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Fare Guide

Estimated lowest fares found within 7 days

The cheapest airline(s) flying from Calgary to Chicago is Air Canada.

Travel Period: January 2025 - December 2025

The cheapest month(s) to fly from Calgary to Chicago is January.

Jan 2025
Feb 2025
Mar 2025
Apr 2025
May 2025
Jun 2025
Jul 2025
Aug 2025
Sep 2025
Oct 2025
Nov 2025
Dec 2025

The cheapest day(s) of the week to fly from Calgary to Chicago is Friday.

Sun Sunday
Mon Monday
Tue Tuesday
Wed Wednesday
Thu Thursday
Fri Friday
Sat Saturday

Flight Schedules

Last Updated: Mon, 2 Dec, 2024

Time Earliest
- Earliest
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Depart Earliest
- Earliest
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- M
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12:41 YYC

17:15 ORD

3Hrs, 34m Direct
YYCCalgary Airport 12:41 - ORD 17:15 3h 34m Direct
YYCCalgary Airport 12:41
ORDChicago O'Hare International Airport 17:15
3h 34m
Direct
United Airlines (UA 1655)Airbus
United Airlines (UA 1655)
- M
- T
- W
- T
- F
- S
- S
Airbus

13:30 YYC

22:56 ORD

8Hrs, 26m Direct
YYCCalgary Airport 13:30 - ORD 22:56 8h 26m Direct
YYCCalgary Airport 13:30
ORDChicago O'Hare International Airport 22:56
8h 26m
Direct
United Airlines (UA 750)Airbus
United Airlines (UA 750)
- -
- -
- W
- -
- -
- S
- -
Airbus

13:30 YYC

23:20 ORD

8Hrs, 50m Direct
YYCCalgary Airport 13:30 - ORD 23:20 8h 50m Direct
YYCCalgary Airport 13:30
ORDChicago O'Hare International Airport 23:20
8h 50m
Direct
United Airlines (UA 750)Airbus
United Airlines (UA 750)
- M
- T
- -
- T
- F
- -
- S
Airbus

19:04 YYC

04:40 ORD

8Hrs, 36m 1 Stop (SEA)
YYCCalgary Airport 19:04 - ORD 04:40 8h 36m 1 Stop (SEA) Seattle
YYCCalgary Airport 19:04

SEASeattle/Tacoma International Airport 22:36
SEASeattle/Tacoma International Airport 19:58

ORDChicago O'Hare International Airport 04:40
8h 36m (2h 38m)
1 Stop SEA · Seattle 2h 38m
Alaska Airlines (AS 2096)Embraer Emb 175

Alaska Airlines (AS 328)Boeing 737 800
Alaska Airlines (AS 2096)
- -
- -
- -
- -
- -
- -
- S

19:04 YYC

04:40 ORD

8Hrs, 36m 1 Stop (SEA)
YYCCalgary Airport 19:04 - ORD 04:40 8h 36m 1 Stop (SEA) Seattle
YYCCalgary Airport 19:04

SEASeattle/Tacoma International Airport 22:36
SEASeattle/Tacoma International Airport 19:58

ORDChicago O'Hare International Airport 04:40
8h 36m (2h 38m)
1 Stop SEA · Seattle 2h 38m
Alaska Airlines (AS 2096)Embraer Emb 175

Alaska Airlines (AS 328)Boeing 737 Max 9 Passenger
Alaska Airlines (AS 2096)
- M
- T
- W
- -
- F
- -
- -

19:04 YYC

04:40 ORD

8Hrs, 36m 1 Stop (SEA)
YYCCalgary Airport 19:04 - ORD 04:40 8h 36m 1 Stop (SEA) Seattle
YYCCalgary Airport 19:04

SEASeattle/Tacoma International Airport 22:36
SEASeattle/Tacoma International Airport 19:58

ORDChicago O'Hare International Airport 04:40
8h 36m (2h 38m)
1 Stop SEA · Seattle 2h 38m
Alaska Airlines (AS 2096)Embraer Emb 175

Alaska Airlines (AS 328)Boeing 737
Alaska Airlines (AS 2096)
- -
- -
- -
- T
- -
- -
- -

00:05 YYC

08:57 ORD

7Hrs, 52m 1 Stop (YYZ)
YYCCalgary Airport 00:05 - ORD 08:57 7h 52m 1 Stop (YYZ) Toronto
YYCCalgary Airport 00:05

YYZToronto Lester B Pearson Intl Airport 08:00
YYZToronto Lester B Pearson Intl Airport 06:02

ORDChicago O'Hare International Airport 08:57
7h 52m (1h 58m)
1 Stop YYZ · Toronto 1h 58m
Air Canada (AC 154)Boeing 737 Max 8 Passenger

Air Canada (AC 501)Airbus
Air Canada (AC 154)
- -
- -
- -
- -
- -
- -
- S

00:05 YYC

08:57 ORD

7Hrs, 52m 1 Stop (YYZ)
YYCCalgary Airport 00:05 - ORD 08:57 7h 52m 1 Stop (YYZ) Toronto
YYCCalgary Airport 00:05

YYZToronto Lester B Pearson Intl Airport 08:00
YYZToronto Lester B Pearson Intl Airport 06:02

ORDChicago O'Hare International Airport 08:57
7h 52m (1h 58m)
1 Stop YYZ · Toronto 1h 58m
Air Canada (AC 154)Boeing 737 Max 8 Passenger

Air Canada (AC 501)Airbus A220 300
Air Canada (AC 154)
- M
- T
- W
- T
- -
- S
- -

00:05 YYC

08:58 ORD

7Hrs, 53m 1 Stop (YYZ)
YYCCalgary Airport 00:05 - ORD 08:58 7h 53m 1 Stop (YYZ) Toronto
YYCCalgary Airport 00:05

YYZToronto Lester B Pearson Intl Airport 08:00
YYZToronto Lester B Pearson Intl Airport 06:02

ORDChicago O'Hare International Airport 08:58
7h 53m (1h 58m)
1 Stop YYZ · Toronto 1h 58m
Air Canada (AC 154)Boeing 737 Max 8 Passenger

Air Canada (AC 8901)Embraer Emb 175
Air Canada (AC 154)
- -
- -
- -
- -
- F
- -
- -

00:05 YYC

10:10 ORD

9Hrs, 05m 1 Stop (YYZ)
YYCCalgary Airport 00:05 - ORD 10:10 9h 05m 1 Stop (YYZ) Toronto
YYCCalgary Airport 00:05

YYZToronto Lester B Pearson Intl Airport 09:00
YYZToronto Lester B Pearson Intl Airport 06:02

ORDChicago O'Hare International Airport 10:10
9h 05m (2h 58m)
1 Stop YYZ · Toronto 2h 58m
Air Canada (AC 154)Boeing 737 Max 8 Passenger

United Airlines (UA 1538)Boeing 737 800
Air Canada (AC 154)
- M
- T
- W
- T
- F
- S
- S

00:50 YYC

08:57 ORD

7Hrs, 07m 1 Stop (YYZ)
YYCCalgary Airport 00:50 - ORD 08:57 7h 07m 1 Stop (YYZ) Toronto
YYCCalgary Airport 00:50

YYZToronto Lester B Pearson Intl Airport 08:00
YYZToronto Lester B Pearson Intl Airport 06:47

ORDChicago O'Hare International Airport 08:57
7h 07m (1h 13m)
1 Stop YYZ · Toronto 1h 13m
Air Canada (AC 156)Airbus

Air Canada (AC 501)Airbus A220 300
Air Canada (AC 156)
- -
- T
- W
- -
- -
- -
- -

00:50 YYC

08:57 ORD

7Hrs, 07m 1 Stop (YYZ)
YYCCalgary Airport 00:50 - ORD 08:57 7h 07m 1 Stop (YYZ) Toronto
YYCCalgary Airport 00:50

YYZToronto Lester B Pearson Intl Airport 08:00
YYZToronto Lester B Pearson Intl Airport 06:47

ORDChicago O'Hare International Airport 08:57
7h 07m (1h 13m)
1 Stop YYZ · Toronto 1h 13m
Air Canada (AC 156)Airbus

Air Canada (AC 501)Airbus
Air Canada (AC 156)
- -
- -
- -
- -
- -
- -
- S

00:50 YYC

08:57 ORD

7Hrs, 07m 1 Stop (YYZ)
YYCCalgary Airport 00:50 - ORD 08:57 7h 07m 1 Stop (YYZ) Toronto
YYCCalgary Airport 00:50

YYZToronto Lester B Pearson Intl Airport 08:00
YYZToronto Lester B Pearson Intl Airport 06:47

ORDChicago O'Hare International Airport 08:57
7h 07m (1h 13m)
1 Stop YYZ · Toronto 1h 13m
Air Canada (AC 156)Airbus

Air Canada (AC 501)Airbus A220 300
Air Canada (AC 156)
- M
- -
- -
- T
- -
- S
- -

00:50 YYC

08:58 ORD

7Hrs, 08m 1 Stop (YYZ)
YYCCalgary Airport 00:50 - ORD 08:58 7h 08m 1 Stop (YYZ) Toronto
YYCCalgary Airport 00:50

YYZToronto Lester B Pearson Intl Airport 08:00
YYZToronto Lester B Pearson Intl Airport 06:47

ORDChicago O'Hare International Airport 08:58
7h 08m (1h 13m)
1 Stop YYZ · Toronto 1h 13m
Air Canada (AC 156)Airbus

Air Canada (AC 8901)Embraer Emb 175
Air Canada (AC 156)
- -
- -
- -
- -
- F
- -
- -

00:50 YYC

10:10 ORD

8Hrs, 20m 1 Stop (YYZ)
YYCCalgary Airport 00:50 - ORD 10:10 8h 20m 1 Stop (YYZ) Toronto
YYCCalgary Airport 00:50

YYZToronto Lester B Pearson Intl Airport 09:00
YYZToronto Lester B Pearson Intl Airport 06:47

ORDChicago O'Hare International Airport 10:10
8h 20m (2h 13m)
1 Stop YYZ · Toronto 2h 13m
Air Canada (AC 156)Airbus

United Airlines (UA 1538)Boeing 737 800
Air Canada (AC 156)
- -
- T
- W
- -
- -
- -
- -

00:50 YYC

10:10 ORD

8Hrs, 20m 1 Stop (YYZ)
YYCCalgary Airport 00:50 - ORD 10:10 8h 20m 1 Stop (YYZ) Toronto
YYCCalgary Airport 00:50

YYZToronto Lester B Pearson Intl Airport 09:00
YYZToronto Lester B Pearson Intl Airport 06:47

ORDChicago O'Hare International Airport 10:10
8h 20m (2h 13m)
1 Stop YYZ · Toronto 2h 13m
Air Canada (AC 156)Airbus

United Airlines (UA 1538)Boeing 737 800
Air Canada (AC 156)
- M
- -
- -
- T
- F
- S
- S

00:50 YYC

10:54 ORD

9Hrs, 04m 1 Stop (YUL)
YYCCalgary Airport 00:50 - ORD 10:54 9h 04m 1 Stop (YUL) Montréal
YYCCalgary Airport 00:50

YULMontreal Pierre Elliott Trudeau Int Airport 09:15
YULMontreal Pierre Elliott Trudeau Int Airport 07:15

ORDChicago O'Hare International Airport 10:54
9h 04m (2h)
1 Stop YUL · Montréal 2h
Air Canada (AC 328)Boeing 737 Max 8 Passenger

Air Canada (AC 8959)Embraer Emb 175
Air Canada (AC 328)
- -
- -
- -
- T
- -
- -
- -

00:55 YYC

10:54 ORD

8Hrs, 59m 1 Stop (YUL)
YYCCalgary Airport 00:55 - ORD 10:54 8h 59m 1 Stop (YUL) Montréal
YYCCalgary Airport 00:55

YULMontreal Pierre Elliott Trudeau Int Airport 09:15
YULMontreal Pierre Elliott Trudeau Int Airport 07:15

ORDChicago O'Hare International Airport 10:54
8h 59m (2h)
1 Stop YUL · Montréal 2h
Air Canada (AC 328)Boeing 777 300 Er

Air Canada (AC 8959)Embraer Emb 175
Air Canada (AC 328)
- -
- T
- W
- -
- F
- -
- S

06:00 YYC

14:39 ORD

7Hrs, 39m 1 Stop (YVR)
YYCCalgary Airport 06:00 - ORD 14:39 7h 39m 1 Stop (YVR) Vancouver
YYCCalgary Airport 06:00

YVRVancouver International Airport 08:30
YVRVancouver International Airport 06:44

ORDChicago O'Hare International Airport 14:39
7h 39m (1h 46m)
1 Stop YVR · Vancouver 1h 46m
Air Canada (AC 201)Boeing 737 Max 8 Passenger

Air Canada (AC 1048)Boeing 737 Max 8 Passenger
Air Canada (AC 201)
- M
- T
- W
- T
- F
- S
- S

06:15 YYC

14:51 ORD

7Hrs, 36m 1 Stop (YYZ)
YYCCalgary Airport 06:15 - ORD 14:51 7h 36m 1 Stop (YYZ) Toronto
YYCCalgary Airport 06:15

YYZToronto Lester B Pearson Intl Airport 14:00
YYZToronto Lester B Pearson Intl Airport 12:12

ORDChicago O'Hare International Airport 14:51
7h 36m (1h 48m)
1 Stop YYZ · Toronto 1h 48m
Air Canada (AC 130)Airbus

Air Canada (AC 505)Airbus A220 300
Air Canada (AC 130)
- M
- T
- W
- T
- F
- S
- -

06:15 YYC

14:58 ORD

7Hrs, 43m 1 Stop (YYZ)
YYCCalgary Airport 06:15 - ORD 14:58 7h 43m 1 Stop (YYZ) Toronto
YYCCalgary Airport 06:15

YYZToronto Lester B Pearson Intl Airport 14:00
YYZToronto Lester B Pearson Intl Airport 12:12

ORDChicago O'Hare International Airport 14:58
7h 43m (1h 48m)
1 Stop YYZ · Toronto 1h 48m
Air Canada (AC 130)Airbus

Air Canada (AC 8905)Embraer Emb 175
Air Canada (AC 130)
- -
- -
- -
- -
- -
- -
- S

06:15 YYC

16:40 ORD

9Hrs, 25m 1 Stop (YYZ)
YYCCalgary Airport 06:15 - ORD 16:40 9h 25m 1 Stop (YYZ) Toronto
YYCCalgary Airport 06:15

YYZToronto Lester B Pearson Intl Airport 15:30
YYZToronto Lester B Pearson Intl Airport 12:12

ORDChicago O'Hare International Airport 16:40
9h 25m (3h 18m)
1 Stop YYZ · Toronto 3h 18m
Air Canada (AC 130)Airbus

United Airlines (UA 2364)Boeing 737 800
Air Canada (AC 130)
- -
- T
- -
- -
- -
- -
- -

06:15 YYC

16:41 ORD

9Hrs, 26m 1 Stop (YYZ)
YYCCalgary Airport 06:15 - ORD 16:41 9h 26m 1 Stop (YYZ) Toronto
YYCCalgary Airport 06:15

YYZToronto Lester B Pearson Intl Airport 15:30
YYZToronto Lester B Pearson Intl Airport 12:12

ORDChicago O'Hare International Airport 16:41
9h 26m (3h 18m)
1 Stop YYZ · Toronto 3h 18m
Air Canada (AC 130)Airbus

United Airlines (UA 2364)Airbus
Air Canada (AC 130)
- M
- -
- W
- T
- F
- S
- S

06:19 YYC

13:15 ORD

5Hrs, 56m 1 Stop (DEN)
YYCCalgary Airport 06:19 - ORD 13:15 5h 56m 1 Stop (DEN) Denver
YYCCalgary Airport 06:19

DENDenver Intl Airport 09:40
DENDenver Intl Airport 08:57

ORDChicago O'Hare International Airport 13:15
5h 56m (43m)
1 Stop DEN · Denver 43m
United Airlines (UA 550)Boeing 737 800

United Airlines (UA 2329)Boeing 757 300 Series
United Airlines (UA 550)
- M
- T
- W
- T
- F
- S
- S

06:19 YYC

14:55 ORD

7Hrs, 36m 1 Stop (DEN)
YYCCalgary Airport 06:19 - ORD 14:55 7h 36m 1 Stop (DEN) Denver
YYCCalgary Airport 06:19

DENDenver Intl Airport 11:18
DENDenver Intl Airport 08:57

ORDChicago O'Hare International Airport 14:55
7h 36m (2h 21m)
1 Stop DEN · Denver 2h 21m
United Airlines (UA 550)Boeing 737 800

United Airlines (UA 2312)Boeing 737 Max 9 Passenger
United Airlines (UA 550)
- -
- T
- -
- -
- -
- -
- -

06:19 YYC

14:55 ORD

7Hrs, 36m 1 Stop (DEN)
YYCCalgary Airport 06:19 - ORD 14:55 7h 36m 1 Stop (DEN) Denver
YYCCalgary Airport 06:19

DENDenver Intl Airport 11:18
DENDenver Intl Airport 08:57

ORDChicago O'Hare International Airport 14:55
7h 36m (2h 21m)
1 Stop DEN · Denver 2h 21m
United Airlines (UA 550)Boeing 737 800

United Airlines (UA 2312)Boeing 737 800
United Airlines (UA 550)
- -
- -
- -
- -
- -
- S
- -

06:19 YYC

14:55 ORD

7Hrs, 36m 1 Stop (DEN)
YYCCalgary Airport 06:19 - ORD 14:55 7h 36m 1 Stop (DEN) Denver
YYCCalgary Airport 06:19

DENDenver Intl Airport 11:18
DENDenver Intl Airport 08:57

ORDChicago O'Hare International Airport 14:55
7h 36m (2h 21m)
1 Stop DEN · Denver 2h 21m
United Airlines (UA 550)Boeing 737 800

United Airlines (UA 2312)Boeing 737 900
United Airlines (UA 550)
- M
- -
- W
- T
- F
- -
- S

06:24 YYC

15:21 ORD

7Hrs, 57m 1 Stop (DFW)
YYCCalgary Airport 06:24 - ORD 15:21 7h 57m 1 Stop (DFW) Dallas
YYCCalgary Airport 06:24

DFWDallas/Fort Worth Intl Airport 12:55
DFWDallas/Fort Worth Intl Airport 11:19

ORDChicago O'Hare International Airport 15:21
7h 57m (1h 36m)
1 Stop DFW · Dallas 1h 36m
American Airlines (AA 2521)Airbus

American Airlines (AA 2723)Boeing 737 800
American Airlines (AA 2521)
- -
- -
- -
- -
- -
- S
- S

06:29 YYC

15:21 ORD

7Hrs, 52m 1 Stop (DFW)
YYCCalgary Airport 06:29 - ORD 15:21 7h 52m 1 Stop (DFW) Dallas
YYCCalgary Airport 06:29

DFWDallas/Fort Worth Intl Airport 12:55
DFWDallas/Fort Worth Intl Airport 11:29

ORDChicago O'Hare International Airport 15:21
7h 52m (1h 26m)
1 Stop DFW · Dallas 1h 26m
American Airlines (AA 2521)Airbus

American Airlines (AA 2723)Boeing 737 800
American Airlines (AA 2521)
- M
- -
- -
- T
- -
- -
- -

06:29 YYC

15:21 ORD

7Hrs, 52m 1 Stop (DFW)
YYCCalgary Airport 06:29 - ORD 15:21 7h 52m 1 Stop (DFW) Dallas
YYCCalgary Airport 06:29

DFWDallas/Fort Worth Intl Airport 12:55
DFWDallas/Fort Worth Intl Airport 11:29

ORDChicago O'Hare International Airport 15:21
7h 52m (1h 26m)
1 Stop DFW · Dallas 1h 26m
American Airlines (AA 2521)Airbus

American Airlines (AA 2723)Airbus A321 Neo
American Airlines (AA 2521)
- -
- -
- -
- -
- F
- -
- -

06:29 YYC

15:32 ORD

8Hrs, 03m 1 Stop (DFW)
YYCCalgary Airport 06:29 - ORD 15:32 8h 03m 1 Stop (DFW) Dallas
YYCCalgary Airport 06:29

DFWDallas/Fort Worth Intl Airport 13:10
DFWDallas/Fort Worth Intl Airport 11:29

ORDChicago O'Hare International Airport 15:32
8h 03m (1h 41m)
1 Stop DFW · Dallas 1h 41m
American Airlines (AA 2521)Airbus

American Airlines (AA 2753)Boeing 737 800
American Airlines (AA 2521)
- -
- T
- W
- -
- -
- -
- -

08:00 YYC

16:40 ORD

7Hrs, 40m 1 Stop (YYZ)
YYCCalgary Airport 08:00 - ORD 16:40 7h 40m 1 Stop (YYZ) Toronto
YYCCalgary Airport 08:00

YYZToronto Lester B Pearson Intl Airport 15:30
YYZToronto Lester B Pearson Intl Airport 13:57

ORDChicago O'Hare International Airport 16:40
7h 40m (1h 33m)
1 Stop YYZ · Toronto 1h 33m
Air Canada (AC 132)Airbus

United Airlines (UA 2364)Boeing 737 800
Air Canada (AC 132)
- -
- T
- -
- -
- -
- -
- -

08:00 YYC

16:41 ORD

7Hrs, 41m 1 Stop (YYZ)
YYCCalgary Airport 08:00 - ORD 16:41 7h 41m 1 Stop (YYZ) Toronto
YYCCalgary Airport 08:00

YYZToronto Lester B Pearson Intl Airport 15:30
YYZToronto Lester B Pearson Intl Airport 13:57

ORDChicago O'Hare International Airport 16:41
7h 41m (1h 33m)
1 Stop YYZ · Toronto 1h 33m
Air Canada (AC 132)Airbus

United Airlines (UA 2364)Airbus
Air Canada (AC 132)
- M
- -
- W
- T
- F
- S
- S

08:30 YYC

18:38 ORD

9Hrs, 08m 1 Stop (YOW)
YYCCalgary Airport 08:30 - ORD 18:38 9h 08m 1 Stop (YOW) Ottawa
YYCCalgary Airport 08:30

YOWOttawa McDonald Cartier Intl Airport 17:00
YOWOttawa McDonald Cartier Intl Airport 14:39

ORDChicago O'Hare International Airport 18:38
9h 08m (2h 21m)
1 Stop YOW · Ottawa 2h 21m
Air Canada (AC 356)Boeing 737 Max 8 Passenger

United Airlines (UA 3664)Embraer 175
Air Canada (AC 356)
- M
- T
- W
- T
- F
- S
- S

10:45 YYC

19:32 ORD

7Hrs, 47m 1 Stop (YYZ)
YYCCalgary Airport 10:45 - ORD 19:32 7h 47m 1 Stop (YYZ) Toronto
YYCCalgary Airport 10:45

YYZToronto Lester B Pearson Intl Airport 18:35
YYZToronto Lester B Pearson Intl Airport 16:42

ORDChicago O'Hare International Airport 19:32
7h 47m (1h 53m)
1 Stop YYZ · Toronto 1h 53m
Air Canada (AC 136)Boeing 737 Max 8 Passenger

Air Canada (AC 509)Airbus A220 300
Air Canada (AC 136)
- M
- T
- W
- T
- F
- -
- -

11:55 YYC

22:13 ORD

9Hrs, 18m 1 Stop (YYZ)
YYCCalgary Airport 11:55 - ORD 22:13 9h 18m 1 Stop (YYZ) Toronto
YYCCalgary Airport 11:55

YYZToronto Lester B Pearson Intl Airport 21:00
YYZToronto Lester B Pearson Intl Airport 17:52

ORDChicago O'Hare International Airport 22:13
9h 18m (3h 08m)
1 Stop YYZ · Toronto 3h 08m
Air Canada (AC 140)Airbus

United Airlines (UA 5728)Embraer 175
Air Canada (AC 140)
- M
- T
- W
- -
- F
- -
- S

11:55 YYC

22:13 ORD

9Hrs, 18m 1 Stop (YYZ)
YYCCalgary Airport 11:55 - ORD 22:13 9h 18m 1 Stop (YYZ) Toronto
YYCCalgary Airport 11:55

YYZToronto Lester B Pearson Intl Airport 21:00
YYZToronto Lester B Pearson Intl Airport 17:52

ORDChicago O'Hare International Airport 22:13
9h 18m (3h 08m)
1 Stop YYZ · Toronto 3h 08m
Air Canada (AC 140)Airbus

United Airlines (UA 5728)Embraer 175
Air Canada (AC 140)
- -
- -
- -
- T
- -
- -
- -

12:45 YYC

21:19 ORD

7Hrs, 34m 1 Stop (DFW)
YYCCalgary Airport 12:45 - ORD 21:19 7h 34m 1 Stop (DFW) Dallas
YYCCalgary Airport 12:45

DFWDallas/Fort Worth Intl Airport 18:55
DFWDallas/Fort Worth Intl Airport 17:40

ORDChicago O'Hare International Airport 21:19
7h 34m (1h 15m)
1 Stop DFW · Dallas 1h 15m
American Airlines (AA 2517)Airbus

American Airlines (AA 566)Boeing 737 800
American Airlines (AA 2517)
- M
- -
- -
- T
- F
- S
- S

12:45 YYC

21:28 ORD

7Hrs, 43m 1 Stop (DFW)
YYCCalgary Airport 12:45 - ORD 21:28 7h 43m 1 Stop (DFW) Dallas
YYCCalgary Airport 12:45

DFWDallas/Fort Worth Intl Airport 19:00
DFWDallas/Fort Worth Intl Airport 17:40

ORDChicago O'Hare International Airport 21:28
7h 43m (1h 20m)
1 Stop DFW · Dallas 1h 20m
American Airlines (AA 2517)Airbus

American Airlines (AA 2881)Boeing 737 800
American Airlines (AA 2517)
- -
- -
- W
- -
- -
- -
- -

12:45 YYC

23:09 ORD

9Hrs, 24m 1 Stop (DFW)
YYCCalgary Airport 12:45 - ORD 23:09 9h 24m 1 Stop (DFW) Dallas
YYCCalgary Airport 12:45

DFWDallas/Fort Worth Intl Airport 20:40
DFWDallas/Fort Worth Intl Airport 17:40

ORDChicago O'Hare International Airport 23:09
9h 24m (3h)
1 Stop DFW · Dallas 3h
American Airlines (AA 2517)Airbus

American Airlines (AA 1125)Boeing 737 800
American Airlines (AA 2517)
- M
- -
- -
- T
- F
- S
- S

14:09 YYC

21:30 ORD

6Hrs, 21m 1 Stop (DEN)
YYCCalgary Airport 14:09 - ORD 21:30 6h 21m 1 Stop (DEN) Denver
YYCCalgary Airport 14:09

DENDenver Intl Airport 18:00
DENDenver Intl Airport 16:43

ORDChicago O'Hare International Airport 21:30
6h 21m (1h 17m)
1 Stop DEN · Denver 1h 17m
United Airlines (UA 1953)Boeing 737 800

United Airlines (UA 521)Boeing 757 300 Series
United Airlines (UA 1953)
- M
- T
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14:09 YYC

23:10 ORD

8Hrs, 01m 1 Stop (DEN)
YYCCalgary Airport 14:09 - ORD 23:10 8h 01m 1 Stop (DEN) Denver
YYCCalgary Airport 14:09

DENDenver Intl Airport 19:40
DENDenver Intl Airport 16:43

ORDChicago O'Hare International Airport 23:10
8h 01m (2h 57m)
1 Stop DEN · Denver 2h 57m
United Airlines (UA 1953)Boeing 737 800

United Airlines (UA 2258)Boeing 757 300 Series
United Airlines (UA 1953)
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14:09 YYC

23:51 ORD

8Hrs, 42m 1 Stop (DEN)
YYCCalgary Airport 14:09 - ORD 23:51 8h 42m 1 Stop (DEN) Denver
YYCCalgary Airport 14:09

DENDenver Intl Airport 20:20
DENDenver Intl Airport 16:43

ORDChicago O'Hare International Airport 23:51
8h 42m (3h 37m)
1 Stop DEN · Denver 3h 37m
United Airlines (UA 1953)Boeing 737 800

United Airlines (UA 377)Boeing 757 300 Series
United Airlines (UA 1953)
- -
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- -
- -

15:05 YYC

01:11 ORD

9Hrs, 06m 1 Stop (SFO)
YYCCalgary Airport 15:05 - ORD 01:11 9h 06m 1 Stop (SFO) San Francisco
YYCCalgary Airport 15:05

SFOSan Francisco International Airport 18:45
SFOSan Francisco International Airport 17:08

ORDChicago O'Hare International Airport 01:11
9h 06m (1h 37m)
1 Stop SFO · San Francisco 1h 37m
United Airlines (UA 490)Boeing 737 Max 8 Passenger

United Airlines (UA 1896)Airbus A321 Neo
United Airlines (UA 490)
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What’s the fastest flight time from Calgary to Chicago?

The fastest flight time for direct flights from Calgary to Chicago is 3 hours 34 minutes. Check latest flight schedules & prices on Wego.

What’s the most popular airline flying from Calgary to Chicago?

The most popular airline flying from Calgary to Chicago is Air Canada. Find the latest flight deals on Wego.

How far is Chicago from Calgary?

The flight distance between Calgary and Chicago is 2251km. Check all available flights on Wego.

When is the earliest and latest flight of the day?

The earliest flight of the day departs at 00:05. The last flight of the day departs at 19:04. See the full list of flight times on Wego.

How many airlines offer direct flights from Calgary to Chicago?

There are 1 airlines that offer direct flights from Calgary to Chicago. Find out the list of airlines on Wego.

Popular Airlines Flying From Calgary to Chicago

Air Canada ‏()

Popular Destinations From Chicago

Popular Destinations From Calgary

Popular Hotels in Chicago

Hotels In Popular Destinations

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