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Cheap flights from Canada to Chicago from C$ 217

YYZ — CHI
29 Oct — 5 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 10/107:43 p.m. -
1 stop4h 48m
Sun 11/1010:43 a.m. -
Nonstop1h 59m
Deal found 25/9C$ 330
Sat 17/107:43 p.m. -
1 stop4h 48m
Sun 18/107:09 a.m. -
Nonstop1h 45m
Deal found 28/9C$ 340
Thu 12/1110:00 a.m. -
1 stop5h 38m
Thu 12/119:21 p.m. -
Nonstop1h 38m
Deal found 28/9C$ 344
Thu 3/121:37 p.m. -
Nonstop2h 33m
Wed 9/128:40 a.m. -
Nonstop4h 55m
Deal found 25/9C$ 367
Sat 10/107:00 a.m. -
1 stop14h 12m
Sun 11/1011:05 a.m. -
1 stop5h 28m
Deal found 24/9C$ 370
Fri 4/129:07 a.m. -
2 stops27h 03m
Wed 9/126:00 a.m. -
1 stop16h 37m
Deal found 25/9C$ 372
Fri 4/123:06 p.m. -
1 stop5h 28m
Wed 9/128:40 a.m. -
Nonstop4h 55m
Deal found 25/9C$ 388
Fri 20/1110:35 a.m. -
Nonstop2h 05m
Sat 21/116:20 p.m. -
Nonstop1h 46m
Deal found 24/9C$ 388
Thu 29/104:35 p.m. -
Nonstop2h 05m
Sun 1/1112:20 p.m. -
Nonstop1h 46m
Deal found 28/9C$ 389
Mon 19/1012:00 p.m. -
Nonstop3h 40m
Fri 23/105:30 p.m. -
Nonstop3h 55m
Deal found 24/9C$ 392
Thu 22/1012:30 p.m. -
Nonstop3h 35m
Wed 28/108:40 a.m. -
Nonstop3h 55m
Deal found 25/9C$ 394
Sat 3/106:30 a.m. -
Nonstop2h 06m
Sun 4/109:45 a.m. -
Nonstop1h 50m
Deal found 26/9C$ 405

Find flight deals from Canada to Chicago

Round-trip from

C$ 330

One-way from

C$ 217

Popular in

October

Cheapest in

February

Average price

C$ 372

Good round-trip deal

C$ 326 or less

Good one-way deal

C$ 237 or less
Lufthansa
  • Lufthansa
  • 10/10-11/10
  • 1 total stop
  • 6h 47m 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. 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
Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 7/10

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$ 244

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Tue 24/11

1:37 p.m.-4:10 p.m.

Nonstop2h 33m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 249

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 25/12

1:37 p.m.-4:10 p.m.

Nonstop2h 33m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 249

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Thu 24/12

1:37 p.m.-4:10 p.m.

Nonstop2h 33m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 249

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Fri 23/10

6:00 a.m.-11:59 p.m.

1 stop16h 59m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 254

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Wed 21/10

6:00 a.m.-7:30 p.m.

1 stop12h 30m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 254

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Mon 19/10

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

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - ORD Chicago O'Hare Intl

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 25/11

6:00 a.m.-8:00 a.m.

Nonstop3h 00m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 261

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - ORD Chicago O'Hare Intl

YULORD

Montreal Pierre Elliott Trudeau Intl

Tue 20/10

9:45 a.m.-11:21 a.m.

Nonstop2h 36m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 261

CalgaryChicago

YYC Calgary - ORD Chicago O'Hare Intl

YYCORD

Calgary

Wed 21/10

7:45 a.m.-8:30 p.m.

2 stops11h 45m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 262

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/9

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$ 397). Flying from Canada to Chicago in December is currently the most expensive (average of C$ 516). 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 Sunday (71 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (52 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
464 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

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
464 reviews
Porter Airlines
8.0
Very good
464 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

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
10,246 reviews
Porter Airlines
8.0
Very good
464 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

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
3,449 reviews
Porter Airlines
8.0
Very good
464 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

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
11,699 reviews
Porter Airlines
8.0
Very good
464 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

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
12,097 reviews
Porter Airlines
8.0
Very good
464 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

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 1h 50m. Delta provides one of the quickest options available for as low as C$ 467. 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 WestJet, which is currently one of the cheapest options available, starting at C$ 147. Air Canada flights start at C$ 154 while deals on Porter Airlines start at C$ 154 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, Toronto Pearson Intl - Chicago Midway or Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl 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 (84%), Egyptair( 81%).

  • What are the cheapest flights from Canada to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 248. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 405 on average, our data indicates C$ 1,409 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$ 397). Flying from Canada to Chicago in December is currently the most expensive (average of C$ 516). 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$ 137AverageC$ 639FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 145AverageC$ 391FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapestC$ 188AverageC$ 633FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapestC$ 201AverageC$ 503FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
WestJetCheapestC$ 205AverageC$ 434FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Porter AirlinesCheapestC$ 248AverageC$ 462FlexibilityNo 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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