Prices are in Canadian Dollars.

Cheap flights from Calgary International to Chicago

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The best prices from Calgary International to Chicago are usually found in January or September, booked 0 days in advance, depart on a Tuesday or Thursday and return on a Monday

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

YYC - CHI
Price
C$ 312 - C$ 478
CHI
Temperature
1 - 29 °C
CHI
Rainfall
17 - 109 mm

Popular in

December

High demand for flights, 13% potential price rise

Cheapest in

January

Best time to find cheap flights, 25% potential price drop

Round-trip from

C$ 312

From Calgary International to Chicago

One-way from

C$ 318

One-way flight from Calgary International to Chicago

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Calgary International to Chicago?

Users have found that leaving on a Monday can be a cost-effective option. It’s possible to save up to 24% on your flight compared to booking on days when demand is much higher.

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

Users have found that booking a flight from Calgary International to Chicago at least 34 days early can save you up to 86% on average compared to booking a flight this week. If booking 34 days before your flight isn’t an option for you, users have found flights from Calgary International to Chicago for as little as C$ 442 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$ 598 for flights departing within the next 3 days.

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

Our data shows that April tends to be the cheapest month to fly to Chicago from Calgary International. Users have commonly found prices around C$ 322 for the month, but tickets can be as low as C$ 243. Due to multiple factors, prepare for potentially higher prices in January.

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

A simple way to save on the total cost of your ticket is to fly from Calgary International to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 17% on your trip compared to booking a flight in the morning.

Calgary International to Chicago 2021 flight deals

Cheap flights to Chicago from Calgary International found for this year
17 Aug - 13 Sep
C$ 419pp
YYC
Calgary
American Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Direct
YYC
Calgary
26 Jun - 27 Jun
C$ 420pp
YYC
Calgary
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YYC
Calgary
1 Sep - 24 Sep
C$ 425pp
YYC
Calgary
American Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
YYC
Calgary

Direct flights to Chicago from Calgary International

Save time with Calgary International to Chicago direct flight deals
26 Jun - 27 Jun
C$ 420pp
YYC
Calgary
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YYC
Calgary
22 Jul - 26 Jul
C$ 429pp
YYC
Calgary
Aer Lingus
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Aer Lingus
Direct
YYC
Calgary
29 Mar - 30 Mar
C$ 433pp
YYC
Calgary
American Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Direct
YYC
Calgary

One-way flights to Chicago from Calgary International

The cheapest one-way flights from Calgary International to Chicago
8:42 a.m. - 4:56 p.m.
Delta
1 stop
7h 14m
YYC - ORD
Delta
C$ 319
Delta
7:55 p.m. - 5:12 a.m.
Air Canada
2 stops
32h 17m
YYC - ORD
Air Canada
C$ 479
6:00 a.m. - 9:30 a.m.
Multiple Airlines
3 stops
26h 30m
YYC - ORD
Multiple Airlines
C$ 791
Kiwi.com

Related info for your journey

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

Flight FAQs

From Calgary International to Chicago

Can I find flights from Calgary International to Chicago for under C$ 509 on Cheapflights?

Yes, there are multiple flights from Calgary International to Chicago for under C$ 509. The cheapest flight booked recently is on United Airlines for just C$ 420, but on average you can expect to pay C$ 470.

What safety measures are being taken by airlines flying from Calgary to Chicago to control the spread of COVID-19?

New policies can now be found on Delta to help keep travellers safe while flying. New policies for travellers booking flights from Calgary to Chicago include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially-distanced seating (for a limited time). Keep in mind that policies will vary by airline.

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 United Airlines, American Airlines, and Air Canada. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Are there direct flights from Calgary International to Chicago for under C$ 509 on Cheapflights?

Cheapflights has 4 direct flights from Calgary International to Chicago under C$ 509. A good price for a direct flight from Calgary International to Chicago is less than C$ 429.

Is Calgary weather warmer or cooler than Chicago?

With an average temperature of 29 °C, peak weather can be found in July. As a traveller, expect to see changes in flight prices during that period. The temperatures in Chicago are hotter than in Calgary.

How long is the flight from Calgary International to Chicago?

For as low as C$ 429, Aer Lingus can have you in Chicago from Calgary International in 3h 19m. Most flights are nonstop.

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

United Airlines, at C$ 420, was found to be the cheapest airline from Calgary International to Chicago.Alternate airlines to your destination round-trip include Aer Lingus and American Airlines.

What are the cheapest airlines to fly from Calgary International to Chicago one-way?

The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as C$ 316. Check flights for Air Canada, as they currently have the next best price.

Destination information for Chicago

Things to know before you go. Useful info for your trip from Calgary International to Chicago
Today's exchange rate
C$ 1 = $0.79
Flight duration
3h 31m
Average temperature for January in Chicago
1.0 °C
Avg rainfall for January in Chicago
17.0 mm

Airports servicing Calgary

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 7 airlines flying from Calgary International to Chicago

The chart below displays the airlines Cheapflights users travelling from Calgary International to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.

Airline Cheapest Average Flexibility On-time COVID-19 safety
Frontier
C$ 182 C$ 268 No cancel fee 62%
Search Frontier flights
Delta
C$ 213 C$ 332 No cancel fee N/A
Search Delta flights
Air Canada
C$ 173 C$ 334 No cancel fee 67%
Search Air Canada flights
American Airlines
C$ 167 C$ 385 No cancel fee 71%
Search American Airlines flights
WestJet
C$ 242 C$ 398 No cancel fee 60%
Search WestJet flights
United Airlines
C$ 234 C$ 449 No cancel fee 69%
Search United Airlines flights
Aer Lingus
C$ 289 C$ 481 No cancel fee N/A
Search Aer Lingus flights
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