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$98+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
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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The best prices from Calgary to Chicago are usually found in February or January, 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 febrero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$166
(Kiwi.com)

One-way from

$103
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$200

Good round-trip deal

$149 or less

Good one-way deal

$189 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. 9% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals
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 febrero 20, 2025.

This Trip.com deal was found by Cheapflights users on 2/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/2711:30 amYYC - ORD
Nonstop3h 26mWestJet
dom. 3/24:45 pmORD - YYC
Nonstop3h 51mWestJet
Deal found 2/19$159
This Air Canada deal was found by Cheapflights users on 2/19. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/78:30 amYYC - ORD
1 stop9h 24mAir Canada
jue. 4/1010:53 amORD - YYC
1 stop10h 30mAir Canada
Deal found 2/19$175
This United Airlines deal was found by Cheapflights users on 2/20. 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.
jue. 3/202:01 pmYYC - ORD
1 stop7h 44mUnited Airlines
jue. 3/275:00 amORD - YYC
1 stop10h 21mUnited Airlines
Deal found 2/20$189
This flygcity.se deal was found by Cheapflights users on 2/19. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/211:30 amYYC - ORD
Nonstop3h 26mMultiple Airlines
dom. 3/95:00 amORD - YYC
1 stop10h 21mMultiple Airlines
Deal found 2/19$210
This Delta deal was found by Cheapflights users on 2/20. 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.
mar. 5/137:15 amYYC - ORD
1 stop9h 46mDelta
sáb. 5/179:30 amORD - YYC
2 stops14h 37mDelta
Deal found 2/20$220
This Delta deal was found by Cheapflights users on 2/20. 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.
lun. 3/36:35 amYYC - MDW
1 stop10h 08mDelta
mié. 3/51:26 pmMDW - YYC
1 stop8h 27mDelta
Deal found 2/20$220
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 3/153:45 pmYYC - MDW
1 stop12h 45mMultiple Airlines
mié. 3/199:25 amMDW - YYC
1 stop8h 37mMultiple Airlines
Deal found 2/19$291
This American Airlines deal was found by Cheapflights users on 2/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/201:32 pmYYC - ORD
Nonstop3h 31mAmerican Airlines
dom. 2/236:48 pmORD - YYC
1 stop18h 02mAmerican Airlines
Deal found 2/19$320
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/134:30 pmYYC - MDW
1 stop22h 54mPorter Airlines
jue. 5/159:15 amMDW - YYC
2 stops14h 15mPorter Airlines
Deal found 2/19$481
This CheapTicketsDeal deal was found by Cheapflights users on 2/19. 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 CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/1310:30 amYYC - MDW
1 stop6h 33mWestJet
lun. 8/189:20 amMDW - YYC
1 stop8h 28mWestJet
Deal found 2/19$501

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 febrero 20, 2025.

Fly from

Calgary

Fly to

Chicago

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

lun. 4/14

11:30 am-3:56 pm

Nonstop3h 26m

Chicago O'Hare Intl

dom. 4/20

4:45 pm-7:36 pm

Nonstop3h 51m

$159

CalgaryChicago

YYC - ORD

YYCORD

Calgary

lun. 4/7

8:30 am-6:54 pm

1 stop9h 24m

Chicago O'Hare Intl

jue. 4/10

10:53 am-8:23 pm

1 stop10h 30m

$175

CalgaryChicago

YYC - ORD

YYCORD

Calgary

jue. 3/20

2:01 pm-10:45 pm

1 stop7h 44m

Chicago O'Hare Intl

jue. 3/27

5:00 am-2:21 pm

1 stop10h 21m

$189

CalgaryChicago

YYC - ORD

YYCORD

Calgary

dom. 3/2

11:30 am-3:56 pm

Nonstop3h 26m

Chicago O'Hare Intl

dom. 3/9

5:00 am-2:21 pm

1 stop10h 21m

$210

CalgaryChicago

YYC - ORD

YYCORD

Calgary

mar. 5/13

7:15 am-6:01 pm

1 stop9h 46m

Chicago O'Hare Intl

sáb. 5/17

9:30 am-11:07 pm

2 stops14h 37m

$220

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

lun. 3/3

6:35 am-5:43 pm

1 stop10h 08m

Chicago Midway

mié. 3/5

1:26 pm-8:53 pm

1 stop8h 27m

$220

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

sáb. 3/15

3:45 pm-5:30 am

1 stop12h 45m

Chicago Midway

mié. 3/19

9:25 am-5:02 pm

1 stop8h 37m

$291

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

mar. 5/13

4:30 pm-4:24 pm

1 stop22h 54m

Chicago Midway

jue. 5/15

9:15 am-10:30 pm

2 stops14h 15m

$481

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

mié. 8/13

10:30 am-6:03 pm

1 stop6h 33m

Chicago Midway

lun. 8/18

9:20 am-4:48 pm

1 stop8h 28m

$501

CalgaryChicago

YYC - ORD

YYCORD

Calgary

jue. 5/1

12:15 pm-4:44 pm

Nonstop3h 29m

$98

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 19 results
1
2

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 February.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 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.

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 February 14, 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 febrero 20, 2025.

Unlike in the morning, 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 febrero 20, 2025.

The most flights from YYC to CHI are scheduled on a Thursday (8 on average). You will have fewer flight options on Saturday, 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 febrero 20, 2025.
Read reviews from past customers who have flown Alaska Airlines, Delta and Porter Airlines 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
9,692 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

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
9,692 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

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
8,220 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

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
7.9
Good
276 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

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
8,766 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

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

American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Boarding

8.2

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 5 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 $166 on this airline. Additional options worth looking into are Air Canada and United Airlines, starting at $177 and $189 round-trip. WestJet is currently priced 50% 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 $103. Air Canada flights start at $110 while deals on United Airlines start at $121 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 (90%), Emirates (90%), United Airlines( 90%).

  • What are the cheapest flights from Calgary to Chicago?

    Looking for the cheapest flight from Calgary to Chicago? While on average our users pay $381, our data indicates the cheapest price to be $94. The most popular route (Calgary - Chicago O'Hare Intl), is priced around $183.

  • 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Top 5 airlines flying from Calgary to Chicago

Discover the top 5 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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$143Average$248FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$154Average$451FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$219Average$443FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$239Average$530FlexibilityNo cancel feeOn-time69%
DeltaCheapest$268Average$327FlexibilityNo cancel feeOn-timeN/A
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