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$109+ 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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
mar. 15 — mar. 221
sáb. 3/15
sáb. 3/22
1 adult, Economy
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1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
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3. Compare prices and book
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The best prices from Calgary to Chicago are usually found in February or May, booked 66 days in advance, depart on a Sunday or Friday 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 marzo 10, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$146
(Mytrip)

One-way from

$109
(Air Canada)

Popular in

December

Cheapest in

February

Average price

$236

Good round-trip deal

$150 or less

Good one-way deal

$187 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.
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From Calgary to Chicago (CHI)
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One-way flight from Calgary to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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).
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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 marzo 10, 2025.

This Mytrip deal was found by Cheapflights users on 3/9. 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.
dom. 4/2011:30 amYYC - ORD
Nonstop3h 26mWestJet
dom. 4/275:30 pmORD - YYC
Nonstop3h 49mWestJet
Deal found 3/9$146
This Air Canada deal was found by Cheapflights users on 3/9. 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.
lun. 3/3112:55 amYYC - ORD
1 stop8h 52mAir Canada
mar. 4/88:52 amORD - YYC
Nonstop3h 49mAir Canada
Deal found 3/9$167
This United Airlines deal was found by Cheapflights users on 3/9. 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.
vie. 5/238:30 amYYC - ORD
Nonstop3h 33mUnited Airlines
lun. 5/265:02 amORD - YYC
1 stop14h 19mUnited Airlines
Deal found 3/9$214
This Delta deal was found by Cheapflights users on 3/9. 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.
mar. 9/97:15 amYYC - ORD
2 stops11h 28mDelta
mié. 9/179:30 amORD - YYC
2 stops14h 33mDelta
Deal found 3/9$218
This American Airlines deal was found by Cheapflights users on 3/8. 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.
jue. 4/106:45 amYYC - ORD
1 stop16h 04mAmerican Airlines
sáb. 4/199:50 amORD - YYC
Nonstop3h 45mAmerican Airlines
Deal found 3/8$233
This United deal was found by Cheapflights users on 3/9. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/11:30 pmYYC - ORD
1 stop9h 59mMultiple Airlines
dom. 5/49:35 amORD - YYC
1 stop14h 33mMultiple Airlines
Deal found 3/9$236
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
mar. 4/16:55 pmYYC - MDW
1 stop9h 28mMultiple Airlines
mar. 4/88:50 pmMDW - YYC
1 stop16h 48mMultiple Airlines
Deal found 3/9$262
This Delta deal was found by Cheapflights users on 3/10. 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.
mar. 4/17:00 amYYC - MDW
2 stops10h 18mDelta
mar. 4/810:36 amMDW - YYC
2 stops13h 40mDelta
Deal found 3/10$264
This Kissandfly.com deal was found by Cheapflights users on 3/10. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/1912:30 amYYC - ORD
2 stops14h 40mKLM
dom. 4/275:30 pmORD - YYC
Nonstop3h 49mKLM
Deal found 3/10$279
This Mytrip deal was found by Cheapflights users on 3/9. 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.
dom. 4/207:40 amYYC - MDW
2 stops25h 40mPorter Airlines
dom. 4/275:35 pmMDW - YYC
2 stops28h 38mPorter Airlines
Deal found 3/9$426
This CheapTicketsDeal deal was found by Cheapflights users on 3/9. 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 CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/2310:30 amYYC - MDW
1 stop25h 45mWestJet
lun. 5/269:20 amMDW - YYC
1 stop8h 28mWestJet
Deal found 3/9$565

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 2,558,603 searches. Data last updated marzo 10, 2025.

Fly from

Calgary

Fly to

Chicago

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

dom. 4/20

11:30 am-3:56 pm

Nonstop3h 26m

Chicago O'Hare Intl

dom. 4/27

5:30 pm-8:19 pm

Nonstop3h 49m

$146

CalgaryChicago

YYC - ORD

YYCORD

Calgary

lun. 3/31

12:55 am-10:47 am

1 stop8h 52m

Chicago O'Hare Intl

mar. 4/8

8:52 am-11:41 am

Nonstop3h 49m

$167

CalgaryChicago

YYC - ORD

YYCORD

Calgary

lun. 4/7

8:30 am-6:54 pm

1 stop9h 24m

Chicago O'Hare Intl

dom. 4/13

4:45 pm-7:36 pm

Nonstop3h 51m

$180

CalgaryChicago

YYC - ORD

YYCORD

Calgary

vie. 5/23

8:30 am-1:03 pm

Nonstop3h 33m

Chicago O'Hare Intl

lun. 5/26

5:02 am-6:21 pm

1 stop14h 19m

$214

CalgaryChicago

YYC - ORD

YYCORD

Calgary

mar. 4/1

6:30 am-5:28 pm

1 stop9h 58m

Chicago O'Hare Intl

mar. 4/8

12:15 pm-11:16 pm

2 stops12h 01m

$218

CalgaryChicago

YYC - ORD

YYCORD

Calgary

jue. 4/10

6:45 am-11:49 pm

1 stop16h 04m

Chicago O'Hare Intl

sáb. 4/19

9:50 am-12:35 pm

Nonstop3h 45m

$233

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

mar. 4/1

6:55 pm-5:23 am

1 stop9h 28m

Chicago Midway

mar. 4/8

8:50 pm-12:38 pm

1 stop16h 48m

$262

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

mar. 4/1

7:00 am-6:18 pm

2 stops10h 18m

Chicago Midway

mar. 4/8

10:36 am-11:16 pm

2 stops13h 40m

$264

CalgaryChicago

YYC - ORD

YYCORD

Calgary

sáb. 4/19

12:30 am-4:10 pm

2 stops14h 40m

Chicago O'Hare Intl

dom. 4/27

5:30 pm-8:19 pm

Nonstop3h 49m

$279

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

dom. 4/20

7:40 am-10:20 am

2 stops25h 40m

Chicago Midway

dom. 4/27

5:35 pm-9:13 pm

2 stops28h 38m

$426

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/9

Showing 1-10 of 23 results
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2
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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 March.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*2 stars
SmartFaresPrice 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 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.

The best insider tips for Calgary to Chicago flights

Find out what our experts recommend to make the most of your Calgary to Chicago trip
Airports
YYC

For a quick check-in, use YYC's spacious area with natural light, ensuring a smooth start to your journey.

Read more about YYCby Jenna Scatena
ORD

Upon arrival at ORD, consider using the 'L' train for a quick trip 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

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.

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 March 7, 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 $327). 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 marzo 10, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 40% 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 marzo 10, 2025.

The most flights from YYC to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 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 marzo 10, 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
9,731 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.1

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines
8.0
Very good
9,731 reviews
Alaska Airlines
8.0
Very good
9,731 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.1

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Porter Airlines
8.0
Very good
280 reviews
Alaska Airlines
8.0
Very good
9,731 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.1

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta
8.0
Very good
7,973 reviews
Alaska Airlines
8.0
Very good
9,731 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.1

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

KLM
7.8
Good
1,320 reviews
Alaska Airlines
8.0
Very good
9,731 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.1

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

United Airlines
7.4
Good
8,631 reviews
Alaska Airlines
8.0
Very good
9,731 reviews

Boarding

8.2

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.1

Entertainment

7.1

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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.

  • 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 $146 on this airline. Additional options worth looking into are Air Canada and United Airlines, starting at $167 and $214 round-trip. WestJet is currently priced 52% 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 $109. WestJet flights start at $110 while deals on American Airlines start at $119 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%), Emirates (92%), United Airlines( 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 $648, our data indicates the cheapest price to be $103. The most popular route (Calgary - Chicago O'Hare Intl), is priced around $172.

  • 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 $327). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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 marzo 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$139Average$219FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$154Average$468FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$219Average$443FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$239Average$490FlexibilityNo cancel feeOn-time69%
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