Cheap flights from Calgary to Chicago

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The best prices from Calgary 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 (YYC) to Chicago (CHI)

YYC - CHI
Price
C$ 321 - C$ 493
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$ 321

From Calgary to Chicago

One-way from

C$ 236

One-way flight from Calgary 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 to Chicago?

Travellers have found that booking a Monday departure is the best way to save up to 24% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

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

To save up to 81% on this flight, we recommend booking at least 61 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Calgary to Chicago from C$ 437 1-2 weeks out and tickets from C$ 584 for flights departing within the next 72 hours.

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

February is one of the best times of the year to fly to Chicago from Calgary. Prices for February average C$ 328 per person but you can even find prices for as low as C$ 240. The most expensive prices can be found in the month of August. Opting for a February flight can save you 9% on your journey compared to booking in February

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

A simple way to save on the total cost of your ticket is to fly from Calgary 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.

Cheap flights from Calgary to Chicago in October, November 2020

The best prices found for YYC to CHI flights for October, November
16 Nov - 14 Dec
C$ 407pp
YYC
Calgary
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Direct
YYC
Calgary
16 Nov - 14 Dec
C$ 429pp
YYC
Calgary
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
YYC
Calgary
25 Nov - 27 Nov
C$ 437pp
YYC
Calgary
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYC
Calgary

Calgary to Chicago 2020 flight deals

Cheap flights to Chicago from Calgary found for this year
9 Dec - 21 Dec
C$ 398pp
YYC
Calgary
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
YYC
Calgary
16 Nov - 14 Dec
C$ 407pp
YYC
Calgary
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Direct
YYC
Calgary
23 Dec - 2 Jan
C$ 411pp
YYC
Calgary
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYC
Calgary

Direct flights to Chicago from Calgary

Save time with Calgary to Chicago direct flight deals
1 Dec - 13 Dec
C$ 419pp
YYC
Calgary
American Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Direct
YYC
Calgary
12 Jan - 13 Jan
C$ 420pp
YYC
Calgary
American Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Direct
YYC
Calgary
12 Jan - 13 Jan
C$ 421pp
YYC
Calgary
American Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Direct
YYC
Calgary

Last minute flights from Calgary to Chicago

Late deals on round-trip flights to Chicago from Calgary, departing today and this week
5 Nov - 19 Nov
C$ 480pp
YYC
Calgary
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
YYC
Calgary
5 Nov - 19 Nov
C$ 510pp
YYC
Calgary
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
   
2 STOPS
YYC
Calgary
4 Nov - 19 Nov
C$ 627pp
YYC
Calgary
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYC
Calgary

One-way flights to Chicago from Calgary

The cheapest one-way flights from Calgary to Chicago
8:38 a.m. - 12:58 p.m.
American Airlines
Direct
3h 20m
YYC - ORD
American Airlines
C$ 237
7:30 a.m. - 10:15 a.m.
Alaska Airlines
2 stops
25h 45m
YYC - ORD
Alaska Airlines
C$ 241
7:55 p.m. - 5:12 a.m.
Air Canada
2 stops
32h 17m
YYC - ORD
Air Canada
C$ 285

Related info for your journey

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

Flight FAQs

From Calgary to Chicago

Can I find flights from Calgary to Chicago for under C$ 525 on Cheapflights?

Yes, there are multiple flights from Calgary to Chicago for under C$ 525. The cheapest flight booked recently is on American Airlines for just C$ 398, but on average you can expect to pay C$ 425.

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 to Chicago for under C$ 525 on Cheapflights?

Cheapflights has 6 direct flights from Calgary to Chicago under C$ 525. A good price for a direct flight from Calgary to Chicago is less than C$ 488.

Are there last-minute flights available from Calgary to Chicago for under C$ 525?

There are currently 6+ open flights from Calgary to Chicago within the next 7 days for less than C$ 525.

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 to Chicago?

A quick flight from Calgary to Chicago can take about 3h 20m. American Airlines provides one of the quickest options available for as low as C$ 419. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

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

Currently priced at C$ 398, American Airlines will fly you from Calgary to Chicago and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Air Canada and Delta - these airlines can fly you to your destination from C$ 411 and C$ 414, respectively. Users have found that American Airlines is 7% cheaper than the other options available to this destination.

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

One-way options have recently been found by users for as low as C$ 229 on Air Canada. Other airlines that offer cheap prices include American Airlines from C$ 237 and Alaska Airlines from C$ 241 one-way.

Destination information for Chicago

Things to know before you go. Useful info for your trip from Calgary to Chicago
Today's exchange rate
C$ 1 = $0.77
Flight duration
3h 34m
Average temperature for October in Chicago
18.0 °C
Avg rainfall for October in Chicago
66.0 mm

Airports servicing Calgary

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)
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