most accurate pricing for Calgary-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Calgary-Chicago (CHI) flights.
Search Deals
From Calgary to Chicago (CHI)
Search Deals
One-way flight from Calgary to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 23% potential increase in price ($85 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Calgary to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Calgary to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
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 2,558,603 searches. Data last updated October 23, 2025.
Use the filters below to find and compare flights from Calgary to Chicago that are best for you.

Fly from

Calgary

Fly to

Chicago

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 12/11

7:35 am-6:45 pm

1 stop10h 10m

Chicago O'Hare Intl

Mon 12/15

1:35 pm-11:13 pm

1 stop10h 38m

$222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 11/11

7:45 am-6:45 pm

1 stop10h 00m

Chicago O'Hare Intl

Sat 11/15

6:00 am-2:06 pm

1 stop9h 06m

$222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 12/12

7:35 am-6:45 pm

1 stop10h 10m

Chicago O'Hare Intl

Tue 12/16

8:50 am-1:40 pm

1 stop5h 50m

$222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 12/6

6:35 am-8:35 pm

2 stops13h 00m

Chicago O'Hare Intl

Sat 12/13

6:00 am-1:40 pm

1 stop8h 40m

$222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 11/11

6:35 am-3:02 pm

1 stop7h 27m

Chicago O'Hare Intl

Tue 11/18

8:50 am-1:53 pm

1 stop6h 03m

$222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 12/11

7:35 am-6:45 pm

1 stop10h 10m

Chicago O'Hare Intl

Tue 12/16

8:50 am-1:40 pm

1 stop5h 50m

$222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 11/21

7:45 am-6:45 pm

1 stop10h 00m

Chicago O'Hare Intl

Fri 11/28

6:00 am-1:53 pm

1 stop8h 53m

$222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 11/18

7:45 am-9:36 pm

2 stops12h 51m

Chicago O'Hare Intl

Tue 11/25

11:03 am-11:10 pm

2 stops13h 07m

$222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 12/10

12:41 pm-9:21 pm

1 stop7h 40m

Chicago O'Hare Intl

Tue 12/16

8:50 am-1:40 pm

1 stop5h 50m

$222

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 12/6

6:35 am-1:08 pm

1 stop5h 33m

Chicago Midway

Sat 12/13

1:50 pm-8:57 pm

1 stop8h 07m

$222

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

Showing 1-10 of 34 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 October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice 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 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.

Cheapflights Insights

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

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 October 17, 2025.

To ensure you get the cheapest price possible for a flight from Calgary to Chicago, you should look to book at least 66 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, April is the cheapest month in which you can book a flight from Calgary to Chicago (average of $108). Flying from Calgary to Chicago in July is currently the most expensive (average of $156). 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 October 23, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 66% 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 October 23, 2025.

The most flights from YYC to CHI are scheduled on a Thursday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

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

The best insider tips for Calgary to Chicago 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 Calgary to Chicago trip
Airports
YYC

Calgary Airport offers a convenient LINK shuttle between terminals, making it easy to navigate during peak travel times.

Read more about YYCby Jenna Scatena
ORD

For a quick city transfer, take the 'L' train from ORD to downtown Chicago, avoiding traffic delays.

Read more about ORDby Ramsey Qubein
Our travel experts
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

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 October 23, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Calgary to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,982 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Delta
7.9
Good
7,982 reviews
Delta
7.9
Good
7,982 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
United Airlines
7.4
Good
8,995 reviews
Delta
7.9
Good
7,982 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
American Airlines
7.2
Good
11,033 reviews
Delta
7.9
Good
7,982 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
WestJet
7.2
Good
3,139 reviews
Delta
7.9
Good
7,982 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!
Air Canada
7.1
Good
10,350 reviews
Delta
7.9
Good
7,982 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

7.9

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Mary,Oct 2025

AMS - PDX

It's specail being able to fly non-stop from Amsterdam all the way home to Portland, Oregon!

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 5 outbound flights to Chicago per day from 4 airlines. Calgary is conveniently located just 5.8 mi from Calgary’s city center.

  • How long is the flight from Calgary to Chicago?

    There are many flights that can get you from Calgary to Chicago in 10h 10m. Fly via Delta to get the fastest option. The distance between Calgary and Chicago is about 1381 mi.

  • 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 $109 on this airline. Additional options worth looking into are WestJet and American Airlines, starting at $138 and $208 round-trip. Air Canada is currently priced 60% below the average price you’ll pay for this route.

  • 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: United Airlines (88%), Emirates (85%), Air Canada( 83%).

  • What are the cheapest flights from Calgary to Chicago?

    Looking for the cheapest flight from Calgary to Chicago? While on average our users pay $425, our data indicates the cheapest price to be $112. The most popular route (Calgary - Chicago O'Hare Intl), is priced around $193.

  • 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, April is the cheapest month in which you can book a flight from Calgary to Chicago (average of $108). Flying from Calgary to Chicago in July is currently the most expensive (average of $156). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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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 2,558,603 searches. Data last updated October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$109Average$468FlexibilityNo cancel feeOn-time67%
WestJetCheapest$138Average$219FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$208Average$376FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$218Average$467FlexibilityNo cancel feeOn-time69%

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