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Cheap flights from Chicago to Canada from C$ 121

CHI — YYZ
15 Oct — 22 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Chicago to Canada

Enter your travel dates to find the best prices.

Cheapest flights from Chicago to Canada

Sat 3/103:20 p.m. -
Nonstop1h 40m
Sun 4/1010:10 a.m. -
Nonstop1h 50m
Deal found 11/9C$ 297
Sun 6/126:20 p.m. -
Nonstop1h 46m
Wed 16/1210:35 a.m. -
Nonstop2h 05m
Deal found 13/9C$ 297
Thu 1/103:20 p.m. -
Nonstop1h 40m
Sun 4/1010:10 a.m. -
Nonstop1h 50m
Deal found 14/9C$ 299
Mon 26/106:20 p.m. -
Nonstop1h 46m
Mon 2/1110:35 a.m. -
Nonstop2h 05m
Deal found 10/9C$ 299
Tue 3/114:30 p.m. -
Nonstop1h 40m
Sat 7/112:35 p.m. -
Nonstop2h 03m
Deal found 10/9C$ 299
Sun 11/103:20 p.m. -
Nonstop1h 40m
Mon 19/101:45 p.m. -
Nonstop1h 50m
Deal found 11/9C$ 300
Sat 21/1112:20 p.m. -
Nonstop1h 46m
Sat 28/114:35 p.m. -
Nonstop2h 05m
Deal found 14/9C$ 300
Thu 10/1212:20 p.m. -
Nonstop1h 46m
Sun 13/1210:35 a.m. -
Nonstop2h 05m
Deal found 13/9C$ 301
Thu 1/109:55 a.m. -
Nonstop1h 45m
Sun 4/108:05 a.m. -
Nonstop1h 55m
Deal found 13/9C$ 301
Fri 16/103:20 p.m. -
Nonstop1h 40m
Tue 20/1010:10 a.m. -
Nonstop1h 50m
Deal found 11/9C$ 303
Thu 22/102:00 p.m. -
Nonstop1h 48m
Sun 25/1010:35 a.m. -
Nonstop2h 05m
Deal found 11/9C$ 303
Thu 22/108:40 p.m. -
Nonstop1h 46m
Sun 25/108:20 a.m. -
Nonstop2h 03m
Deal found 13/9C$ 303

Find flight deals from Chicago to Canada

Round-trip from

C$ 297

One-way from

C$ 121

Popular in

August

Cheapest in

March

Average price

C$ 414

Good round-trip deal

C$ 265 or less

Good one-way deal

C$ 140 or less
Porter Airlines
  • Porter Airlines
  • 3/10-4/10
  • Nonstop
  • 3h 30m total
  • Chicago to Canada
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Porter Airlines
  • Porter Airlines
  • 1/11-31/12
  • Nonstop
  • 1h 46m total
  • Chicago to Canada
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 30 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 September 2026
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Price to beat on a round-trip flight from Chicago (CHI) to Canada.
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Price to beat on a one-way flight from Chicago (CHI) to Canada.
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Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Sat 24/10

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

Nonstop1h 40m

Toronto Island

Wed 31/12

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

Nonstop0h 00m

C$ 138

ChicagoToronto

ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl

ORDYYZ

Chicago O'Hare Intl

Sat 5/12

10:25 a.m.-6:43 p.m.

1 stop7h 18m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 146

ChicagoToronto

ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl

ORDYYZ

Chicago O'Hare Intl

Thu 1/10

7:05 a.m.-3:15 p.m.

1 stop7h 10m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 146

ChicagoToronto

ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl

ORDYYZ

Chicago O'Hare Intl

Mon 28/9

3:00 p.m.-10:23 p.m.

1 stop6h 23m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 146

ChicagoToronto

ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl

ORDYYZ

Chicago O'Hare Intl

Wed 25/11

8:29 a.m.-1:30 p.m.

1 stop4h 01m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 146

ChicagoToronto

ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl

ORDYYZ

Chicago O'Hare Intl

Thu 15/10

1:55 p.m.-10:56 p.m.

1 stop8h 01m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 146

ChicagoToronto

ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl

ORDYYZ

Chicago O'Hare Intl

Mon 26/10

4:40 p.m.-11:26 p.m.

1 stop5h 46m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 146

ChicagoToronto

ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl

ORDYYZ

Chicago O'Hare Intl

Sat 21/11

5:05 p.m.-10:57 p.m.

1 stop4h 52m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 146

ChicagoToronto

ORD Chicago O'Hare Intl - YYZ Toronto Pearson Intl

ORDYYZ

Chicago O'Hare Intl

Sat 10/10

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

1 stop5h 43m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 146

ChicagoToronto

MDW Chicago Midway - YYZ Toronto Pearson Intl

MDWYYZ

Chicago Midway

Tue 20/10

1:27 p.m.-10:56 p.m.

1 stop8h 29m

Toronto Pearson Intl

Wed 31/12

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

Nonstop0h 00m

C$ 146

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/9

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

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

Cheapflights Insights

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

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

Currently, February is the cheapest month in which you can book a flight from Chicago to Canada (average of C$ 463). Flying from Chicago to Canada in July is currently the most expensive (average of C$ 613). 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 CHI to CA?

It’s typically best to fly out from Chicago to Canada in the afternoon. Doing so could potentially save you 38% on the flight price compared to flying at noon, which is usually more expensive.

Weekly flight availability from Chicago to Canada

The most flights from CHI to CA0 are scheduled on a Friday (70 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (52 on average).

How often are flights from Chicago to Canada delayed?

About 22% of weekly flights between Chicago and Canada have experienced delays in the past year, with the average delay time being 138 minutes.

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

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

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

Over the past year, American Airlines has had the lowest number of delays on this route, with just 18% of flights being delayed.

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

Booking 47 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Canada. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

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

Reviews of airlines servicing Canada

Get a feel of what it's like to fly with Porter Airlines,United Airlines, andWestJet from Chicago to Canada by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
461 reviews
Check prices

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.6

Entertainment

6.9

Boarding

8.2

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
461 reviews
Porter Airlines
8.0
Very good
461 reviews
Check prices

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.6

Entertainment

6.9

Boarding

8.2

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
10,213 reviews
Porter Airlines
8.0
Very good
461 reviews
Check prices

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.6

Entertainment

6.9

Boarding

8.2

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
3,443 reviews
Porter Airlines
8.0
Very good
461 reviews
Check prices

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.6

Entertainment

6.9

Boarding

8.2

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
11,627 reviews
Porter Airlines
8.0
Very good
461 reviews
Check prices

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.6

Entertainment

6.9

Boarding

8.2

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 Chicago to Canada?

    Porter Airlines, United Airlines, and Delta can get you from Chicago to Canada in just under 1h 40m. Your travel time can differ by up to 1h 20m. Airlines will cover a distance of 711 km. Both multi-stop and direct flights can be found to your destination and back.

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

    The cheapest airline one-way is WestJet, with whom users have recently found tickets for as low as C$ 79. However, be on the lookout for offers from United Airlines and American Airlines, as they are both options that can get you from Chicago to Canada for a low price.

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

    Most travellers choose Chicago O'Hare Intl - Toronto Pearson Intl, Chicago O'Hare Intl - Montreal Pierre Elliott Trudeau Intl or Chicago O'Hare Intl - Vancouver Intl when deciding on the best route from Chicago to Canada.

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

    Before booking your flight to Canada from Chicago, check out the most reliable airlines to get you to your destination on time: Korean Air (86%), Royal Jordanian (82%), Republic Airways( 75%).

  • What are the cheapest flights from Chicago to Canada?

    Looking for the cheapest flight from Chicago to Canada? While on average our users pay C$ 409, our data indicates the cheapest price to be C$ 134. The most popular route (Chicago O'Hare Intl - Toronto Pearson Intl), is priced around C$ 297.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Canada 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 Chicago to Canada?

    Currently, February is the cheapest month in which you can book a flight from Chicago to Canada (average of C$ 463). Flying from Chicago to Canada in July is currently the most expensive (average of C$ 613). 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 4 airlines flying from Chicago to Canada

AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapestC$ 135AverageC$ 660FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapestC$ 235AverageC$ 628FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
WestJetCheapestC$ 256AverageC$ 514FlexibilityNo cancel feeOn-time60%
Search WestJet flights
United AirlinesCheapestC$ 345AverageC$ 561FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

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Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Chicago to Canada. 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 Chicago to Canada?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago to Canada.

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

Cheapflights does show flights with no change fees to all users. To see these options for flights from Chicago to Canada, users can toggle the no change fees filter when performing a flight search.

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Not ready to book yet? You can track prices for flights from Chicago to Canada on Cheapflights with our Price Alert feature and get notified when better prices are available.

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