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$93+ 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Find cheap flights from Calgary to Chicago with Cheapflights

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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Cheapflights Tip: The best prices from Calgary to Chicago are usually found in April or February, booked 47 days in advance, depart on a Sunday or Wednesday and return on a Thursday

Cheap 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 December 23, 2025.

This American Airlines deal was found by Cheapflights users on 12/22. 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.
Mon 12/297:00 amYYC - ORD
1 stop9h 40mAmerican Airlines
Mon 1/58:25 amORD - YYC
1 stop14h 21mAmerican Airlines
Deal found 12/22$505
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/299:00 amYYC - ORD
Nonstop3h 35mWestJet
Mon 1/52:20 pmORD - YYC
Nonstop3h 55mWestJet
Deal found 12/22$513
This American Airlines deal was found by Cheapflights users on 12/22. 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.
Fri 12/266:30 amYYC - ORD
1 stop14h 50mAmerican Airlines
Fri 1/28:58 pmORD - YYC
1 stop15h 41mAmerican Airlines
Deal found 12/22$554
This CheapOair deal was found by Cheapflights users on 12/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/297:20 pmYYC - ORD
1 stop10h 55mMultiple Airlines
Mon 1/52:20 pmORD - YYC
Nonstop3h 55mMultiple Airlines
Deal found 12/22$562
This Air Canada deal was found by Cheapflights users on 12/21. 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.
Thu 12/2512:37 pmYYC - ORD
Nonstop3h 31mAir Canada
Fri 12/268:30 pmORD - YYC
1 stop13h 13mAir Canada
Deal found 12/21$620
This Air Canada deal was found by Cheapflights users on 12/22. 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 12/275:35 amYYC - ORD
1 stop8h 38mAir Canada
Sat 1/311:15 amORD - YYC
1 stop10h 44mAir Canada
Deal found 12/22$651
This Air Canada deal was found by Cheapflights users on 12/21. 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.
Mon 12/2212:37 pmYYC - ORD
Nonstop3h 31mAir Canada
Wed 12/312:00 pmORD - YYC
1 stop7h 39mAir Canada
Deal found 12/21$672
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/222:45 pmYYC - ORD
1 stop5h 49mDelta
Wed 12/3112:30 pmORD - YYC
2 stops11h 45mDelta
Deal found 12/21$677
This FlightHub deal was found by Cheapflights users on 12/23. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:30 amYYC - MDW
1 stop9h 49mWestJet
Wed 12/319:50 amMDW - YYC
2 stops31h 25mWestJet
Deal found 12/23$818
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/261:05 amYYC - MDW
2 stops33h 01mMultiple Airlines
Sat 1/36:12 amMDW - YYC
1 stop30h 32mMultiple Airlines
Deal found 12/22$930
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Thu 12/256:30 amYYC - MDW
1 stop9h 49mWestJet
Fri 12/2611:48 amMDW - YYC
2 stops11h 33mWestJet
Deal found 12/21$947
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Thu 12/257:00 amYYC - MDW
1 stop26h 05mMultiple Airlines
Fri 12/264:15 pmMDW - YYC
1 stop17h 50mMultiple Airlines
Deal found 12/21$1,234

Find 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 December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$168
(FlightHub)

One-way from

$93
(Kiwi.com)

Popular in

July

Cheapest in

April

Average price

$291

Good round-trip deal

$196 or less

Good one-way deal

$154 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. 14% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 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

Tue 2/3

6:15 am-11:59 pm

1 stop16h 44m

Chicago O'Hare Intl

Wed 2/4

8:45 am-11:35 am

Nonstop3h 50m

$190

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 2/2

7:00 am-5:44 pm

1 stop9h 44m

Chicago O'Hare Intl

Mon 2/9

2:20 pm-5:15 pm

Nonstop3h 55m

$224

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 2/2

6:30 am-3:19 pm

1 stop7h 49m

Chicago O'Hare Intl

Mon 2/9

1:50 pm-11:02 pm

1 stop10h 12m

$224

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 2/1

6:30 am-5:55 pm

1 stop10h 25m

Chicago O'Hare Intl

Fri 4/17

1:22 pm-11:00 pm

1 stop10h 38m

$232

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 1/19

9:45 pm-6:27 pm

2 stops19h 42m

Chicago O'Hare Intl

Mon 1/26

2:20 pm-5:15 pm

Nonstop3h 55m

$238

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 1/22

5:35 am-6:51 pm

2 stops12h 16m

Chicago O'Hare Intl

Wed 1/28

7:00 am-2:21 pm

1 stop8h 21m

$242

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 1/31

12:30 am-1:37 pm

1 stop12h 07m

Chicago O'Hare Intl

Fri 4/17

2:20 pm-5:15 pm

Nonstop3h 55m

$243

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 1/22

6:30 am-9:05 pm

2 stops13h 35m

Chicago O'Hare Intl

Wed 1/28

6:50 am-8:54 pm

2 stops15h 04m

$244

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 2/4

6:30 am-9:05 pm

2 stops13h 35m

Chicago O'Hare Intl

Wed 2/11

6:50 am-8:54 pm

2 stops15h 04m

$244

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 1/22

6:30 am-1:09 pm

1 stop5h 39m

Chicago Midway

Wed 1/28

9:33 am-8:54 pm

2 stops12h 21m

$244

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 31 results
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4

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 December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Calgary-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 December 19, 2025.

To ensure you get the cheapest price possible for a flight from Calgary to Chicago, you should look to book at least 47 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 $155). 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 December 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 December 23, 2025.

The most flights from YYC to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Wednesday, 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

AI-powered summary based on content written by travel experts. AI can make mistakes.
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 December 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
8,014 reviews

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,014 reviews
Delta
7.9
Good
8,014 reviews

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,106 reviews
Delta
7.9
Good
8,014 reviews

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,050 reviews
Delta
7.9
Good
8,014 reviews

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
WestJet
7.2
Good
3,216 reviews
Delta
7.9
Good
8,014 reviews

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Air Canada
7.1
Good
10,551 reviews
Delta
7.9
Good
8,014 reviews

Overall

7.9

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 6 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 7h 49m. Fly via United Airlines 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 $101 on this airline. Additional options worth looking into are WestJet and American Airlines, starting at $138 and $185 round-trip. Air Canada is currently priced 59% 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 $94. American Airlines flights start at $102 while deals on Air Canada start at $102 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: Delta (85%), WestJet (79%), Avianca( 74%).

  • What are the cheapest flights from Calgary to Chicago?

    Looking for the cheapest flight from Calgary to Chicago? While on average our users pay $295, our data indicates the cheapest price to be $93. The most popular route (Calgary - Chicago O'Hare Intl), is priced around $192.

  • 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 $155). 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
Lansing
Merrillville
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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$101Average$338FlexibilityNo cancel feeOn-time67%
WestJetCheapest$138Average$237FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$185Average$376FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$218Average$461FlexibilityNo cancel feeOn-time69%

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