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Cheap flights from Canada to Chicago from C$ 184

YYZ — CHI
27 Sep — 4 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 2/1010:10 a.m. -
Nonstop1h 50m
Mon 5/103:20 p.m. -
Nonstop1h 40m
Deal found 24/8C$ 280
Thu 17/91:45 p.m. -
Nonstop1h 50m
Sun 20/911:45 a.m. -
Nonstop1h 40m
Deal found 23/8C$ 283
Wed 16/97:35 p.m. -
Nonstop2h 06m
Wed 23/92:00 p.m. -
Nonstop1h 42m
Deal found 23/8C$ 283
Thu 17/912:25 p.m. -
Nonstop1h 58m
Sun 20/98:40 p.m. -
Nonstop1h 46m
Deal found 26/8C$ 284
Thu 17/91:45 p.m. -
Nonstop1h 50m
Wed 30/93:20 p.m. -
Nonstop1h 40m
Deal found 24/8C$ 284
Thu 17/99:30 a.m. -
1 stop6h 22m
Sun 20/97:25 a.m. -
Nonstop1h 42m
Deal found 27/8C$ 284
Fri 2/1012:25 p.m. -
Nonstop1h 58m
Sun 4/109:55 a.m. -
Nonstop1h 45m
Deal found 27/8C$ 286
Wed 7/101:45 p.m. -
Nonstop1h 50m
Sat 10/1011:45 a.m. -
Nonstop1h 40m
Deal found 26/8C$ 286
Tue 6/101:45 p.m. -
Nonstop1h 50m
Fri 9/103:20 p.m. -
Nonstop1h 40m
Deal found 27/8C$ 287
Sat 26/912:15 p.m. -
Nonstop2h 06m
Sat 3/108:45 a.m. -
1 stop6h 05m
Deal found 27/8C$ 288
Sat 19/910:30 a.m. -
1 stop5h 22m
Mon 21/93:40 p.m. -
1 stop4h 58m
Deal found 26/8C$ 291
Fri 18/91:45 p.m. -
Nonstop1h 50m
Sun 20/911:45 a.m. -
Nonstop1h 40m
Deal found 24/8C$ 291

Find flight deals from Canada to Chicago

Round-trip from

C$ 280

One-way from

C$ 184

Popular in

July

Cheapest in

February

Average price

C$ 362

Good round-trip deal

C$ 283 or less

Good one-way deal

C$ 193 or less
Porter Airlines
  • Porter Airlines
  • 17/9-20/9
  • Nonstop
  • 3h 30m total
  • Canada to Chicago
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United Airlines
  • United Airlines
  • 24/9
  • Nonstop
  • 2h 00m 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 August 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 18/9

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

Nonstop1h 50m

Chicago Midway

Tue 6/10

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

Nonstop1h 40m

C$ 294

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 18/9

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

Nonstop1h 50m

Chicago Midway

Thu 1/10

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

Nonstop1h 40m

C$ 294

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 16/9

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

Nonstop1h 50m

Chicago Midway

Sun 4/10

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 294

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sun 20/9

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

Nonstop1h 50m

Chicago Midway

Tue 6/10

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 294

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

Fri 2/10

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 294

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sun 27/9

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

Nonstop2h 00m

Chicago O'Hare Intl

Wed 30/9

11:05 a.m.-6:12 p.m.

1 stop6h 07m

C$ 308

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$ 320

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 21/9

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

Nonstop1h 50m

Chicago Midway

Sat 3/10

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

Nonstop1h 40m

C$ 325

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Sat 26/9

9:44 a.m.-5:20 p.m.

1 stop8h 36m

Chicago O'Hare Intl

Mon 28/9

3:40 p.m.-11:18 p.m.

1 stop6h 38m

C$ 330

TorontoChicago

YYZ Toronto Pearson Intl - ORD Chicago O'Hare Intl

YYZORD

Toronto Pearson Intl

Fri 18/9

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

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/8

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$ 498). 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 Wednesday (68 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (33 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

Food

7.6

Entertainment

6.9

Boarding

8.2

Overall

8.0

Crew

8.6

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

Food

7.6

Entertainment

6.9

Boarding

8.2

Overall

8.0

Crew

8.6

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
10,136 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Comfort

8.0

Food

7.6

Entertainment

6.9

Boarding

8.2

Overall

8.0

Crew

8.6

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
3,440 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Comfort

8.0

Food

7.6

Entertainment

6.9

Boarding

8.2

Overall

8.0

Crew

8.6

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
12,022 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Comfort

8.0

Food

7.6

Entertainment

6.9

Boarding

8.2

Overall

8.0

Crew

8.6

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
11,548 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Comfort

8.0

Food

7.6

Entertainment

6.9

Boarding

8.2

Overall

8.0

Crew

8.6

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$ 294. 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$ 150 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$ 249. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 295 on average, our data indicates C$ 1,437 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$ 498). 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$ 634FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 142AverageC$ 383FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 184AverageC$ 552FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapestC$ 196AverageC$ 468FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 199AverageC$ 435FlexibilityNo 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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