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 2022: compare Calgary to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
YYC - CHI
Price
C$ 245 - C$ 376
CHI
Temperature
-5 - 23 °C
CHI
Precipitation
43 - 125 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$ 307

From Calgary to Chicago (CHI)

One-way from

C$ 250

One-way flight from Calgary to Chicago (CHI)

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
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 afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 21% on airfare.

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.

Cheap flights from Calgary to Chicago in January, February 2022

The best prices found for YYC to CHI flights for January, February
1 Feb - 5 Feb
C$ 395pp
YYC
Calgary
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
 
1 STOP
YYC
Calgary
1 Feb - 5 Feb
C$ 396pp
YYC
Calgary
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
 
1 STOP
YYC
Calgary
11 Feb - 13 Feb
C$ 404pp
YYC
Calgary
Alaska Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
 
1 STOP
YYC
Calgary

Calgary to Chicago 2022 flight deals

Cheap flights to Chicago from Calgary found for this year
1 Feb - 5 Feb
C$ 395pp
YYC
Calgary
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
 
1 STOP
YYC
Calgary
1 Feb - 5 Feb
C$ 396pp
YYC
Calgary
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
 
1 STOP
YYC
Calgary
11 Feb - 13 Feb
C$ 404pp
YYC
Calgary
Alaska Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
 
1 STOP
YYC
Calgary

Direct flights to Chicago from Calgary

Save time with Calgary to Chicago direct flight deals
19 May - 23 May
C$ 511pp
YYC
Calgary
American Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Direct
YYC
Calgary
19 May - 23 May
C$ 513pp
YYC
Calgary
American Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Direct
YYC
Calgary
19 May - 23 May
C$ 514pp
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
21 Jan - 24 Jan
C$ 468pp
YYC
Calgary
Multiple Airlines
     
3 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
YYC
Calgary
21 Jan - 24 Jan
C$ 508pp
YYC
Calgary
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
YYC
Calgary
21 Jan - 24 Jan
C$ 531pp
YYC
Calgary
Multiple Airlines
     
3 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
 
1 STOP
YYC
Calgary

One-way flights to Chicago from Calgary

The cheapest one-way flights from Calgary to Chicago
1:55 p.m. - 3:40 a.m.
Flair Airlines
1 stop
12h 45m
YYC - ORD
Flair Airlines
C$ 250
Supersaver
3:35 a.m. - 3:40 a.m.
Multiple Airlines
2 stops
23h 05m
YYC - ORD
Multiple Airlines
C$ 271
Supersaver
8:05 p.m. - 12:40 p.m.
WestJet
2 stops
15h 35m
YYC - ORD
WestJet
C$ 275

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$ 400 on Cheapflights?

Yes, there are multiple flights from Calgary to Chicago for under C$ 400. The cheapest flight booked recently is on Multiple Airlines for just C$ 395, but on average you can expect to pay C$ 432.

Are there direct flights from Calgary to Chicago for under C$ 600 on Cheapflights?

Cheapflights has 17 direct flights from Calgary to Chicago under C$ 600. A good price for a direct flight from Calgary to Chicago is less than C$ 764.

Are there last-minute flights available from Calgary to Chicago for under C$ 500?

There are currently 14+ open flights from Calgary to Chicago within the next 7 days for less than C$ 500.

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

According to our current data, Alaska Airlines (C$ 404), American Airlines (C$ 430), and Flair Airlines (C$ 444) offers the cheapest pricing from Calgary to Chicago. Users have found that Alaska Airlines is 1% 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 Flair Airlines, which is currently one of the cheapest options available, starting at C$ 250. Delta flights start at C$ 258 while deals on American Airlines start at C$ 267 one-way.

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

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

What are the cheapest flights from Calgary to Chicago?

The cheapest flight price from Calgary to Chicago is C$ 218. On average you can expect to pay C$ 286. The most popular route, (Calgary - Chicago O'Hare Intl), can usually be booked for C$ 395.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from Calgary?

Information is based on travel restrictions from Calgary to Chicago

Most visitors from Calgary need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Calgary must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Chicago.

Quarantine requirements
Visitors from Calgary are not required to quarantine after entering Chicago.

Do I need a test to fly back to Calgary from Chicago?

Returning to Calgary from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) test taken 72 hours before departing to Calgary.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Calgary.

Hide COVID Travel Restrictions for Chicago, IL

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 from YYC to Chicago
3h 29m
Average temperature for January in Chicago
1.0 °C
Avg rainfall for January in Chicago
17.0 mm

Airports servicing Calgary

Airports servicing 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
American Airlines
C$ 209 C$ 482 No cancel fee 71%
Search American Airlines flights
Air Canada
C$ 217 C$ 419 No cancel fee 67%
Search Air Canada flights
Frontier
C$ 228 C$ 337 No cancel fee 62%
Search Frontier flights
Delta
C$ 268 C$ 416 No cancel fee N/A
Search Delta flights
United Airlines
C$ 294 C$ 563 No cancel fee 69%
Search United Airlines flights
WestJet
C$ 304 C$ 499 No cancel fee 60%
Search WestJet flights
Aer Lingus
C$ 362 C$ 604 No cancel fee N/A
Search Aer Lingus flights
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