Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Calgary to Chicago from C$ 139

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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
25 Feb — 4 Mar1
1 adult

The best prices from Calgary to Chicago are usually found in February or January, booked 66 days in advance, depart on a Thursday 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 20 February 2025.

Round-trip from

C$ 226

One-way from

C$ 139

Popular in

December

Cheapest in

February

Average price

C$ 284

Good round-trip deal

C$ 402 or less

Good one-way deal

C$ 245 or less
WestJet
  • WestJet
  • 14/4-20/4
  • Nonstop
  • 7h 17m total
  • Calgary to Chicago
Search Deals
WestJet
  • WestJet
  • 1/5
  • Nonstop
  • 3h 29m total
  • Calgary to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 66 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 25 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).
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 20 February 2025.

Thu 27/211:30 a.m.YYC - ORD
Nonstop3h 26mWestJet
Sun 2/34:45 p.m.ORD - YYC
Nonstop3h 51mWestJet
Deal found 19/2C$ 226
Mon 7/48:30 a.m.YYC - ORD
1 stop9h 24mAir Canada
Thu 10/410:53 a.m.ORD - YYC
1 stop10h 30mAir Canada
Deal found 19/2C$ 249
Thu 10/412:43 p.m.YYC - ORD
Nonstop3h 27mUnited Airlines
Sat 12/41:05 p.m.ORD - YYC
1 stop9h 43mUnited Airlines
Deal found 19/2C$ 274
Sun 2/311:30 a.m.YYC - ORD
Nonstop3h 26mMultiple Airlines
Sun 9/35:00 a.m.ORD - YYC
1 stop10h 21mMultiple Airlines
Deal found 19/2C$ 298
Fri 7/312:40 p.m.YYC - ORD
1 stop7h 47mDelta
Tue 11/31:26 p.m.ORD - YYC
2 stops10h 50mDelta
Deal found 19/2C$ 313
Wed 12/36:30 a.m.YYC - MDW
1 stop6h 45mDelta
Wed 10/910:10 a.m.MDW - YYC
2 stops13h 53mDelta
Deal found 19/2C$ 313
Sat 15/33:45 p.m.YYC - MDW
1 stop12h 45mMultiple Airlines
Wed 19/39:25 a.m.MDW - YYC
1 stop8h 37mMultiple Airlines
Deal found 19/2C$ 413
Thu 15/51:18 p.m.YYC - ORD
Nonstop3h 30mAmerican Airlines
Sun 18/56:00 a.m.ORD - YYC
1 stop16h 50mAmerican Airlines
Deal found 19/2C$ 452
Tue 13/54:30 p.m.YYC - MDW
1 stop22h 54mPorter Airlines
Thu 15/59:15 a.m.MDW - YYC
2 stops14h 15mPorter Airlines
Deal found 19/2C$ 683
Wed 13/810:30 a.m.YYC - MDW
1 stop6h 33mWestJet
Mon 18/89:20 a.m.MDW - YYC
1 stop8h 28mWestJet
Deal found 19/2C$ 712

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 20 February 2025.

Fly from

Calgary

Fly to

Chicago

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 14/4

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

Nonstop3h 26m

Chicago O'Hare Intl

Sun 20/4

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

Nonstop3h 51m

C$ 226

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 7/4

8:30 a.m.-6:54 p.m.

1 stop9h 24m

Chicago O'Hare Intl

Thu 10/4

10:53 a.m.-8:23 p.m.

1 stop10h 30m

C$ 249

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 10/4

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

Nonstop3h 27m

Chicago O'Hare Intl

Sat 12/4

1:05 p.m.-9:48 p.m.

1 stop9h 43m

C$ 274

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 2/3

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

Nonstop3h 26m

Chicago O'Hare Intl

Sun 9/3

5:00 a.m.-2:21 p.m.

1 stop10h 21m

C$ 298

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 7/3

12:40 p.m.-9:27 p.m.

1 stop7h 47m

Chicago O'Hare Intl

Tue 11/3

1:26 p.m.-11:16 p.m.

2 stops10h 50m

C$ 313

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 12/3

6:30 a.m.-2:15 p.m.

1 stop6h 45m

Chicago Midway

Wed 10/9

10:10 a.m.-11:03 p.m.

2 stops13h 53m

C$ 313

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 15/3

3:45 p.m.-5:30 a.m.

1 stop12h 45m

Chicago Midway

Wed 19/3

9:25 a.m.-5:02 p.m.

1 stop8h 37m

C$ 413

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 15/5

1:18 p.m.-5:48 p.m.

Nonstop3h 30m

Chicago O'Hare Intl

Sun 18/5

6:00 a.m.-9:50 p.m.

1 stop16h 50m

C$ 452

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 13/5

4:30 p.m.-4:24 p.m.

1 stop22h 54m

Chicago Midway

Thu 15/5

9:15 a.m.-10:30 p.m.

2 stops14h 15m

C$ 683

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 13/8

10:30 a.m.-6:03 p.m.

1 stop6h 33m

Chicago Midway

Mon 18/8

9:20 a.m.-4:48 p.m.

1 stop8h 28m

C$ 712

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/2

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 14 February 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 20 February 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 20 February 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 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 20 February 2025.
See what other customers who have flown with Delta, Porter Airlines and United 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.
Delta
8.0
Very good
8,227 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Food

7.3

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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

Delta
8.0
Very good
8,227 reviews
Delta
8.0
Very good
8,227 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Food

7.3

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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
8,227 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Food

7.3

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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

United Airlines
7.4
Good
8,771 reviews
Delta
8.0
Very good
8,227 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Food

7.3

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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
8,227 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Food

7.3

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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

WestJet
7.2
Good
2,799 reviews
Delta
8.0
Very good
8,227 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Food

7.3

Comfort

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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 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, WestJet (C$ 226), Air Canada (C$ 249), and United Airlines (C$ 274) offers the cheapest pricing from Calgary to Chicago. Users have found that WestJet is 52% 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$ 139. Air Canada flights start at C$ 156 while deals on United Airlines start at C$ 172 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?

    The cheapest flight price from Calgary to Chicago is C$ 142. On average you can expect to pay C$ 1,596. The most popular route, (Calgary - Chicago O'Hare Intl), can usually be booked for C$ 226.

  • 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 20 February 2025.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 189AverageC$ 358FlexibilityNo cancel feeOn-time60%
Search WestJet flights
American AirlinesCheapestC$ 201AverageC$ 433FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 239AverageC$ 490FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 291AverageC$ 406FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 335AverageC$ 635FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJet EncoreCheapestC$ 572AverageC$ 1,011FlexibilityNo cancel feeOn-timeN/A
Search WestJet Encore flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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.

100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.