$411 Business Class Flight Deals from Calgary to Chicago

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Stops

Nonstop
from $939
Up to 1 stop
$897

Airlines

Air Canada
$897
American Airlines
$898

Cabin Class

Business
$897

Departure Airports

Calgary International Airport
$897

Arrival Airports

Chicago O Hare Airport
$897

Layover Airports

Dallas Fort Worth International Airport
$898
Denver International Airport
$924
Montreal Trudeau Airport
$897
Seattle Tacoma International Airport
$1097
Toronto Pearson Airport
$904

Best Price. GUARANTEED.

Exclusively for Priceline Members
Tired of searching? Book now!
We'll refund the difference if you find a lower price.

BUNDLE & SAVE

Book a flight & hotel together for extra savings.

On average save $240 per traveler

Air Canada

08/11/25

1:05am

YYC

7h 47m

YUL

08/11/25

9:52am

ORD

Air Canada

08/18/25

8:03pm

ORD

3h 50m

Direct

08/18/25

10:53pm

YYC

^$897

Air Canada

08/11/25

1:05am

YYC

7h 47m

YUL

08/11/25

9:52am

ORD

Air Canada

08/18/25

8:45am

ORD

3h 53m

Direct

08/18/25

11:38am

YYC

^$897

American Airlines

08/11/25

6:29am

YYC

3h 25m

Direct

08/11/25

10:54am

ORD

American Airlines

08/18/25

6:00am

ORD

16h 58m

DFW

08/18/25

9:58pm

YYC

^$898

Air Canada

08/11/25

12:20am

YYC

7h 49m

YYZ

08/11/25

9:09am

ORD

Air Canada

08/18/25

8:45am

ORD

3h 53m

Direct

08/18/25

11:38am

YYC

^$904

Air Canada

08/11/25

6:00am

YYC

8h 4m

YYZ

08/11/25

3:04pm

ORD

Air Canada

08/18/25

8:03pm

ORD

3h 50m

Direct

08/18/25

10:53pm

YYC

^$904

Air Canada

08/11/25

11:45pm

YYC

8h 24m

YYZ

08/12/25

9:09am

ORD

Air Canada

08/18/25

8:03pm

ORD

3h 50m

Direct

08/18/25

10:53pm

YYC

^$904

Air Canada

08/11/25

1:10am

YYC

6h 59m

YYZ

08/11/25

9:09am

ORD

Air Canada

08/18/25

8:45am

ORD

3h 53m

Direct

08/18/25

11:38am

YYC

^$904

Air Canada

08/11/25

12:20am

YYC

7h 49m

YYZ

08/11/25

9:09am

ORD

Air Canada

08/18/25

8:03pm

ORD

3h 50m

Direct

08/18/25

10:53pm

YYC

^$904

Air Canada

08/11/25

1:10am

YYC

6h 59m

YYZ

08/11/25

9:09am

ORD

Air Canada

08/18/25

8:03pm

ORD

3h 50m

Direct

08/18/25

10:53pm

YYC

^$904

Air Canada

08/11/25

6:00am

YYC

8h 4m

YYZ

08/11/25

3:04pm

ORD

Air Canada

08/18/25

8:45am

ORD

3h 53m

Direct

08/18/25

11:38am

YYC

^$904

Air Canada

08/11/25

11:45pm

YYC

8h 24m

YYZ

08/12/25

9:09am

ORD

Air Canada

08/18/25

8:45am

ORD

3h 53m

Direct

08/18/25

11:38am

YYC

^$904

American Airlines

08/11/25

6:29am

YYC

3h 25m

Direct

08/11/25

10:54am

ORD

American Airlines

08/18/25

2:55pm

ORD

8h 3m

DFW

08/18/25

9:58pm

YYC

^$915

Air Canada

08/11/25

7:30pm

YYC

13h 11m

DEN

08/12/25

9:41am

ORD

Air Canada

08/18/25

8:45am

ORD

3h 53m

Direct

08/18/25

11:38am

YYC

^$924

Air Canada

08/11/25

7:30pm

YYC

13h 11m

DEN

08/12/25

9:41am

ORD

Air Canada

08/18/25

8:03pm

ORD

3h 50m

Direct

08/18/25

10:53pm

YYC

^$924

Air Canada

08/11/25

1:05am

YYC

7h 47m

YUL

08/11/25

9:52am

ORD

Air Canada

08/18/25

9:14pm

ORD

15h 41m

YYZ

08/19/25

11:55am

YYC

^$933

Air Canada

08/11/25

1:05am

YYC

7h 47m

YUL

08/11/25

9:52am

ORD

Air Canada

08/18/25

9:14pm

ORD

13h 16m

YYZ

08/19/25

9:30am

YYC

^$933

Air Canada

08/11/25

1:05am

YYC

7h 47m

YUL

08/11/25

9:52am

ORD

Air Canada

08/18/25

8:50am

ORD

15h 20m

YYZ

08/18/25

11:10pm

YYC

^$933

Air Canada

08/11/25

1:05am

YYC

7h 47m

YUL

08/11/25

9:52am

ORD

Air Canada

08/18/25

9:14pm

ORD

12h 26m

YYZ

08/19/25

8:40am

YYC

^$933

Air Canada

08/11/25

1:05am

YYC

7h 47m

YUL

08/11/25

9:52am

ORD

Air Canada

08/18/25

7:15am

ORD

16h 58m

YUL

08/18/25

11:13pm

YYC

^$936

American Airlines

08/11/25

6:29am

YYC

3h 25m

Direct

08/11/25

10:54am

ORD

American Airlines

08/18/25

8:34pm

ORD

3h 55m

Direct

08/18/25

11:29pm

YYC

^$939

American Airlines

08/11/25

6:45am

YYC

23h 39m

DFW

08/12/25

7:24am

ORD

American Airlines

08/18/25

6:00am

ORD

16h 58m

DFW

08/18/25

9:58pm

YYC

^$979

American Airlines

08/11/25

6:45am

YYC

23h 39m

DFW

08/12/25

7:24am

ORD

American Airlines

08/18/25

2:55pm

ORD

8h 3m

DFW

08/18/25

9:58pm

YYC

^$995

American Airlines

08/11/25

6:45am

YYC

23h 39m

DFW

08/12/25

7:24am

ORD

American Airlines

08/18/25

8:34pm

ORD

3h 55m

Direct

08/18/25

11:29pm

YYC

^$1018

Air Canada

08/11/25

1:10am

YYC

6h 59m

YYZ

08/11/25

9:09am

ORD

Alaska Airlines

08/18/25

5:54pm

ORD

6h 56m

SEA

08/18/25

11:50pm

YYC

^$1097

American Airlines

08/11/25

6:29am

YYC

3h 25m

Direct

08/11/25

10:54am

ORD

American Airlines

08/18/25

9:55am

ORD

3h 39m

Direct

08/18/25

12:34pm

YYC

^$1102

American Airlines

08/11/25

6:45am

YYC

28h 37m

DFW

08/12/25

12:22pm

ORD

American Airlines

08/18/25

6:00am

ORD

16h 58m

DFW

08/18/25

9:58pm

YYC

^$1159

Air Canada

08/11/25

8:30am

YYC

3h 31m

Direct

08/11/25

1:01pm

ORD

Air Canada

08/18/25

8:03pm

ORD

3h 50m

Direct

08/18/25

10:53pm

YYC

^$1324

Air Canada

08/11/25

12:38pm

YYC

3h 32m

Direct

08/11/25

5:10pm

ORD

Air Canada

08/18/25

8:03pm

ORD

3h 50m

Direct

08/18/25

10:53pm

YYC

^$1324

Air Canada

08/11/25

8:30am

YYC

3h 31m

Direct

08/11/25

1:01pm

ORD

Air Canada

08/18/25

8:45am

ORD

3h 53m

Direct

08/18/25

11:38am

YYC

^$1324

Air Canada

08/11/25

12:38pm

YYC

3h 32m

Direct

08/11/25

5:10pm

ORD

Air Canada

08/18/25

8:45am

ORD

3h 53m

Direct

08/18/25

11:38am

YYC

^$1324

Top Deals on flights Business Class from Calgary to Chicago

Calgary, CA (YYC) - Chicago, US (CHI)

American Airlines

Aug 13

6:29am

YYC

3h 25m

Direct

Aug 13

10:54am

ORD

as low as

^$411

Calgary, CA (YYC) - Chicago, US (CHI)

American Airlines

Aug 13

1:29pm

YYC

3h 25m

Direct

Aug 13

5:54pm

ORD

as low as

^$452

Calgary, CA (YYC) - Chicago, US (CHI)

Air Canada

Aug 13

6:00am

YYC

7h 55m

YUL

Aug 13

2:55pm

ORD

as low as

^$466

Calgary, CA (YYC) - Chicago, US (CHI)

American Airlines

Aug 13

6:45am

YYC

23h 40m

DFW

Aug 14

7:25am

ORD

as low as

^$468

Calgary, CA (YYC) - Chicago, US (CHI)

American Airlines

Aug 13

6:45am

YYC

7h 2m

DFW

Aug 13

2:47pm

ORD

as low as

^$468

Calgary, CA (YYC) - Chicago, US (CHI)

Air Canada

Aug 13

9:40am

YYC

6h 57m

YYZ

Aug 13

5:37pm

ORD

as low as

^$473

Calgary, CA (YYC) - Chicago, US (CHI)

Air Canada

Aug 13

12:20am

YYC

7h 49m

YYZ

Aug 13

9:09am

ORD

as low as

^$473

Calgary, CA (YYC) - Chicago, US (CHI)

Air Canada

Aug 13

7:10am

YYC

6h 54m

YYZ

Aug 13

3:04pm

ORD

as low as

^$473

Calgary, CA (YYC) - Chicago, US (CHI)

Air Canada

Aug 13

12:38pm

YYC

3h 32m

Direct

Aug 13

5:10pm

ORD

as low as

^$477

Calgary, CA (YYC) - Chicago, US (CHI)

American Airlines

Aug 13

6:45am

YYC

8h 5m

DFW

Aug 13

3:50pm

ORD

as low as

^$590

Calgary, CA (YYC) - Chicago, US (CHI)

Air Canada

Aug 13

1:05am

YYC

7h 47m

YUL

Aug 13

9:52am

ORD

as low as

^$726

Calgary, CA (YYC) - Chicago, US (CHI)

Air Canada

Aug 13

7:00am

YYC

6h 54m

YVR

Aug 13

2:54pm

ORD

as low as

^$1009

Frequently Asked Questions

Are there convenient layover flights from Calgary to Chicago?

Yes, convenient layover flights from Calgary to Chicago include Air Canada for $173 (10h 28m, layover in Montreal), United Airlines for $181 (7h, layover in Denver), Delta Air Lines for $216 (10h 42m, layover in Salt Lake City), American Airlines for $365 (9h 20m, layover in Dallas), and WestJet for $418 (10h 9m, layover in Seattle).

What are the most convenient layover airports for my flight from Calgary to Chicago?

The most convenient layover airports for your flight are Montreal Trudeau, Denver International, Salt Lake City International, Dallas Fort Worth International, and Seattle Tacoma International.

What is the cheapest and fastest flight from Calgary to Chicago?

The cheapest flight is with Air Canada at $173, taking 10 hours 28 minutes with 1 stop. The fastest flight is with United Airlines at $352, taking 4 hours 20 minutes non-stop.

What are all possible destination arrival airports?

The possible arrival airport for your flight from Calgary is Chicago O'Hare Airport.

What is the time difference between destination and arrival?

The time difference between Calgary, Canada and Chicago, USA is typically one hour, with Chicago being ahead of Calgary.

Is there a direct flight from Calgary to Chicago?

Yes, there are direct flights from Calgary to Chicago. United Airlines offers a non-stop flight for $180 with a flight time of 4 hours 33 minutes. Air Canada also provides a non-stop option for $225 with the same flight duration. WestJet and Delta Air Lines have similar non-stop flights priced at $311.

Flights to Chicago

Top Destinations

Origins

Return flights

Cabin Class

Flights
North America
Canada
Alberta
Calgary

➔ Business Class Flights From Chicago To Calgary

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Business Class Flight Deals from Calgary to Chicago from $411

Stops

Airlines

Cabin Class

Departure Airports

Arrival Airports

Layover Airports

Best Price. GUARANTEED.

Top Deals on flights Business Class from Calgary to Chicago

Frequently Asked Questions

Flights to Chicago