Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Calgary to Chicago from C$ 153

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 18/8. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
17 Jun — 24 Jun1
1 adult

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 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 12 June 2025.

Round-trip from

C$ 205

One-way from

C$ 153

Popular in

December

Cheapest in

April

Average price

C$ 334

Good round-trip deal

C$ 459 or less

Good one-way deal

C$ 290 or less
WestJet
  • WestJet
  • 31/7-4/8
  • Nonstop
  • 7h 18m total
  • Calgary to Chicago
Search Deals
Air Canada
  • Air Canada
  • 18/8
  • 1 total stop
  • 7h 47m total
  • Calgary to Chicago
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (C$ 153 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
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

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 12 June 2025.

Thu 31/712:15 p.m.YYC - ORD
Nonstop3h 29mWestJet
Mon 4/85:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Deal found 11/6C$ 205
Fri 13/66:29 a.m.YYC - ORD
Nonstop3h 25mAmerican Airlines
Tue 17/61:28 p.m.ORD - YYC
1 stop9h 29mAmerican Airlines
Deal found 12/6C$ 238
Tue 17/612:38 p.m.YYC - ORD
Nonstop3h 32mUnited Airlines
Tue 24/65:02 a.m.ORD - YYC
1 stop14h 19mUnited Airlines
Deal found 11/6C$ 261
Sat 6/91:10 a.m.YYC - ORD
1 stop7h 41mAir Canada
Wed 17/96:20 p.m.ORD - YYC
1 stop7h 52mAir Canada
Deal found 11/6C$ 275
Mon 14/78:00 a.m.YYC - ORD
2 stops12h 30mMultiple Airlines
Wed 23/75:30 p.m.ORD - YYC
Nonstop3h 49mMultiple Airlines
Deal found 12/6C$ 287
Sat 13/96:35 a.m.YYC - ORD
2 stops14h 11mDelta
Fri 19/91:55 p.m.ORD - YYC
1 stop10h 17mDelta
Deal found 11/6C$ 308
Tue 17/66:45 a.m.YYC - MDW
1 stop9h 55mDelta
Tue 24/61:47 p.m.MDW - YYC
1 stop8h 10mDelta
Deal found 11/6C$ 328
Fri 25/712:30 a.m.YYC - MDW
1 stop21h 05mMultiple Airlines
Sat 2/86:20 a.m.MDW - YYC
2 stops19h 24mMultiple Airlines
Deal found 11/6C$ 476
Mon 21/77:00 a.m.YYC - MDW
2 stops32h 24mPorter Airlines
Tue 5/85:20 p.m.MDW - YYC
2 stops29h 00mPorter Airlines
Deal found 11/6C$ 629
Fri 25/712:30 a.m.YYC - MDW
1 stop20h 12mWestJet
Sat 2/812:43 p.m.MDW - YYC
1 stop10h 32mWestJet
Deal found 11/6C$ 882

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 12 June 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

Thu 31/7

12:15 p.m.-4:44 p.m.

Nonstop3h 29m

Chicago O'Hare Intl

Mon 4/8

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

Nonstop3h 49m

C$ 205

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 13/9

6:45 a.m.-9:24 p.m.

1 stop13h 39m

Chicago O'Hare Intl

Sat 20/9

8:30 p.m.-11:19 p.m.

Nonstop3h 49m

C$ 273

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 6/9

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

1 stop7h 41m

Chicago O'Hare Intl

Wed 17/9

6:20 p.m.-1:12 a.m.

1 stop7h 52m

C$ 275

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 14/7

8:00 a.m.-9:30 p.m.

2 stops12h 30m

Chicago O'Hare Intl

Wed 23/7

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

Nonstop3h 49m

C$ 287

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 13/9

6:35 a.m.-9:46 p.m.

2 stops14h 11m

Chicago O'Hare Intl

Fri 19/9

1:55 p.m.-11:12 p.m.

1 stop10h 17m

C$ 308

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Tue 9/9

6:40 a.m.-5:37 p.m.

1 stop9h 57m

Chicago Midway

Wed 17/9

1:00 p.m.-8:54 p.m.

2 stops8h 54m

C$ 328

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 25/7

12:30 a.m.-10:35 p.m.

1 stop21h 05m

Chicago Midway

Sat 2/8

6:20 a.m.-12:44 a.m.

2 stops19h 24m

C$ 476

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Mon 21/7

7:00 a.m.-4:24 p.m.

2 stops32h 24m

Chicago Midway

Tue 5/8

5:20 p.m.-9:20 p.m.

2 stops29h 00m

C$ 629

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

Fri 25/7

12:30 a.m.-9:42 p.m.

1 stop20h 12m

Chicago Midway

Sat 2/8

12:43 p.m.-10:15 p.m.

1 stop10h 32m

C$ 882

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 18/8

1:05 a.m.-9:52 a.m.

1 stop7h 47m

C$ 153

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

Showing 1-10 of 20 results
1
2

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 June 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$ 352). 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 12 June 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 12 June 2025.

The most flights from YYC to CHI are scheduled on a Monday (14 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 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 12 June 2025.
See what other customers who have flown with Alaska Airlines, Porter Airlines and Delta 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
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Porter Airlines
8.0
Very good
288 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Overall

8.0

Food

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

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

    According to our current data, WestJet (C$ 205), American Airlines (C$ 273), and Air Canada (C$ 275) offers the cheapest pricing from Calgary to Chicago. Users have found that WestJet is 47% 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$ 153. United Airlines flights start at C$ 160 while deals on American Airlines start at C$ 175 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 (91%), Air Canada (84%), United Airlines( 84%).

  • What are the cheapest flights from Calgary to Chicago?

    The cheapest flight price from Calgary to Chicago is C$ 197. On average you can expect to pay C$ 1,852. The most popular route, (Calgary - Chicago O'Hare Intl), can usually be booked for C$ 261.

  • 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$ 352). 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 12 June 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 148AverageC$ 336FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 169AverageC$ 420FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 176AverageC$ 271FlexibilityNo cancel feeOn-time60%
Search WestJet flights
DeltaCheapestC$ 197AverageC$ 363FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 248AverageC$ 564FlexibilityNo 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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.