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Cheap flights from Calgary to Chicago from C$ 247

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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
26 Aug — 2 Sep1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Calgary to Chicago are usually found in November or January, booked 26 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap 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 27 July 2026.

Sat 29/812:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Mon 31/85:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 24/7C$ 310
Sat 5/98:30 a.m.
YYC
-
ORD
Nonstop3h 35m
United Airlines
Sun 13/97:45 p.m.
ORD
-
YYC
Nonstop3h 50m
United Airlines
Deal found 25/7C$ 354
Fri 28/81:00 a.m.
YYC
-
ORD
1 stop8h 16m
Air Canada
Mon 31/89:50 a.m.
ORD
-
YYC
1 stop17h 06m
Air Canada
Deal found 24/7C$ 362
Mon 28/912:00 p.m.
YYC
-
ORD
Nonstop3h 40m
WestJet
Mon 5/105:30 p.m.
ORD
-
YYC
Nonstop3h 55m
WestJet
Deal found 23/7C$ 368
Sat 29/86:45 a.m.
YYC
-
ORD
1 stop7h 45m
Delta
Mon 31/82:00 p.m.
ORD
-
YYC
1 stop10h 04m
Delta
Deal found 24/7C$ 369
Wed 12/86:45 a.m.
YYC
-
ORD
1 stop9h 56m
Delta
Fri 11/92:05 p.m.
ORD
-
YYC
1 stop10h 01m
Delta
Deal found 23/7C$ 373
Thu 24/126:00 a.m.
YYC
-
ORD
1 stop13h 20m
United Airlines
Sat 2/19:00 a.m.
ORD
-
YYC
Nonstop3h 54m
United Airlines
Deal found 25/7C$ 375
Thu 27/812:34 p.m.
YYC
-
ORD
Nonstop3h 32m
Multiple Airlines
Mon 31/89:50 a.m.
ORD
-
YYC
1 stop17h 06m
Multiple Airlines
Deal found 24/7C$ 376
Mon 23/117:45 a.m.
YYC
-
MDW
2 stops13h 25m
Delta
Thu 26/111:00 p.m.
MDW
-
YYC
2 stops8h 54m
Delta
Deal found 21/7C$ 387
Sat 24/107:45 a.m.
YYC
-
MDW
1 stop8h 02m
Delta
Mon 26/1012:27 p.m.
MDW
-
YYC
2 stops11h 43m
Delta
Deal found 26/7C$ 392
Wed 9/96:35 a.m.
YYC
-
MDW
1 stop5h 45m
Delta
Wed 16/99:29 a.m.
MDW
-
YYC
2 stops12h 13m
Delta
Deal found 26/7C$ 426
Thu 29/1012:30 a.m.
YYC
-
MDW
1 stop8h 22m
Delta
Mon 2/119:59 a.m.
MDW
-
YYC
2 stops10h 16m
Delta
Deal found 24/7C$ 472

Find 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 27 July 2026.

Round-trip from

C$ 310

One-way from

C$ 247

Popular in

June

Cheapest in

November

Average price

C$ 373

Good round-trip deal

C$ 588 or less

Good one-way deal

C$ 348 or less
WestJet
  • WestJet
  • 29/8-31/8
  • Nonstop
  • 7h 35m total
  • Calgary to Chicago
Search Deals
Air Canada
  • Air Canada
  • 4/9
  • 1 total stop
  • 8h 16m total
  • Calgary to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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

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 27 July 2026.
Use the filters below to find and compare flights from Calgary to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 24/12

6:00 a.m.-7:20 p.m.

1 stop13h 20m

Chicago O'Hare Intl

Sat 2/1

9:00 a.m.-12:54 p.m.

Nonstop3h 54m

C$ 375

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 24/10

7:45 a.m.-6:00 p.m.

2 stops9h 15m

Chicago Midway

Mon 26/10

12:27 p.m.-11:10 p.m.

2 stops11h 43m

C$ 392

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 19/8

7:45 a.m.-6:19 p.m.

1 stop9h 34m

Chicago O'Hare Intl

Sat 22/8

12:29 p.m.-8:35 p.m.

1 stop9h 06m

C$ 418

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Wed 9/9

6:35 a.m.-1:20 p.m.

1 stop5h 45m

Chicago Midway

Wed 16/9

9:29 a.m.-8:42 p.m.

2 stops12h 13m

C$ 426

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 11/8

7:45 a.m.-6:19 p.m.

1 stop9h 34m

Chicago O'Hare Intl

Fri 14/8

2:00 p.m.-11:04 p.m.

1 stop10h 04m

C$ 426

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 13/8

7:45 a.m.-6:19 p.m.

1 stop9h 34m

Chicago O'Hare Intl

Wed 16/9

2:05 p.m.-11:06 p.m.

1 stop10h 01m

C$ 433

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 30/10

12:33 p.m.-10:00 p.m.

1 stop8h 27m

Chicago O'Hare Intl

Mon 2/11

12:33 p.m.-12:12 a.m.

2 stops11h 39m

C$ 435

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 23/11

7:45 a.m.-3:50 p.m.

1 stop8h 05m

Chicago Midway

Thu 26/11

10:35 a.m.-9:54 p.m.

2 stops11h 19m

C$ 452

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 8/8

6:45 a.m.-5:41 p.m.

1 stop9h 56m

Chicago O'Hare Intl

Tue 11/8

2:00 p.m.-11:04 p.m.

1 stop10h 04m

C$ 454

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 29/10

12:30 a.m.-10:03 a.m.

1 stop8h 33m

Chicago Midway

Mon 2/11

12:27 p.m.-12:10 a.m.

2 stops11h 43m

C$ 472

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/7

Showing 1-10 of 36 resultsSorted by cheapest first
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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

What is the cheapest month to book a flight from Calgary to Chicago?

Currently, November is the cheapest month in which you can book a flight from Calgary to Chicago (average of C$ 331). Flying from Calgary to Chicago in June is currently the most expensive (average of C$ 510). 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 27 July 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 27 July 2026.

The most flights from YYC to CHI are scheduled on a Tuesday (14 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (11 on average).

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

Airfare is typical for this route at the moment.
Calgary to Chicago flights typically cost between C$ 297 and C$ 571 in August.
The cheapest round-trip price found within the last 5 days was C$ 310 on WestJet (29 Aug-31 Aug).

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 65% 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.

Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of C$ 434.

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 Toronto (YYZ) have the shortest average one-way travel time for 1-stop routes: 7h 19m.

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 57m.

How far ahead should I book a flight from Calgary to Chicago?

To ensure you get the cheapest price possible for a flight from Calgary to Chicago, you should look to book at least 44 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.

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 27 July 2026.
Read through reviews of airlines operating flights from Calgary to Chicago, such as Delta,United Airlines, andWestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.8
Good
8,485 reviews
Check prices

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Food

7.2

Crew

8.5

Overall

7.8

Reviews

1 / 20
8.0
Excellent

Rakshith,May 2026

TPE - SEA

I got middle seat, but it was cheap $340 for Taipei to PDX ,
Delta
7.8
Good
8,485 reviews
Delta
7.8
Good
8,485 reviews
Check prices

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Food

7.2

Crew

8.5

Overall

7.8

Reviews

1 / 20
8.0
Excellent

Rakshith,May 2026

TPE - SEA

I got middle seat, but it was cheap $340 for Taipei to PDX ,
United Airlines
7.4
Good
10,042 reviews
Delta
7.8
Good
8,485 reviews
Check prices

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Food

7.2

Crew

8.5

Overall

7.8

Reviews

1 / 20
8.0
Excellent

Rakshith,May 2026

TPE - SEA

I got middle seat, but it was cheap $340 for Taipei to PDX ,
WestJet
7.2
Good
3,415 reviews
Delta
7.8
Good
8,485 reviews
Check prices

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Food

7.2

Crew

8.5

Overall

7.8

Reviews

1 / 20
8.0
Excellent

Rakshith,May 2026

TPE - SEA

I got middle seat, but it was cheap $340 for Taipei to PDX ,
American Airlines
7.1
Good
11,843 reviews
Delta
7.8
Good
8,485 reviews
Check prices

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Food

7.2

Crew

8.5

Overall

7.8

Reviews

1 / 20
8.0
Excellent

Rakshith,May 2026

TPE - SEA

I got middle seat, but it was cheap $340 for Taipei to PDX ,
Air Canada
7.1
Good
11,391 reviews
Delta
7.8
Good
8,485 reviews
Check prices

Comfort

7.8

Entertainment

7.8

Boarding

8.1

Food

7.2

Crew

8.5

Overall

7.8

Reviews

1 / 20
8.0
Excellent

Rakshith,May 2026

TPE - SEA

I got middle seat, but it was cheap $340 for Taipei to PDX ,

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 12 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$ 392, United Airlines can have you in Chicago from Calgary in 9h 15m. The distance between Calgary and Chicago is about 2247 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, Air Canada (C$ 123), Delta (C$ 144), and WestJet (C$ 188) offers the cheapest pricing from Calgary to Chicago. Users have found that Air Canada is 69% 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$ 138. Air Canada flights start at C$ 153 while deals on American 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: Qatar Airways (85%), Avianca (80%), Emirates( 79%).

  • What are the cheapest flights from Calgary to Chicago?

    The cheapest flight price from Calgary to Chicago is C$ 266. On average you can expect to pay C$ 2,922. The most popular route, (Calgary - Chicago O'Hare Intl), can usually be booked for C$ 328.

  • 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, November is the cheapest month in which you can book a flight from Calgary to Chicago (average of C$ 331). Flying from Calgary to Chicago in June is currently the most expensive (average of C$ 510). 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 27 July 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 123AverageC$ 437FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 144AverageC$ 389FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
WestJetCheapestC$ 188AverageC$ 360FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 190AverageC$ 534FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapestC$ 200AverageC$ 465FlexibilityNo cancel feeOn-time71%
Search American 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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