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$112+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 Friday

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 June 12, 2025.

Round-trip from

$150
(Kiwi.com)

One-way from

$112
(Air Canada)

Popular in

December

Cheapest in

April

Average price

$244

Good round-trip deal

$183 or less

Good one-way deal

$177 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. 22% potential increase in price ($82 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Thu 7/3112:15 pmYYC - ORD
Nonstop3h 29mWestJet
Mon 8/45:30 pmORD - YYC
Nonstop3h 49mWestJet
Deal found 6/11$150
This American Airlines deal was found by Cheapflights users on 6/12. 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 6/136:29 amYYC - ORD
Nonstop3h 25mAmerican Airlines
Tue 6/171:28 pmORD - YYC
1 stop9h 29mAmerican Airlines
Deal found 6/12$174
This United Airlines deal was found by Cheapflights users on 6/11. 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 6/1712:38 pmYYC - ORD
Nonstop3h 32mUnited Airlines
Tue 6/245:02 amORD - YYC
1 stop14h 19mUnited Airlines
Deal found 6/11$191
This Air Canada deal was found by Cheapflights users on 6/11. 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 9/61:10 amYYC - ORD
1 stop7h 41mAir Canada
Wed 9/176:20 pmORD - YYC
1 stop7h 52mAir Canada
Deal found 6/11$201
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 7/148:00 amYYC - ORD
2 stops12h 30mMultiple Airlines
Wed 7/235:30 pmORD - YYC
Nonstop3h 49mMultiple Airlines
Deal found 6/12$210
This Delta deal was found by Cheapflights users on 6/11. 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 9/136:35 amYYC - ORD
2 stops14h 11mDelta
Fri 9/191:55 pmORD - YYC
1 stop10h 17mDelta
Deal found 6/11$225
This Delta deal was found by Cheapflights users on 6/11. 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 6/176:45 amYYC - MDW
1 stop9h 55mDelta
Tue 6/241:47 pmMDW - YYC
1 stop8h 10mDelta
Deal found 6/11$240
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 7/2512:30 amYYC - MDW
1 stop21h 05mMultiple Airlines
Sat 8/26:20 amMDW - YYC
2 stops19h 24mMultiple Airlines
Deal found 6/11$348
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Mon 7/217:00 amYYC - MDW
2 stops32h 24mPorter Airlines
Tue 8/55:20 pmMDW - YYC
2 stops29h 00mPorter Airlines
Deal found 6/11$460
This Jettzy deal was found by Cheapflights users on 6/11. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/2512:30 amYYC - MDW
1 stop20h 12mWestJet
Sat 8/212:43 pmMDW - YYC
1 stop10h 32mWestJet
Deal found 6/11$645

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 June 12, 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 7/31

12:15 pm-4:44 pm

Nonstop3h 29m

Chicago O'Hare Intl

Mon 8/4

5:30 pm-8:19 pm

Nonstop3h 49m

$150

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 9/13

6:45 am-9:24 pm

1 stop13h 39m

Chicago O'Hare Intl

Sat 9/20

8:30 pm-11:19 pm

Nonstop3h 49m

$200

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 9/6

1:10 am-9:51 am

1 stop7h 41m

Chicago O'Hare Intl

Wed 9/17

6:20 pm-1:12 am

1 stop7h 52m

$201

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 7/14

8:00 am-9:30 pm

2 stops12h 30m

Chicago O'Hare Intl

Wed 7/23

5:30 pm-8:19 pm

Nonstop3h 49m

$210

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 9/13

6:35 am-9:46 pm

2 stops14h 11m

Chicago O'Hare Intl

Fri 9/19

1:55 pm-11:12 pm

1 stop10h 17m

$225

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 9/9

6:40 am-5:37 pm

1 stop9h 57m

Chicago Midway

Wed 9/17

1:00 pm-8:54 pm

2 stops8h 54m

$240

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 7/25

12:30 am-10:35 pm

1 stop21h 05m

Chicago Midway

Sat 8/2

6:20 am-12:44 am

2 stops19h 24m

$348

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 7/21

7:00 am-4:24 pm

2 stops32h 24m

Chicago Midway

Tue 8/5

5:20 pm-9:20 pm

2 stops29h 00m

$460

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 7/25

12:30 am-9:42 pm

1 stop20h 12m

Chicago Midway

Sat 8/2

12:43 pm-10:15 pm

1 stop10h 32m

$645

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 8/18

1:05 am-9:52 am

1 stop7h 47m

$112

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 20 results
1
2

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 June 9, 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 June 12, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 51% 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 June 12, 2025.

The most flights from YYC to CHI are scheduled on a Monday (14 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 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 June 12, 2025.
Read reviews from past customers who have flown Alaska Airlines, Porter Airlines and Delta 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
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Porter Airlines
8.0
Very good
288 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Crew

8.5

Entertainment

7.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 11 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 WestJet. Our recent data shows that you can find tickets from as low as $150 on this airline. Additional options worth looking into are American Airlines and Air Canada, starting at $200 and $201 round-trip. WestJet is currently priced 47% 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 Air Canada, which is currently one of the cheapest options available, starting at $112. United Airlines flights start at $117 while deals on American Airlines start at $128 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: Avianca (91%), Air Canada (84%), United Airlines( 84%).

  • What are the cheapest flights from Calgary to Chicago?

    Looking for the cheapest flight from Calgary to Chicago? While on average our users pay $527, our data indicates the cheapest price to be $109. The most popular route (Calgary - Chicago O'Hare Intl), is priced around $191.

  • 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 Calgary?

Book flights to Calgary if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$109Average$388FlexibilityNo cancel feeOn-time67%
WestJetCheapest$139Average$195FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$205Average$356FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$239Average$473FlexibilityNo cancel feeOn-time69%

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