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Cheap flights from Calgary to Chicago from C$ 143

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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
14 Feb — 21 Feb1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Calgary to Chicago are usually found in April or November, booked 47 days in advance, depart on a Friday or Thursday 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 15 January 2026.

Round-trip from

C$ 229

One-way from

C$ 143

Popular in

July

Cheapest in

April

Average price

C$ 325

Good round-trip deal

C$ 494 or less

Good one-way deal

C$ 231 or less
Air Canada
  • Air Canada
  • 28/2-7/3
  • 2 total stops
  • 17h 44m total
  • Calgary to Chicago
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WestJet
  • WestJet
  • 10/4
  • Nonstop
  • 3h 35m total
  • Calgary to Chicago
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Highest demand for flights based on searches. 11% potential increase in price (C$ 64 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 18 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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

Enter your travel dates to find the best prices.

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 15 January 2026.

Fri 27/29:00 a.m.
YYC
-
ORD
Nonstop3h 35m
WestJet
Fri 6/32:20 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 12/1C$ 206
Sat 28/25:30 a.m.
YYC
-
ORD
1 stop8h 40m
Air Canada
Sat 7/33:55 p.m.
ORD
-
YYC
1 stop9h 04m
Air Canada
Deal found 14/1C$ 229
Fri 6/29:00 a.m.
YYC
-
ORD
Nonstop3h 35m
WestJet
Fri 13/22:20 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 13/1C$ 233
Thu 30/412:15 p.m.
YYC
-
ORD
Nonstop3h 28m
WestJet
Sun 3/55:30 p.m.
ORD
-
YYC
Nonstop3h 49m
WestJet
Deal found 13/1C$ 240
Sat 30/512:15 p.m.
YYC
-
ORD
Nonstop3h 28m
WestJet
Sun 31/55:30 p.m.
ORD
-
YYC
Nonstop3h 49m
WestJet
Deal found 14/1C$ 243
Wed 26/811:55 p.m.
YYC
-
ORD
1 stop8h 05m
Air Canada
Sat 29/82:15 p.m.
ORD
-
YYC
1 stop7h 45m
Air Canada
Deal found 13/1C$ 252
Tue 31/36:00 a.m.
YYC
-
ORD
1 stop14h 17m
United Airlines
Wed 8/412:55 p.m.
ORD
-
YYC
1 stop9h 53m
United Airlines
Deal found 13/1C$ 257
Wed 5/812:15 p.m.
YYC
-
ORD
Nonstop3h 28m
WestJet
Sun 9/85:30 p.m.
ORD
-
YYC
Nonstop3h 49m
WestJet
Deal found 13/1C$ 264
Thu 14/512:15 p.m.
YYC
-
ORD
Nonstop3h 28m
WestJet
Mon 18/55:30 p.m.
ORD
-
YYC
Nonstop3h 49m
WestJet
Deal found 15/1C$ 272
Fri 27/27:00 a.m.
YYC
-
ORD
1 stop9h 44m
Multiple Airlines
Fri 6/32:20 p.m.
ORD
-
YYC
Nonstop3h 55m
Multiple Airlines
Deal found 12/1C$ 274
Thu 6/812:15 p.m.
YYC
-
ORD
Nonstop3h 28m
WestJet
Sun 9/85:30 p.m.
ORD
-
YYC
Nonstop3h 49m
WestJet
Deal found 14/1C$ 277
Wed 25/36:45 a.m.
YYC
-
MDW
1 stop5h 40m
Delta
Tue 31/32:05 p.m.
MDW
-
YYC
1 stop7h 40m
Delta
Deal found 15/1C$ 317

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 15 January 2026.
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 27/2

9:00 a.m.-1:35 p.m.

Nonstop3h 35m

Chicago O'Hare Intl

Fri 6/3

2:20 p.m.-5:15 p.m.

Nonstop3h 55m

C$ 206

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 31/3

6:00 a.m.-9:17 p.m.

1 stop14h 17m

Chicago O'Hare Intl

Wed 8/4

12:55 p.m.-9:48 p.m.

1 stop9h 53m

C$ 257

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 17/3

7:20 a.m.-6:06 p.m.

1 stop9h 46m

Chicago O'Hare Intl

Tue 24/3

12:15 p.m.-11:02 p.m.

2 stops11h 47m

C$ 317

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 26/3

6:45 a.m.-1:25 p.m.

1 stop5h 40m

Chicago Midway

Tue 31/3

2:05 p.m.-8:45 p.m.

1 stop7h 40m

C$ 317

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 27/2

6:30 a.m.-6:01 p.m.

1 stop10h 31m

Chicago O'Hare Intl

Fri 6/3

1:20 p.m.-11:05 p.m.

1 stop10h 45m

C$ 338

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 6/2

6:30 a.m.-5:55 p.m.

1 stop10h 25m

Chicago O'Hare Intl

Wed 11/2

8:50 a.m.-11:02 p.m.

2 stops15h 12m

C$ 338

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 27/1

7:40 a.m.-9:05 p.m.

2 stops12h 25m

Chicago O'Hare Intl

Thu 29/1

1:50 p.m.-11:02 p.m.

1 stop10h 12m

C$ 338

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 6/2

6:30 a.m.-1:06 p.m.

1 stop5h 36m

Chicago Midway

Wed 11/2

9:33 a.m.-8:54 p.m.

2 stops12h 21m

C$ 338

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 5/4

7:20 a.m.-6:06 p.m.

1 stop9h 46m

Chicago O'Hare Intl

Wed 8/4

1:18 p.m.-11:02 p.m.

1 stop10h 44m

C$ 339

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 27/3

7:20 a.m.-6:06 p.m.

1 stop9h 46m

Chicago O'Hare Intl

Wed 1/4

8:55 a.m.-11:02 p.m.

2 stops15h 07m

C$ 361

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/1

Showing 1-10 of 35 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 9 January 2026.

To ensure you get the cheapest price possible for a flight from Calgary to Chicago, you should look to book at least 47 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, April is the cheapest month in which you can book a flight from Calgary to Chicago (average of C$ 150). Flying from Calgary to Chicago in July is currently the most expensive (average of C$ 215). 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 15 January 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Calgary to Chicago as you normally would.

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 15 January 2026.

The most flights from YYC to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 on average).

How much does it cost to fly round-trip from Calgary to Chicago?

What’s the top layover airport for flights from Calgary to Chicago?

Share of one-stop round-trip flights from Calgary to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Toronto (YYZ) – chosen by Cheapflights users on 60% of one-stop itineraries from Calgary to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Calgary to Chicago?

Average round-trip fare for 1-stop flights from Calgary to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Ottawa (YOW) is the most affordable 1-stop option, with an average round-trip price of C$ 258.

What’s the fastest layover option from Calgary to Chicago?

Shortest average travel time for 1-stop one-way flights from Calgary to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Minneapolis (MSP) have the shortest average one-way travel time for 1-stop routes: 5h 31m.

Which airport typically offers the quickest layover for flights from Calgary to Chicago?

Average layover duration for 1-stop one-way flights from Calgary to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Toronto (YYZ) offer the fastest connection on this route, with an average layover time of 1h 33m.

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 15 January 2026.
Read through reviews of airlines operating flights from Calgary to Chicago, such as Delta,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,049 reviews
Check prices

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,049 reviews
Delta
7.9
Good
8,049 reviews
Check prices

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,163 reviews
Delta
7.9
Good
8,049 reviews
Check prices

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,131 reviews
Delta
7.9
Good
8,049 reviews
Check prices

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
WestJet
7.2
Good
3,242 reviews
Delta
7.9
Good
8,049 reviews
Check prices

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Air Canada
7.1
Good
10,622 reviews
Delta
7.9
Good
8,049 reviews
Check prices

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Crew

8.5

Overall

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 7 outbound flights to Chicago per day. 5 airlines have flights to Chicago from Calgary on a regular basis.

  • How long is the flight from Calgary to Chicago?

    For as low as C$ 206, WestJet can have you in Chicago from Calgary in 3h 35m. The distance between Calgary and Chicago is about 2223 km. Both multi-stop and direct flights can be found to your destination and back.

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

    According to our current data, Delta (C$ 149), Air Canada (C$ 150), and American Airlines (C$ 172) offers the cheapest pricing from Calgary to Chicago. Users have found that Delta is 56% 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$ 136. Air Canada flights start at C$ 156 while deals on United Airlines start at C$ 164 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: WestJet (78%), Delta (78%), Air Canada( 63%).

  • What are the cheapest flights from Calgary to Chicago?

    The cheapest flight price from Calgary to Chicago is C$ 162. On average you can expect to pay C$ 690. The most popular route, (Calgary - Chicago O'Hare Intl), can usually be booked for C$ 243.

  • 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, April is the cheapest month in which you can book a flight from Calgary to Chicago (average of C$ 150). Flying from Calgary to Chicago in July is currently the most expensive (average of C$ 215). 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 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 629,999 searches. Data last updated 15 January 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapestC$ 149AverageC$ 342FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Air CanadaCheapestC$ 150AverageC$ 302FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 172AverageC$ 350FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 177AverageC$ 257FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 180AverageC$ 455FlexibilityNo cancel feeOn-time69%
Search United Airlines 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.

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