Cheap flights from Calgary to Chicago

YYC — CHI
10 Dec — 17 Dec1
Return
1 adult
Economy
From?
To?
Sat 10/12
Sat 17/12

The best prices from Calgary to Chicago are usually found in March or November, booked 60 days in advance, depart on a Tuesday or Wednesday and return on a Monday

How to find the cheapest flight from Calgary (YYC) to Chicago (CHI)

All the information you need to plan the best YYC to CHI flight in 2022: compare Calgary to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.

YYC - CHI

Price

C$ 433 - C$ 596

CHI

Temperature

-5 - 23 °C

CHI

Rainfall

43 - 125 mm

Popular inJulyHigh demand for flights, 16% potential price rise
Cheapest inMarchBest time to find cheap flights, 14% potential price drop
Round-trip fromC$ 583From Calgary to Chicago (CHI)
One-way fromC$ 277One-way flight from Calgary to Chicago (CHI)

What is the cheapest day to fly round-trip from Calgary to Chicago?

Users have found that leaving on a Monday can be a cost-effective option. It’s possible to save up to 19% on your flight compared to booking on days when demand is much higher.

How far in advance should I book a flight from Calgary to Chicago?

Users have found that booking a flight from Calgary to Chicago at least 60 days early can save you up to 45% on average compared to booking a flight this week. If booking 60 days before your flight isn’t an option for you, users have found flights from Calgary to Chicago for as little as C$ 853 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as C$ 964 for flights departing within the next 3 days.

What is the cheapest month to fly from Calgary to Chicago?

March is one of the best times of the year to fly to Chicago from Calgary. Prices for March average C$ 674 per person but you can even find prices for as low as C$ 479. The most expensive prices can be found in the month of July. Opting for a March flight can save you 19% on your journey compared to booking in July

When is the cheapest time to fly from Calgary to Chicago (YYC - CHI)?

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 5% on airfare.

Cheap United Airlines flights from Calgary to Chicago

20 Apr. - 23 Apr.
YYC

Calgary

ORD

Chicago O'Hare Intl

Nonstop

3h 19m
ORD

Chicago O'Hare Intl

YYC

Calgary

Nonstop

3h 44m
C$ 455

United Airlines

Deal found 2/12

21 Apr. - 23 Apr.
YYC

Calgary

ORD

Chicago O'Hare Intl

1 stop

6h 14m
ORD

Chicago O'Hare Intl

YYC

Calgary

Nonstop

3h 44m
C$ 461

United Airlines

Deal found 2/12

25 Jan. - 5 Feb.
YYC

Calgary

ORD

Chicago O'Hare Intl

Nonstop

3h 18m
ORD

Chicago O'Hare Intl

YYC

Calgary

1 stop

8h 31m
C$ 474

United Airlines

Deal found 4/12

  • One of the most popular airlines travelling from Calgary to Chicago is United Airlines. Flights on this route from United Airlines typically cost C$ 561.92 RT, a price that is 81% more expensive than the average Calgary to Chicago flight. The cheapest flight found was C$ 366 RT. Calgary Airport is the most common Calgary airport to take off from when flying to Chicago. Chicago O'Hare Intl Airport is the most popular arrival airport in Chicago. When flying from Calgary to Chicago, United Airlines flights are 9% more popular than any other airline flying that same route.

Cheap British Airways flights from Calgary to Chicago

26 Jan. - 4 Feb.
YYC

Calgary

ORD

Chicago O'Hare Intl

1 stop

8h 44m
ORD

Chicago O'Hare Intl

YYC

Calgary

1 stop

16h 37m
C$ 462

British Airways

Deal found 4/12

27 Jan. - 30 Jan.
YYC

Calgary

ORD

Chicago O'Hare Intl

1 stop

8h 44m
ORD

Chicago O'Hare Intl

YYC

Calgary

1 stop

21h 57m
C$ 463

British Airways

Deal found 3/12

18 May - 22 May
YYC

Calgary

ORD

Chicago O'Hare Intl

Nonstop

3h 39m
ORD

Chicago O'Hare Intl

YYC

Calgary

Nonstop

3h 47m
C$ 568

British Airways

Deal found 3/12

  • One of the most popular airlines travelling from Calgary to Chicago is British Airways. Flights from British Airways travelling this route typically cost C$ 489.29 RT. This price is typically 94% more expensive than other airlines that offer Calgary to Chicago flights. When booking this route, the cheapest RT price found was C$ 349. The most popular departure airport in Calgary when flying to Chicago is Calgary Airport. The most popular airport to fly into when visiting Chicago is Chicago O'Hare Intl Airport. When flying from Calgary to Chicago, British Airways flights are -7% more popular than any other airline flying that same route.

Related info for your journey

Useful info, stats and facts about Calgary to Chicago flights.

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 2 outbound flights to Chicago per day. 10 airlines have flights to Chicago from Calgary on a regular basis.

Which airlines flying from Calgary to Chicago have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Calgary to Chicago that may be offering flexible cancellation policies are Air Canada, American Airlines, and United Airlines. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Can I find flights from Calgary to Chicago for under C$ 500 on Cheapflights?

Yes, there are multiple flights from Calgary to Chicago for under C$ 500. The cheapest flight booked recently is on Multiple Airlines for just C$ 430, but on average you can expect to pay C$ 473.

Are there direct flights from Calgary to Chicago for under C$ 500 on Cheapflights?

Cheapflights has 20 direct flights from Calgary to Chicago under C$ 500. A good price for a direct flight from Calgary to Chicago is less than C$ 696.

Are there last-minute flights available from Calgary to Chicago for under C$ 700?

There are currently 20+ open flights from Calgary to Chicago within the next 7 days for less than C$ 700.

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

According to our current data, United Airlines (C$ 455), British Airways (C$ 462), and Air Canada (C$ 469) offers the cheapest pricing from Calgary to Chicago. Users have found that United Airlines is 32% 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$ 246. British Airways flights start at C$ 271 while deals on Aer Lingus start at C$ 292 one-way.

What are the most popular airlines that fly from Calgary to Chicago?

The most popular airlines flying from Calgary to Chicago are Endeavor Airlines, American Airlines and Air Canada. Something to consider prior to booking your flight.

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: American Airlines (89%), Qatar Airways (89%), British Airways( 89%).

What are the cheapest flights from Calgary to Chicago?

The cheapest flight price from Calgary to Chicago is C$ 352. On average you can expect to pay C$ 647. The most popular route, (Calgary - Chicago O'Hare Intl), can usually be booked for C$ 430.

Top 7 airlines flying from Calgary to Chicago

The chart below displays the airlines Cheapflights users travelling from Calgary to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
FrontierCheapestC$ 245AverageC$ 361FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search Frontier flights
American AirlinesCheapestC$ 408AverageC$ 625FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
Air CanadaCheapestC$ 470AverageC$ 659FlexibilityNo cancel feeOn-time67%COVID-19 safety
Search Air Canada flights
United AirlinesCheapestC$ 492AverageC$ 757FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
DeltaCheapestC$ 522AverageC$ 637FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
WestJetCheapestC$ 542AverageC$ 642FlexibilityNo cancel feeOn-time60%COVID-19 safety
Search WestJet flights
British AirwaysCheapestC$ 595AverageC$ 884FlexibilityNo cancel feeOn-time70%COVID-19 safety
Search British Airways flights

Hourly flight availability from Calgary to Chicago

See what time of day planes typically take off from Calgary to Chicago
0%of flight departuresEarly morningMidnight to 6 am
100%of flight departuresMorning6 am to noon
0%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Calgary to Chicago

See how many times per day planes take to the skies headed from Calgary to Chicago
Sunday3daily flights
Monday3daily flights
Tuesday3daily flights
Wednesday1daily flight
Thursday1daily flight
Friday3daily flights
Saturday3daily flights