Chicago

$135+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Jul 16 — Jul 231
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Cheap 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 June 16, 2026.

This Air Canada deal was found by Cheapflights users on 6/15. 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.
Sat 9/56:55 pm
YYZ
-
ORD
Nonstop1h 57m
Air Canada
Mon 9/79:50 am
ORD
-
YYZ
Nonstop1h 45m
Air Canada
Deal found 6/15$206
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 6/298:50 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 6/293:20 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/12$206
This Kissandfly.com deal was found by Cheapflights users on 6/11. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/267:25 pm
YTZ
-
ORD
Nonstop2h 04m
Air Canada
Sun 8/27:25 am
ORD
-
YTZ
Nonstop1h 42m
Air Canada
Deal found 6/11$206
This United Airlines deal was found by Cheapflights users on 6/12. 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.
Fri 10/211:00 am
YYZ
-
ORD
Nonstop2h 00m
United Airlines
Mon 10/57:09 am
ORD
-
YYZ
Nonstop1h 45m
United Airlines
Deal found 6/12$207
This Mytrip deal was found by Cheapflights users on 6/13. 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 7/28:50 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 7/510:25 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/13$207
This Trip.com deal was found by Cheapflights users on 6/15. 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 7/37:25 pm
YTZ
-
ORD
Nonstop2h 04m
Air Canada
Mon 7/62:00 pm
ORD
-
YTZ
Nonstop1h 42m
Air Canada
Deal found 6/15$207
This Trip.com deal was found by Cheapflights users on 6/15. 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.
Thu 9/246:15 am
YYZ
-
ORD
1 stop5h 02m
Air Canada
Sat 9/265:35 pm
ORD
-
YYZ
Nonstop1h 43m
Air Canada
Deal found 6/15$208
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/268:50 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 8/210:20 am
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/11$208
This Trip.com deal was found by Cheapflights users on 6/15. 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.
Thu 8/207:25 pm
YTZ
-
ORD
Nonstop2h 04m
Air Canada
Sun 8/238:45 am
ORD
-
YTZ
1 stop6h 06m
Air Canada
Deal found 6/15$208
This Trip.com deal was found by Cheapflights users on 6/14. 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.
Thu 7/24:00 pm
YYZ
-
ORD
Nonstop1h 57m
Air Canada
Sun 7/59:50 am
ORD
-
YYZ
Nonstop1h 45m
Air Canada
Deal found 6/14$209
This Trip.com deal was found by Cheapflights users on 6/15. 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 9/196:15 am
YYZ
-
ORD
1 stop5h 02m
Air Canada
Sun 9/205:35 pm
ORD
-
YYZ
Nonstop1h 43m
Air Canada
Deal found 6/15$210
This Porter Airlines deal was found by Cheapflights users on 6/11. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/128:50 am
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 7/303:20 pm
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 6/11$210

Find flight deals from Canada to Chicago

Keep the following information in mind while searching for Canada to Chicago flight deals. Data was last updated June 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$206
(Air Canada)

One-way from

$135
(Flightnetwork)

Popular in

June

Cheapest in

September

Average price

$284

Good round-trip deal

$217 or less

Good one-way deal

$134 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago (CHI) flights.
From Canada to Chicago (CHI)
One-way flight from Canada to Chicago (CHI)
Highest demand for flights based on searches. 3% potential increase in price ($10 potential increase over avg. RT price).
Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
Average for round-trip flights in June 2026
Price to beat on a round-trip flight from Canada to Chicago (CHI).
Price to beat on a one-way flight from Canada to Chicago (CHI).

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 June 16, 2026.
Use the filters below to find and compare flights from Canada to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 7/2

8:50 am-9:40 am

Nonstop1h 50m

Chicago Midway

Sun 7/5

10:25 am-1:05 pm

Nonstop1h 40m

$207

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 8/14

1:45 pm-2:35 pm

Nonstop1h 50m

Chicago Midway

Sun 8/16

10:20 am-1:00 pm

Nonstop1h 40m

$208

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 7/2

8:50 am-9:40 am

Nonstop1h 50m

Chicago Midway

Sat 7/4

10:25 am-1:05 pm

Nonstop1h 40m

$209

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 7/10

1:45 pm-2:35 pm

Nonstop1h 50m

Chicago Midway

Tue 7/28

3:20 pm-6:00 pm

Nonstop1h 40m

$210

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 7/10

1:45 pm-2:35 pm

Nonstop1h 50m

Chicago Midway

Wed 7/29

10:25 am-1:05 pm

Nonstop1h 40m

$210

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 8/23

7:00 am-8:00 am

Nonstop2h 00m

Chicago O'Hare Intl

Mon 8/24

2:15 pm-5:01 pm

Nonstop1h 46m

$219

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 7/15

1:00 pm-2:06 pm

Nonstop2h 06m

Chicago O'Hare Intl

Sun 7/19

7:09 am-9:54 am

Nonstop1h 45m

$219

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 8/12

1:45 pm-2:35 pm

Nonstop1h 50m

Chicago Midway

Thu 8/20

3:15 pm-5:55 pm

Nonstop1h 40m

$222

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sun 9/13

1:40 pm-2:35 pm

Nonstop1h 55m

Chicago O'Hare Intl

Thu 9/17

11:45 am-2:25 pm

Nonstop1h 40m

$225

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 7/18

7:43 pm-11:31 pm

1 stop4h 48m

Chicago O'Hare Intl

Mon 8/17

9:29 pm-12:13 am

Nonstop1h 44m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/13

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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, April is the cheapest month in which you can book a flight from Canada to Chicago (average of $255). Flying from Canada to Chicago in June is currently the most expensive (average of $363). 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 June 16, 2026.

A simple way to save on the total cost of your ticket is to fly from Canada to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 25% on your trip compared to booking a flight at noon.

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 June 16, 2026.

The most flights from CA0 to CHI are scheduled on a Tuesday (71 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (41 on average).

How often are flights from Canada to Chicago delayed?

About 13% of weekly flights between Canada and Chicago have experienced delays in the past year, with the average delay time being 136 minutes.

What is the most punctual flight time for Canada to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Thursday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Canada to Chicago flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 8% of flights being delayed.

How far ahead should I book a flight from Canada to Chicago?

Booking 83 days in advance of your planned departure date is, on average, the best time to get cheap flights from Canada to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 June 13, 2026.

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 June 16, 2026.
Read through reviews of airlines operating flights from Canada to Chicago, such as Porter Airlines,United Airlines, andWestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Crew

8.6

Food

7.6

Boarding

8.2

Entertainment

6.9

Overall

8.0

Comfort

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

Crew

8.6

Food

7.6

Boarding

8.2

Entertainment

6.9

Overall

8.0

Comfort

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

Crew

8.6

Food

7.6

Boarding

8.2

Entertainment

6.9

Overall

8.0

Comfort

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

Crew

8.6

Food

7.6

Boarding

8.2

Entertainment

6.9

Overall

8.0

Comfort

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

Crew

8.6

Food

7.6

Boarding

8.2

Entertainment

6.9

Overall

8.0

Comfort

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

Crew

8.6

Food

7.6

Boarding

8.2

Entertainment

6.9

Overall

8.0

Comfort

8.0

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

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?

    Porter Airlines, United Airlines, and Air Canada 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 ($98), Porter Airlines ($101), and American Airlines ($102).

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

  • 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 (100%), EVA Air (100%) and Qatar Airways (91%).

  • What are the cheapest flights from Canada to Chicago?

    The cheapest flight price from Canada to Chicago is $143. On average you can expect to pay $902. The most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl), can usually be booked for $207.

  • 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, April is the cheapest month in which you can book a flight from Canada to Chicago (average of $255). Flying from Canada to Chicago in June is currently the most expensive (average of $363). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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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.

Top 6 airlines flying from Canada to Chicago

Discover the top 6 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 June 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$90Average$446FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$119Average$412FlexibilityNo cancel feeOn-time67%
WestJetCheapest$138Average$314FlexibilityNo cancel feeOn-time60%
Porter AirlinesCheapest$163Average$370FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$167Average$379FlexibilityNo cancel feeOn-time71%
DeltaCheapest$241Average$288FlexibilityNo cancel feeOn-timeN/A

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