HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$96+ 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 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
jan. 26 — feb. 21
søn. 1/26
søn. 2/2
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

Discover tips and strategies to find the most affordable flight options for your journey from Canada (CA0) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated januar 21, 2025.

Round-trip from

$136
(Mytrip)

One-way from

$96
(Trip.com)

Good round-trip deal

$237 or less

Good one-way deal

$155 or less
From Canada to Chicago (CHI)
Search Deals
One-way flight from Canada to Chicago (CHI)
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

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 januar 21, 2025.

This Mytrip deal was found by Cheapflights users on 1/20. 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.
tor. 2/2011:30 amYYC - ORD
Nonstop3h 26mWestJet
tor. 2/274:45 pmORD - YYC
Nonstop3h 51mWestJet
Deal found 1/20$136
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tor. 2/2011:30 amYYC - ORD
Nonstop3h 26mMultiple Airlines
lør. 3/14:21 pmORD - YYC
1 stop8h 29mMultiple Airlines
Deal found 1/20$176
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
man. 3/177:20 pmYYC - ORD
1 stop13h 13mUnited Airlines
tir. 3/181:05 pmORD - YYC
1 stop9h 36mUnited Airlines
Deal found 1/20$192
This Air Canada deal was found by Cheapflights users on 1/20. 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.
man. 2/38:30 amYYC - ORD
1 stop9h 08mAir Canada
tir. 2/114:51 pmORD - YYC
1 stop9h 27mAir Canada
Deal found 1/20$203
This Delta deal was found by Cheapflights users on 1/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tor. 2/206:35 amYYC - ORD
2 stops13h 18mDelta
ons. 2/2612:15 pmORD - YYC
1 stop9h 38mDelta
Deal found 1/20$216
This Cheapflightsfares deal was found by Cheapflights users on 1/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
tor. 2/1311:20 amYTZ - MDW
Nonstop1h 50mPorter Airlines
man. 2/171:05 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 1/21$236
This American Airlines deal was found by Cheapflights users on 1/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lør. 3/16:20 pmYYZ - ORD
Nonstop2h 00mAmerican Airlines
ons. 3/58:11 amORD - YYZ
Nonstop1h 40mAmerican Airlines
Deal found 1/20$238
This Cheapflightsfares deal was found by Cheapflights users on 1/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
fre. 3/149:30 amYTZ - MDW
Nonstop1h 50mAir Transat
søn. 3/1611:15 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 1/20$243
This Air Canada deal was found by Cheapflights users on 1/21. 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.
fre. 2/216:40 pmYYZ - ORD
Nonstop1h 57mAir Canada
man. 2/247:12 amORD - YYZ
Nonstop1h 46mAir Canada
Deal found 1/21$244
This United deal was found by Cheapflights users on 1/20. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ons. 2/126:40 pmYYZ - ORD
Nonstop1h 57mMultiple Airlines
lør. 2/229:50 amORD - YYZ
Nonstop1h 35mMultiple Airlines
Deal found 1/20$247
This Air Canada deal was found by Cheapflights users on 1/21. 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.
fre. 2/148:50 amYTZ - ORD
1 stop5h 09mAir Canada
man. 2/171:58 pmORD - YTZ
1 stop5h 45mAir Canada
Deal found 1/21$248
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lør. 3/15:30 pmYVR - MDW
1 stop10h 01mMultiple Airlines
tir. 3/47:05 amMDW - YVR
2 stops17h 25mMultiple Airlines
Deal found 1/20$250

Find flights from Canada to Chicago within your budget

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 januar 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

tor. 2/20

11:30 am-3:56 pm

Nonstop3h 26m

Chicago O'Hare Intl

tor. 2/27

4:45 pm-7:36 pm

Nonstop3h 51m

$136

CalgaryChicago

YYC - ORD

YYCORD

Calgary

tor. 2/20

11:30 am-3:56 pm

Nonstop3h 26m

Chicago O'Hare Intl

lør. 3/1

4:21 pm-11:50 pm

1 stop8h 29m

$176

CalgaryChicago

YYC - ORD

YYCORD

Calgary

man. 3/17

7:20 pm-9:33 am

1 stop13h 13m

Chicago O'Hare Intl

tir. 3/18

1:05 pm-9:41 pm

1 stop9h 36m

$192

CalgaryChicago

YYC - ORD

YYCORD

Calgary

man. 2/3

8:30 am-6:38 pm

1 stop9h 08m

Chicago O'Hare Intl

tir. 2/11

4:51 pm-1:18 am

1 stop9h 27m

$203

CalgaryChicago

YYC - ORD

YYCORD

Calgary

tor. 2/20

6:35 am-8:53 pm

2 stops13h 18m

Chicago O'Hare Intl

fre. 2/28

1:40 pm-11:15 pm

1 stop10h 35m

$216

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

tor. 2/13

11:20 am-12:10 pm

Nonstop1h 50m

Chicago Midway

man. 2/17

1:05 pm-3:47 pm

Nonstop1h 42m

$236

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

lør. 3/1

11:31 am-12:31 pm

Nonstop2h 00m

Chicago O'Hare Intl

ons. 3/5

8:11 am-10:51 am

Nonstop1h 40m

$238

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

fre. 3/14

9:30 am-10:20 am

Nonstop1h 50m

Chicago Midway

søn. 3/16

11:15 am-1:57 pm

Nonstop1h 42m

$243

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

søn. 2/16

12:20 pm-1:11 pm

Nonstop1h 51m

Chicago O'Hare Intl

søn. 2/23

8:30 pm-11:11 pm

Nonstop1h 41m

$244

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

ons. 2/12

6:40 pm-7:37 pm

Nonstop1h 57m

Chicago O'Hare Intl

lør. 2/22

9:50 am-12:25 pm

Nonstop1h 35m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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.

Travel insights for flights from Canada to Chicago

Get recent, data-driven insights about flights from Canada to Chicago including ideal travel times, pricing trends, and more.

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 $320). 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 januar 21, 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 januar 21, 2025.

The most flights from CA0 to CHI are scheduled on a Monday (52 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (33 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 januar 21, 2025.
Read through reviews of airlines operating flights from Canada to Chicago, such as KLM, Air Canada and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Overall

8.0

Comfort

8.0

Entertainment

7.9

Crew

8.6

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,521 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Overall

8.0

Comfort

8.0

Entertainment

7.9

Crew

8.6

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Alaska Airlines
8.0
Very good
9,706 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Overall

8.0

Comfort

8.0

Entertainment

7.9

Crew

8.6

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Porter Airlines
7.9
Good
277 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Overall

8.0

Comfort

8.0

Entertainment

7.9

Crew

8.6

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

KLM
7.8
Good
1,341 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Overall

8.0

Comfort

8.0

Entertainment

7.9

Crew

8.6

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Air Transat
7.8
Good
381 reviews
Delta
8.0
Very good
8,521 reviews

Boarding

8.2

Overall

8.0

Comfort

8.0

Entertainment

7.9

Crew

8.6

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

  • 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 ($96), United Airlines ($119), and Air Canada ($120).

  • 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 Vancouver 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 Emirates (92%), Japan Airlines (92%) and Republic Airways (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 $682. The most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl), can usually be booked for $247.

  • 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 $320). 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 Canada?

Book flights to Canada if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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
Boston to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Los Angeles to O'Hare Intl flights
Orlando to O'Hare Intl flights
Newark to Midway flights
Seattle to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Baltimore to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Atlanta to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Los Angeles to Midway flights
Denver to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
LaGuardia to Midway flights
Atlanta to Midway flights
Minneapolis to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
San Francisco to Midway flights
Baltimore to Midway flights
Austin to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
San Diego to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Tampa to O'Hare Intl flights
Minneapolis to Midway flights
Miami to O'Hare Intl flights
Reagan-National to Midway flights
Ontario to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Philadelphia to Midway flights
Mexico City to O'Hare Intl flights
Orlando to Midway flights
Hartford to O'Hare Intl flights
Burbank to O'Hare Intl flights
Denver to Midway flights
Hobby to O'Hare Intl flights
Newark to St. Louis flights
Dulles Intl to Midway flights
Hobby to Midway flights
George Bush Intcntl to O'Hare Intl flights
Nashville to O'Hare Intl flights
Boston to Midway flights
Detroit to O'Hare Intl flights

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 januar 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$112Average$442FlexibilityNo cancel feeOn-time69%
WestJetCheapest$149Average$341FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$166Average$355FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$179Average$466FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$209Average$320FlexibilityNo cancel feeOn-time52%
DeltaCheapest$268Average$332FlexibilityNo cancel feeOn-timeN/A
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.