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$ 308 - C$ 472
CHI
Temperature
1 - 29 °C
CHI
Precipitation
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$ 308

From Calgary to Chicago

One-way from

C$ 280

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$ 436 1-2 weeks out and tickets from C$ 591 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$ 318 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 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 July, August 2021

The best prices found for YYC to CHI flights for July, August
30 Aug - 8 Sep
C$ 486pp
YYC
Calgary
WestJet
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
WestJet
 
1 STOP
YYC
Calgary
27 Aug - 30 Aug
C$ 496pp
YYC
Calgary
WestJet
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
WestJet
 
1 STOP
YYC
Calgary
28 Aug - 30 Aug
C$ 514pp
YYC
Calgary
WestJet
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
WestJet
 
1 STOP
YYC
Calgary

Calgary to Chicago 2021 flight deals

Cheap flights to Chicago from Calgary found for this year
29 Dec - 12 Jan
C$ 466pp
YYC
Calgary
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YYC
Calgary
29 Dec - 12 Jan
C$ 478pp
YYC
Calgary
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
YYC
Calgary
25 Nov - 29 Nov
C$ 479pp
YYC
Calgary
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YYC
Calgary

Direct flights to Chicago from Calgary

Save time with Calgary to Chicago direct flight deals
29 Dec - 12 Jan
C$ 466pp
YYC
Calgary
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YYC
Calgary
16 Dec - 4 Jan
C$ 478pp
YYC
Calgary
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Direct
YYC
Calgary
25 Nov - 29 Nov
C$ 479pp
YYC
Calgary
United Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United 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
4 Aug - 11 Aug
C$ 1,580pp
YYC
Calgary
Air Canada
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYC
Calgary
4 Aug - 11 Aug
C$ 1,629pp
YYC
Calgary
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYC
Calgary
3 Aug - 11 Aug
C$ 2,289pp
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
10:30 a.m. - 7:10 p.m.
United Airlines
1 stop
7h 40m
YYC - ORD
United Airlines
C$ 281
United
3:00 a.m. - 7:01 p.m.
American Airlines
1 stop
15h 01m
YYC - ORD
American Airlines
C$ 286
5:55 a.m. - 5:13 a.m.
Delta
1 stop
22h 18m
YYC - MDW
Delta
C$ 357
Delta

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 0 outbound flights to Chicago per day. 7 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 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$ 503 on Cheapflights?

Yes, there are multiple flights from Calgary to Chicago for under C$ 503. The cheapest flight booked recently is on United Airlines for just C$ 466, but on average you can expect to pay C$ 500.

Are there direct flights from Calgary to Chicago for under C$ 503 on Cheapflights?

Cheapflights has 4 direct flights from Calgary to Chicago under C$ 503. A good price for a direct flight from Calgary to Chicago is less than C$ 478.

Are there last-minute flights available from Calgary to Chicago for under C$ 1,634?

There are currently 5+ open flights from Calgary to Chicago within the next 7 days for less than C$ 1,634.

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$ 466. 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$ 466, United Airlines will fly you from Calgary to Chicago and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from WestJet and Air Canada - these airlines can fly you to your destination from C$ 486 and C$ 495, 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$ 261 on United Airlines. Other airlines that offer cheap prices include Air Canada from C$ 271 and Delta from C$ 275 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 = $0.80
Flight duration
3h 35m
Average temperature for July in Chicago
29.0 °C
Avg rainfall for July in Chicago
95.0 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
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