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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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
May 5 — May 121
Mon 5/5
Mon 5/12
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”

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Cheapflights Tip: The best prices from Calgary to Chicago are usually found in May 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 April 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$186
(United Airlines)

One-way from

$113
(Air Canada)

Popular in

December

Cheapest in

May

Average price

$205

Good round-trip deal

$162 or less

Good one-way deal

$228 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. 19% potential increase in price ($73 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 April 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

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 April 30, 2025.

This United Airlines deal was found by Cheapflights users on 4/28. 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.
Fri 5/238:30 amYYC - ORD
Nonstop3h 33mUnited Airlines
Tue 5/277:10 amORD - YYC
1 stop15h 38mUnited Airlines
Deal found 4/28$186
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Tue 6/1012:15 pmYYC - ORD
Nonstop3h 29mWestJet
Tue 6/245:30 pmORD - YYC
Nonstop3h 49mWestJet
Deal found 4/28$191
This Air Canada deal was found by Cheapflights users on 4/28. 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 5/238:10 amYYC - ORD
1 stop7h 41mAir Canada
Tue 5/274:43 pmORD - YYC
1 stop9h 20mAir Canada
Deal found 4/28$192
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Wed 8/136:29 amYYC - ORD
Nonstop3h 25mAmerican Airlines
Mon 8/188:34 pmORD - YYC
Nonstop3h 55mAmerican Airlines
Deal found 4/28$218
This United deal was found by Cheapflights users on 4/28. 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.
Mon 5/121:30 pmYYC - ORD
1 stop6h 47mMultiple Airlines
Tue 5/132:22 pmORD - YYC
1 stop9h 16mMultiple Airlines
Deal found 4/28$222
This Delta deal was found by Cheapflights users on 4/28. 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.
Wed 5/286:30 amYYC - ORD
1 stop6h 58mDelta
Thu 5/293:33 pmORD - YYC
2 stops8h 28mDelta
Deal found 4/28$223
This Delta deal was found by Cheapflights users on 4/28. 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 5/266:30 amYYC - MDW
1 stop5h 45mDelta
Mon 6/29:20 amMDW - YYC
2 stops14h 41mDelta
Deal found 4/28$223
This Vliegwinkel deal was found by Cheapflights users on 4/29. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/298:30 amYYC - ORD
Nonstop3h 33mSWISS
Fri 6/67:58 pmORD - YYC
1 stop12h 27mSWISS
Deal found 4/29$230
This Kissandfly.com deal was found by Cheapflights users on 4/28. 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.
Thu 5/86:30 amYYC - ORD
1 stop6h 58mKLM
Sun 5/111:40 pmORD - YYC
1 stop10h 21mKLM
Deal found 4/28$272
This Kissandfly.com deal was found by Cheapflights users on 4/28. 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.
Wed 5/76:30 amYYC - MDW
1 stop5h 45mKLM
Sat 5/101:55 pmMDW - YYC
1 stop7h 45mKLM
Deal found 4/28$291
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 6/137:00 amYYC - MDW
2 stops15h 18mMultiple Airlines
Mon 6/166:20 amMDW - YYC
1 stop14h 45mMultiple Airlines
Deal found 4/28$346
This Mytrip deal was found by Cheapflights users on 4/28. 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.
Tue 5/277:55 amYYC - MDW
2 stops23h 50mPorter Airlines
Tue 6/39:40 amMDW - YYC
2 stops12h 44mPorter Airlines
Deal found 4/28$455

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 April 30, 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 5/23

8:30 am-1:03 pm

Nonstop3h 33m

Chicago O'Hare Intl

Tue 5/27

7:10 am-9:48 pm

1 stop15h 38m

$186

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 6/10

12:15 pm-4:44 pm

Nonstop3h 29m

Chicago O'Hare Intl

Tue 6/24

5:30 pm-8:19 pm

Nonstop3h 49m

$191

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 5/23

8:10 am-4:51 pm

1 stop7h 41m

Chicago O'Hare Intl

Tue 5/27

4:43 pm-1:03 am

1 stop9h 20m

$192

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 8/13

6:29 am-10:54 am

Nonstop3h 25m

Chicago O'Hare Intl

Mon 8/18

8:34 pm-11:29 pm

Nonstop3h 55m

$218

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 5/12

1:30 pm-9:17 pm

1 stop6h 47m

Chicago O'Hare Intl

Tue 5/13

2:22 pm-10:38 pm

1 stop9h 16m

$222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 5/28

2:00 pm-9:40 pm

1 stop6h 40m

Chicago O'Hare Intl

Mon 6/2

11:03 am-11:01 pm

2 stops12h 58m

$223

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 5/26

6:30 am-1:15 pm

1 stop5h 45m

Chicago Midway

Mon 6/2

9:20 am-11:01 pm

2 stops14h 41m

$223

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 5/29

8:30 am-1:03 pm

Nonstop3h 33m

Chicago O'Hare Intl

Fri 6/6

7:58 pm-7:25 am

1 stop12h 27m

$230

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 6/13

7:00 am-11:18 pm

2 stops15h 18m

Chicago Midway

Mon 6/16

6:20 am-8:05 pm

1 stop14h 45m

$346

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 5/27

7:55 am-8:45 am

2 stops23h 50m

Chicago Midway

Tue 6/3

9:40 am-9:24 pm

2 stops12h 44m

$455

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

Showing 1-10 of 23 results
1
2
3

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 April.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*2 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
SmartFaresPrice Accuracy1 starTrust Score*1 star

*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 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.

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

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

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 April 25, 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 April 30, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 46% 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 April 30, 2025.

The most flights from YYC to CHI are scheduled on a Tuesday (6 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (3 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 April 30, 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
9,961 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

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
9,961 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

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
285 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

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
7,936 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
SWISS
7.5
Good
1,588 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

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
8,696 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

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 4 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 United Airlines. Our recent data shows that you can find tickets from as low as $186 on this airline. Additional options worth looking into are WestJet and Air Canada, starting at $191 and $192 round-trip. United Airlines is currently priced 36% 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 $113. American Airlines flights start at $116 while deals on United Airlines start at $117 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 (84%), Emirates (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 $495, our data indicates the cheapest price to be $100. 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, 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
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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$123Average$468FlexibilityNo cancel feeOn-time67%
WestJetCheapest$139Average$189FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$205Average$354FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$239Average$479FlexibilityNo cancel feeOn-time69%

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