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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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$151
(Trip.com)

One-way from

$100
(Air Canada)

Popular in

December

Cheapest in

July

Average price

$250

Good round-trip deal

$155 or less

Good one-way deal

$153 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 ($19 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 September 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 September 11, 2025.

This oojo deal was found by Cheapflights users on 9/9. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/176:00 amYVR - ORD
1 stop8h 43mWestJet
Sun 10/195:30 pmORD - YVR
1 stop8h 41mWestJet
Deal found 9/9$144
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/177:00 amYVR - ORD
1 stop7h 43mWestJet
Thu 10/235:30 pmORD - YVR
1 stop7h 06mWestJet
Deal found 9/9$150
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/247:00 amYVR - ORD
1 stop7h 43mWestJet
Sat 10/255:30 pmORD - YVR
1 stop8h 41mWestJet
Deal found 9/9$151
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/186:00 amYVR - ORD
1 stop8h 43mWestJet
Sat 10/255:30 pmORD - YVR
1 stop8h 41mWestJet
Deal found 9/9$152
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/126:00 amYVR - ORD
1 stop8h 43mWestJet
Thu 10/165:30 pmORD - YVR
1 stop7h 06mWestJet
Deal found 9/9$153
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/237:00 amYVR - ORD
1 stop7h 43mWestJet
Mon 10/272:20 pmORD - YVR
1 stop7h 25mWestJet
Deal found 9/9$154
This Air Canada deal was found by Cheapflights users on 9/10. 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 10/248:45 amYVR - ORD
Nonstop4h 15mAir Canada
Sun 10/263:40 pmORD - YVR
Nonstop4h 35mAir Canada
Deal found 9/10$160
This Booking.com deal was found by Cheapflights users on 9/9. 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.
Fri 10/248:45 amYVR - ORD
Nonstop4h 15mMultiple Airlines
Fri 10/312:20 pmORD - YVR
1 stop7h 25mMultiple Airlines
Deal found 9/9$161
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/254:14 pmYQB - ORD
Nonstop2h 50mAmerican Airlines
Sat 11/19:56 amORD - YQB
Nonstop2h 40mAmerican Airlines
Deal found 9/10$162
This Trip.com deal was found by Cheapflights users on 9/10. 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.
Sat 11/228:30 amYVR - ORD
Nonstop4h 11mAir Canada
Tue 11/2512:50 pmORD - YVR
1 stop10h 00mAir Canada
Deal found 9/10$162
This FlightHub deal was found by Cheapflights users on 9/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1712:15 pmYYC - ORD
Nonstop3h 28mWestJet
Sun 10/195:30 pmORD - YYC
Nonstop3h 49mWestJet
Deal found 9/11$163
This Booking.com deal was found by Cheapflights users on 9/10. 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 10/228:45 amYVR - ORD
Nonstop4h 15mAir Canada
Sat 10/259:55 amORD - YVR
2 stops13h 21mAir Canada
Deal found 9/10$163

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 September 11, 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

Fri 10/17

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-8:19 pm

Nonstop3h 49m

$163

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 10/27

11:40 pm-9:15 am

1 stop8h 35m

Chicago O'Hare Intl

Thu 10/30

10:00 am-6:54 pm

1 stop9h 54m

$167

Québec CityChicago

YQB - ORD

YQBORD

Québec City

Fri 10/24

5:20 am-9:09 am

1 stop4h 49m

Chicago O'Hare Intl

Fri 10/31

3:35 pm-10:14 pm

1 stop5h 39m

$169

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 10/15

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Wed 10/15

5:20 pm-8:02 pm

Nonstop1h 42m

$173

Québec CityChicago

YQB - ORD

YQBORD

Québec City

Fri 10/24

4:55 pm-11:30 pm

1 stop7h 35m

Chicago O'Hare Intl

Fri 10/31

10:46 am-2:13 pm

Nonstop2h 27m

$174

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 10/31

11:00 pm-6:39 pm

1 stop17h 39m

Chicago Midway

Tue 11/4

1:56 pm-2:45 pm

2 stops26h 49m

$177

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 10/3

1:45 pm-8:04 pm

Nonstop4h 19m

Chicago O'Hare Intl

Mon 10/6

5:01 am-9:51 am

1 stop6h 50m

$178

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 10/4

1:45 pm-8:04 pm

Nonstop4h 19m

Chicago O'Hare Intl

Sun 10/12

5:01 am-9:51 am

1 stop6h 50m

$178

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Wed 10/8

1:45 pm-8:04 pm

Nonstop4h 19m

Chicago O'Hare Intl

Wed 10/15

5:01 am-9:51 am

1 stop6h 50m

$178

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 9/23

7:20 pm-6:15 am

1 stop8h 55m

Chicago O'Hare Intl

Wed 9/24

8:51 am-11:33 am

Nonstop4h 42m

$178

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

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 September 11, 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 September 11, 2025.

The most flights from CA0 to CHI are scheduled on a Friday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (41 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 September 11, 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
7.9
Good
363 reviews

Comfort

7.9

Entertainment

7.0

Overall

7.9

Food

7.6

Crew

8.6

Boarding

8.1

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
7.9
Good
363 reviews
Porter Airlines
7.9
Good
363 reviews

Comfort

7.9

Entertainment

7.0

Overall

7.9

Food

7.6

Crew

8.6

Boarding

8.1

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
8,937 reviews
Porter Airlines
7.9
Good
363 reviews

Comfort

7.9

Entertainment

7.0

Overall

7.9

Food

7.6

Crew

8.6

Boarding

8.1

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
10,000 reviews
Porter Airlines
7.9
Good
363 reviews

Comfort

7.9

Entertainment

7.0

Overall

7.9

Food

7.6

Crew

8.6

Boarding

8.1

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
3,091 reviews
Porter Airlines
7.9
Good
363 reviews

Comfort

7.9

Entertainment

7.0

Overall

7.9

Food

7.6

Crew

8.6

Boarding

8.1

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
10,000 reviews
Porter Airlines
7.9
Good
363 reviews

Comfort

7.9

Entertainment

7.0

Overall

7.9

Food

7.6

Crew

8.6

Boarding

8.1

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?

    WestJet, Air Canada, and Porter Airlines can get you from Canada to Chicago in just under 1h 49m. Your travel time can differ by up to 6h 46m. The distance from Canada to Chicago 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 Canada to Chicago one-way?

    The cheapest airlines for a one-way flight from Canada to Chicago are United Airlines ($103), American Airlines ($103), and Air Canada ($103).

  • 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 Montreal Pierre Elliott Trudeau 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 EVA Air (83%), SkyWest Airlines (83%) and ANA (83%).

  • What are the cheapest flights from Canada to Chicago?

    The cheapest flight price from Canada to Chicago is $127. On average you can expect to pay $1,182. The most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl), can usually be booked for $186.

  • 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
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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$109Average$466FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$112Average$420FlexibilityNo cancel feeOn-time69%
WestJetCheapest$138Average$217FlexibilityNo cancel feeOn-time60%
Porter AirlinesCheapest$158Average$289FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$193Average$339FlexibilityNo cancel feeOn-time71%

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