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Cheap flights from Calgary to Chicago from C$ 125

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 16/3. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
22 Jan — 29 Jan1
1 adult

The best prices from Calgary to Chicago are usually found in January or February, booked 89 days in advance, depart on a Saturday or Friday and return on a Monday

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 17 January 2025.

Round-trip from

C$ 218

One-way from

C$ 125

Popular in

December

Cheapest in

January

Average price

C$ 333
WestJet
  • WestJet
  • 20/2-27/2
  • Nonstop
  • 7h 17m total
  • Calgary to Chicago
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WestJet
  • WestJet
  • 16/3
  • Nonstop
  • 3h 26m total
  • Calgary to Chicago
Search Deals
High demand for flights, 3% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in January 2025
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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 17 January 2025.

Thu 11/912:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Sun 14/95:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Deal found 14/1C$ 194
Thu 20/211:30 a.m.YYC - ORD
Nonstop3h 26mMultiple Airlines
Thu 27/25:10 a.m.ORD - YYC
2 stops19h 40mMultiple Airlines
Deal found 15/1C$ 287
Thu 20/28:30 a.m.YYC - ORD
1 stop9h 04mAir Canada
Tue 25/24:00 p.m.ORD - YYC
1 stop8h 17mAir Canada
Deal found 14/1C$ 292
Sat 8/26:35 a.m.YYC - ORD
1 stop7h 55mDelta
Wed 19/21:45 p.m.ORD - YYC
1 stop10h 30mDelta
Deal found 16/1C$ 312
Fri 21/26:35 a.m.YYC - MDW
1 stop10h 08mDelta
Tue 25/29:33 a.m.MDW - YYC
2 stops12h 20mDelta
Deal found 14/1C$ 325
Thu 20/26:35 a.m.YYC - MDW
1 stop10h 08mMultiple Airlines
Thu 27/25:10 a.m.MDW - YYC
2 stops17h 42mMultiple Airlines
Deal found 16/1C$ 451
Thu 16/112:41 p.m.YYC - ORD
Nonstop3h 34mUnited Airlines
Tue 21/18:50 a.m.ORD - YYC
Nonstop3h 49mUnited Airlines
Deal found 15/1C$ 466
Thu 16/16:29 a.m.YYC - ORD
1 stop6h 56mAmerican Airlines
Wed 22/110:00 a.m.ORD - YYC
1 stop12h 57mAmerican Airlines
Deal found 15/1C$ 507
Thu 10/47:44 a.m.YYC - MDW
1 stop9h 34mWestJet
Sat 12/411:22 a.m.MDW - YYC
2 stops9h 18mWestJet
Deal found 16/1C$ 719
Thu 10/47:40 a.m.YYC - MDW
2 stops25h 40mPorter Airlines
Sat 12/412:55 p.m.MDW - YYC
2 stops9h 36mPorter Airlines
Deal found 15/1C$ 753

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 629,999 searches. Data last updated 17 January 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 20/2

11:30 a.m.-3:56 p.m.

Nonstop3h 26m

Chicago O'Hare Intl

Thu 27/2

4:45 p.m.-7:36 p.m.

Nonstop3h 51m

C$ 218

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 20/2

11:30 a.m.-3:56 p.m.

Nonstop3h 26m

Chicago O'Hare Intl

Thu 27/2

5:10 a.m.-11:50 p.m.

2 stops19h 40m

C$ 287

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 20/2

8:30 a.m.-6:34 p.m.

1 stop9h 04m

Chicago O'Hare Intl

Tue 25/2

4:00 p.m.-11:17 p.m.

1 stop8h 17m

C$ 292

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 8/2

6:35 a.m.-3:30 p.m.

1 stop7h 55m

Chicago O'Hare Intl

Wed 19/2

1:45 p.m.-11:15 p.m.

1 stop10h 30m

C$ 312

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 21/2

6:35 a.m.-5:43 p.m.

1 stop10h 08m

Chicago Midway

Tue 25/2

9:33 a.m.-8:53 p.m.

2 stops12h 20m

C$ 325

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 20/2

6:35 a.m.-5:43 p.m.

1 stop10h 08m

Chicago Midway

Thu 27/2

5:10 a.m.-9:52 p.m.

2 stops17h 42m

C$ 451

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 7/3

7:20 p.m.-9:33 a.m.

1 stop13h 13m

Chicago O'Hare Intl

Tue 11/3

8:47 a.m.-11:41 a.m.

Nonstop3h 54m

C$ 526

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 21/2

1:32 p.m.-6:03 p.m.

Nonstop3h 31m

Chicago O'Hare Intl

Tue 25/2

5:00 a.m.-11:50 a.m.

1 stop7h 50m

C$ 540

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 10/4

7:44 a.m.-6:18 p.m.

1 stop9h 34m

Chicago Midway

Sat 12/4

11:22 a.m.-7:40 p.m.

2 stops9h 18m

C$ 719

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 10/4

7:40 a.m.-10:20 a.m.

2 stops25h 40m

Chicago Midway

Sat 12/4

12:55 p.m.-9:31 p.m.

2 stops9h 36m

C$ 753

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/1

Showing 1-10 of 20 results
1
2

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 10 January 2025.

To ensure you get the cheapest price possible for a flight from Calgary to Chicago, you should look to book at least 89 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 17 January 2025.

One of the essential ways to save on airfare from Calgary to Chicago is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 31% 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 17 January 2025.
See what other customers who have flown with WestJet, Delta and Air Canada 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.
Delta
8.0
Very good
8,511 reviews
Check prices

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,511 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Porter Airlines
7.9
Good
276 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines
7.4
Good
8,965 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

WestJet
7.2
Good
2,824 reviews
Delta
8.0
Very good
8,511 reviews
Check prices

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.9

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 2 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$ 218), Air Canada (C$ 302), and Delta (C$ 312) offers the cheapest pricing from Calgary to Chicago. Users have found that WestJet is 57% 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$ 125. Air Canada flights start at C$ 158 while deals on United Airlines start at C$ 171 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 (79%), Emirates (79%), United Airlines( 79%).

  • What are the cheapest flights from Calgary to Chicago?

    The cheapest flight price from Calgary to Chicago is C$ 155. On average you can expect to pay C$ 1,319. The most popular route, (Calgary - Chicago O'Hare Intl), can usually be booked for C$ 257.

  • 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

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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 17 January 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapestC$ 204AverageC$ 438FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 238AverageC$ 412FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 275AverageC$ 554FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 318AverageC$ 418FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 331AverageC$ 629FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJet EncoreCheapestC$ 579AverageC$ 1,023FlexibilityNo 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?

Cheapflights helps you search for flights from Calgary to Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

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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