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$108+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
YYZ — CHI
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
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 November 21, 2024.

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 November 21, 2024.

This Delta deal was found by Cheapflights users on 11/20. 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.
Sat 12/77:00 amYYC - ORD
1 stop8h 58mDelta
Tue 12/1012:35 pmORD - YYC
2 stops11h 41mDelta
Deal found 11/20$221
This oojo deal was found by Cheapflights users on 11/20. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/129:40 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 12/265:35 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/20$228
This United Airlines deal was found by Cheapflights users on 11/20. 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.
Thu 12/122:00 pmYYZ - ORD
Nonstop1h 51mUnited Airlines
Mon 12/168:25 pmORD - YYZ
Nonstop1h 41mUnited Airlines
Deal found 11/20$245
This Air Canada deal was found by Cheapflights users on 11/21. 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.
Fri 12/135:30 pmYYZ - ORD
Nonstop2h 07mAir Canada
Sun 12/157:19 amORD - YYZ
Nonstop1h 39mAir Canada
Deal found 11/21$246
This Air Canada deal was found by Cheapflights users on 11/20. 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.
Wed 12/48:30 amYYC - ORD
1 stop9h 06mAir Canada
Sat 12/712:52 pmORD - YYC
1 stop11h 26mAir Canada
Deal found 11/20$250
This Flysmarter deal was found by Cheapflights users on 11/20. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/132:05 pmYYZ - ORD
1 stop5h 31mMultiple Airlines
Tue 12/176:38 pmORD - YYZ
Nonstop1h 47mMultiple Airlines
Deal found 11/20$259
This Booking.com deal was found by Cheapflights users on 11/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1210:25 amYTZ - ORD
1 stop5h 20mAir Canada
Sun 12/152:01 pmORD - YTZ
1 stop4h 49mAir Canada
Deal found 11/19$261
This Mytrip deal was found by Cheapflights users on 11/20. 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.
Thu 12/129:40 amYTZ - MDW
Nonstop1h 50mAir Transat
Sun 12/1511:15 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 11/20$262
This Kissandfly.com deal was found by Cheapflights users on 11/20. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/126:52 amYYZ - ORD
Nonstop2h 13mLufthansa
Sun 12/157:19 amORD - YYZ
Nonstop1h 39mLufthansa
Deal found 11/20$266
This CheapTicketsDeal deal was found by Cheapflights users on 11/20. 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 CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/126:30 amYYZ - MDW
1 stop13h 02mWestJet
Mon 12/169:38 amMDW - YYZ
1 stop12h 56mWestJet
Deal found 11/20$267
This American Airlines deal was found by Cheapflights users on 11/20. 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.
Thu 12/127:30 amYUL - ORD
1 stop16h 15mAmerican Airlines
Mon 12/162:55 pmORD - YUL
1 stop18h 10mAmerican Airlines
Deal found 11/20$281
This United Airlines deal was found by Cheapflights users on 11/21. 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.
Wed 12/47:00 amYVR - ORD
1 stop12h 05mUnited Airlines
Mon 12/99:36 pmORD - YVR
1 stop14h 55mUnited Airlines
Deal found 11/21$282

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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 1/9

8:30 am-6:38 pm

1 stop9h 08m

Chicago O'Hare Intl

Mon 1/13

4:00 pm-11:18 pm

1 stop8h 18m

$215

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 12/7

7:00 am-4:58 pm

1 stop8h 58m

Chicago O'Hare Intl

Tue 12/10

12:35 pm-11:16 pm

2 stops11h 41m

$221

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/12

9:40 am-10:30 am

Nonstop1h 50m

Chicago Midway

Thu 12/26

5:35 pm-8:17 pm

Nonstop1h 42m

$228

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/12

2:00 pm-2:51 pm

Nonstop1h 51m

Chicago O'Hare Intl

Mon 12/16

8:25 pm-11:06 pm

Nonstop1h 41m

$245

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 12/13

5:30 pm-6:37 pm

Nonstop2h 07m

Chicago O'Hare Intl

Sun 12/15

7:19 am-9:58 am

Nonstop1h 39m

$246

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 4/30

7:00 am-10:21 pm

2 stops14h 21m

Chicago O'Hare Intl

Mon 5/5

5:30 pm-8:19 pm

Nonstop3h 49m

$253

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 12/13

2:05 pm-6:36 pm

1 stop5h 31m

Chicago O'Hare Intl

Tue 12/17

6:38 pm-9:25 pm

Nonstop1h 47m

$259

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 12/12

10:25 am-2:45 pm

1 stop5h 20m

Chicago O'Hare Intl

Sun 12/15

2:01 pm-7:50 pm

1 stop4h 49m

$261

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/12

9:40 am-10:30 am

Nonstop1h 50m

Chicago Midway

Sun 12/15

11:15 am-1:57 pm

Nonstop1h 42m

$262

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 1/10

8:30 am-2:39 pm

Nonstop4h 09m

Chicago O'Hare Intl

Tue 1/14

3:40 pm-6:13 pm

Nonstop4h 33m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

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, September is the cheapest month in which you can book a flight from Canada to Chicago (average of $232). Flying from Canada to Chicago in June is currently the most expensive (average of $308). 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 November 21, 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 November 21, 2024.

The most flights from CA0 to CHI are scheduled on a Monday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (45 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 November 21, 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.
Alaska Airlines
8.0
Very good
9,458 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

Alaska Airlines
8.0
Very good
9,458 reviews
Alaska Airlines
8.0
Very good
9,458 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

Delta
8.0
Very good
8,759 reviews
Alaska Airlines
8.0
Very good
9,458 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

Porter Airlines
7.8
Good
286 reviews
Alaska Airlines
8.0
Very good
9,458 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

Air Transat
7.8
Good
389 reviews
Alaska Airlines
8.0
Very good
9,458 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

Aeromexico
7.5
Good
2,004 reviews
Alaska Airlines
8.0
Very good
9,458 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.2

Reviews

1 / 10

Service was good. We pre-ordered a snack but never made it to us.

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 ($108), Air Canada ($118), and Delta ($136).

  • 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 Egyptair (100%), Jazz (100%) and Lufthansa (100%).

  • What are the cheapest flights from Canada to Chicago?

    The cheapest flight price from Canada to Chicago is $145. On average you can expect to pay $894. The most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl), can usually be booked for $262.

  • 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, September is the cheapest month in which you can book a flight from Canada to Chicago (average of $232). Flying from Canada to Chicago in June is currently the most expensive (average of $308). 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.

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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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$112Average$438FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$157Average$444FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$166Average$361FlexibilityNo cancel feeOn-time71%
WestJetCheapest$186Average$348FlexibilityNo cancel feeOn-time60%
Porter AirlinesCheapest$205Average$298FlexibilityNo cancel feeOn-time52%
DeltaCheapest$370Average$671FlexibilityNo cancel feeOn-timeN/A
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