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$92+ Cheap flights from Canada to Chicago (CHI)

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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
1 adult, Economy
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Cheap flight deals from Canada to Chicago

Keep the following information in mind while searching for Canada to Chicago flight deals. Data was last updated April 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$132
(Kiwi.com)

One-way from

$92
(oojo)

Popular in

December

Cheapest in

April

Average price

$234

Good round-trip deal

$118 or less

Good one-way deal

$119 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago (CHI) flights.
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From Canada to Chicago (CHI)
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One-way flight from Canada to Chicago (CHI)
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Highest demand for flights based on searches. 4% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Canada to Chicago (CHI).
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Price to beat on a one-way flight from Canada to Chicago (CHI).
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Find flight deals from Canada to Chicago

Cheapest flights from Canada to Chicago
Explore the most affordable flight options available from Canada to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2025.

This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Sat 5/312:15 pmYYC - ORD
Nonstop3h 29mWestJet
Fri 5/95:30 pmORD - YYC
Nonstop3h 49mWestJet
Deal found 3/31$132
This Jettzy deal was found by Cheapflights users on 3/31. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/111:55 pmYYC - ORD
1 stop7h 55mAir Canada
Wed 5/74:00 pmORD - YYC
1 stop7h 58mAir Canada
Deal found 3/31$158
This United deal was found by Cheapflights users on 3/31. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/312:43 pmYYC - ORD
Nonstop3h 27mMultiple Airlines
Fri 5/94:00 pmORD - YYC
1 stop7h 58mMultiple Airlines
Deal found 3/31$163
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Thu 6/126:29 amYYC - ORD
Nonstop3h 25mAmerican Airlines
Sun 6/158:30 pmORD - YYC
Nonstop3h 59mAmerican Airlines
Deal found 3/31$182
This Trip.com deal was found by Cheapflights users on 3/31. 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.
Wed 4/239:30 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 4/3011:15 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 3/31$199
This Justfly.com deal was found by Cheapflights users on 3/31. 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.
Sun 6/810:15 pmYVR - ORD
1 stop16h 29mWestJet
Mon 6/165:30 pmORD - YVR
1 stop7h 05mWestJet
Deal found 3/31$204
This Trip.com deal was found by Cheapflights users on 3/31. 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.
Mon 4/289:30 amYVR - ORD
1 stop23h 15mMultiple Airlines
Fri 5/25:30 pmORD - YVR
1 stop8h 40mMultiple Airlines
Deal found 3/31$208
This Booking.com deal was found by Cheapflights users on 3/31. 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.
Wed 5/146:35 pmYYZ - ORD
Nonstop1h 55mAir Canada
Wed 5/218:25 pmORD - YYZ
Nonstop1h 42mAir Canada
Deal found 3/31$213
This Trip.com deal was found by Cheapflights users on 3/31. 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.
Fri 4/259:30 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Sun 4/275:35 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 3/31$217
This Mytrip deal was found by Cheapflights users on 3/30. 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.
Thu 5/158:25 amYTZ - ORD
1 stop7h 22mAir Canada
Thu 5/222:07 pmORD - YTZ
1 stop6h 28mAir Canada
Deal found 3/30$219
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/127:40 amYYC - ORD
2 stops8h 47mDelta
Mon 4/141:55 pmORD - YYC
1 stop10h 10mDelta
Deal found 3/31$221
This United Airlines deal was found by Cheapflights users on 3/31. 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.
Mon 4/289:00 pmYYZ - ORD
Nonstop2h 06mUnited Airlines
Mon 5/512:00 pmORD - YYZ
Nonstop1h 38mUnited Airlines
Deal found 3/31$229

Cheapflights Fare Finder

Customize your flight search to find flights from Canada to Chicago 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 April 1, 2025.
Use the filters below to find and compare flights from Canada to Chicago that are best for you.

Fly from

Canada

Fly to

Chicago

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 5/3

12:15 pm-4:44 pm

Nonstop3h 29m

Chicago O'Hare Intl

Fri 5/9

5:30 pm-8:19 pm

Nonstop3h 49m

$132

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 5/1

11:55 pm-8:50 am

1 stop7h 55m

Chicago O'Hare Intl

Wed 5/7

4:00 pm-10:58 pm

1 stop7h 58m

$158

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 5/3

12:43 pm-5:10 pm

Nonstop3h 27m

Chicago O'Hare Intl

Fri 5/9

4:00 pm-10:58 pm

1 stop7h 58m

$163

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 6/12

6:29 am-10:54 am

Nonstop3h 25m

Chicago O'Hare Intl

Sun 6/15

8:30 pm-11:29 pm

Nonstop3h 59m

$182

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 4/23

9:30 am-10:20 am

Nonstop1h 50m

Chicago Midway

Wed 4/30

11:15 am-1:57 pm

Nonstop1h 42m

$199

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sun 6/8

10:15 pm-4:44 pm

1 stop16h 29m

Chicago O'Hare Intl

Mon 6/16

5:30 pm-10:35 pm

1 stop7h 05m

$204

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Mon 4/28

9:30 am-10:45 am

1 stop23h 15m

Chicago O'Hare Intl

Fri 5/2

5:30 pm-12:10 am

1 stop8h 40m

$208

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 5/14

6:35 pm-7:30 pm

Nonstop1h 55m

Chicago O'Hare Intl

Wed 5/21

8:25 pm-11:07 pm

Nonstop1h 42m

$213

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 4/25

9:30 am-10:20 am

Nonstop1h 50m

Chicago Midway

Sun 4/27

5:35 pm-8:17 pm

Nonstop1h 42m

$217

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 5/15

8:25 am-2:47 pm

1 stop7h 22m

Chicago O'Hare Intl

Thu 5/22

2:07 pm-9:35 pm

1 stop6h 28m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 60 results
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Best time to book a flight from Canada to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Canada 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 Canada to Chicago

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

Currently, August is the cheapest month in which you can book a flight from Canada to Chicago (average of $245). Flying from Canada to Chicago in March is currently the most expensive (average of $323). 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 CA to CHI?

Find hourly flight availability from Canada to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 1, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Canada to Chicago as you normally would.

Weekly flight availability from Canada to Chicago

Explore weekly flight availability from Canada to Chicago. 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 April 1, 2025.

The most flights from CA0 to CHI are scheduled on a Sunday (57 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (29 on average).

Rainfall in Chicago by month

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

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

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

If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated April 1, 2025.
Read through reviews of airlines operating flights from Canada to Chicago, such as Japan Airlines, Delta and Alaska Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Japan Airlines
8.3
Very good
1,440 reviews

Crew

8.7

Comfort

8.2

Food

7.7

Entertainment

7.8

Overall

8.3

Boarding

8.4

Reviews

1 / 20
10.0
Excellent

mark,Nov 2024

YVR - NRT

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority
Japan Airlines
8.3
Very good
1,440 reviews
Japan Airlines
8.3
Very good
1,440 reviews

Crew

8.7

Comfort

8.2

Food

7.7

Entertainment

7.8

Overall

8.3

Boarding

8.4

Reviews

1 / 20
10.0
Excellent

mark,Nov 2024

YVR - NRT

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority
Delta
8.0
Very good
7,898 reviews
Japan Airlines
8.3
Very good
1,440 reviews

Crew

8.7

Comfort

8.2

Food

7.7

Entertainment

7.8

Overall

8.3

Boarding

8.4

Reviews

1 / 20
10.0
Excellent

mark,Nov 2024

YVR - NRT

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority
Alaska Airlines
8.0
Very good
9,820 reviews
Japan Airlines
8.3
Very good
1,440 reviews

Crew

8.7

Comfort

8.2

Food

7.7

Entertainment

7.8

Overall

8.3

Boarding

8.4

Reviews

1 / 20
10.0
Excellent

mark,Nov 2024

YVR - NRT

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority
Porter Airlines
7.9
Good
278 reviews
Japan Airlines
8.3
Very good
1,440 reviews

Crew

8.7

Comfort

8.2

Food

7.7

Entertainment

7.8

Overall

8.3

Boarding

8.4

Reviews

1 / 20
10.0
Excellent

mark,Nov 2024

YVR - NRT

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority
Air Transat
7.8
Good
381 reviews
Japan Airlines
8.3
Very good
1,440 reviews

Crew

8.7

Comfort

8.2

Food

7.7

Entertainment

7.8

Overall

8.3

Boarding

8.4

Reviews

1 / 20
10.0
Excellent

mark,Nov 2024

YVR - NRT

I like that flight because super nice and friendly. I’m a senior and quick not comfortable to ask what I need help. But would be nicer if they check us if we need any more help because we are not able to leave our seat. However Japan Aniline is my on top priority

Related info for your journey

Find useful and relevant information for your journey from Canada to Chicago. 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 Canada to Chicago one-way?

    The cheapest airlines for a one-way flight from Canada to Chicago are WestJet ($92), Air Canada ($99), and United Airlines ($115).

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

    The most popular route from Canada to Chicago is Toronto Pearson Intl - Chicago O'Hare Intl. You may also consider Vancouver Intl - Chicago O'Hare Intl or Toronto Island - Chicago Midway.

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

    The top 3 most reliable airlines when flying from Canada to Chicago are Copa Airlines (88%), Emirates (87%) and ANA (86%).

  • What are the cheapest flights from Canada to Chicago?

    The cheapest flight price from Canada to Chicago is $133. On average you can expect to pay $2,224. The most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl), can usually be booked for $229.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Canada to Chicago (average of $245). Flying from Canada to Chicago in March is currently the most expensive (average of $323). 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

Traveling to a place near Canada?

Book flights to Canada if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Canada to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Canada to Chicago

Discover the top 5 airlines that operate flights from Canada to Chicago. 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 April 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$112Average$486FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$129Average$455FlexibilityNo cancel feeOn-time67%
WestJetCheapest$139Average$314FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$166Average$356FlexibilityNo cancel feeOn-time71%
Porter AirlinesCheapest$170Average$311FlexibilityNo cancel feeOn-time52%
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