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Cheap flights from Calgary to Chicago from C$ 155

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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
11 Oct — 18 Oct1
1 adult
1 adult, Economy

Cheapflights Tip: The best prices from Calgary to Chicago are usually found in April or February, booked 66 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 11 September 2025.

Round-trip from

C$ 226

One-way from

C$ 155

Popular in

December

Cheapest in

April

Average price

C$ 319

Good round-trip deal

C$ 516 or less

Good one-way deal

C$ 278 or less
WestJet
  • WestJet
  • 17/10-19/10
  • Nonstop
  • 7h 17m total
  • Calgary to Chicago
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WestJet
  • WestJet
  • 10/11
  • Nonstop
  • 3h 35m total
  • Calgary to Chicago
Search Deals
Highest demand for flights based on searches. 23% potential increase in price (C$ 166 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease (C$ 33 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 2025.

Fri 17/1012:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Sun 19/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Deal found 11/9C$ 226
Fri 24/101:10 a.m.YYC - ORD
1 stop7h 41mAir Canada
Sat 1/112:00 p.m.ORD - YYC
1 stop7h 39mAir Canada
Deal found 10/9C$ 229
Mon 27/1011:40 p.m.YYC - ORD
1 stop8h 35mAir Canada
Thu 30/1010:00 a.m.ORD - YYC
1 stop9h 54mAir Canada
Deal found 10/9C$ 231
Thu 11/1212:35 p.m.YYC - ORD
Nonstop3h 35mUnited Airlines
Mon 15/1210:35 a.m.ORD - YYC
1 stop12h 18mUnited Airlines
Deal found 10/9C$ 262
Tue 30/91:10 a.m.YYC - ORD
1 stop7h 41mAir Canada
Tue 4/1110:00 a.m.ORD - YYC
1 stop9h 54mAir Canada
Deal found 11/9C$ 265
Fri 24/101:29 p.m.YYC - ORD
Nonstop3h 25mAmerican Airlines
Tue 28/109:49 a.m.ORD - YYC
Nonstop3h 45mAmerican Airlines
Deal found 11/9C$ 266
Fri 3/108:15 p.m.YYC - ORD
1 stop15h 24mWestJet
Thu 9/105:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Deal found 9/9C$ 267
Fri 31/109:00 a.m.YYC - ORD
Nonstop3h 35mMultiple Airlines
Sun 2/111:26 p.m.ORD - YYC
1 stop8h 00mMultiple Airlines
Deal found 11/9C$ 270
Sat 25/106:45 a.m.YYC - MDW
1 stop5h 23mDelta
Sat 1/119:20 a.m.MDW - YYC
1 stop5h 34mDelta
Deal found 10/9C$ 309
Wed 19/116:20 a.m.YYC - MDW
1 stop5h 47mDelta
Wed 7/12:00 p.m.MDW - YYC
1 stop7h 58mDelta
Deal found 11/9C$ 321
Wed 19/116:20 a.m.YYC - MDW
1 stop5h 47mDelta
Mon 12/12:00 p.m.MDW - YYC
1 stop7h 58mDelta
Deal found 11/9C$ 345
Wed 1/106:40 a.m.YYC - MDW
1 stop9h 55mDelta
Tue 4/119:35 a.m.MDW - YYC
2 stops12h 12mDelta
Deal found 11/9C$ 352

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 September 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 24/10

1:10 a.m.-9:51 a.m.

1 stop7h 41m

Chicago O'Hare Intl

Sat 1/11

2:00 p.m.-8:39 p.m.

1 stop7h 39m

C$ 229

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 27/10

11:40 p.m.-9:15 a.m.

1 stop8h 35m

Chicago O'Hare Intl

Thu 30/10

10:00 a.m.-6:54 p.m.

1 stop9h 54m

C$ 231

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 11/12

12:35 p.m.-5:10 p.m.

Nonstop3h 35m

Chicago O'Hare Intl

Mon 15/12

10:35 a.m.-9:53 p.m.

1 stop12h 18m

C$ 262

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 25/10

1:29 p.m.-5:54 p.m.

Nonstop3h 25m

Chicago O'Hare Intl

Sat 1/11

9:49 a.m.-12:34 p.m.

Nonstop3h 45m

C$ 267

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 3/10

8:15 p.m.-12:39 p.m.

1 stop15h 24m

Chicago O'Hare Intl

Thu 9/10

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

Nonstop3h 49m

C$ 267

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 31/10

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

Nonstop3h 35m

Chicago O'Hare Intl

Sun 2/11

1:26 p.m.-8:26 p.m.

1 stop8h 00m

C$ 270

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 2/10

9:00 a.m.-10:45 p.m.

1 stop12h 45m

Chicago O'Hare Intl

Sun 5/10

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

Nonstop3h 49m

C$ 303

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 25/10

6:45 a.m.-4:50 p.m.

1 stop9h 05m

Chicago O'Hare Intl

Sat 1/11

11:05 a.m.-11:02 p.m.

2 stops12h 57m

C$ 309

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 25/10

6:45 a.m.-1:08 p.m.

1 stop5h 23m

Chicago Midway

Sat 1/11

9:20 a.m.-1:54 p.m.

1 stop5h 34m

C$ 309

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 12/10

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

Chicago O'Hare Intl

Sat 1/11

10:00 a.m.-6:15 p.m.

2 stops33h 15m

C$ 309

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/9

Showing 1-10 of 39 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 29 August 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$ 349). 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 September 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 September 2025.

The most flights from YYC to CHI are scheduled on a Thursday (14 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).

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 64% 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$ 257.

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 Minneapolis (MSP) offer the fastest connection on this route, with an average layover time of 0h 49m.

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 September 2025.
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
8.0
Very good
7,960 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
United Airlines
7.4
Good
8,937 reviews
Delta
8.0
Very good
7,960 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
WestJet
7.2
Good
3,091 reviews
Delta
8.0
Very good
7,960 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others
Air Canada
7.1
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews
Check prices

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

Reviews

1 / 20
6.0
Good

Morgan Rae,Aug 2025

BRU - JFK

Typically I choose delta because they do a great job but this time the flight attendant in my zone was very rude and didnt offer the same treatment as she did to others

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 11 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$ 267, Air Canada can have you in Chicago from Calgary in 3h 25m. 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, Air Canada (C$ 150), WestJet (C$ 177), and Delta (C$ 185) offers the cheapest pricing from Calgary to Chicago. Users have found that Air Canada is 61% 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$ 157. WestJet flights start at C$ 158 while deals on Delta start at C$ 219 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: Avianca (80%), Air Canada (76%), United Airlines( 76%).

  • What are the cheapest flights from Calgary to Chicago?

    The cheapest flight price from Calgary to Chicago is C$ 149. On average you can expect to pay C$ 1,381. 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$ 349). 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 11 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 150AverageC$ 343FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 177AverageC$ 252FlexibilityNo cancel feeOn-time60%
Search WestJet flights
DeltaCheapestC$ 185AverageC$ 346FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
American AirlinesCheapestC$ 186AverageC$ 425FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapestC$ 253AverageC$ 531FlexibilityNo 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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