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Cheap flights from Canada to Chicago from C$ 218

YYZ — CHI
3 Nov — 10 Nov1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Canada to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Canada to Chicago

Sat 24/102:00 p.m. -
Nonstop1h 55m
Fri 30/1010:15 a.m. -
Nonstop1h 37m
Deal found 1/10C$ 312
Sat 24/1012:15 p.m. -
Nonstop2h 10m
Fri 30/101:55 p.m. -
Nonstop1h 47m
Deal found 2/10C$ 323
Fri 30/102:45 p.m. -
1 stop7h 59m
Sat 31/107:03 a.m. -
Nonstop1h 44m
Deal found 30/9C$ 349
Fri 6/114:30 p.m. -
Nonstop2h 13m
Mon 9/118:45 a.m. -
Nonstop1h 42m
Deal found 2/10C$ 372
Tue 17/1110:45 a.m. -
1 stop5h 17m
Tue 24/111:55 p.m. -
Nonstop1h 47m
Deal found 3/10C$ 372
Sat 28/1110:35 a.m. -
Nonstop2h 05m
Tue 1/126:20 p.m. -
Nonstop1h 46m
Deal found 1/10C$ 376
Sat 31/1010:35 a.m. -
Nonstop2h 05m
Tue 3/1112:20 p.m. -
Nonstop1h 46m
Deal found 1/10C$ 378
Sat 21/114:35 p.m. -
Nonstop2h 05m
Mon 23/1112:20 p.m. -
Nonstop1h 46m
Deal found 30/9C$ 379
Wed 25/118:30 a.m. -
1 stop7h 32m
Sun 29/117:05 a.m. -
1 stop6h 16m
Deal found 3/10C$ 383
Sat 31/107:00 a.m. -
1 stop5h 07m
Sat 7/1110:15 a.m. -
Nonstop1h 37m
Deal found 3/10C$ 385
Tue 27/1012:05 p.m. -
Nonstop2h 15m
Sat 31/101:55 p.m. -
Nonstop1h 47m
Deal found 3/10C$ 385
Fri 30/104:30 p.m. -
Nonstop2h 13m
Sat 31/108:45 a.m. -
Nonstop1h 42m
Deal found 30/9C$ 388

Find flight deals from Canada to Chicago

Round-trip from

C$ 312

One-way from

C$ 218

Popular in

October

Cheapest in

February

Average price

C$ 432

Good round-trip deal

C$ 328 or less

Good one-way deal

C$ 186 or less
Air Canada
  • Air Canada
  • 24/10-30/10
  • Nonstop
  • 3h 32m total
  • Canada to Chicago
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Air Transat
  • Air Transat
  • 15/11-31/12
  • Nonstop
  • 2h 05m total
  • Canada to Chicago
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Highest demand for flights based on searches. 2% potential increase in price (C$ 12 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease (C$ 5 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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Price to beat on a round-trip flight from Canada to Chicago (CHI).
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Price to beat on a one-way flight from Canada to Chicago (CHI).
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Canada to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 23/10

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 239

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 22/10

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 239

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Thu 29/10

10:35 a.m.-11:40 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 251

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 15/1

1:35 p.m.-8:53 p.m.

1 stop7h 18m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 252

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Sat 21/11

2:20 p.m.-10:54 p.m.

2 stops8h 34m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 252

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 14/11

5:55 p.m.-7:05 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 255

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sun 29/11

6:45 a.m.-7:54 a.m.

Nonstop2h 09m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 255

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Sat 24/10

6:35 a.m.-8:30 p.m.

2 stops12h 55m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 255

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Tue 27/10

6:35 a.m.-6:10 p.m.

1 stop10h 35m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 255

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 22/10

6:30 a.m.-2:55 p.m.

1 stop7h 25m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 258

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/9

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Canada to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Canada with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Canada to Chicago

What is the cheapest month to book a flight from Canada to Chicago?

Currently, January is the cheapest month in which you can book a flight from Canada to Chicago (average of C$ 405). Flying from Canada to Chicago in December is currently the most expensive (average of C$ 519). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CA to CHI?

It’s typically best to fly out from Canada to Chicago in the evening. Doing so could potentially save you 23% on the flight price compared to flying at noon, which is usually more expensive.

Weekly flight availability from Canada to Chicago

The most flights from CA0 to CHI are scheduled on a Friday (65 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (41 on average).

How often are flights from Canada to Chicago delayed?

About 14% of weekly flights between Canada and Chicago have experienced delays in the past year, with the average delay time being 134 minutes.

What is the most punctual flight time for Canada to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Thursday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Canada to Chicago flights?

Over the past year, United Airlines has had the lowest number of delays on this route, with just 9% of flights being delayed.

How far ahead should I book a flight from Canada to Chicago?

The price you pay for your flight from Canada to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 87 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest day to fly from Canada to Chicago?

Travelers seeking maximum savings on their Canada to Chicago flight should consider departing on Friday mornings when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Chicago

Check out reviews from past customers who have flown with Porter Airlines,United Airlines, andWestJet from Canada to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
466 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Porter Airlines
8.0
Very good
466 reviews
Porter Airlines
8.0
Very good
466 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
United Airlines
7.4
Good
10,283 reviews
Porter Airlines
8.0
Very good
466 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
WestJet
7.2
Good
3,450 reviews
Porter Airlines
8.0
Very good
466 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Air Canada
7.1
Good
11,717 reviews
Porter Airlines
8.0
Very good
466 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
American Airlines
7.0
Good
12,131 reviews
Porter Airlines
8.0
Very good
466 reviews
Check prices

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Related info for your journey

  • How long is the flight from Canada to Chicago?

    A quick flight from Canada to Chicago can take about 2h 05m. Porter Airlines provides one of the quickest options available for as low as C$ 409. Canada and Chicago are separated by a distance of 716 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What are the cheapest airlines to fly from Canada to Chicago one-way?

    To fly one-way, consider booking your trip with WestJet, which is currently one of the cheapest options available, starting at C$ 148. Air Canada flights start at C$ 155 while deals on Porter Airlines start at C$ 155 one-way.

  • What are the most popular routes from Canada to Chicago?

    When deciding which route to take from Canada to Chicago consider Toronto Pearson Intl - Chicago O'Hare Intl, Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl or Toronto Pearson Intl - Chicago Midway as they are the most popular.

  • What are the most reliable airlines from Canada to Chicago?

    Before booking your flight to Chicago from Canada, check out the most reliable airlines to get you to your destination on time: Sun Country Air (100%), Copa Airlines (86%), Egyptair( 76%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 249. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 426 on average, our data indicates C$ 1,417 when flying from Canada to Chicago.

  • Can I find deals for flights from Canada to Chicago that include hotel bookings?

    Yes. In addition to deals on Canada to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Canada to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Canada to Chicago.

  • Can I find deals for business class flights from Canada to Chicago?

    Yes. Cheapflights offers flight deals from Canada to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Canada to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Canada to Chicago (average of C$ 405). Flying from Canada to Chicago in December is currently the most expensive (average of C$ 519). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Top 6 airlines flying from Canada to Chicago

AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 138AverageC$ 643FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 145AverageC$ 394FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 189AverageC$ 638FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapestC$ 202AverageC$ 507FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 206AverageC$ 439FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Porter AirlinesCheapestC$ 249AverageC$ 464FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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How does Cheapflights help users find flights from Canada to Chicago?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Canada to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Canada to Chicago?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Canada to Chicago for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Canada to Chicago with no change fees?

Certainly. Search results for flights to Chicago from Canada shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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