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$86+ 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 3/13. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
1 adult, Economy
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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 December 22, 2024.

Round-trip from

$181
(United)

One-way from

$86
(Trip.com)
From Canada to Chicago (CHI)
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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 December 22, 2024.

This American Airlines deal was found by Cheapflights users on 12/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/266:29 amYYC - ORD
1 stop15h 40mAmerican Airlines
Wed 1/17:09 amORD - YYC
1 stop15h 46mAmerican Airlines
Deal found 12/21$302
This oojo deal was found by Cheapflights users on 12/21. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/289:40 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 1/311:05 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/21$323
This Air Canada deal was found by Cheapflights users on 12/21. 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.
Tue 12/248:10 amYVR - ORD
1 stop6h 41mAir Canada
Tue 12/248:02 pmORD - YVR
Nonstop4h 50mAir Canada
Deal found 12/21$337
This Air Canada deal was found by Cheapflights users on 12/21. 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.
Tue 12/319:00 pmYYZ - ORD
Nonstop2h 13mAir Canada
Tue 1/78:30 pmORD - YYZ
Nonstop1h 41mAir Canada
Deal found 12/21$365
This American Airlines deal was found by Cheapflights users on 12/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/3011:40 amYYZ - ORD
Nonstop2h 00mAmerican Airlines
Tue 1/77:22 amORD - YYZ
1 stop4h 38mAmerican Airlines
Deal found 12/21$374
This Trip.com deal was found by Cheapflights users on 12/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/286:50 amYUL - MDW
1 stop4h 40mPorter Airlines
Wed 1/151:05 pmMDW - YUL
1 stop5h 20mPorter Airlines
Deal found 12/21$377
This American Airlines deal was found by Cheapflights users on 12/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/307:00 amYVR - ORD
1 stop15h 19mAmerican Airlines
Tue 1/71:13 pmORD - YVR
1 stop10h 11mAmerican Airlines
Deal found 12/21$382
This United deal was found by Cheapflights users on 12/20. 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.
Fri 12/2712:20 pmYYZ - ORD
Nonstop1h 51mMultiple Airlines
Fri 1/36:06 pmORD - YYZ
1 stop12h 59mMultiple Airlines
Deal found 12/20$392
This Air Transat deal was found by Cheapflights users on 12/21. 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 Transat is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/289:40 amYTZ - MDW
Nonstop1h 50mAir Transat
Sat 1/45:35 pmMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 12/21$398
This United Airlines deal was found by Cheapflights users on 12/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/306:30 amYVR - ORD
Nonstop4h 13mUnited Airlines
Tue 1/76:22 pmORD - YVR
1 stop17h 03mUnited Airlines
Deal found 12/21$406
This United Airlines deal was found by Cheapflights users on 12/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/299:00 amYYZ - ORD
Nonstop2h 10mUnited Airlines
Tue 12/314:00 pmORD - YYZ
Nonstop1h 41mUnited Airlines
Deal found 12/19$410
This FlightHub deal was found by Cheapflights users on 12/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/265:15 pmYYZ - ORD
1 stop24h 25mWestJet
Wed 1/296:45 amORD - YYZ
1 stop15h 07mWestJet
Deal found 12/21$415

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 3/17

7:20 pm-9:33 am

1 stop13h 13m

Chicago O'Hare Intl

Tue 3/18

12:58 pm-11:18 pm

1 stop11h 20m

$181

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 1/9

8:30 am-6:38 pm

1 stop9h 08m

Chicago O'Hare Intl

Sat 1/11

6:28 pm-1:18 am

1 stop7h 50m

$193

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 5/22

12:15 pm-4:44 pm

Nonstop3h 29m

Chicago O'Hare Intl

Sun 5/25

5:30 pm-8:19 pm

Nonstop3h 49m

$197

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sun 1/19

6:35 am-5:29 pm

1 stop9h 54m

Chicago O'Hare Intl

Sun 1/26

1:45 pm-11:18 pm

1 stop10h 33m

$216

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 2/14

11:20 am-12:10 pm

Nonstop1h 50m

Chicago Midway

Mon 2/17

1:05 pm-3:47 pm

Nonstop1h 42m

$230

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 1/26

7:00 am-2:23 pm

1 stop8h 23m

Chicago O'Hare Intl

Wed 1/29

5:11 am-11:55 pm

1 stop17h 44m

$247

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 1/23

1:14 pm-2:14 pm

Nonstop2h 00m

Chicago O'Hare Intl

Mon 1/27

6:35 pm-9:20 pm

Nonstop1h 45m

$256

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 2/13

11:20 am-12:10 pm

Nonstop1h 50m

Chicago Midway

Sun 2/16

1:05 pm-3:47 pm

Nonstop1h 42m

$264

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 2/4

11:31 am-12:31 pm

Nonstop2h 00m

Chicago O'Hare Intl

Tue 2/11

3:00 pm-5:35 pm

Nonstop1h 35m

$272

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 2/4

8:30 am-6:38 pm

1 stop8h 08m

Chicago O'Hare Intl

Tue 2/11

6:30 am-1:19 pm

1 stop8h 49m

$276

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

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 $317). 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 December 22, 2024.

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 December 22, 2024.

The most flights from CA0 to CHI are scheduled on a Monday (51 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (36 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 December 22, 2024.
Read through reviews of airlines operating flights from Canada to Chicago, such as Air Canada, Delta 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
8,594 reviews

Overall

8.0

Food

7.3

Crew

8.6

Entertainment

7.9

Comfort

8.0

Boarding

8.2

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
8,594 reviews
Delta
8.0
Very good
8,594 reviews

Overall

8.0

Food

7.3

Crew

8.6

Entertainment

7.9

Comfort

8.0

Boarding

8.2

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
9,537 reviews
Delta
8.0
Very good
8,594 reviews

Overall

8.0

Food

7.3

Crew

8.6

Entertainment

7.9

Comfort

8.0

Boarding

8.2

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
283 reviews
Delta
8.0
Very good
8,594 reviews

Overall

8.0

Food

7.3

Crew

8.6

Entertainment

7.9

Comfort

8.0

Boarding

8.2

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
384 reviews
Delta
8.0
Very good
8,594 reviews

Overall

8.0

Food

7.3

Crew

8.6

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Reviews

1 / 10

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

Austrian Airlines
7.6
Good
785 reviews
Delta
8.0
Very good
8,594 reviews

Overall

8.0

Food

7.3

Crew

8.6

Entertainment

7.9

Comfort

8.0

Boarding

8.2

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 ($86), Air Canada ($97), and United Airlines ($113).

  • 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 Montreal Pierre Elliott Trudeau Intl - 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 Lufthansa (100%), Royal Jordanian (97%) and SkyWest Airlines (97%).

  • What are the cheapest flights from Canada to Chicago?

    The cheapest flight price from Canada to Chicago is $158. On average you can expect to pay $1,064. The most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl), can usually be booked for $245.

  • 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 $317). 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

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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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$112Average$436FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$157Average$444FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$166Average$361FlexibilityNo cancel feeOn-time71%
WestJetCheapest$186Average$346FlexibilityNo cancel feeOn-time60%
Porter AirlinesCheapest$206Average$317FlexibilityNo cancel feeOn-time52%
DeltaCheapest$268Average$501FlexibilityNo cancel feeOn-timeN/A
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