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Cheap flights from Calgary to Chicago from C$ 148

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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
25 Nov — 2 Dec1
1 adult

The best prices from Calgary to Chicago are usually found in September or February, booked 84 days in advance, depart on a Friday or Wednesday and return on a Wednesday

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 645,034 searches. Data last updated 20 November 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 10/4

8:30 a.m.-12:49 p.m.

Nonstop3h 19m

Chicago O'Hare Intl

Tue 15/4

9:03 a.m.-4:52 p.m.

1 stop8h 49m

C$ 294

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 7/12

7:00 a.m.-2:39 p.m.

1 stop6h 39m

Chicago O'Hare Intl

Tue 10/12

12:35 p.m.-11:16 p.m.

2 stops11h 41m

C$ 307

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 7/12

7:00 a.m.-6:32 p.m.

1 stop10h 32m

Chicago Midway

Tue 10/12

9:30 a.m.-8:38 p.m.

2 stops12h 08m

C$ 308

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 10/4

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

Nonstop3h 26m

Chicago O'Hare Intl

Tue 15/4

7:45 p.m.-10:29 p.m.

Nonstop3h 44m

C$ 311

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 23/1

12:30 a.m.-11:54 a.m.

1 stop10h 24m

Chicago Midway

Sun 26/1

12:43 p.m.-10:55 p.m.

1 stop11h 12m

C$ 379

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 1/4

8:30 a.m.-12:49 p.m.

Nonstop3h 19m

Chicago O'Hare Intl

Tue 8/4

12:45 p.m.-9:38 p.m.

1 stop9h 53m

C$ 385

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 30/4

1:20 p.m.-5:45 p.m.

Nonstop3h 25m

Chicago O'Hare Intl

Mon 5/5

9:45 a.m.-12:30 p.m.

Nonstop3h 45m

C$ 531

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 29/4

12:30 a.m.-10:02 a.m.

1 stop8h 32m

Chicago O'Hare Intl

Mon 5/5

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

Nonstop3h 49m

C$ 589

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 1/3

6:59 p.m.-6:00 p.m.

1 stop22h 01m

Chicago O'Hare Intl

Fri 7/3

7:00 p.m.-6:09 p.m.

2 stops24h 09m

C$ 592

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sun 8/12

12:50 p.m.-11:10 a.m.

1 stop21h 20m

Chicago Midway

Thu 12/12

5:35 p.m.-3:28 p.m.

1 stop22h 53m

C$ 708

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/11

Showing 1-10 of 22 results
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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 November 2024.

Round-trip from

C$ 294

One-way from

C$ 148

Popular in

December

Cheapest in

September
Air Canada
  • Air Canada
  • 10/4-15/4
  • 1 total stop
  • 12h 08m total
  • Calgary to Chicago
Search Deals
WestJet
  • WestJet
  • 7/4
  • Nonstop
  • 3h 26m total
  • Calgary to Chicago
Search Deals
High demand for flights, 17% potential price rise
Search Deals
Best time to find cheap flights, 20% potential price drop
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 November 2024.

Tue 26/118:30 a.m.YYC - ORD
1 stop9h 06mAir Canada
Sat 30/1112:52 p.m.ORD - YYC
1 stop9h 26mAir Canada
Deal found 19/11C$ 307
Sat 7/127:00 a.m.YYC - ORD
2 stops13h 12mDelta
Tue 10/128:35 a.m.ORD - YYC
2 stops13h 03mDelta
Deal found 19/11C$ 308
Sat 7/127:00 a.m.YYC - MDW
1 stop10h 32mDelta
Tue 10/129:30 a.m.MDW - YYC
2 stops12h 08mDelta
Deal found 19/11C$ 308
Tue 17/126:55 p.m.YYC - ORD
1 stop9h 47mMultiple Airlines
Thu 19/128:34 p.m.ORD - YYC
1 stop27h 21mMultiple Airlines
Deal found 19/11C$ 414
Thu 21/1112:41 p.m.YYC - ORD
Nonstop3h 28mUnited Airlines
Fri 29/118:45 a.m.ORD - YYC
Nonstop3h 54mUnited Airlines
Deal found 19/11C$ 438
Thu 28/116:29 a.m.YYC - ORD
1 stop7h 34mAmerican Airlines
Sun 1/125:00 a.m.ORD - YYC
1 stop7h 45mAmerican Airlines
Deal found 18/11C$ 580
Tue 3/129:45 p.m.YYC - MDW
2 stops12h 57mMultiple Airlines
Mon 9/1212:05 p.m.MDW - YYC
1 stop12h 20mMultiple Airlines
Deal found 19/11C$ 622
Sat 7/1211:30 a.m.YYC - ORD
2 stops24h 32mAlaska Airlines
Tue 10/121:58 p.m.ORD - YYC
2 stops21h 42mAlaska Airlines
Deal found 19/11C$ 685
Sun 8/1212:50 p.m.YYC - MDW
1 stop21h 20mPorter Airlines
Thu 12/125:35 p.m.MDW - YYC
1 stop22h 53mPorter Airlines
Deal found 18/11C$ 708
Sat 7/127:00 a.m.YYC - MDW
1 stop10h 32mWestJet
Tue 10/129:38 a.m.MDW - YYC
1 stop12h 00mWestJet
Deal found 19/11C$ 756
Fri 6/1212:20 a.m.YYC - ORD
2 stops18h 09mWestJet
Tue 10/125:25 p.m.ORD - YYC
1 stop28h 13mWestJet
Deal found 20/11C$ 818

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 15 November 2024.

To ensure you get the cheapest price possible for a flight from Calgary to Chicago, you should look to book at least 84 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 May is currently the most expensive (average of C$ 342). 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 November 2024.

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 30% 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 November 2024.

The most flights from YYC to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, 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 November 2024.
See what other customers who have flown with Air Canada, Delta and American 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.
Alaska Airlines
8.0
Very good
9,461 reviews
Check prices

Overall

8.0

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Food

7.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

Alaska Airlines
8.0
Very good
9,461 reviews
Alaska Airlines
8.0
Very good
9,461 reviews
Check prices

Overall

8.0

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Food

7.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

Delta
8.0
Very good
8,756 reviews
Alaska Airlines
8.0
Very good
9,461 reviews
Check prices

Overall

8.0

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Food

7.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

Porter Airlines
7.8
Good
288 reviews
Alaska Airlines
8.0
Very good
9,461 reviews
Check prices

Overall

8.0

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Food

7.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

United Airlines
7.4
Good
9,171 reviews
Alaska Airlines
8.0
Very good
9,461 reviews
Check prices

Overall

8.0

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Food

7.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

WestJet
7.3
Good
2,811 reviews
Alaska Airlines
8.0
Very good
9,461 reviews
Check prices

Overall

8.0

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Food

7.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

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 3 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, Air Canada (C$ 294), Delta (C$ 307), and United Airlines (C$ 385) offers the cheapest pricing from Calgary to Chicago. Users have found that Air Canada is 42% 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$ 148. Air Canada flights start at C$ 164 while deals on United Airlines start at C$ 179 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 (92%), United Airlines (92%), WestJet( 92%).

  • What are the cheapest flights from Calgary to Chicago?

    The cheapest flight price from Calgary to Chicago is C$ 304. On average you can expect to pay C$ 934. The most popular route, (Calgary - Chicago O'Hare Intl), can usually be booked for C$ 279.

  • 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 May is currently the most expensive (average of C$ 342). 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 645,034 searches. Data last updated 20 November 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapestC$ 198AverageC$ 426FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 234AverageC$ 420FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 284AverageC$ 556FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 310AverageC$ 407FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 322AverageC$ 603FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJet EncoreCheapestC$ 564AverageC$ 996FlexibilityNo 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.

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