HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Canada

$56+ 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 2/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
déc. 19 — déc. 261
ven. 12/19
ven. 12/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Canada with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Canada

Keep the following information in mind while searching for Chicago to Canada flight deals. Data was last updated novembre 19, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$145
(Kiwi.com)

One-way from

$56
(Kiwi.com)

Popular in

November

Cheapest in

September

Average price

$344

Good round-trip deal

$198 or less

Good one-way deal

$72 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 ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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

Find 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 novembre 19, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/16. 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.
lun. 12/111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
dim. 12/79:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/16$192
This American Airlines deal was found by Cheapflights users on 11/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/86:04 amORD - YYZ
1 stop4h 52mAmerican Airlines
mar. 12/1611:36 amYYZ - ORD
Nonstop1h 55mAmerican Airlines
Deal found 11/17$194
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/234:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
lun. 1/59:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/17$199
This Air Canada deal was found by Cheapflights users on 11/19. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 12/267:05 amORD - YYC
1 stop9h 49mAir Canada
jeu. 1/15:35 amYYC - ORD
1 stop8h 20mAir Canada
Deal found 11/19$200
This American Airlines deal was found by Cheapflights users on 11/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/98:10 amORD - YYZ
Nonstop1h 46mAmerican Airlines
mar. 12/93:56 pmYYZ - ORD
1 stop5h 54mAmerican Airlines
Deal found 11/18$200
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/224:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
lun. 1/59:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/17$202
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 12/2411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
lun. 1/59:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/17$204
This American Airlines deal was found by Cheapflights users on 11/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 12/125:00 amORD - YYZ
1 stop5h 12mAmerican Airlines
lun. 12/156:15 pmYYZ - ORD
1 stop5h 39mAmerican Airlines
Deal found 11/18$209
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
ven. 12/52:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/17$210
This Air Canada deal was found by Cheapflights users on 11/18. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 12/138:15 pmORD - YYZ
Nonstop1h 39mAir Canada
ven. 1/96:30 pmYYZ - ORD
Nonstop2h 00mAir Canada
Deal found 11/18$210
This Mytrip deal was found by Cheapflights users on 11/17. 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.
lun. 12/84:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
sam. 1/39:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/17$212
This American Airlines deal was found by Cheapflights users on 11/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 12/78:10 amORD - YYZ
Nonstop1h 46mAmerican Airlines
dim. 12/146:00 amYYZ - ORD
Nonstop2h 15mAmerican Airlines
Deal found 11/19$213

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 novembre 19, 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

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

ven. 1/23

8:45 am-11:35 am

Nonstop3h 50m

Calgary

mer. 2/4

12:37 pm-5:08 pm

Nonstop3h 31m

$185

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

mar. 1/27

8:45 am-11:35 am

Nonstop3h 50m

Calgary

mar. 2/3

12:37 pm-5:08 pm

Nonstop3h 31m

$185

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

dim. 5/3

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

mer. 5/13

7:55 am-8:45 am

Nonstop1h 50m

$186

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

dim. 5/3

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

ven. 5/8

7:55 am-8:45 am

Nonstop1h 50m

$186

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

dim. 3/8

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

mer. 3/11

9:15 am-10:05 am

Nonstop1h 50m

$188

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

dim. 1/18

5:40 am-1:08 pm

1 stop8h 28m

Calgary

mer. 1/28

12:37 pm-5:08 pm

Nonstop3h 31m

$190

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

dim. 1/18

5:40 am-1:08 pm

1 stop8h 28m

Calgary

mer. 1/21

12:37 pm-5:08 pm

Nonstop3h 31m

$190

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

sam. 1/10

8:52 am-7:48 pm

1 stop9h 56m

Montreal Pierre Elliott Trudeau Intl

dim. 1/18

6:00 am-8:05 am

Nonstop3h 05m

$191

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

sam. 1/10

8:52 am-7:48 pm

1 stop9h 56m

Montreal Pierre Elliott Trudeau Intl

jeu. 1/15

6:00 am-8:05 am

Nonstop3h 05m

$191

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

mar. 1/13

7:10 am-1:28 pm

1 stop5h 18m

Montreal Pierre Elliott Trudeau Intl

dim. 1/18

4:45 pm-6:51 pm

Nonstop3h 06m

$191

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Showing 1-10 of 60 results
1
2
3
...
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, 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 $151). 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 novembre 19, 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 17% 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 novembre 19, 2025.

The most flights from CHI to CA0 are scheduled on a Monday (64 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (42 on average).

How often are flights $[0, preposition:'from ']$[0, article:'from ']$[0, place:'from'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] delayed?

About 18% of weekly flights between $[0, place:'genitive'] and $[1, place:'genitive'] have experienced delays in the past year, with the average delay time being 136 minutes.

What is the most punctual flight time for $[0,article:'genitive ']$[0,place:'genitive'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] 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.

Which airline has the best punctuality record on $[0,article:'genitive ']$[0,place:'genitive'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] flights?

Over the last year, Air Antilles have had the lowest number of delays on this route, with no flights being classified as 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 novembre 19, 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
392 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Porter Airlines
8.0
Very good
392 reviews
Porter Airlines
8.0
Very good
392 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
United Airlines
7.4
Good
9,019 reviews
Porter Airlines
8.0
Very good
392 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
American Airlines
7.2
Good
11,045 reviews
Porter Airlines
8.0
Very good
392 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
WestJet
7.2
Good
3,164 reviews
Porter Airlines
8.0
Very good
392 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Air Canada
7.1
Good
10,462 reviews
Porter Airlines
8.0
Very good
392 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

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 $193, United 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?

    $57 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on United Airlines and American Airlines, with prices starting from $70 and $86, 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 - Montreal Pierre Elliott Trudeau Intl, 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 Japan Airlines (89%), Korean Air (88%) or SkyWest Airlines (84%) 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 $96. While the most popular route (Chicago O'Hare Intl - Vancouver Intl) can be booked for $230 on average, our data indicates $836 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 $151). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Canada

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Cancún flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Mexico City flights
O'Hare Intl to Orlando flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Newark flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Miami flights
O'Hare Intl to Tampa flights
O'Hare Intl to Denver flights
O'Hare Intl to Seattle flights
O'Hare Intl to San Francisco flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Atlanta flights
O'Hare Intl to Honolulu flights
Midway to Cancún flights
Midway to Orlando flights
O'Hare Intl to Fort Myers flights
Midway to John F Kennedy Intl flights
Midway to Sky Harbor Intl flights
O'Hare Intl to Boston flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to Santa Ana flights
Midway to Miami flights
O'Hare Intl to Baltimore flights
O'Hare Intl to New Orleans flights
Midway to Las Vegas flights
Midway to LaGuardia flights
O'Hare Intl to Salt Lake City flights
Midway to Los Angeles flights
O'Hare Intl to Puerto Vallarta flights
Midway to Mexico City flights
O'Hare Intl to Guadalajara flights
O'Hare Intl to George Bush Intcntl flights
Midway to Atlanta flights
O'Hare Intl to Dulles Intl flights
Midway to Hobby flights
O'Hare Intl to Ontario flights
O'Hare Intl to Cozumel flights
Midway to Tampa flights
St. Louis to Las Vegas flights
Midway to Fort Lauderdale flights
O'Hare Intl to San Diego flights
O'Hare Intl to Sarasota flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Hobby flights

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 novembre 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$88Average$451FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$91Average$417FlexibilityNo cancel feeOn-time67%
DeltaCheapest$109Average$424FlexibilityNo cancel feeOn-timeN/A
WestJetCheapest$142Average$273FlexibilityNo cancel feeOn-time60%
Porter AirlinesCheapest$185Average$377FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$192Average$460FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$464Average$716FlexibilityNo cancel feeOn-time75%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.