Is Air Canada cheaper than other airlines flying to Chicago?

With an average return price of C$ 815, Air Canada is the most expensive airline flying into Chicago. The cheapest airline flying to Chicago is American Airlines.

Which other airlines fly to Chicago?

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

How much is a flight to Chicago with Air Canada?

On average, Air Canada flights to Chicago cost C$ 815 for a round-trip.

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 flights to Chicago (CHI) from C$ 152

Flight Deals

Cheap Air Canada Flight Deals to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip Air Canada flight deals to Chicago

Mon, 27 Apr - Fri, 1 May

1:20 p.m. - 2:55 p.m.

YUL

ORD

2h 35mdirect

3:40 p.m. - 7:04 p.m.

ORD

YUL

2h 24mdirect

C$ 238Air Canada

Sat, 14 Mar - Mon, 16 Mar

9:25 a.m. - 11:18 a.m.

YUL

ORD

2h 53mdirect

7:15 a.m. - 10:20 a.m.

ORD

YUL

2h 05mdirect

C$ 239Air Canada

Thu, 12 Mar - Mon, 16 Mar

6:25 p.m. - 8:10 p.m.

YUL

ORD

2h 45mdirect

7:15 a.m. - 10:20 a.m.

ORD

YUL

2h 05mdirect

C$ 242Air Canada

Thu, 12 Mar - Mon, 16 Mar

6:25 p.m. - 8:10 p.m.

YUL

ORD

2h 45mdirect

7:15 a.m. - 10:20 a.m.

ORD

YUL

2h 05mdirect

C$ 243Air Canada

Wed, 18 Mar - Mon, 23 Mar

1:10 p.m. - 2:55 p.m.

YUL

ORD

2h 45mdirect

3:35 p.m. - 6:40 p.m.

ORD

YUL

2h 05mdirect

C$ 250Air Canada

Fri, 1 May - Mon, 4 May

6:30 p.m. - 8:08 p.m.

YUL

ORD

2h 38mdirect

8:45 a.m. - 12:00 p.m.

ORD

YUL

2h 15mdirect

C$ 251Air Canada

Sun, 29 Mar - Sun, 5 Apr

12:05 p.m. - 1:05 p.m.

YYZ

ORD

2h 00mdirect

9:50 a.m. - 12:26 p.m.

ORD

YYZ

1h 36mdirect

C$ 261Air Canada

Fri, 27 Mar - Fri, 3 Apr

12:05 p.m. - 1:01 p.m.

YYZ

ORD

1h 56mdirect

4:15 p.m. - 6:57 p.m.

ORD

YYZ

1h 42mdirect

C$ 262Air Canada

Thu, 5 Mar - Sun, 8 Mar

8:15 a.m. - 9:13 a.m.

YYZ

ORD

1h 58mdirect

8:40 p.m. - 11:19 p.m.

ORD

YYZ

1h 39mdirect

C$ 264Air Canada

Fri, 5 Jun - Sun, 7 Jun

8:40 a.m. - 10:18 a.m.

YUL

ORD

2h 38mdirect

8:45 a.m. - 11:56 a.m.

ORD

YUL

2h 11mdirect

C$ 264Air Canada

Useful Info

Low season	January
High season	April
Cheapest flight	C$ 152
Average price round-trip	C$ 815
Good deal round-trip	C$ 692

Best time to beat the crowds but there is an average 5% increase in price.

Most popular time to fly and prices are also 6% lower on average.

Flight from Montreal 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

Is Air Canada cheaper than other airlines flying to Chicago?
With an average return price of C$ 815, Air Canada is the most expensive airline flying into Chicago. The cheapest airline flying to Chicago is American Airlines.
Which other airlines fly to Chicago?
Along with Air Canada, you can also fly to Chicago with American Airlines, Porter Airlines, United Airlines and WestJet.
How much is a flight to Chicago with Air Canada?
On average, Air Canada flights to Chicago cost C$ 815 for a round-trip.
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.

The cheapest flight to Chicago with Air Canada found on KAYAK in the last 2 weeks departed from Winnipeg and cost C$ 332.
If you’re intending to fly with Air Canada, book your flight to Chicago at least 2 weeks before departure to ensure a below-average price.
High season for flights to Chicago with Air Canada is May and prices are highest at this time. The cheapest month to fly is January.

7.1

Good10,000 verified ratings

6.3Food

7.8Crew

6.8Entertainment

7.3Boarding

7.1Comfort

8.0 Very good

Anonymous, Feb 2026

its all good

8.0 Very good

Anonymous, Feb 2026

there was no food or entertainment on that short 1.5 hour flight unless you mean the cookie and the overhead announcements... Those Q-400's are the workhorse of the rugged coast and mountains for sure.

6.0 Okay

Alfred, Feb 2026

For the amount of money I spent, I definitely expected a better experience

2.0 Poor

Kendall Lynn, Feb 2026

The last 3 hours it was freezing cold in row 56. Multiple people had their winter coats on and were utilizing the blankets provided by the airline. I also did not have easy access to figure out how to book my food allergy and advance for my meals. Most of everything I received was something I couldn't eat. This needs to be made more accessible. Also, I'm 5'10 which is the average height of the American male. I flew from Philadelphia to Toronto and then to Tokyo and the seats were absolutely unbearable. For that long of a flight it is impossible to get comfortable when doing anything. Flights need to have more space and stop prioritizing costs over people.

10.0 Wonderful

Anonymous, Feb 2026

They do a good job.

10.0 Wonderful

Beth, Feb 2026

they were super helpful. Agents at the desk got me on an earlier flight and I was able to get home several hours earlier.

10.0 Wonderful

Grant, Feb 2026

Everything good

2.0 Poor

Michael, Feb 2026

Delays and very uncomfortable seating