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$66+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
Nov 20 — Nov 271
Thu 11/20
Thu 11/27
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 October 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$178
(Air Canada)

One-way from

$66
(Trip.com)

Popular in

January

Cheapest in

September

Average price

$294

Good round-trip deal

$193 or less

Good one-way deal

$72 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. 11% potential increase in price ($35 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 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 October 21, 2025.

This American Airlines deal was found by Cheapflights users on 10/21. 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 12/29:45 amORD - YYZ
Nonstop1h 47mAmerican Airlines
Fri 12/126:24 pmYYZ - ORD
Nonstop2h 00mAmerican Airlines
Deal found 10/21$184
This Trip.com deal was found by Cheapflights users on 10/20. 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 12/52:20 pmORD - YYC
Nonstop3h 55mWestJet
Fri 12/129:00 amYYC - ORD
Nonstop3h 35mWestJet
Deal found 10/20$187
This American Airlines deal was found by Cheapflights users on 10/19. 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 11/208:20 amORD - YYZ
1 stop6h 37mAmerican Airlines
Thu 12/46:00 amYYZ - ORD
Nonstop2h 15mAmerican Airlines
Deal found 10/19$194
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Sat 11/110:46 amORD - YQB
Nonstop2h 27mUnited Airlines
Wed 11/52:55 pmYQB - ORD
Nonstop3h 02mUnited Airlines
Deal found 10/19$198
This Flightnetwork deal was found by Cheapflights users on 10/20. 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.
Thu 12/43:55 pmORD - YVR
1 stop10h 55mAir Canada
Thu 12/118:30 amYVR - ORD
Nonstop4h 11mAir Canada
Deal found 10/20$199
This American Airlines deal was found by Cheapflights users on 10/21. 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 12/59:39 amORD - YYZ
Nonstop1h 51mAmerican Airlines
Sun 12/76:00 amYYZ - ORD
1 stop6h 03mAmerican Airlines
Deal found 10/21$200
This United deal was found by Cheapflights users on 10/21. 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.
Wed 11/510:46 amORD - YQB
Nonstop2h 27mMultiple Airlines
Sat 11/86:00 amYQB - ORD
1 stop6h 18mMultiple Airlines
Deal found 10/21$203
This Air Canada deal was found by Cheapflights users on 10/20. 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.
Tue 11/182:00 pmORD - YYC
1 stop7h 39mAir Canada
Sat 11/225:35 amYYC - ORD
1 stop8h 20mAir Canada
Deal found 10/20$206
This Mytrip deal was found by Cheapflights users on 10/20. 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.
Fri 12/52:20 pmORD - YYC
Nonstop3h 55mMultiple Airlines
Fri 12/125:35 amYYC - ORD
1 stop8h 35mMultiple Airlines
Deal found 10/20$207
This Air Canada deal was found by Cheapflights users on 10/21. 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.
Tue 12/212:50 pmORD - YQB
1 stop4h 24mAir Canada
Thu 12/116:00 amYQB - ORD
1 stop6h 18mAir Canada
Deal found 10/21$208
This American Airlines deal was found by Cheapflights users on 10/21. 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 11/208:20 amORD - YYZ
1 stop6h 37mAmerican Airlines
Mon 11/2410:57 amYYZ - ORD
1 stop6h 56mAmerican Airlines
Deal found 10/21$209
This Air Canada deal was found by Cheapflights users on 10/19. 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.
Tue 11/183:40 pmORD - YVR
Nonstop4h 35mAir Canada
Sun 11/238:30 amYVR - ORD
Nonstop4h 11mAir Canada
Deal found 10/19$210

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 October 21, 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

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sun 3/22

7:10 am-9:55 am

Nonstop1h 45m

Toronto Pearson Intl

Thu 3/26

11:00 am-11:59 am

Nonstop1h 59m

$178

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 3/5

6:40 pm-9:28 pm

Nonstop1h 48m

Toronto Pearson Intl

Sun 3/15

9:00 pm-9:59 pm

Nonstop1h 59m

$178

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Mon 11/17

10:46 am-2:13 pm

Nonstop2h 27m

Québec City

Mon 11/24

2:55 pm-4:57 pm

Nonstop3h 02m

$198

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Sat 11/1

10:46 am-2:13 pm

Nonstop2h 27m

Québec City

Wed 11/5

2:55 pm-4:57 pm

Nonstop3h 02m

$198

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Wed 11/12

10:46 am-2:13 pm

Nonstop2h 27m

Québec City

Fri 11/14

2:55 pm-4:57 pm

Nonstop3h 02m

$198

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Sat 11/15

10:46 am-2:13 pm

Nonstop2h 27m

Québec City

Sat 11/22

2:55 pm-4:57 pm

Nonstop3h 02m

$198

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Wed 11/5

10:46 am-2:13 pm

Nonstop2h 27m

Québec City

Sat 11/8

6:00 am-11:18 am

1 stop6h 18m

$203

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Wed 11/19

10:46 am-2:13 pm

Nonstop2h 27m

Québec City

Sat 11/22

6:00 am-11:18 am

1 stop6h 18m

$203

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Sat 11/1

10:46 am-2:13 pm

Nonstop2h 27m

Québec City

Tue 11/4

6:00 am-11:18 am

1 stop6h 18m

$203

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 2/20

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Wed 2/25

9:15 am-10:05 am

Nonstop1h 50m

$206

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/20

Showing 1-10 of 60 results
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6

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, April is the cheapest month in which you can book a flight from Chicago to Canada (average of $80). Flying from Chicago to Canada in August is currently the most expensive (average of $132). 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 October 21, 2025.

When flying from Chicago to Canada, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 17% versus a flight at noon.

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

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

Travelers seeking maximum savings on their Chicago to Canada flight should consider departing on Thursday at noon 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.

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 October 21, 2025.

The most flights from CHI to CA0 are scheduled on a Monday (64 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (11 on average).

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 October 21, 2025.
Peruse reviews from past customers who have flown with Porter Airlines, United Airlines, and American Airlines from Chicago to Canada to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
381 reviews

Comfort

8.0

Food

7.6

Entertainment

7.0

Overall

8.0

Crew

8.6

Boarding

8.2

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
381 reviews
Porter Airlines
8.0
Very good
381 reviews

Comfort

8.0

Food

7.6

Entertainment

7.0

Overall

8.0

Crew

8.6

Boarding

8.2

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
8,988 reviews
Porter Airlines
8.0
Very good
381 reviews

Comfort

8.0

Food

7.6

Entertainment

7.0

Overall

8.0

Crew

8.6

Boarding

8.2

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
11,023 reviews
Porter Airlines
8.0
Very good
381 reviews

Comfort

8.0

Food

7.6

Entertainment

7.0

Overall

8.0

Crew

8.6

Boarding

8.2

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
3,131 reviews
Porter Airlines
8.0
Very good
381 reviews

Comfort

8.0

Food

7.6

Entertainment

7.0

Overall

8.0

Crew

8.6

Boarding

8.2

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
10,338 reviews
Porter Airlines
8.0
Very good
381 reviews

Comfort

8.0

Food

7.6

Entertainment

7.0

Overall

8.0

Crew

8.6

Boarding

8.2

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 Chicago to Canada. 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 Chicago to Canada?

    For as low as $206, United Airlines can have you in Canada from Chicago in 1h 42m. The distance from Chicago to Canada 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 Chicago to Canada one-way?

    $66 is the cheapest one-way deal found within the past few days, from Air Canada. You may also be able to find cheap deals on United Airlines and American Airlines, with prices starting from $73 and $77, respectively.

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

    While some choose either Chicago O'Hare Intl - Vancouver Intl or Chicago O'Hare Intl - Montreal Pierre Elliott Trudeau Intl, Chicago O'Hare Intl - Toronto Pearson 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 Finnair (92%), Qatar Airways (91%) or British Airways (89%) 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 $122. While the most popular route (Chicago O'Hare Intl - Toronto Pearson Intl) can be booked for $166 on average, our data indicates $762 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, April is the cheapest month in which you can book a flight from Chicago to Canada (average of $80). Flying from Chicago to Canada in August is currently the most expensive (average of $132). 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.

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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 October 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$91Average$452FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$98Average$422FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$109Average$337FlexibilityNo cancel feeOn-time52%
DeltaCheapest$109Average$424FlexibilityNo cancel feeOn-timeN/A
WestJetCheapest$142Average$273FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$192Average$463FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$464Average$715FlexibilityNo cancel feeOn-time75%

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