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$117+ 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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$176
(Cheapflightsfares)

One-way from

$117
(Air Canada)

Popular in

December

Cheapest in

March

Average price

$261

Good round-trip deal

$143 or less

Good one-way deal

$115 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago (CHI) flights.
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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. 5% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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.
Sat 5/247:55 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 5/285:50 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 4/29$176
This flugladen.de deal was found by Cheapflights users on 4/29. 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/137:55 amYTZ - MDW
Nonstop1h 50mAir Transat
Fri 6/205:50 pmMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 4/29$179
This Ticket deal was found by Cheapflights users on 4/30. 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 Ticket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/56:15 amYYZ - ORD
1 stop4h 37mAir Canada
Sun 6/89:14 pmORD - YYZ
Nonstop1h 44mAir Canada
Deal found 4/30$187
This Trip.com deal was found by Cheapflights users on 4/29. 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.
Sun 6/14:05 pmYTZ - MDW
Nonstop1h 49mMultiple Airlines
Mon 6/25:50 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 4/29$190
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Tue 6/1012:15 pmYYC - ORD
Nonstop3h 29mWestJet
Tue 6/245:30 pmORD - YYC
Nonstop3h 49mWestJet
Deal found 4/29$191
This Air Canada deal was found by Cheapflights users on 4/30. 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.
Thu 6/197:25 amYTZ - ORD
1 stop4h 59mAir Canada
Mon 6/232:16 pmORD - YTZ
1 stop5h 20mAir Canada
Deal found 4/30$198
This Air Canada deal was found by Cheapflights users on 4/30. 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 5/238:30 amYYC - ORD
Nonstop3h 33mAir Canada
Tue 5/275:55 pmORD - YYC
1 stop8h 08mAir Canada
Deal found 4/30$205
This United deal was found by Cheapflights users on 4/30. 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.
Thu 5/298:30 amYYC - ORD
Nonstop3h 33mMultiple Airlines
Thu 6/510:56 amORD - YYC
1 stop12h 42mMultiple Airlines
Deal found 4/30$222
This Delta deal was found by Cheapflights users on 4/30. 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.
Mon 5/266:30 amYYC - ORD
1 stop6h 58mDelta
Fri 5/308:40 amORD - YYC
2 stops15h 21mDelta
Deal found 4/30$223
This American Airlines deal was found by Cheapflights users on 4/30. 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 6/53:14 pmYYZ - ORD
Nonstop1h 55mAmerican Airlines
Sun 6/85:00 amORD - YYZ
1 stop4h 21mAmerican Airlines
Deal found 4/30$228
This Trip.com deal was found by Cheapflights users on 4/30. 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.
Tue 6/310:45 amYUL - MDW
1 stop6h 39mPorter Airlines
Tue 6/109:40 amMDW - YUL
1 stop5h 20mPorter Airlines
Deal found 4/30$229
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 6/97:00 amYVR - ORD
1 stop7h 44mWestJet
Tue 6/245:30 pmORD - YVR
1 stop7h 05mWestJet
Deal found 4/30$246

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 May 1, 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

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 5/24

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

Wed 5/28

9:40 am-12:22 pm

Nonstop1h 42m

$176

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 6/12

7:55 am-8:45 am

Nonstop1h 50m

Chicago Midway

Sun 6/15

9:40 am-12:22 pm

Nonstop1h 42m

$186

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 6/5

6:15 am-9:52 am

1 stop4h 37m

Chicago O'Hare Intl

Sun 6/8

9:14 pm-11:58 pm

Nonstop1h 44m

$187

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 6/10

12:15 pm-4:44 pm

Nonstop3h 29m

Chicago O'Hare Intl

Tue 6/24

5:30 pm-8:19 pm

Nonstop3h 49m

$191

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 5/27

12:55 am-9:52 am

1 stop7h 57m

Chicago O'Hare Intl

Thu 5/29

2:16 pm-10:38 pm

1 stop9h 22m

$195

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 6/19

7:25 am-11:24 am

1 stop4h 59m

Chicago O'Hare Intl

Mon 6/23

2:16 pm-8:36 pm

1 stop5h 20m

$198

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 5/21

4:05 pm-4:54 pm

Nonstop1h 49m

Chicago Midway

Sun 5/25

5:50 pm-8:32 pm

Nonstop1h 42m

$206

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 5/12

1:30 pm-9:17 pm

1 stop6h 47m

Chicago O'Hare Intl

Tue 5/13

2:22 pm-10:38 pm

1 stop9h 16m

$222

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 5/26

6:30 am-2:28 pm

1 stop6h 58m

Chicago O'Hare Intl

Fri 5/30

8:40 am-11:01 pm

2 stops15h 21m

$223

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 6/7

6:29 am-10:54 am

Nonstop3h 25m

Chicago O'Hare Intl

Mon 6/9

8:30 pm-11:29 pm

Nonstop3h 59m

$226

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 May 1, 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 May 1, 2025.

The most flights from CA0 to CHI are scheduled on a Thursday (61 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (42 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 May 1, 2025.
Read through reviews of airlines operating flights from Canada to Chicago, such as Delta, Alaska Airlines and Porter 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
7,934 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Alaska Airlines
8.0
Very good
9,968 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Porter Airlines
8.0
Very good
285 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
KLM
7.8
Good
1,334 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Air Transat
7.8
Good
385 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

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 Air Canada ($117), WestJet ($120), and Porter Airlines ($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 Vancouver 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 Copa Airlines (90%), Egyptair (89%) and ANA (85%).

  • What are the cheapest flights from Canada to Chicago?

    The cheapest flight price from Canada to Chicago is $124. On average you can expect to pay $491. The most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl), can usually be booked for $212.

  • 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 Canada?

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

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$112Average$444FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$123Average$458FlexibilityNo cancel feeOn-time67%
WestJetCheapest$139Average$298FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$166Average$338FlexibilityNo cancel feeOn-time71%
Porter AirlinesCheapest$170Average$320FlexibilityNo cancel feeOn-time52%

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