HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$89+ 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 5/22. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
ene. 14 — ene. 211
mié. 1/14
mié. 1/21
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Canada to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 diciembre 15, 2025.

This FlightHub deal was found by Cheapflights users on 12/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/276:45 amYUL - MDW
1 stop4h 20mPorter Airlines
lun. 2/2311:00 amMDW - YUL
1 stop5h 45mPorter Airlines
Deal found 12/13$196
This Air Canada deal was found by Cheapflights users on 12/15. 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.
jue. 12/185:35 amYYC - ORD
1 stop13h 10mAir Canada
mié. 1/78:00 amORD - YYC
1 stop10h 04mAir Canada
Deal found 12/15$262
This United Airlines deal was found by Cheapflights users on 12/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/316:40 pmYYZ - ORD
1 stop5h 55mUnited Airlines
mié. 3/256:25 pmORD - YYZ
Nonstop1h 53mUnited Airlines
Deal found 12/14$268
This United Airlines deal was found by Cheapflights users on 12/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/299:00 amYYZ - ORD
Nonstop2h 05mUnited Airlines
dom. 4/54:43 pmORD - YYZ
Nonstop1h 54mUnited Airlines
Deal found 12/13$277
This United Airlines deal was found by Cheapflights users on 12/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/316:40 pmYYZ - ORD
1 stop5h 55mUnited Airlines
mar. 3/241:06 pmORD - YYZ
1 stop4h 51mUnited Airlines
Deal found 12/14$278
This United Airlines deal was found by Cheapflights users on 12/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/316:40 pmYYZ - ORD
1 stop5h 55mUnited Airlines
vie. 3/274:30 pmORD - YYZ
1 stop5h 50mUnited Airlines
Deal found 12/14$282
This United Airlines deal was found by Cheapflights users on 12/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/316:40 pmYYZ - ORD
1 stop5h 55mUnited Airlines
dom. 1/48:46 pmORD - YYZ
1 stop10h 49mUnited Airlines
Deal found 12/14$291
This United Airlines deal was found by Cheapflights users on 12/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/317:40 pmYYZ - ORD
1 stop5h 04mUnited Airlines
sáb. 4/43:00 pmORD - YYZ
Nonstop1h 58mUnited Airlines
Deal found 12/13$297
This FlightHub deal was found by Cheapflights users on 12/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/309:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
vie. 1/24:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/12$304
This FlightHub deal was found by Cheapflights users on 12/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/296:45 amYUL - MDW
1 stop4h 20mPorter Airlines
dom. 1/411:05 amMDW - YUL
1 stop5h 40mPorter Airlines
Deal found 12/14$305
This Trip.com deal was found by Cheapflights users on 12/14. 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.
mié. 12/319:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
dom. 1/411:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/14$308
This FlightHub deal was found by Cheapflights users on 12/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/252:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
jue. 1/1511:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/13$309

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 diciembre 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$155
(Booking.com)

One-way from

$89
(Mytrip)

Popular in

December

Cheapest in

July

Average price

$321

Good round-trip deal

$195 or less

Good one-way deal

$117 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago (CHI) flights.
Search Deals
From Canada to Chicago (CHI)
Search Deals
One-way flight from Canada to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Canada to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Canada to Chicago (CHI).
Search Deals

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 diciembre 15, 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

mié. 1/28

5:35 am-3:10 pm

1 stop8h 35m

Chicago O'Hare Intl

mié. 2/4

7:15 am-8:19 pm

2 stops14h 04m

$167

CalgaryChicago

YYC - ORD

YYCORD

Calgary

jue. 2/19

5:35 am-3:10 pm

1 stop8h 35m

Chicago O'Hare Intl

sáb. 2/28

3:55 pm-12:14 am

1 stop9h 19m

$176

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

vie. 2/20

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

lun. 2/23

11:00 am-1:42 pm

Nonstop1h 42m

$179

CalgaryChicago

YYC - ORD

YYCORD

Calgary

vie. 1/16

9:00 am-1:35 pm

Nonstop3h 35m

Chicago O'Hare Intl

lun. 1/19

2:20 pm-5:15 pm

Nonstop3h 55m

$181

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

dom. 2/8

11:00 am-12:08 pm

Nonstop2h 08m

Chicago O'Hare Intl

lun. 2/16

6:28 pm-9:21 pm

Nonstop1h 53m

$186

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

jue. 1/29

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

jue. 2/5

11:05 am-1:47 pm

Nonstop1h 42m

$186

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

mar. 2/24

10:51 am-12:00 pm

Nonstop2h 09m

Chicago O'Hare Intl

vie. 2/27

6:28 pm-9:21 pm

Nonstop1h 53m

$186

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

lun. 2/9

9:00 pm-10:05 pm

Nonstop2h 05m

Chicago O'Hare Intl

lun. 2/16

9:15 pm-11:59 pm

Nonstop1h 44m

$186

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

jue. 2/5

9:00 am-10:06 am

Nonstop2h 06m

Chicago O'Hare Intl

dom. 2/8

7:10 am-9:58 am

Nonstop1h 48m

$186

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

mié. 2/4

3:30 pm-4:28 pm

Nonstop1h 58m

Chicago O'Hare Intl

vie. 2/6

9:15 pm-11:59 pm

Nonstop1h 44m

$186

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 60 results
1
2
3
...
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 $82). Flying from Canada to Chicago in December is currently the most expensive (average of $135). 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 diciembre 15, 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 32% 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. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 diciembre 15, 2025.

The most flights from CA0 to CHI are scheduled on a Monday (60 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (14 on average).

How often are flights from Canada to Chicago delayed?

About 11% of weekly flights between Canada and Chicago have experienced delays in the past year, with the average delay time being 139 minutes.

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

Historically, flights departing at night 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?

Tuesday tends to have the lowest number of delays on this route, whereas Saturday 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 6% of flights being delayed.

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 diciembre 15, 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
399 reviews

Comfort

7.9

Overall

8.0

Food

7.6

Boarding

8.2

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
8.0
Very good
399 reviews
Porter Airlines
8.0
Very good
399 reviews

Comfort

7.9

Overall

8.0

Food

7.6

Boarding

8.2

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
United Airlines
7.4
Good
9,094 reviews
Porter Airlines
8.0
Very good
399 reviews

Comfort

7.9

Overall

8.0

Food

7.6

Boarding

8.2

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
American Airlines
7.2
Good
11,050 reviews
Porter Airlines
8.0
Very good
399 reviews

Comfort

7.9

Overall

8.0

Food

7.6

Boarding

8.2

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
WestJet
7.2
Good
3,202 reviews
Porter Airlines
8.0
Very good
399 reviews

Comfort

7.9

Overall

8.0

Food

7.6

Boarding

8.2

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Canada
7.1
Good
10,526 reviews
Porter Airlines
8.0
Very good
399 reviews

Comfort

7.9

Overall

8.0

Food

7.6

Boarding

8.2

Entertainment

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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, Porter Airlines, and WestJet can get you from Canada to Chicago in just under 1h 50m. Your travel time can differ by up to 6h 45m. 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 WestJet ($94), Porter Airlines ($101), and American Airlines ($102).

  • 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 Montreal Pierre Elliott Trudeau 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 Qatar Airways (86%), EVA Air (85%) and SkyWest Airlines (84%).

  • What are the cheapest flights from Canada to Chicago?

    The cheapest flight price from Canada to Chicago is $129. On average you can expect to pay $1,110. The most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl), can usually be booked for $155.

  • 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 $82). Flying from Canada to Chicago in December is currently the most expensive (average of $135). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Canada to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Seattle to O'Hare Intl flights
Denver to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
San Francisco to O'Hare Intl flights
Los Angeles to Midway flights
Baltimore to O'Hare Intl flights
Boston to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Ontario to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Atlanta to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Tampa to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Austin to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Orlando to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Hobby to O'Hare Intl flights
Love Field to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
LaGuardia to Midway flights
Hobby to Midway flights
Mexico City to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Nashville to O'Hare Intl flights
Dulles Intl to Midway flights
San Francisco to Midway flights
Orlando to Midway flights
Minneapolis to Midway flights
San Diego to O'Hare Intl flights
Detroit to O'Hare Intl flights
Baltimore to Midway flights
Denver to Midway flights
Newark to St. Louis flights
Philadelphia to Midway flights
Las Vegas to O'Hare Intl flights
Boston to Midway flights
Portland to O'Hare Intl flights
Miami to O'Hare Intl flights

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 diciembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$101Average$410FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$110Average$395FlexibilityNo cancel feeOn-time69%
WestJetCheapest$138Average$244FlexibilityNo cancel feeOn-time60%
Porter AirlinesCheapest$158Average$327FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$167Average$377FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.