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Find cheap Air Canada flights to Chicago from C$ 167

1 adult
0 bags
Wed 29/5
Wed 5/6

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Good to know

Low season

January

High season

August

Cheapest flight

C$ 167

Average price round-trip

C$ 644

Good deal one-way

C$ 493
Best time to beat the crowds (16% less expensive on average)
Most popular time to fly and prices are also 5% lower on average.
Flight from Calgary to Chicago O'Hare Airport
(avg. price over the last 2 weeks)
or less

When to book flights with Air Canada to Chicago

Average price per month
Flight prices as travel date approaches

FAQs for flying to Chicago with Air Canada

  • Which other airlines fly to Chicago?

    Along with Air Canada, you can also fly to Chicago with Porter Airlines, United Airlines and Porter Airlines.

  • Which airport do Air Canada flights to Chicago fly into?

    Air Canada flights to Chicago will fly into either Chicago O'Hare Airport, Chicago Midway Airport and Chicago Greater Rockford.

  • Are there any other airlines in Star Alliance that fly to Chicago?

    The only other Star Alliance airline flying to Chicago is United Airlines.

Air Canada customer reviews

7.0
GoodBased on 6,883 verified guest reviews
6.8Entertainment
7.0Comfort
7.8Crew
7.2Boarding
6.2Food
Traveler rating:
Sort by:
A
10.0 Wonderful
Pros:Wel,l my flight out of SFO was delayed by an hour and ~20 minutes, which was the length of my layover in Toronto. The pilot was able to make up some time in the air, but I still had to go through customs, security, and then run through most of the Toronto airport with only 25 minutes (before my flight left, probably even less because they close the doors before take off). I was off the plane at 7:30. My flight to Charlottetown was on-time, leaving at 7:55. The nicest male flight attendant on the plane moved me to a seat right before first class and put my carry-on in the closet at the front so I could be of the first off the plane! I ran through the airport, customs, security and all. I got to the gate at 7:41. The lady at the gate saw me running from far off and asked if I was Michelle. She was so happy that I had made it and let me catch me breath before I boarded. The delay on the first flight was very unfortunate and stress-inducing, but all the Air Canada people I interacted with along the way were very wonderful.
Cons:The delay.
S
7.0 Good
Cons:Air Canada not even offering a snack on a 3 hour flight now. Ridiculous.
P
8.6 Very good
Cons:dirt and stuff on floor between floor and wall, bad, never seen that before in a nearly new plane
A
7.3 Good
Pros:Brand new aircraft
Cons:Not gourmet not even fast food. A lot of area for improvement.
A
7.6 Good
Pros:The movie selection was fantastic, the check-in and security was quick, the accommodation for my kosher meal was much appreciated.
Cons:The plane was cramped with very little legroom.
A
4.0 Mediocre
Pros:Nothing
Cons:Everything
A
8.0 Very good
Pros:Service good
A
9.3 Wonderful
Pros:Tat everyone was so friendly
Cons:Couldn't sleep
S
10.0 Wonderful
Pros:Everything
Cons:Nothing
A
5.3 Fair
Pros:Difficult to find employees in the Toronto airport. Security needed to help me locate someone after my plane was delayed causing me to miss my connection. On the way back had a delay again lucky if was my final leg.
Read more about Air Canada

Book Cheap flights with Air Canada to Chicago

Recent round-trip flight deals

10/8Sat
directAir Canada
1h 54mYYZ-ORD
14/8Wed
directAir Canada
1h 48mORD-YYZ
C$ 350
31/7Wed
directAir Canada
1h 56mYYZ-ORD
6/8Tue
directAir Canada
1h 48mORD-YYZ
C$ 351
10/8Sat
directAir Canada
1h 54mYYZ-ORD
14/8Wed
1 stopAir Canada
6h 47mORD-YYZ
C$ 354
20/5Mon
1 stopAir Canada
4h 31mYYZ-ORD
27/5Mon
directAir Canada
1h 52mORD-YYZ
C$ 358
12/5Sun
directAir Canada
1h 54mYYZ-ORD
31/5Fri
directAir Canada
1h 48mORD-YYZ
C$ 360
13/8Tue
directAir Canada
1h 57mYYZ-ORD
15/8Thu
1 stopAir Canada
6h 47mORD-YYZ
C$ 366
12/5Sun
1 stopAir Canada
4h 36mYYZ-ORD
31/5Fri
directAir Canada
1h 48mORD-YYZ
C$ 367
25/9Wed
1 stopAir Canada
8h 43mYYC-ORD
2/10Wed
1 stopAir Canada
9h 49mORD-YYC
C$ 367
30/5Thu
directAir Canada
1h 54mYYZ-ORD
2/6Sun
directAir Canada
1h 48mORD-YYZ
C$ 369
11/5Sat
directAir Canada
2h 04mYYZ-ORD
11/5Sat
directAir Canada
1h 42mORD-YYZ
C$ 371
4/6Tue
directAir Canada
2h 31mYUL-ORD
11/6Tue
1 stopAir Canada
6h 18mORD-YUL
C$ 377
20/7Sat
1 stopAir Canada
7h 40mYYZ-ORD
27/7Sat
1 stopAir Canada
5h 57mORD-YYZ
C$ 378
26/5Sun
directAir Canada
2h 43mYUL-ORD
2/6Sun
1 stopAir Canada
6h 18mORD-YUL
C$ 378
24/5Fri
1 stopAir Canada
6h 53mYTZ-ORD
27/5Mon
1 stopAir Canada
6h 28mORD-YTZ
C$ 378
29/6Sat
directAir Canada
1h 56mYYZ-ORD
7/7Sun
directAir Canada
1h 48mORD-YYZ
C$ 380
30/5Thu
directAir Canada
1h 54mYYZ-ORD
31/5Fri
directAir Canada
1h 48mORD-YYZ
C$ 381
4/7Thu
1 stopAir Canada
6h 40mYYZ-ORD
8/7Mon
1 stopAir Canada
5h 57mORD-YYZ
C$ 385
30/5Thu
directAir Canada
1h 54mYYZ-ORD
3/6Mon
directAir Canada
1h 45mORD-YYZ
C$ 389
4/6Tue
1 stopAir Canada
4h 44mYUL-ORD
11/6Tue
1 stopAir Canada
6h 18mORD-YUL
C$ 392
30/5Thu
directAir Canada
1h 54mYYZ-ORD
3/6Mon
directAir Canada
1h 45mORD-YYZ
C$ 393

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Recent one-way flight deals

12/5Sun
directAir Canada
3h 30mYYC-ORD
C$ 167
27/5Mon
1 stopAir Canada
7h 54mYYC-ORD
C$ 182
5/5Sun
directAir Canada
3h 30mYYC-ORD
C$ 194
3/7Wed
1 stopAir Canada
7h 54mYYC-ORD
C$ 202
28/5Tue
directAir Canada
1h 54mYYZ-ORD
C$ 203
27/7Sat
directAir Canada
1h 57mYYZ-ORD
C$ 206
18/6Tue
1 stopAir Canada
5h 53mYTZ-ORD
C$ 206
6/5Mon
1 stopAir Canada
7h 48mYYC-ORD
C$ 208
1/6Sat
1 stopAir Canada
4h 31mYYZ-ORD
C$ 213
4/9Wed
1 stopAir Canada
7h 51mYYC-ORD
C$ 213
4/6Tue
directAir Canada
2h 31mYUL-ORD
C$ 216
27/8Tue
1 stopAir Canada
4h 22mYTZ-ORD
C$ 216
15/5Wed
directAir Canada
1h 59mYYZ-ORD
C$ 217
15/5Wed
1 stopAir Canada
5h 55mYTZ-ORD
C$ 217
22/6Sat
directAir Canada
1h 54mYYZ-ORD
C$ 218
29/5Wed
directAir Canada
1h 54mYYZ-ORD
C$ 220
6/5Mon
directAir Canada
4h 13mYVR-ORD
C$ 220
21/5Tue
directAir Canada
1h 54mYYZ-ORD
C$ 221
27/8Tue
1 stopAir Canada
5h 32mYYZ-ORD
C$ 223
15/5Wed
1 stopAir Canada
4h 31mYYZ-ORD
C$ 224

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Flights to Chicago - Air Canada

Return flight deals:

Chicago - Canada

Cabin classes:

C$ 987
First Class flights to Chicago
C$ 827
Business Class flights to Chicago
C$ 542
C$ 279

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