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$100+ 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$174
(Kiwi.com)

One-way from

$100
(Kiwi.com)

Popular in

October

Cheapest in

July

Average price

$296

Good round-trip deal

$268 or less

Good one-way deal

$124 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. 5% potential increase in price ($15 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 October 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 October 30, 2025.

This SmartFares deal was found by Cheapflights users on 10/29. 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.
Fri 11/147:00 amYYZ - ORD
1 stop5h 18mAir Canada
Mon 11/178:15 pmORD - YYZ
Nonstop1h 39mAir Canada
Deal found 10/29$181
This Air Canada deal was found by Cheapflights users on 10/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/37:00 amYYZ - ORD
1 stop5h 18mAir Canada
Thu 2/122:00 pmORD - YYZ
Nonstop1h 39mAir Canada
Deal found 10/29$183
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/310:58 amYYZ - ORD
1 stop9h 23mAmerican Airlines
Thu 2/127:19 amORD - YYZ
1 stop4h 43mAmerican Airlines
Deal found 10/29$184
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Sun 11/239:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 12/1211:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/30$185
This Air Canada deal was found by Cheapflights users on 10/28. 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 11/1210:55 amYQB - ORD
1 stop5h 15mAir Canada
Tue 11/187:05 amORD - YQB
1 stop6h 09mAir Canada
Deal found 10/28$187
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Mon 11/249:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 12/811:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/30$187
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Mon 11/179:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 11/2212:45 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/30$188
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:00 amYYZ - ORD
Nonstop2h 15mAmerican Airlines
Sun 12/148:10 amORD - YYZ
Nonstop1h 46mAmerican Airlines
Deal found 10/29$189
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/186:00 amYYZ - ORD
Nonstop2h 15mAmerican Airlines
Thu 11/207:35 amORD - YYZ
1 stop4h 27mAmerican Airlines
Deal found 10/29$190
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/149:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 11/174:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/29$190
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 11/11:29 pmYYC - ORD
Nonstop3h 25mAmerican Airlines
Mon 11/38:45 pmORD - YYC
1 stop15h 59mAmerican Airlines
Deal found 10/28$192
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 12/64:44 pmYYZ - ORD
Nonstop2h 00mAmerican Airlines
Tue 12/96:22 amORD - YYZ
1 stop5h 38mAmerican Airlines
Deal found 10/28$193

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 October 30, 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 1/16

2:15 pm-3:10 pm

Nonstop1h 55m

Chicago O'Hare Intl

Mon 1/19

3:35 pm-11:04 pm

1 stop6h 29m

$183

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 2/27

3:30 pm-4:39 pm

Nonstop2h 09m

Chicago O'Hare Intl

Sun 3/1

4:47 pm-7:45 pm

Nonstop1h 58m

$184

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 2/24

8:55 am-10:02 am

Nonstop2h 07m

Chicago O'Hare Intl

Sat 2/28

8:15 pm-10:54 pm

Nonstop1h 39m

$184

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/26

6:30 pm-7:30 pm

Nonstop2h 00m

Chicago O'Hare Intl

Sun 3/1

2:00 pm-4:39 pm

Nonstop1h 39m

$185

Québec CityChicago

YQB - ORD

YQBORD

Québec City

Wed 11/12

10:55 am-3:10 pm

1 stop5h 15m

Chicago O'Hare Intl

Tue 11/18

7:05 am-2:14 pm

1 stop6h 09m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 11/22

11:00 am-11:50 am

Nonstop1h 50m

Chicago Midway

Tue 11/25

11:00 am-1:42 pm

Nonstop1h 42m

$197

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 11/24

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Mon 12/1

11:00 am-1:42 pm

Nonstop1h 42m

$199

Québec CityChicago

YQB - ORD

YQBORD

Québec City

Thu 11/13

2:55 pm-4:57 pm

Nonstop3h 02m

Chicago O'Hare Intl

Sun 11/16

8:02 pm-11:02 am

1 stop14h 00m

$201

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 11/28

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Fri 12/5

4:15 pm-6:57 pm

Nonstop1h 42m

$201

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/4

6:24 pm-7:24 pm

Nonstop2h 00m

Chicago O'Hare Intl

Fri 12/5

9:39 am-12:30 pm

Nonstop1h 51m

$202

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

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, June is the cheapest month in which you can book a flight from Canada to Chicago (average of $83). Flying from Canada to Chicago in December is currently the most expensive (average of $142). 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 October 30, 2025.

A simple way to save on the total cost of your ticket is to fly from Canada to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 29% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Canada to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Canada to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Canada to Chicago flight should consider departing on Thursday mornings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 30, 2025.
Read through reviews of airlines operating flights from Canada to Chicago, such as Porter Airlines, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
384 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Food

7.6

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
8.0
Very good
384 reviews
Porter Airlines
8.0
Very good
384 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Food

7.6

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
United Airlines
7.4
Good
8,996 reviews
Porter Airlines
8.0
Very good
384 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Food

7.6

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
American Airlines
7.2
Good
11,034 reviews
Porter Airlines
8.0
Very good
384 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Food

7.6

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
WestJet
7.2
Good
3,152 reviews
Porter Airlines
8.0
Very good
384 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Food

7.6

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Canada
7.1
Good
10,383 reviews
Porter Airlines
8.0
Very good
384 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Food

7.6

Comfort

8.0

Entertainment

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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.

  • How long is the flight from Canada to Chicago?

    Air Canada, United Airlines, and Porter Airlines can get you from Canada to Chicago in just under 1h 50m. Your travel time will be generally consistent. The distance from Canada to Chicago is about 442 mi. Generally, flights for this route are nonstop.

  • 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 ($110), United Airlines ($112), and American Airlines ($114).

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

    The most popular route from Canada to Chicago is Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl. You may also consider Toronto Pearson 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 EVA Air (94%), Egyptair (90%) and Copa Airlines (90%).

  • What are the cheapest flights from Canada to Chicago?

    The cheapest flight price from Canada to Chicago is $153. On average you can expect to pay $1,238. The most popular route, (Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl), can usually be booked for $183.

  • 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, June is the cheapest month in which you can book a flight from Canada to Chicago (average of $83). Flying from Canada to Chicago in December is currently the most expensive (average of $142). 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
Porter
Benton Harbor

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$109Average$436FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$110Average$389FlexibilityNo cancel feeOn-time69%
WestJetCheapest$138Average$272FlexibilityNo cancel feeOn-time60%
Porter AirlinesCheapest$158Average$326FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$167Average$376FlexibilityNo cancel feeOn-time71%

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