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$54+ 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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
janv. 22 — janv. 291
jeu. 1/22
jeu. 1/29
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 décembre 23, 2025.

This Trip.com deal was found by Cheapflights users on 12/22. 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.
lun. 12/294:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
lun. 1/129:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/22$383
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
mar. 12/307:30 amORD - YYZ
1 stop14h 50mMultiple Airlines
lun. 1/123:40 pmYYZ - ORD
1 stop20h 42mMultiple Airlines
Deal found 12/22$385
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
mer. 12/316:35 amORD - YYZ
1 stop15h 45mMultiple Airlines
lun. 1/123:40 pmYYZ - ORD
1 stop20h 42mMultiple Airlines
Deal found 12/22$407
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
mer. 12/245:45 amORD - YYZ
1 stop33h 05mMultiple Airlines
lun. 1/127:00 amYYZ - ORD
1 stop29h 22mMultiple Airlines
Deal found 12/22$425
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
lun. 12/297:00 amORD - YYZ
1 stop3h 19mMultiple Airlines
lun. 1/123:40 pmYYZ - ORD
1 stop20h 42mMultiple Airlines
Deal found 12/22$436
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
jeu. 12/255:25 amORD - YYZ
2 stops31h 55mMultiple Airlines
lun. 1/127:00 amYYZ - ORD
1 stop29h 22mMultiple Airlines
Deal found 12/22$441
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
mar. 12/307:20 amORD - YTZ
2 stops13h 43mMultiple Airlines
lun. 1/126:15 pmYTZ - ORD
1 stop5h 27mMultiple Airlines
Deal found 12/22$452
This FlightHub deal was found by Cheapflights users on 12/22. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 12/3111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
lun. 1/129:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/22$464
This FlightHub deal was found by Cheapflights users on 12/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/304:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
ven. 1/22:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/21$466
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
lun. 12/297:00 amORD - YYZ
1 stop3h 19mWestJet
lun. 1/1210:15 pmYYZ - ORD
2 stops20h 40mWestJet
Deal found 12/22$468
This FlightHub deal was found by Cheapflights users on 12/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 12/284:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
ven. 1/99:20 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/20$471
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
mar. 12/304:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
mer. 12/319:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/21$479

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 décembre 23, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$145
(Trip.com)

One-way from

$54
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$319

Good round-trip deal

$205 or less

Good one-way deal

$95 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
Highest demand for flights based on searches. 8% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 décembre 23, 2025.
Use the filters below to find and compare flights from Chicago to Canada that are best for you.

Fly from

Chicago

Fly to

Canada

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

jeu. 2/19

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

lun. 2/23

9:15 am-10:05 am

Nonstop1h 50m

$194

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

mer. 2/18

11:00 am-4:30 pm

1 stop4h 30m

Montreal Pierre Elliott Trudeau Intl

ven. 2/20

6:45 am-10:05 am

1 stop4h 20m

$203

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

jeu. 2/19

11:05 am-5:45 pm

1 stop5h 40m

Montreal Pierre Elliott Trudeau Intl

mer. 2/25

6:45 am-10:10 am

1 stop4h 25m

$203

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

ven. 1/23

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

mar. 1/27

9:20 am-10:10 am

Nonstop1h 50m

$203

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

dim. 1/18

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

dim. 1/25

2:30 pm-3:20 pm

Nonstop1h 50m

$203

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

jeu. 1/15

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

lun. 1/19

9:20 am-10:10 am

Nonstop1h 50m

$204

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

lun. 1/26

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

sam. 1/31

11:00 am-11:50 am

Nonstop1h 50m

$206

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

mer. 1/28

7:00 am-9:53 pm

1 stop15h 53m

Calgary

lun. 2/2

6:15 am-11:59 pm

1 stop16h 44m

$221

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

jeu. 2/5

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

dim. 2/8

7:00 am-7:52 pm

2 stops13h 52m

$223

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

ven. 1/16

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

dim. 1/18

2:30 pm-3:20 pm

Nonstop1h 50m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 60 results
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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
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, March is the cheapest month in which you can book a flight from Chicago to Canada (average of $79). Flying from Chicago to Canada in December is currently the most expensive (average of $161). 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 décembre 23, 2025.

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 in the evening, which can drop the price by up to 22% versus a flight at noon.

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 December 16, 2024.

Travelers seeking maximum savings on their Chicago to Canada flight should consider departing on Monday 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.

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 décembre 23, 2025.

The most flights from CHI to CA0 are scheduled on a Monday (62 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (32 on average).

How often are flights from Chicago to Canada delayed?

About 18% of weekly flights between Chicago and Canada have experienced delays in the past year, with the average delay time being 136 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 Friday 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, Korean Air have had the lowest number of delays on this route, with just 11% of flights being delayed.

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 décembre 23, 2025.
Peruse reviews from past customers who have flown with Porter Airlines, United Airlines, and American Airlines 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
399 reviews

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
8.0
Very good
399 reviews
Porter Airlines
8.0
Very good
399 reviews

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
United Airlines
7.4
Good
9,104 reviews
Porter Airlines
8.0
Very good
399 reviews

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
American Airlines
7.2
Good
11,055 reviews
Porter Airlines
8.0
Very good
399 reviews

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
WestJet
7.2
Good
3,210 reviews
Porter Airlines
8.0
Very good
399 reviews

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Canada
7.1
Good
10,551 reviews
Porter Airlines
8.0
Very good
399 reviews

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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 $194, Porter Airlines can have you in Canada from Chicago in 1h 42m. The distance from Chicago to Canada is about 442 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $54 is the cheapest one-way deal found within the past few days, from Air Canada. You may also be able to find cheap deals on Porter Airlines and WestJet, with prices starting from $58 and $63, 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 (89%), Japan Airlines (75%) or SkyWest Airlines (74%) 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 $67. While the most popular route (Chicago O'Hare Intl - Vancouver Intl) can be booked for $210 on average, our data indicates $1,257 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, March is the cheapest month in which you can book a flight from Chicago to Canada (average of $79). Flying from Chicago to Canada in December is currently the most expensive (average of $161). 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 7 airlines flying from Chicago to Canada

Discover the top 7 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 décembre 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$85Average$406FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$90Average$448FlexibilityNo cancel feeOn-time69%
DeltaCheapest$109Average$418FlexibilityNo cancel feeOn-timeN/A
WestJetCheapest$142Average$367FlexibilityNo cancel feeOn-time60%
Porter AirlinesCheapest$185Average$380FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$192Average$458FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$343Average$707FlexibilityNo cancel feeOn-time75%

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