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Cheap flights from Calgary to Chicago from C$ 140

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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
16 Apr — 23 Apr1
1 adult

Cheapflights Tip: The best prices from Calgary to Chicago are usually found in May or February, 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 11 April 2025.

Round-trip from

C$ 227

One-way from

C$ 140

Popular in

December

Cheapest in

May

Average price

C$ 279

Good round-trip deal

C$ 461 or less

Good one-way deal

C$ 267 or less
United Airlines
  • United Airlines
  • 9/5-11/5
  • 1 total stop
  • 13h 15m total
  • Calgary to Chicago
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Air Canada
  • Air Canada
  • 3/5
  • Nonstop
  • 3h 27m total
  • Calgary to Chicago
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Highest demand for flights based on searches. 18% potential increase in price (C$ 136 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 April 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 11 April 2025.

Fri 9/512:43 p.m.YYC - ORD
Nonstop3h 27mUnited Airlines
Sun 11/55:05 a.m.ORD - YYC
1 stop9h 48mUnited Airlines
Deal found 9/4C$ 227
Fri 9/512:15 p.m.YYC - ORD
Nonstop3h 29mWestJet
Mon 12/55:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Deal found 10/4C$ 243
Fri 9/512:43 p.m.YYC - ORD
Nonstop3h 27mAir Canada
Sun 11/55:05 a.m.ORD - YYC
1 stop9h 48mAir Canada
Deal found 10/4C$ 251
Fri 29/86:29 a.m.YYC - ORD
Nonstop3h 25mAmerican Airlines
Sun 31/88:25 p.m.ORD - YYC
Nonstop4h 04mAmerican Airlines
Deal found 10/4C$ 261
Wed 23/77:15 a.m.YYC - ORD
1 stop9h 50mDelta
Tue 29/712:17 p.m.ORD - YYC
2 stops11h 46mDelta
Deal found 10/4C$ 309
Fri 9/512:43 p.m.YYC - ORD
Nonstop3h 27mMultiple Airlines
Sun 11/55:30 p.m.ORD - YYC
Nonstop3h 49mMultiple Airlines
Deal found 10/4C$ 314
Mon 14/46:45 a.m.YYC - MDW
2 stops14h 37mDelta
Sun 20/49:20 a.m.MDW - YYC
2 stops12h 27mDelta
Deal found 10/4C$ 340
Tue 17/612:30 a.m.YYC - MDW
1 stop9h 11mMultiple Airlines
Mon 14/76:20 a.m.MDW - YYC
1 stop14h 40mMultiple Airlines
Deal found 9/4C$ 445
Fri 2/56:19 p.m.YYC - ORD
2 stops17h 48mAlaska Airlines
Fri 9/57:19 p.m.ORD - YYC
1 stop23h 10mAlaska Airlines
Deal found 10/4C$ 479
Fri 30/57:55 a.m.YYC - MDW
2 stops23h 50mPorter Airlines
Sun 1/69:40 a.m.MDW - YYC
2 stops12h 39mPorter Airlines
Deal found 10/4C$ 768
Fri 13/610:30 a.m.YYC - MDW
1 stop6h 10mWestJet
Tue 17/612:44 p.m.MDW - YYC
1 stop8h 21mWestJet
Deal found 10/4C$ 889

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 11 April 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 9/5

12:43 p.m.-5:10 p.m.

Nonstop3h 27m

Chicago O'Hare Intl

Sun 11/5

5:05 a.m.-1:53 p.m.

1 stop9h 48m

C$ 227

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 9/5

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

Nonstop3h 29m

Chicago O'Hare Intl

Mon 12/5

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

Nonstop3h 49m

C$ 243

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 9/5

12:43 p.m.-5:10 p.m.

Nonstop3h 27m

Chicago O'Hare Intl

Sun 11/5

5:05 a.m.-1:53 p.m.

1 stop9h 48m

C$ 251

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 29/8

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

Nonstop3h 25m

Chicago O'Hare Intl

Sun 31/8

8:25 p.m.-11:29 p.m.

Nonstop4h 04m

C$ 261

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 23/7

7:15 a.m.-6:05 p.m.

1 stop9h 50m

Chicago O'Hare Intl

Tue 29/7

12:17 p.m.-11:03 p.m.

2 stops11h 46m

C$ 309

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 9/5

12:43 p.m.-5:10 p.m.

Nonstop3h 27m

Chicago O'Hare Intl

Sun 11/5

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

Nonstop3h 49m

C$ 314

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 26/4

1:00 a.m.-12:35 p.m.

2 stops10h 35m

Chicago Midway

Tue 29/4

10:20 a.m.-6:40 p.m.

2 stops9h 20m

C$ 416

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 17/6

12:30 a.m.-10:41 a.m.

1 stop9h 11m

Chicago Midway

Mon 14/7

6:20 a.m.-8:00 p.m.

1 stop14h 40m

C$ 445

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 2/5

6:19 p.m.-1:07 p.m.

2 stops17h 48m

Chicago O'Hare Intl

Fri 9/5

7:19 p.m.-5:29 p.m.

1 stop23h 10m

C$ 479

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 30/5

7:55 a.m.-8:45 a.m.

2 stops23h 50m

Chicago Midway

Sun 1/6

9:40 a.m.-9:19 p.m.

2 stops12h 39m

C$ 768

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/4

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 4 April 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 11 April 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.

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 11 April 2025.

The most flights from YYC to CHI are scheduled on a Thursday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 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 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 11 April 2025.
See what other customers who have flown with Alaska Airlines, Porter Airlines and Delta 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
9,851 reviews
Check prices

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,851 reviews
Alaska Airlines
8.0
Very good
9,851 reviews
Check prices

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Porter Airlines
8.0
Very good
280 reviews
Alaska Airlines
8.0
Very good
9,851 reviews
Check prices

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,911 reviews
Alaska Airlines
8.0
Very good
9,851 reviews
Check prices

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,636 reviews
Alaska Airlines
8.0
Very good
9,851 reviews
Check prices

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,851 reviews
Check prices

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 5 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, United Airlines (C$ 227), WestJet (C$ 243), and Air Canada (C$ 251) offers the cheapest pricing from Calgary to Chicago. Users have found that United Airlines is 45% 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 Air Canada, which is currently one of the cheapest options available, starting at C$ 140. WestJet flights start at C$ 146 while deals on United Airlines start at C$ 161 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 (87%), Emirates (87%), United Airlines( 87%).

  • What are the cheapest flights from Calgary to Chicago?

    The cheapest flight price from Calgary to Chicago is C$ 197. On average you can expect to pay C$ 555. The most popular route, (Calgary - Chicago O'Hare Intl), can usually be booked for C$ 250.

  • 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 11 April 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 160AverageC$ 428FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 181AverageC$ 327FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 199AverageC$ 427FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
DeltaCheapestC$ 202AverageC$ 388FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 323AverageC$ 612FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJet EncoreCheapestC$ 566AverageC$ 999FlexibilityNo 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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