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$59+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
abr. 2 — abr. 91
mié. 4/2
mié. 4/9
1 adult, Economy
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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 marzo 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$145
(Flightnetwork)

One-way from

$59
(Justfly.com)

Popular in

March

Cheapest in

April

Average price

$400

Good round-trip deal

$196 or less

Good one-way deal

$91 or less
Provider with most accurate pricing for Chicago (CHI)-Toronto (YTO) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Toronto (YTO) flights.
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From Chicago (CHI) to Canada
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One-way flight from Chicago (CHI) to Canada
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Highest demand for flights based on searches. 5% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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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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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 marzo 28, 2025.

This Flightnetwork deal was found by Cheapflights users on 3/27. 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.
jue. 5/15:30 pmORD - YYC
Nonstop3h 49mMultiple Airlines
lun. 5/511:55 pmYYC - ORD
1 stop7h 55mMultiple Airlines
Deal found 3/27$145
This Trip.com deal was found by Cheapflights users on 3/27. 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.
sáb. 5/35:30 pmORD - YYC
Nonstop3h 49mWestJet
sáb. 5/1012:15 pmYYC - ORD
Nonstop3h 29mWestJet
Deal found 3/27$147
This Flightnetwork deal was found by Cheapflights users on 3/27. 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.
mar. 5/137:10 amORD - YYC
1 stop15h 38mAir Canada
sáb. 5/2412:55 amYYC - ORD
1 stop7h 57mAir Canada
Deal found 3/27$151
This American Airlines deal was found by Cheapflights users on 3/27. 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.
jue. 6/128:25 pmORD - YYC
Nonstop4h 00mAmerican Airlines
jue. 6/196:29 amYYC - ORD
Nonstop3h 25mAmerican Airlines
Deal found 3/27$180
This United Airlines deal was found by Cheapflights users on 3/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/17:10 amORD - YYC
1 stop15h 38mUnited Airlines
sáb. 5/1012:43 pmYYC - ORD
Nonstop3h 27mUnited Airlines
Deal found 3/27$189
This Mytrip deal was found by Cheapflights users on 3/26. 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.
mié. 5/148:40 amORD - YTZ
2 stops8h 57mAir Canada
vie. 5/2310:20 amYTZ - ORD
2 stops10h 52mAir Canada
Deal found 3/26$204
This Trip.com deal was found by Cheapflights users on 3/27. 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.
jue. 4/2411:15 amMDW - YTZ
Nonstop1h 42mPorter Airlines
jue. 5/17:55 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 3/27$220
This Flightnetwork deal was found by Cheapflights users on 3/27. 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.
dom. 5/116:30 pmORD - YYZ
Nonstop1h 46mAir Canada
dom. 5/186:35 pmYYZ - ORD
Nonstop1h 55mAir Canada
Deal found 3/27$227
This Trip.com deal was found by Cheapflights users on 3/27. 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.
jue. 5/15:30 pmORD - YVR
1 stop7h 05mWestJet
sáb. 5/107:00 amYVR - ORD
1 stop7h 44mWestJet
Deal found 3/27$228
This Mytrip deal was found by Cheapflights users on 3/27. 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.
mar. 5/139:02 pmORD - YVR
1 stop27h 23mMultiple Airlines
sáb. 5/173:55 pmYVR - ORD
1 stop11h 30mMultiple Airlines
Deal found 3/27$229
This Flightnetwork deal was found by Cheapflights users on 3/27. 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.
vie. 4/1811:15 amMDW - YUL
1 stop4h 32mPorter Airlines
lun. 4/216:50 amYUL - MDW
1 stop4h 30mPorter Airlines
Deal found 3/27$233
This Flightnetwork deal was found by Cheapflights users on 3/27. 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.
sáb. 5/39:40 amMDW - YTZ
Nonstop1h 42mMultiple Airlines
sáb. 5/107:55 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 3/27$234

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 marzo 28, 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

jue. 5/1

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

lun. 5/5

11:55 pm-8:50 am

1 stop7h 55m

$145

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

sáb. 5/3

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

sáb. 5/10

12:15 pm-4:44 pm

Nonstop3h 29m

$147

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

mar. 5/13

7:10 am-9:48 pm

1 stop15h 38m

Calgary

sáb. 5/24

12:55 am-9:52 am

1 stop7h 57m

$151

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

jue. 6/12

8:25 pm-11:25 pm

Nonstop4h 00m

Calgary

jue. 6/19

6:29 am-10:54 am

Nonstop3h 25m

$180

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

jue. 5/1

5:05 am-1:53 pm

1 stop9h 48m

Calgary

sáb. 5/10

12:43 pm-5:10 pm

Nonstop3h 27m

$189

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

mié. 5/14

8:40 am-6:37 pm

2 stops8h 57m

Toronto Island

vie. 5/23

10:20 am-8:12 pm

2 stops10h 52m

$204

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

jue. 4/24

11:15 am-1:57 pm

Nonstop1h 42m

Toronto Island

jue. 5/1

7:55 am-8:45 am

Nonstop1h 50m

$220

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

dom. 5/11

6:30 pm-9:16 pm

Nonstop1h 46m

Toronto Pearson Intl

dom. 5/18

6:35 pm-7:30 pm

Nonstop1h 55m

$227

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

jue. 5/1

5:30 pm-10:35 pm

1 stop7h 05m

Vancouver Intl

sáb. 5/10

7:00 am-4:44 pm

1 stop7h 44m

$228

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

mar. 5/13

9:02 pm-10:25 pm

1 stop27h 23m

Vancouver Intl

sáb. 5/17

3:55 pm-5:25 am

1 stop11h 30m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

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, January is the cheapest month in which you can book a flight from Chicago to Canada (average of $243). Flying from Chicago to Canada in July is currently the most expensive (average of $359). 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 marzo 28, 2025.

When flying from Chicago to Canada, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 marzo 28, 2025.

The most flights from CHI to CA0 are scheduled on a Friday (55 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).

Rainfall in Canada by month

Plan your trip to Canada by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Canada ranges from 2.0 - 3.3 inches per month. June is typically the wettest month, when rainfall can reach 3.3 in. February is typically the driest time to visit Canada when rainfall is around 2.0 in.

Temperature in Canada by month

Plan your trip to Canada by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Canada, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 21.2 F).

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 marzo 28, 2025.
Read through reviews of airlines operating flights from Chicago to Canada, such as Alaska Airlines, Delta and Porter Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,798 reviews

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,798 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,896 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Porter Airlines
7.9
Good
276 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Air Transat
7.8
Good
381 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,603 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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.

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

    $59 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 $75 and $77, 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 Sun Country Air (100%), Korean Air (83%) or Air New Zealand (80%) 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 $111. While the most popular route (Chicago O'Hare Intl - Vancouver Intl) can be booked for $208 on average our data indicates $1,514 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, January is the cheapest month in which you can book a flight from Chicago to Canada (average of $243). Flying from Chicago to Canada in July is currently the most expensive (average of $359). 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 marzo 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$92Average$500FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$117Average$483FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$122Average$357FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$122Average$494FlexibilityNo cancel feeOn-time71%
WestJetCheapest$133Average$308FlexibilityNo cancel feeOn-time60%
DeltaCheapest$137Average$403FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$154Average$474FlexibilityNo cancel feeOn-time75%
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