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$103+ 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 9/18. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Aug 6 — Aug 131
Wed 8/6
Wed 8/13
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 August 1, 2025.

Round-trip from

$147
(Air Canada)

One-way from

$103
(Booking.com)

Popular in

December

Cheapest in

June

Average price

$249

Good round-trip deal

$170 or less

Good one-way deal

$101 or less
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. 7% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 1, 2025.

This Air Canada deal was found by Cheapflights users on 7/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/712:05 pmYYZ - ORD
Nonstop1h 56mAir Canada
Sun 11/93:55 pmORD - YYZ
Nonstop1h 39mAir Canada
Deal found 7/30$147
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/412:15 pmYYC - ORD
Nonstop3h 28mWestJet
Tue 9/95:30 pmORD - YYC
Nonstop3h 49mWestJet
Deal found 7/30$153
This SmartFares deal was found by Cheapflights users on 7/29. 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.
Sat 9/67:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 9/89:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 7/29$153
This Booking.com deal was found by Cheapflights users on 7/29. 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.
Sat 9/133:25 pmYTZ - ORD
1 stop5h 46mAir Canada
Sat 9/203:35 pmORD - YTZ
1 stop4h 59mAir Canada
Deal found 7/29$155
This Trip.com deal was found by Cheapflights users on 7/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2412:15 pmYYC - ORD
Nonstop3h 28mMultiple Airlines
Thu 10/238:47 amORD - YYC
Nonstop3h 51mMultiple Airlines
Deal found 7/30$158
This American Airlines deal was found by Cheapflights users on 8/1. 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 9/186:30 amYYZ - ORD
Nonstop1h 55mAmerican Airlines
Sun 9/218:15 amORD - YYZ
Nonstop1h 44mAmerican Airlines
Deal found 8/1$171
This United Airlines deal was found by Cheapflights users on 7/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/59:00 amYYZ - ORD
Nonstop1h 55mUnited Airlines
Fri 10/176:01 pmORD - YYZ
Nonstop1h 43mUnited Airlines
Deal found 7/30$172
This Air Canada deal was found by Cheapflights users on 8/1. 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.
Thu 9/188:20 amYUL - ORD
Nonstop2h 31mAir Canada
Mon 9/228:40 amORD - YUL
Nonstop2h 17mAir Canada
Deal found 8/1$175
This Kissandfly.com deal was found by Cheapflights users on 7/30. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/45:15 pmYYZ - ORD
Nonstop1h 57mLufthansa
Sun 9/79:12 pmORD - YYZ
Nonstop1h 46mLufthansa
Deal found 7/30$182
This American Airlines deal was found by Cheapflights users on 7/31. 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.
Fri 9/512:30 pmYUL - ORD
Nonstop2h 35mAmerican Airlines
Tue 9/95:00 amORD - YUL
1 stop16h 32mAmerican Airlines
Deal found 7/31$184
This Air Canada deal was found by Cheapflights users on 7/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/31:10 amYYC - ORD
1 stop7h 41mAir Canada
Tue 9/93:50 pmORD - YYC
1 stop8h 32mAir Canada
Deal found 7/30$185
This Mytrip deal was found by Cheapflights users on 7/29. 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 9/257:50 amYTZ - MDW
Nonstop1h 49mMultiple Airlines
Mon 9/295:20 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 7/29$196

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 August 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

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 11/7

12:05 pm-1:01 pm

Nonstop1h 56m

Chicago O'Hare Intl

Sun 11/9

3:55 pm-6:34 pm

Nonstop1h 39m

$147

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 9/4

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

Tue 9/9

5:30 pm-8:19 pm

Nonstop3h 49m

$153

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 9/6

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Mon 9/8

9:35 am-12:17 pm

Nonstop1h 42m

$153

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 9/13

3:25 pm-8:11 pm

1 stop5h 46m

Chicago O'Hare Intl

Sat 9/20

3:35 pm-9:34 pm

1 stop4h 59m

$155

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 9/24

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

Thu 10/23

8:47 am-11:38 am

Nonstop3h 51m

$158

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 9/18

6:30 am-7:25 am

Nonstop1h 55m

Chicago O'Hare Intl

Sun 9/21

8:15 am-10:59 am

Nonstop1h 44m

$171

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 10/5

9:00 am-9:55 am

Nonstop1h 55m

Chicago O'Hare Intl

Fri 10/17

6:01 pm-8:44 pm

Nonstop1h 43m

$172

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 9/18

8:20 am-9:51 am

Nonstop2h 31m

Chicago O'Hare Intl

Mon 9/22

8:40 am-11:57 am

Nonstop2h 17m

$175

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 9/4

5:15 pm-6:12 pm

Nonstop1h 57m

Chicago O'Hare Intl

Sun 9/7

9:12 pm-11:58 pm

Nonstop1h 46m

$182

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 9/5

12:30 pm-2:05 pm

Nonstop2h 35m

Chicago O'Hare Intl

Tue 9/9

5:00 am-10:32 pm

1 stop16h 32m

$184

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 $321). 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 August 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 August 1, 2025.

The most flights from CA0 to CHI are scheduled on a Friday (60 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (39 on average).

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 August 1, 2025.
Read through reviews of airlines operating flights from Canada to Chicago, such as Porter Airlines, Delta, and Air Transat. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Comfort

8.0

Crew

8.7

Boarding

8.2

Entertainment

7.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
318 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Comfort

8.0

Crew

8.7

Boarding

8.2

Entertainment

7.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,981 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Comfort

8.0

Crew

8.7

Boarding

8.2

Entertainment

7.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Transat
7.7
Good
424 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Comfort

8.0

Crew

8.7

Boarding

8.2

Entertainment

7.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,900 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Comfort

8.0

Crew

8.7

Boarding

8.2

Entertainment

7.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
8.0
Very good
318 reviews

Overall

8.0

Comfort

8.0

Crew

8.7

Boarding

8.2

Entertainment

7.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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 Air Canada ($103), Porter Airlines ($107), and United Airlines ($111).

  • 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 Toronto Island - Chicago Midway or Vancouver Intl - Chicago O'Hare Intl.

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

    The top 3 most reliable airlines when flying from Canada to Chicago are Cathay Pacific (100%), SkyWest Airlines (91%) and Egyptair (90%).

  • What are the cheapest flights from Canada to Chicago?

    The cheapest flight price from Canada to Chicago is $122. On average you can expect to pay $2,979. The most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl), can usually be booked for $172.

  • 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 $321). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 August 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$109Average$471FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$112Average$425FlexibilityNo cancel feeOn-time69%
WestJetCheapest$137Average$265FlexibilityNo cancel feeOn-time60%
Porter AirlinesCheapest$158Average$291FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$167Average$375FlexibilityNo cancel feeOn-time71%

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