Cheap flights from Calgary to Chicago

Round-trip
Economy
Calgary (YYC)
Chicago (CHI)
Depart
Return
Any month
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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 Wednesday and return on a Tuesday

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 2021: compare Calgary to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
YYC - CHI
Price
C$ 302 - C$ 463
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$ 302

From Calgary to Chicago

One-way from

C$ 345

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 19% 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 86% on this flight, we recommend booking at least 34 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$ 427 1-2 weeks out and tickets from C$ 578 for flights departing within the next 72 hours.

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

April is one of the best times of the year to fly to Chicago from Calgary. Prices for April average C$ 311 per person but you can even find prices for as low as C$ 235. The most expensive prices can be found in the month of January. Opting for a April flight can save you 10% on your journey compared to booking in April

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 21% on your trip compared to booking a flight in the afternoon.

Cheap flights from Calgary to Chicago in May, June 2021

The best prices found for YYC to CHI flights for May, June
2 Jun - 9 Jun
C$ 464pp
YYC
Calgary
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
YYC
Calgary
10 Jun - 15 Jun
C$ 482pp
YYC
Calgary
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
YYC
Calgary
24 May - 31 May
C$ 484pp
YYC
Calgary
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
British Airways
 
1 STOP
YYC
Calgary

Calgary to Chicago 2021 flight deals

Cheap flights to Chicago from Calgary found for this year
4 Sep - 7 Sep
C$ 443pp
YYC
Calgary
American Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Direct
YYC
Calgary
4 Sep - 7 Sep
C$ 454pp
YYC
Calgary
American Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
YYC
Calgary
7 Sep - 8 Sep
C$ 455pp
YYC
Calgary
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
YYC
Calgary

Direct flights to Chicago from Calgary

Save time with Calgary to Chicago direct flight deals
4 Sep - 7 Sep
C$ 443pp
YYC
Calgary
American Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Direct
YYC
Calgary
7 Sep - 8 Sep
C$ 457pp
YYC
Calgary
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YYC
Calgary
10 Sep - 13 Sep
C$ 604pp
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

The cheapest one-way flights from Calgary to Chicago
8:15 p.m. - 5:48 a.m.
Air Canada
2 stops
32h 33m
YYC - ORD
Air Canada
C$ 345
4:00 a.m. - 1:07 p.m.
Delta
1 stop
8h 07m
YYC - MDW
Delta
C$ 370
Delta
3:00 a.m. - 1:00 a.m.
American Airlines
3 stops
21h 00m
YYC - ORD
American Airlines
C$ 396

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Calgary</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From Calgary to Chicago

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 1 outbound flight to Chicago per day. 7 airlines have flights to Chicago from Calgary on a regular basis.

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.

Can I find flights from Calgary to Chicago for under C$ 492 on Cheapflights?

Yes, there are multiple flights from Calgary to Chicago for under C$ 492. The cheapest flight booked recently is on American Airlines for just C$ 443, but on average you can expect to pay C$ 497.

Are there direct flights from Calgary to Chicago for under C$ 492 on Cheapflights?

Cheapflights has 3 direct flights from Calgary to Chicago under C$ 492. A good price for a direct flight from Calgary to Chicago is less than C$ 501.

What days are direct flights available from Calgary to Chicago?

Direct flights are available for this route on the following days: Sunday, Monday, Friday, Saturday.

How many flights depart from Calgary to Chicago on average per day?

2 flight departures from Calgary to Chicago per day on average.
Morning (6am - Noon) - 100% of flight departures

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 19m. United Airlines provides one of the quickest options available for as low as C$ 456. There are 2235 km between Calgary and Chicago. 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$ 444, 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 United Airlines and Delta - these airlines can fly you to your destination from C$ 456 and C$ 463, respectively.

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$ 269 on American Airlines. Other airlines that offer cheap prices include Air Canada from C$ 292 and Delta from C$ 330 one-way.

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Calgary to Chicago.
Today's exchange rate
C$ 1 = $0.82
Flight duration
3h 32m
Average temperature for May in Chicago
22.0 °C
Avg rainfall for May in Chicago
109.0 mm

Airports servicing Calgary

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

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.
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

Hourly flight availability from Calgary to Chicago

See what time of day planes typically take off from Calgary towards Chicago.
Morning 6 AM to noon 100% of flight departures
Early morning Midnight to 6 AM 0% of flight departures
Afternoon Noon to 6 PM 0% of flight departures
Evening 6 PM to midnight 0% of flight departures
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.
Sunday
1 daily flight
Monday
2 daily flights
Tuesday
1 daily flight
Wednesday
2 daily flights
Thursday
1 daily flight
Friday
2 daily flights
Saturday
0 flights
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