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Cheap flights from Canada to Chicago from C$ 183

YYZ — CHI
1 Oct — 8 Oct1
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

Fri 18/912:25 p.m. -
Nonstop1h 58m
Mon 21/93:40 p.m. -
1 stop4h 58m
Deal found 29/8C$ 284
Thu 1/1010:45 a.m. -
1 stop5h 07m
Sun 4/107:25 a.m. -
Nonstop1h 53m
Deal found 27/8C$ 284
Fri 25/910:10 a.m. -
Nonstop1h 50m
Fri 25/93:20 p.m. -
Nonstop1h 40m
Deal found 28/8C$ 286
Thu 24/910:45 a.m. -
1 stop5h 07m
Sun 27/97:25 a.m. -
Nonstop1h 42m
Deal found 30/8C$ 286
Thu 17/99:30 a.m. -
1 stop6h 22m
Sun 20/97:25 a.m. -
Nonstop1h 42m
Deal found 27/8C$ 287
Wed 30/910:30 a.m. -
1 stop5h 22m
Sat 3/103:45 p.m. -
Nonstop1h 46m
Deal found 27/8C$ 289
Thu 24/98:05 a.m. -
Nonstop1h 55m
Sun 27/99:55 a.m. -
Nonstop1h 45m
Deal found 31/8C$ 290
Sat 19/93:00 p.m. -
1 stop6h 12m
Sun 20/98:40 p.m. -
Nonstop1h 46m
Deal found 29/8C$ 291
Sat 19/912:15 p.m. -
Nonstop2h 06m
Sat 3/102:00 p.m. -
Nonstop1h 42m
Deal found 27/8C$ 293
Mon 21/99:00 p.m. -
Nonstop2h 05m
Fri 25/97:09 a.m. -
Nonstop1h 45m
Deal found 28/8C$ 294
Tue 22/99:30 a.m. -
1 stop6h 22m
Thu 24/92:00 p.m. -
Nonstop1h 42m
Deal found 28/8C$ 294
Fri 18/99:00 p.m. -
Nonstop2h 05m
Sun 20/99:18 p.m. -
Nonstop1h 41m
Deal found 28/8C$ 296

Find flight deals from Canada to Chicago

Round-trip from

C$ 284

One-way from

C$ 183

Popular in

October

Cheapest in

February

Average price

C$ 359

Good round-trip deal

C$ 293 or less

Good one-way deal

C$ 199 or less
Air Canada
  • Air Canada
  • 18/9-21/9
  • 1 total stop
  • 6h 56m total
  • Canada to Chicago
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Air Canada
  • Air Canada
  • 13/10
  • 1 total stop
  • 6h 12m total
  • Canada to Chicago
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Highest demand for flights based on searches. 0% potential increase in price (C$ 1 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 6 potential savings vs. average RT price).
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Average for round-trip flights in September 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

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 10/10

7:00 p.m.-11:21 p.m.

1 stop5h 21m

Chicago O'Hare Intl

Tue 20/10

8:45 a.m.-3:53 p.m.

1 stop6h 08m

C$ 303
Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sun 11/10

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

Nonstop1h 50m

Chicago Midway

Sun 18/10

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 307

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Thu 24/9

1:00 p.m.-2:05 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Sun 27/9

12:59 p.m.-3:46 p.m.

Nonstop1h 47m

C$ 309

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 25/9

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

Nonstop2h 00m

Chicago O'Hare Intl

Mon 28/9

9:55 a.m.-12:40 p.m.

Nonstop1h 45m

C$ 309

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 17/9

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

Nonstop1h 50m

Chicago Midway

Mon 21/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 321

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 23/9

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

Nonstop1h 50m

Chicago Midway

Thu 24/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 321

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 21/9

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

Nonstop1h 50m

Chicago Midway

Sat 3/10

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 328

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 18/9

7:00 a.m.-8:00 a.m.

Nonstop2h 00m

Chicago O'Hare Intl

Sun 20/9

12:59 p.m.-3:46 p.m.

Nonstop1h 47m

C$ 333

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Tue 22/9

9:00 p.m.-10:05 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Thu 24/9

7:09 a.m.-9:54 a.m.

Nonstop1h 45m

C$ 333

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Tue 22/9

7:00 a.m.-8:00 a.m.

Nonstop2h 00m

Chicago O'Hare Intl

Wed 23/9

5:00 a.m.-11:43 a.m.

1 stop5h 43m

C$ 333

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/8

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$ 390). Flying from Canada to Chicago in August is currently the most expensive (average of C$ 502). 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 33% 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 Monday (70 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (29 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 135 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 8% 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
458 reviews
Check prices

Comfort

8.0

Crew

8.6

Entertainment

6.9

Boarding

8.2

Food

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Porter Airlines
8.0
Very good
458 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Comfort

8.0

Crew

8.6

Entertainment

6.9

Boarding

8.2

Food

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
United Airlines
7.4
Good
10,154 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Comfort

8.0

Crew

8.6

Entertainment

6.9

Boarding

8.2

Food

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
WestJet
7.2
Good
3,444 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Comfort

8.0

Crew

8.6

Entertainment

6.9

Boarding

8.2

Food

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
American Airlines
7.1
Good
12,023 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Comfort

8.0

Crew

8.6

Entertainment

6.9

Boarding

8.2

Food

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Air Canada
7.1
Good
11,566 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Comfort

8.0

Crew

8.6

Entertainment

6.9

Boarding

8.2

Food

7.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

Related info for your journey

  • How long is the flight from Canada to Chicago?

    A quick flight from Canada to Chicago can take about 1h 50m. Porter Airlines provides one of the quickest options available for as low as C$ 307. Canada and Chicago are separated by a distance of 711 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 Porter Airlines, which is currently one of the cheapest options available, starting at C$ 134. WestJet flights start at C$ 136 while deals on Air Canada start at C$ 151 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: Egyptair (88%), Japan Airlines (82%), ANA( 76%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 256. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 269 on average, our data indicates C$ 2,437 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$ 390). Flying from Canada to Chicago in August is currently the most expensive (average of C$ 502). 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$ 121AverageC$ 624FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 142AverageC$ 384FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 185AverageC$ 607FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapestC$ 197AverageC$ 472FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 199AverageC$ 434FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Porter AirlinesCheapestC$ 220AverageC$ 432FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

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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Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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