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$98+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
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 febrero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$166
(Kiwi.com)

One-way from

$103
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$285

Good round-trip deal

$149 or less

Good one-way deal

$119 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. 4% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in February 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 febrero 20, 2025.

This Trip.com deal was found by Cheapflights users on 2/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/2711:30 amYYC - ORD
Nonstop3h 26mWestJet
dom. 3/24:45 pmORD - YYC
Nonstop3h 51mWestJet
Deal found 2/19$159
This Air Canada deal was found by Cheapflights users on 2/19. 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.
lun. 4/78:30 amYYC - ORD
1 stop9h 24mAir Canada
jue. 4/1010:53 amORD - YYC
1 stop10h 30mAir Canada
Deal found 2/19$175
This United Airlines deal was found by Cheapflights users on 2/20. 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.
jue. 3/202:01 pmYYC - ORD
1 stop7h 44mUnited Airlines
jue. 3/275:00 amORD - YYC
1 stop10h 21mUnited Airlines
Deal found 2/20$189
This Kiwi.com deal was found by Cheapflights users on 2/18. 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.
sáb. 5/37:00 amYVR - ORD
1 stop7h 44mWestJet
lun. 5/265:30 pmORD - YVR
1 stop7h 05mWestJet
Deal found 2/18$198
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/287:00 amYVR - ORD
1 stop7h 44mMultiple Airlines
mar. 4/298:00 amORD - YVR
1 stop16h 25mMultiple Airlines
Deal found 2/19$199
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
mié. 4/23:55 pmYVR - MDW
1 stop11h 28mMultiple Airlines
mar. 4/88:50 pmMDW - YVR
1 stop27h 40mMultiple Airlines
Deal found 2/20$200
This 123 Milhas deal was found by Cheapflights users on 2/20. 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 123 Milhas is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/244:00 pmYYZ - ORD
1 stop5h 12mAir Canada
sáb. 6/710:40 amORD - YYZ
1 stop6h 18mAir Canada
Deal found 2/20$204
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/203:50 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
lun. 3/245:35 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 2/19$204
This 123 Milhas deal was found by Cheapflights users on 2/20. 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 123 Milhas is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/2410:25 amYTZ - ORD
1 stop5h 30mAir Canada
sáb. 6/710:40 amORD - YTZ
1 stop6h 10mAir Canada
Deal found 2/20$204
This flygcity.se deal was found by Cheapflights users on 2/19. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/211:30 amYYC - ORD
Nonstop3h 26mMultiple Airlines
dom. 3/95:00 amORD - YYC
1 stop10h 21mMultiple Airlines
Deal found 2/19$210
This Delta deal was found by Cheapflights users on 2/20. 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.
mar. 5/137:15 amYYC - ORD
1 stop9h 46mDelta
sáb. 5/179:30 amORD - YYC
2 stops14h 37mDelta
Deal found 2/20$220
This Trip.com deal was found by Cheapflights users on 2/18. 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.
jue. 3/203:50 pmYTZ - MDW
Nonstop1h 50mAir Transat
jue. 3/275:35 pmMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 2/18$223

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 febrero 20, 2025.

Fly from

Canada

Fly to

Chicago

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

lun. 4/14

11:30 am-3:56 pm

Nonstop3h 26m

Chicago O'Hare Intl

dom. 4/20

4:45 pm-7:36 pm

Nonstop3h 51m

$159

CalgaryChicago

YYC - ORD

YYCORD

Calgary

lun. 4/7

8:30 am-6:54 pm

1 stop9h 24m

Chicago O'Hare Intl

jue. 4/10

10:53 am-8:23 pm

1 stop10h 30m

$175

CalgaryChicago

YYC - ORD

YYCORD

Calgary

jue. 3/20

2:01 pm-10:45 pm

1 stop7h 44m

Chicago O'Hare Intl

jue. 3/27

5:00 am-2:21 pm

1 stop10h 21m

$189

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

sáb. 5/3

7:00 am-4:44 pm

1 stop7h 44m

Chicago O'Hare Intl

lun. 5/26

5:30 pm-10:35 pm

1 stop7h 05m

$198

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

lun. 4/28

7:00 am-4:44 pm

1 stop7h 44m

Chicago O'Hare Intl

mar. 4/29

8:00 am-10:25 pm

1 stop16h 25m

$199

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

mié. 4/2

3:55 pm-5:23 am

1 stop11h 28m

Chicago Midway

mar. 4/8

8:50 pm-10:30 pm

1 stop27h 40m

$200

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

jue. 3/20

3:50 pm-4:40 pm

Nonstop1h 50m

Chicago Midway

lun. 3/24

5:35 pm-8:17 pm

Nonstop1h 42m

$204

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

sáb. 5/24

4:00 pm-8:12 pm

1 stop5h 12m

Chicago O'Hare Intl

sáb. 6/7

10:40 am-5:58 pm

1 stop6h 18m

$204

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

sáb. 5/24

10:25 am-2:55 pm

1 stop5h 30m

Chicago O'Hare Intl

sáb. 6/7

10:40 am-5:50 pm

1 stop6h 10m

$204

CalgaryChicago

YYC - ORD

YYCORD

Calgary

dom. 3/2

11:30 am-3:56 pm

Nonstop3h 26m

Chicago O'Hare Intl

dom. 3/9

5:00 am-2:21 pm

1 stop10h 21m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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.

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 $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 febrero 20, 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 febrero 20, 2025.

The most flights from CA0 to CHI are scheduled on a Thursday (53 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (38 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 febrero 20, 2025.
Read through reviews of airlines operating flights from Canada to Chicago, such as Alaska Airlines, Delta and Porter Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,697 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines
8.0
Very good
9,697 reviews
Alaska Airlines
8.0
Very good
9,697 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta
8.0
Very good
8,219 reviews
Alaska Airlines
8.0
Very good
9,697 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Porter Airlines
7.9
Good
276 reviews
Alaska Airlines
8.0
Very good
9,697 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

KLM
7.8
Good
1,333 reviews
Alaska Airlines
8.0
Very good
9,697 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Air Transat
7.8
Good
380 reviews
Alaska Airlines
8.0
Very good
9,697 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 ($103), Air Canada ($110), and United Airlines ($121).

  • 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 (90%), Republic Airways (89%) and ANA (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 $858. The most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl), can usually be booked for $221.

  • 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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.
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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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$112Average$460FlexibilityNo cancel feeOn-time69%
WestJetCheapest$143Average$318FlexibilityNo cancel feeOn-time60%
Air CanadaCheapest$154Average$475FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$166Average$355FlexibilityNo cancel feeOn-time71%
Porter AirlinesCheapest$194Average$312FlexibilityNo cancel feeOn-time52%
DeltaCheapest$268Average$327FlexibilityNo cancel feeOn-timeN/A
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