Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Calgary to Chicago from C$ 163

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 24/7. Fares are subject to change and may not be available on all flights or dates of travel.
YYC — CHI
14 jul. — 21 jul.1
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 9 julio 2025.

Round-trip from

C$ 199

One-way from

C$ 163

Popular in

December

Cheapest in

April

Average price

C$ 477

Good round-trip deal

C$ 504 or less

Good one-way deal

C$ 229 or less
WestJet
  • WestJet
  • 25/9-29/9
  • Nonstop
  • 7h 17m total
  • Calgary to Chicago
Search Deals
WestJet
  • WestJet
  • 24/7
  • Nonstop
  • 3h 29m total
  • Calgary to Chicago
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (C$ 155 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 July 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 9 julio 2025.

jue. 25/912:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
lun. 29/95:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Deal found 7/7C$ 199
sáb. 11/1012:15 p.m.YYC - ORD
Nonstop3h 28mMultiple Airlines
sáb. 18/105:01 a.m.ORD - YYC
1 stop9h 52mMultiple Airlines
Deal found 7/7C$ 225
sáb. 22/1112:30 p.m.YYC - ORD
Nonstop3h 20mUnited Airlines
dom. 23/119:00 a.m.ORD - YYC
Nonstop3h 54mUnited Airlines
Deal found 7/7C$ 232
mar. 16/91:10 a.m.YYC - ORD
1 stop7h 41mAir Canada
vie. 19/96:20 p.m.ORD - YYC
1 stop7h 52mAir Canada
Deal found 9/7C$ 238
dom. 31/86:15 a.m.YYC - ORD
1 stop6h 00mLufthansa
dom. 7/98:08 p.m.ORD - YYC
Nonstop3h 45mLufthansa
Deal found 9/7C$ 292
sáb. 23/86:40 a.m.YYC - ORD
1 stop9h 24mDelta
lun. 25/82:15 p.m.ORD - YYC
1 stop9h 42mDelta
Deal found 9/7C$ 312
lun. 6/106:29 a.m.YYC - ORD
Nonstop3h 25mAmerican Airlines
mié. 8/105:00 a.m.ORD - YYC
1 stop7h 52mAmerican Airlines
Deal found 6/7C$ 332
jue. 14/86:40 a.m.YYC - MDW
1 stop9h 57mDelta
lun. 18/89:31 a.m.MDW - YYC
2 stops12h 12mDelta
Deal found 7/7C$ 357
jue. 4/912:30 a.m.YYC - MDW
1 stop14h 28mMultiple Airlines
mié. 10/99:00 a.m.MDW - YYC
1 stop12h 00mMultiple Airlines
Deal found 8/7C$ 398
jue. 21/811:55 p.m.YYC - MDW
2 stops15h 29mPorter Airlines
jue. 28/89:40 a.m.MDW - YYC
2 stops12h 40mPorter Airlines
Deal found 7/7C$ 642

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 9 julio 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

jue. 25/9

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

Nonstop3h 28m

Chicago O'Hare Intl

lun. 29/9

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

Nonstop3h 49m

C$ 199

CalgaryChicago

YYC - ORD

YYCORD

Calgary

sáb. 11/10

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

Nonstop3h 28m

Chicago O'Hare Intl

sáb. 18/10

5:01 a.m.-1:53 p.m.

1 stop9h 52m

C$ 225

CalgaryChicago

YYC - ORD

YYCORD

Calgary

sáb. 22/11

12:30 p.m.-4:50 p.m.

Nonstop3h 20m

Chicago O'Hare Intl

dom. 23/11

9:00 a.m.-11:54 a.m.

Nonstop3h 54m

C$ 232

CalgaryChicago

YYC - ORD

YYCORD

Calgary

mar. 16/9

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

1 stop7h 41m

Chicago O'Hare Intl

vie. 19/9

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

1 stop7h 52m

C$ 238

CalgaryChicago

YYC - ORD

YYCORD

Calgary

dom. 31/8

6:15 a.m.-1:15 p.m.

1 stop6h 00m

Chicago O'Hare Intl

dom. 7/9

8:08 p.m.-10:53 p.m.

Nonstop3h 45m

C$ 292

CalgaryChicago

YYC - ORD

YYCORD

Calgary

sáb. 23/8

6:40 a.m.-5:04 p.m.

1 stop9h 24m

Chicago O'Hare Intl

lun. 25/8

2:15 p.m.-10:57 p.m.

1 stop9h 42m

C$ 312

CalgaryChicago

YYC - ORD

YYCORD

Calgary

lun. 6/10

6:29 a.m.-10:54 a.m.

Nonstop3h 25m

Chicago O'Hare Intl

mié. 8/10

5:00 a.m.-11:52 a.m.

1 stop7h 52m

C$ 332

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

jue. 14/8

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

1 stop9h 57m

Chicago Midway

lun. 18/8

9:31 a.m.-8:43 p.m.

2 stops12h 12m

C$ 357

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

jue. 4/9

12:30 a.m.-3:58 p.m.

1 stop14h 28m

Chicago Midway

mié. 10/9

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

1 stop12h 00m

C$ 398

CalgaryChicago

YYC - MDW

YYCMDW

Calgary

dom. 31/8

11:55 p.m.-4:24 p.m.

2 stops15h 29m

Chicago Midway

dom. 7/9

9:15 a.m.-10:28 p.m.

2 stops14h 13m

C$ 635

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/7

Showing 1-10 of 19 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 27 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 9 julio 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 75% 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 9 julio 2025.

The most flights from YYC to CHI are scheduled on a Monday (15 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (7 on average).

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

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 9 julio 2025.
Read through reviews of airlines operating flights from Calgary to Chicago, such as Alaska Airlines,Porter Airlines, andDelta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Comfort

7.8

Boarding

8.1

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

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Comfort

7.8

Boarding

8.1

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
303 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Comfort

7.8

Boarding

8.1

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
7,954 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Comfort

7.8

Boarding

8.1

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
8,844 reviews
Alaska Airlines
8.0
Very good
10,000 reviews
Check prices

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Comfort

7.8

Boarding

8.1

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

Crew

8.5

Overall

8.0

Entertainment

7.1

Food

7.1

Comfort

7.8

Boarding

8.1

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$ 199), United Airlines (C$ 232), and Air Canada (C$ 238) offers the cheapest pricing from Calgary to Chicago. Users have found that WestJet is 48% 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$ 163. American Airlines flights start at C$ 165 while deals on United Airlines start at C$ 168 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 (93%), Envoy Air (85%), Air Canada( 85%).

  • What are the cheapest flights from Calgary to Chicago?

    The cheapest flight price from Calgary to Chicago is C$ 166. On average you can expect to pay C$ 2,406. The most popular route, (Calgary - Chicago O'Hare Intl), can usually be booked for C$ 232.

  • 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 9 julio 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 148AverageC$ 337FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
American AirlinesCheapestC$ 169AverageC$ 419FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 175AverageC$ 270FlexibilityNo cancel feeOn-time60%
Search WestJet flights
DeltaCheapestC$ 184AverageC$ 366FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 250AverageC$ 548FlexibilityNo 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.
Site
©2025 Cheapflights
OSZAR »