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Cheap flights from Calgary to Chicago from C$ 132

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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
30 Mar — 6 Apr1
1 adult

Cheapflights Tip: The best prices from Calgary to Chicago are usually found in February or May, booked 66 days in advance, depart on a Thursday or Friday and return on a Wednesday

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 25 March 2025.

Round-trip from

C$ 225

One-way from

C$ 132

Popular in

December

Cheapest in

February

Average price

C$ 382

Good round-trip deal

C$ 452 or less

Good one-way deal

C$ 272 or less
WestJet
  • WestJet
  • 11/5-13/5
  • Nonstop
  • 7h 18m total
  • Calgary to Chicago
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WestJet
  • WestJet
  • 2/6
  • Nonstop
  • 3h 29m total
  • Calgary to Chicago
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Highest demand for flights based on searches. 16% potential increase in price (C$ 122 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease (C$ 30 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from Calgary to Chicago (CHI).
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Price to beat on a one-way flight from Calgary to Chicago (CHI).
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Find flight deals from Calgary to Chicago

Cheapest flights from Calgary to Chicago
Explore the most affordable flight options available from Calgary to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 25 March 2025.

Sun 11/512:15 p.m.YYC - ORD
Nonstop3h 29mWestJet
Tue 13/55:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Deal found 24/3C$ 225
Fri 23/512:38 p.m.YYC - ORD
Nonstop3h 32mUnited Airlines
Mon 26/55:02 a.m.ORD - YYC
1 stop14h 19mUnited Airlines
Deal found 23/3C$ 305
Fri 2/512:25 a.m.YYC - ORD
1 stop9h 29mAir Canada
Fri 9/54:00 p.m.ORD - YYC
1 stop8h 43mAir Canada
Deal found 24/3C$ 307
Tue 15/48:00 a.m.YYC - ORD
2 stops12h 31mDelta
Tue 22/412:15 p.m.ORD - YYC
2 stops11h 50mDelta
Deal found 24/3C$ 312
Fri 6/66:29 a.m.YYC - ORD
Nonstop3h 25mAmerican Airlines
Tue 10/68:25 p.m.ORD - YYC
Nonstop4h 00mAmerican Airlines
Deal found 24/3C$ 315
Fri 23/58:30 a.m.YYC - ORD
Nonstop3h 33mMultiple Airlines
Mon 26/57:58 p.m.ORD - YYC
1 stop12h 27mMultiple Airlines
Deal found 23/3C$ 318
Tue 15/46:45 a.m.YYC - MDW
1 stop9h 34mDelta
Tue 22/49:20 a.m.MDW - YYC
2 stops12h 27mDelta
Deal found 24/3C$ 335
Fri 2/512:30 a.m.YYC - MDW
1 stop8h 03mMultiple Airlines
Fri 9/58:30 a.m.MDW - YYC
2 stops12h 10mMultiple Airlines
Deal found 24/3C$ 569
Thu 14/86:00 a.m.YYC - ORD
2 stops16h 39mAlaska Airlines
Mon 18/88:42 p.m.ORD - YYC
1 stop14h 47mAlaska Airlines
Deal found 24/3C$ 653
Sun 11/57:00 a.m.YYC - MDW
2 stops32h 54mPorter Airlines
Tue 13/59:40 a.m.MDW - YYC
2 stops12h 30mPorter Airlines
Deal found 24/3C$ 752
Tue 15/46:45 a.m.YYC - MDW
1 stop9h 34mWestJet
Tue 22/41:16 p.m.MDW - YYC
1 stop8h 31mWestJet
Deal found 24/3C$ 844

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 629,999 searches. Data last updated 25 March 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

Sun 11/5

12:15 p.m.-4:44 p.m.

Nonstop3h 29m

Chicago O'Hare Intl

Tue 13/5

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

C$ 225

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 23/5

12:38 p.m.-5:10 p.m.

Nonstop3h 32m

Chicago O'Hare Intl

Mon 26/5

5:02 a.m.-6:21 p.m.

1 stop14h 19m

C$ 305

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 2/5

12:25 a.m.-10:54 a.m.

1 stop9h 29m

Chicago O'Hare Intl

Fri 9/5

4:00 p.m.-11:43 p.m.

1 stop8h 43m

C$ 307

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 15/4

8:00 a.m.-9:31 p.m.

2 stops12h 31m

Chicago O'Hare Intl

Tue 22/4

12:15 p.m.-11:05 p.m.

2 stops11h 50m

C$ 312

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 6/6

6:29 a.m.-10:54 a.m.

Nonstop3h 25m

Chicago O'Hare Intl

Tue 10/6

8:25 p.m.-11:25 p.m.

Nonstop4h 00m

C$ 315

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 23/5

8:30 a.m.-1:03 p.m.

Nonstop3h 33m

Chicago O'Hare Intl

Mon 26/5

7:58 p.m.-7:25 a.m.

1 stop12h 27m

C$ 318

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 15/4

6:45 a.m.-5:19 p.m.

1 stop9h 34m

Chicago Midway

Tue 22/4

9:20 a.m.-8:47 p.m.

2 stops12h 27m

C$ 335

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 2/5

12:30 a.m.-9:33 a.m.

1 stop8h 03m

Chicago Midway

Fri 9/5

8:30 a.m.-7:40 p.m.

2 stops12h 10m

C$ 569

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 14/8

6:00 a.m.-11:39 p.m.

2 stops16h 39m

Chicago O'Hare Intl

Mon 18/8

8:42 p.m.-10:29 a.m.

1 stop14h 47m

C$ 653

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 11/5

7:00 a.m.-4:54 p.m.

2 stops32h 54m

Chicago Midway

Tue 13/5

9:40 a.m.-9:10 p.m.

2 stops12h 30m

C$ 752

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/3

Showing 1-10 of 22 results
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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 21 March 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, January is the cheapest month in which you can book a flight from Calgary to Chicago (average of C$ 261). Flying from Calgary to Chicago in March is currently the most expensive (average of C$ 355). 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 25 March 2025.

One of the essential ways to save on airfare from Calgary to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 76% on airfare.

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 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

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 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 25 March 2025.
See what other customers who have flown with Alaska Airlines, Delta and Porter Airlines from Calgary to Chicago have to say. 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
9,785 reviews
Check prices

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

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
9,785 reviews
Alaska Airlines
8.0
Very good
9,785 reviews
Check prices

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

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
7,890 reviews
Alaska Airlines
8.0
Very good
9,785 reviews
Check prices

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

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
9,785 reviews
Check prices

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

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
8,605 reviews
Alaska Airlines
8.0
Very good
9,785 reviews
Check prices

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

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
9,785 reviews
Check prices

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

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?

    For a flight from Calgary to Chicago, you will be flying from Calgary. Calgary (YYC) is just 9.3 km from the centre of the city. Calgary is the only Calgary airport and it handles 4 outbound flights to Chicago per day. 6 airlines have flights to Chicago from Calgary on a regular basis.

  • What are the cheapest airlines flying from Calgary to Chicago round-trip?

    According to our current data, WestJet (C$ 225), United Airlines (C$ 305), and Air Canada (C$ 307) offers the cheapest pricing from Calgary to Chicago. Users have found that WestJet is 48% cheaper than the other options available to this destination.

  • 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 C$ 132. American Airlines flights start at C$ 155 while deals on Air Canada start at C$ 162 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 (89%), Emirates (89%), United Airlines( 89%).

  • What are the cheapest flights from Calgary to Chicago?

    The cheapest flight price from Calgary to Chicago is C$ 203. On average you can expect to pay C$ 2,218. The most popular route, (Calgary - Chicago O'Hare Intl), can usually be booked for C$ 288.

  • 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, January is the cheapest month in which you can book a flight from Calgary to Chicago (average of C$ 261). Flying from Calgary to Chicago in March is currently the most expensive (average of C$ 355). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 6 airlines flying from Calgary to Chicago

Discover the top 6 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 629,999 searches. Data last updated 25 March 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 186AverageC$ 341FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 190AverageC$ 480FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 203AverageC$ 436FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
DeltaCheapestC$ 207AverageC$ 409FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 330AverageC$ 627FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJet EncoreCheapestC$ 577AverageC$ 1,019FlexibilityNo cancel feeOn-timeN/A
Search WestJet Encore flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Calgary to Chicago?

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Why should you use Cheapflights to find cheap flight tickets from Calgary to Chicago?

Cheapflights helps you find that perfect flight to Chicago from Calgary by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Calgary to Chicago with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Calgary to Chicago, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Calgary to Chicago become cheaper?

Of course! You can now track prices for flights from Calgary to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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