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$106+ Cheap flights from Chicago (CHI) to Canada

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
Aug 19 — Aug 261
Wed 8/19
Wed 8/26
1 adult, Economy
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Cheap flight deals from Chicago to Canada

Cheapest flights from Chicago to Canada
Explore the most affordable flight options available from Chicago to Canada. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 20, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/910:20 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Mon 8/178:55 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/18$238
This Trip.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:45 am
ORD
-
YTZ
1 stop6h 05m
Air Canada
Sun 9/137:35 pm
YTZ
-
ORD
Nonstop2h 06m
Air Canada
Deal found 7/19$238
This Flightnetwork deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/111:05 am
ORD
-
YYZ
1 stop6h 20m
Air Canada
Tue 9/88:05 am
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Deal found 7/18$238
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/133:15 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Thu 8/201:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/16$239
This Mytrip deal was found by Cheapflights users on 7/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:25 am
ORD
-
YTZ
Nonstop1h 42m
Air Canada
Sun 9/1312:15 pm
YTZ
-
ORD
Nonstop2h 06m
Air Canada
Deal found 7/17$239
This Kissandfly.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/254:30 pm
ORD
-
YYZ
Nonstop1h 40m
Air Canada
Tue 10/272:35 pm
YYZ
-
ORD
Nonstop2h 03m
Air Canada
Deal found 7/19$239
This Kiwi.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/710:25 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Wed 8/121:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/16$240
This Flightnetwork deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:40 am
ORD
-
YTZ
1 stop6h 11m
Air Canada
Wed 9/99:30 am
YTZ
-
ORD
1 stop6h 22m
Air Canada
Deal found 7/18$240
This SmartFares deal was found by Cheapflights users on 7/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/192:15 pm
ORD
-
YYZ
Nonstop1h 46m
Air Canada
Thu 10/222:00 pm
YYZ
-
ORD
Nonstop1h 55m
Air Canada
Deal found 7/18$240
This Justfly.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/183:15 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sun 8/238:50 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/19$241
This Booking.com deal was found by Cheapflights users on 7/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:45 am
ORD
-
YYZ
1 stop7h 08m
Air Canada
Sun 10/257:10 pm
YYZ
-
ORD
Nonstop2h 03m
Air Canada
Deal found 7/16$241
This Kiwi.com deal was found by Cheapflights users on 7/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1410:25 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Fri 8/211:45 pm
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 7/15$242

Find flight deals from Chicago to Canada

Keep the following information in mind while searching for Chicago to Canada flight deals. Data was last updated July 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$238
(Kiwi.com)

One-way from

$106
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$296

Good round-trip deal

$237 or less

Good one-way deal

$106 or less
Provider with most accurate pricing for Chicago (CHI)-Toronto (YTO) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Toronto (YTO) flights.
Search Deals
From Chicago (CHI) to Canada
Search Deals
One-way flight from Chicago (CHI) to Canada
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Canada.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Canada.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Canada that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 20, 2026.
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
Quickest round-trip

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 8/27

3:15 pm-5:55 pm

Nonstop1h 40m

Toronto Island

Mon 8/31

8:55 am-9:45 am

Nonstop1h 50m

$239

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 8/14

10:25 am-1:05 pm

Nonstop1h 40m

Toronto Island

Sat 8/22

8:50 am-9:40 am

Nonstop1h 50m

$239

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Thu 9/24

7:25 am-10:07 am

Nonstop1h 42m

Toronto Island

Wed 9/30

10:45 am-2:52 pm

1 stop5h 07m

$253

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 9/24

5:53 pm-8:44 pm

Nonstop1h 51m

Toronto Pearson Intl

Tue 9/29

10:15 am-11:21 am

Nonstop2h 06m

$253

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 9/12

9:29 pm-12:13 am

Nonstop1h 44m

Toronto Pearson Intl

Sat 9/19

7:00 am-8:00 am

Nonstop2h 00m

$253

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 9/24

2:52 pm-5:56 pm

Nonstop2h 04m

Toronto Pearson Intl

Tue 9/29

3:00 pm-8:12 pm

1 stop6h 12m

$262

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 8/8

10:20 am-1:00 pm

Nonstop1h 40m

Toronto Island

Sun 8/9

8:50 am-9:40 am

Nonstop1h 50m

$262

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 9/5

9:39 pm-10:04 am

1 stop11h 25m

Toronto Pearson Intl

Tue 9/8

8:05 am-9:00 am

Nonstop1h 55m

$263

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 8/22

10:20 am-1:00 pm

Nonstop1h 40m

Toronto Island

Mon 8/24

8:55 am-9:45 am

Nonstop1h 50m

$264

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 9/24

8:50 am-7:02 pm

1 stop9h 12m

Toronto Pearson Intl

Wed 9/30

3:00 pm-8:12 pm

1 stop6h 12m

$272

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/17

Showing 1-10 of 60 resultsSorted by cheapest first
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2
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6

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
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

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, October is the cheapest month in which you can book a flight from Chicago to Canada (average of $305). Flying from Chicago to Canada in July is currently the most expensive (average of $431). 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?

Find hourly flight availability from Chicago to Canada. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 20, 2026.

When flying from Chicago to Canada, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 15% versus a flight in the evening.

Weekly flight availability from Chicago to Canada

Explore weekly flight availability from Chicago to Canada. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 20, 2026.

The most flights from CHI to CA0 are scheduled on a Friday (70 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (55 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 137 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 last year, United Airlines have had the lowest number of delays on this route, with just 19% of flights being delayed.

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

Booking 38 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?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Canada. Price data was last updated on July 18, 2026.

Travelers seeking maximum savings on their Chicago to Canada flight should consider departing on Tuesday at noon 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 Canada

Get insights into the airlines that provide service to Canada. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Canada. Reviews last updated July 20, 2026.
Peruse reviews from past customers who have flown with Porter Airlines,United Airlines, andWestJet from Chicago to Canada 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
448 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.5

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Porter Airlines
8.0
Very good
448 reviews
Porter Airlines
8.0
Very good
448 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.5

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
United Airlines
7.4
Good
10,016 reviews
Porter Airlines
8.0
Very good
448 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.5

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
WestJet
7.2
Good
3,412 reviews
Porter Airlines
8.0
Very good
448 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.5

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
American Airlines
7.1
Good
11,826 reviews
Porter Airlines
8.0
Very good
448 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.5

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Air Canada
7.1
Good
11,360 reviews
Porter Airlines
8.0
Very good
448 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.5

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats

Related info for your journey

Find useful and relevant information for your journey from Chicago to Canada. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Canada?

    For as low as $239, Porter Airlines can have you in Canada from Chicago in 1h 40m. The distance from Chicago to Canada is about 442 mi. Generally, flights for this route are nonstop.

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

    $66 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on Air Canada and United Airlines, with prices starting from $69 and $72, respectively.

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

    While some choose either Chicago O'Hare Intl - Toronto Pearson Intl or Chicago O'Hare Intl - Calgary, Chicago O'Hare Intl - Vancouver Intl is the most popular route from Chicago to Canada.

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

    No one likes to see their flight delayed. When booking a flight from Chicago to Canada consider choosing Korean Air (91%), Royal Jordanian (91%) or Republic Airways (83%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Canada?

    Looking at all options, your cheapest flight can be booked for $106. While the most popular route (Chicago O'Hare Intl - Vancouver Intl) can be booked for $326 on average, our data indicates $1,537 when flying from Chicago to Canada.

  • 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, October is the cheapest month in which you can book a flight from Chicago to Canada (average of $305). Flying from Chicago to Canada in July is currently the most expensive (average of $431). 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

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Alternative routes for Chicago to Canada

See prices for flight routes from nearby airports that may be better suited for you.
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Top 9 airlines flying from Chicago to Canada

Discover the top 9 airlines that operate flights from Chicago to Canada. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$88Average$322FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$106Average$410FlexibilityNo cancel feeOn-time67%
WestJetCheapest$121Average$354FlexibilityNo cancel feeOn-time60%
United AirlinesCheapest$123Average$557FlexibilityNo cancel feeOn-time69%
Qantas AirwaysCheapest$160Average$403FlexibilityNo cancel feeOn-time74%
Porter AirlinesCheapest$160Average$337FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$208Average$471FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$217Average$343FlexibilityNo cancel feeOn-time75%
Qatar AirwaysCheapest$381Average$385FlexibilityNo cancel feeOn-time68%

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