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Cheap flights from Calgary to Chicago from C$ 125

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 24/3. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
16 Feb — 23 Feb1
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 11 February 2025.

Round-trip from

C$ 186

One-way from

C$ 125

Popular in

December

Cheapest in

February

Average price

C$ 287

Good round-trip deal

C$ 329 or less

Good one-way deal

C$ 247 or less
WestJet
  • WestJet
  • 20/3-24/3
  • Nonstop
  • 7h 17m total
  • Calgary to Chicago
WestJet
  • WestJet
  • 24/3
  • Nonstop
  • 3h 26m total
  • Calgary to Chicago
Highest demand for flights based on searches. 7% potential increase in price (C$ 59 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease (C$ 24 potential savings vs. average RT price).
Average for round-trip flights in February 2025
Price to beat on a round-trip flight from Calgary to Chicago (CHI).
Price to beat on a one-way flight from Calgary to Chicago (CHI).

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 February 2025.

Thu 20/211:30 a.m.YYC - ORD
Nonstop3h 26mWestJet
Thu 27/24:45 p.m.ORD - YYC
Nonstop3h 51mWestJet
Deal found 10/2C$ 186
Fri 2/51:30 p.m.YYC - ORD
1 stop9h 59mMultiple Airlines
Mon 5/55:30 p.m.ORD - YYC
Nonstop3h 49mMultiple Airlines
Deal found 11/2C$ 238
Mon 17/37:20 p.m.YYC - ORD
1 stop13h 13mUnited Airlines
Wed 26/32:35 p.m.ORD - YYC
1 stop8h 06mUnited Airlines
Deal found 11/2C$ 245
Thu 13/38:30 a.m.YYC - ORD
1 stop9h 11mAir Canada
Thu 20/312:58 p.m.ORD - YYC
1 stop11h 20mAir Canada
Deal found 11/2C$ 287
Tue 11/37:40 a.m.YYC - ORD
1 stop9h 06mDelta
Tue 18/312:15 p.m.ORD - YYC
2 stops12h 01mDelta
Deal found 11/2C$ 312
Fri 21/24:35 p.m.YYC - MDW
1 stop11h 46mMultiple Airlines
Sun 23/28:44 p.m.MDW - YYC
1 stop27h 11mMultiple Airlines
Deal found 10/2C$ 396
Fri 7/36:59 p.m.YYC - ORD
2 stops17h 05mAlaska Airlines
Tue 11/32:00 p.m.ORD - YYC
1 stop29h 09mAlaska Airlines
Deal found 10/2C$ 426
Thu 10/46:30 a.m.YYC - MDW
1 stop6h 47mDelta
Sun 13/410:25 a.m.MDW - YYC
2 stops13h 51mDelta
Deal found 11/2C$ 428
Fri 7/31:28 p.m.YYC - ORD
Nonstop3h 31mAmerican Airlines
Tue 11/35:00 a.m.ORD - YYC
1 stop7h 49mAmerican Airlines
Deal found 10/2C$ 460
Sat 12/44:20 p.m.YYC - MDW
1 stop17h 00mPorter Airlines
Mon 21/411:15 a.m.MDW - YYC
1 stop13h 15mPorter Airlines
Deal found 11/2C$ 712
Tue 8/46:30 a.m.YYC - MDW
1 stop10h 48mWestJet
Sat 12/47:13 p.m.MDW - YYC
1 stop26h 29mWestJet
Deal found 11/2C$ 737

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 11 February 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 20/3

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

Nonstop3h 26m

Chicago O'Hare Intl

Mon 24/3

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

Nonstop3h 51m

C$ 186

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 2/5

1:30 p.m.-12:29 a.m.

1 stop9h 59m

Chicago O'Hare Intl

Mon 5/5

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

Nonstop3h 49m

C$ 238

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 17/3

7:20 p.m.-9:33 a.m.

1 stop13h 13m

Chicago O'Hare Intl

Wed 26/3

2:35 p.m.-9:41 p.m.

1 stop8h 06m

C$ 245

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 13/3

8:30 a.m.-6:41 p.m.

1 stop9h 11m

Chicago O'Hare Intl

Thu 20/3

12:58 p.m.-11:18 p.m.

1 stop11h 20m

C$ 287

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 11/3

7:40 a.m.-5:46 p.m.

1 stop9h 06m

Chicago O'Hare Intl

Tue 18/3

1:45 p.m.-11:16 p.m.

1 stop10h 31m

C$ 312

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 21/2

4:35 p.m.-5:21 a.m.

1 stop11h 46m

Chicago Midway

Sun 23/2

8:44 p.m.-10:55 p.m.

1 stop27h 11m

C$ 396

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 7/3

6:59 p.m.-1:04 p.m.

2 stops17h 05m

Chicago O'Hare Intl

Tue 11/3

2:00 p.m.-6:09 p.m.

1 stop29h 09m

C$ 426

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Thu 10/4

6:30 a.m.-2:17 p.m.

1 stop6h 47m

Chicago Midway

Sun 13/4

10:25 a.m.-11:16 p.m.

2 stops13h 51m

C$ 428

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 7/3

1:28 p.m.-5:59 p.m.

Nonstop3h 31m

Chicago O'Hare Intl

Tue 11/3

5:00 a.m.-11:49 a.m.

1 stop7h 49m

C$ 460

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Sat 12/4

4:20 p.m.-10:20 a.m.

1 stop17h 00m

Chicago Midway

Mon 21/4

11:15 a.m.-11:30 p.m.

1 stop13h 15m

C$ 712

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/2

Showing 1-10 of 22 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.

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 7 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 11 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.

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 11 February 2025.
See what other customers who have flown with Alaska Airlines, Delta and Porter 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.

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Overall

8.0

Entertainment

7.1

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them