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$113+ 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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
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

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 August 20, 2025.

Round-trip from

$156
(FlightHub)

One-way from

$113
(Air Canada)

Popular in

December

Cheapest in

April

Average price

$268

Good round-trip deal

$161 or less

Good one-way deal

$204 or less
From Calgary to Chicago (CHI)
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One-way flight from Calgary to Chicago (CHI)
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Highest demand for flights based on searches. 24% potential increase in price ($91 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Calgary to Chicago (CHI).
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Price to beat on a 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 August 20, 2025.

This FlightHub deal was found by Cheapflights users on 8/18. 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 10/1712:15 pmYYC - ORD
Nonstop3h 28mWestJet
Sun 10/195:30 pmORD - YYC
Nonstop3h 49mWestJet
Deal found 8/18$156
This KAYAK deal was found by Cheapflights users on 8/19. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1612:15 pmYYC - ORD
Nonstop3h 28mWestJet
Sun 10/195:30 pmORD - YYC
Nonstop3h 49mWestJet
Deal found 8/19$165
This Air Canada deal was found by Cheapflights users on 8/18. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/151:10 amYYC - ORD
1 stop7h 41mAir Canada
Tue 9/233:50 pmORD - YYC
1 stop8h 32mAir Canada
Deal found 8/18$174
This Mytrip deal was found by Cheapflights users on 8/18. 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.
Wed 10/11:10 amYYC - ORD
1 stop7h 41mMultiple Airlines
Fri 10/105:30 pmORD - YYC
Nonstop3h 49mMultiple Airlines
Deal found 8/18$175
This FlightHub deal was found by Cheapflights users on 8/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1812:15 pmYYC - ORD
Nonstop3h 28mWestJet
Sun 10/195:30 pmORD - YYC
Nonstop3h 49mWestJet
Deal found 8/20$176
This Trip.com deal was found by Cheapflights users on 8/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/11:10 amYYC - ORD
1 stop7h 41mMultiple Airlines
Thu 10/95:30 pmORD - YYC
Nonstop3h 49mMultiple Airlines
Deal found 8/18$177
This Air Canada deal was found by Cheapflights users on 8/20. 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 10/31:10 amYYC - ORD
1 stop7h 41mAir Canada
Sat 10/113:35 pmORD - YYC
1 stop8h 41mAir Canada
Deal found 8/20$178
This deal was found by Cheapflights users on 8/18. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1612:15 pmYYC - ORD
Nonstop3h 28mWestJet
Thu 10/235:30 pmORD - YYC
Nonstop3h 49mWestJet
Deal found 8/18$180
This United Airlines deal was found by Cheapflights users on 8/20. 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.
Tue 10/2812:37 pmYYC - ORD
Nonstop3h 33mUnited Airlines
Fri 10/311:55 pmORD - YYC
1 stop8h 58mUnited Airlines
Deal found 8/20$185
This Trip.com deal was found by Cheapflights users on 8/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/111:40 pmYYC - ORD
1 stop16h 48mMultiple Airlines
Fri 12/52:20 pmORD - YYC
Nonstop3h 55mMultiple Airlines
Deal found 8/20$188
This Delta deal was found by Cheapflights users on 8/20. 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.
Tue 10/287:45 amYYC - MDW
2 stops8h 58mDelta
Fri 10/319:20 amMDW - YYC
1 stop5h 34mDelta
Deal found 8/20$223
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Wed 10/112:30 amYYC - MDW
1 stop14h 28mMultiple Airlines
Wed 10/88:05 amMDW - YYC
1 stop12h 55mMultiple Airlines
Deal found 8/18$269

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 August 20, 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

Fri 10/17

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-8:19 pm

Nonstop3h 49m

$156

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 11/21

9:00 am-1:35 pm

Nonstop3h 35m

Chicago O'Hare Intl

Mon 11/24

2:20 pm-5:15 pm

Nonstop3h 55m

$156

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 10/16

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-8:19 pm

Nonstop3h 49m

$165

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 9/15

1:10 am-9:51 am

1 stop7h 41m

Chicago O'Hare Intl

Tue 9/23

3:50 pm-11:22 pm

1 stop8h 32m

$174

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 10/1

1:10 am-9:51 am

1 stop7h 41m

Chicago O'Hare Intl

Fri 10/10

5:30 pm-8:19 pm

Nonstop3h 49m

$175

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 10/18

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-8:19 pm

Nonstop3h 49m

$176

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 10/1

1:10 am-9:51 am

1 stop7h 41m

Chicago O'Hare Intl

Thu 10/9

5:30 pm-8:19 pm

Nonstop3h 49m

$177

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 10/3

1:10 am-9:51 am

1 stop7h 41m

Chicago O'Hare Intl

Sat 10/11

3:35 pm-11:16 pm

1 stop8h 41m

$178

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 10/16

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

Thu 10/23

5:30 pm-8:19 pm

Nonstop3h 49m

$180

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 10/28

12:37 pm-5:10 pm

Nonstop3h 33m

Chicago O'Hare Intl

Fri 10/31

8:45 am-11:35 am

Nonstop3h 50m

$185

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 40 results
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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

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 August 8, 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, August is the cheapest month in which you can book a flight from Calgary to Chicago (average of $245). Flying from Calgary to Chicago in March is currently the most expensive (average of $321). 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 August 20, 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 August 20, 2025.

The most flights from YYC to CHI are scheduled on a Tuesday (15 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (10 on average).

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

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 August 20, 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
8.0
Very good
7,982 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
United Airlines
7.4
Good
8,928 reviews
Delta
8.0
Very good
7,982 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,982 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
WestJet
7.2
Good
3,032 reviews
Delta
8.0
Very good
7,982 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Air Canada
7.1
Good
10,000 reviews
Delta
8.0
Very good
7,982 reviews

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

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 13 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 3h 28m. Fly via WestJet, Air Canada, or Delta to get the fastest option. The distance between Calgary and Chicago is about 1381 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 United Airlines, starting at $137 and $239 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: Avianca (80%), Air Canada (72%), United Airlines( 72%).

  • What are the cheapest flights from Calgary to Chicago?

    Looking for the cheapest flight from Calgary to Chicago? While on average our users pay $309, our data indicates the cheapest price to be $115. The most popular route (Calgary - Chicago O'Hare Intl), is priced around $171.

  • 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, August is the cheapest month in which you can book a flight from Calgary to Chicago (average of $245). Flying from Calgary to Chicago in March is currently the most expensive (average of $321). 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
Benton Harbor
Porter
Chesterton

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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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$109Average$468FlexibilityNo cancel feeOn-time67%
WestJetCheapest$137Average$222FlexibilityNo cancel feeOn-time60%
United AirlinesCheapest$239Average$468FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$250Average$376FlexibilityNo cancel feeOn-time71%

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