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$64+ Cheap flights from Chicago (CHI) to Canada

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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
Dec 24 — Dec 311
Tue 12/24
Tue 12/31
1 adult, Economy
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Cheap flight deals from Chicago to Canada

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Canada (CA0). 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 19, 2024.

Round-trip from

$178
(Air Canada)

One-way from

$64
(Air Canada)
From Chicago (CHI) to Canada
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One-way flight from Chicago (CHI) to Canada
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Find flight deals from Chicago to Canada

Cheapest flights from Chicago to Canada
Explore the most affordable flight options available from Chicago to Canada. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 19, 2024.

This Kiwi.com deal was found by Cheapflights users on 12/17. 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 12/245:45 amORD - YYZ
1 stop29h 00mMultiple Airlines
Fri 1/107:00 amYYZ - ORD
1 stop15h 16mMultiple Airlines
Deal found 12/17$310
This Kiwi.com deal was found by Cheapflights users on 12/18. 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.
Sat 12/285:35 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Wed 1/811:20 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/18$349
This Booking.com deal was found by Cheapflights users on 12/18. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/3012:05 pmMDW - YUL
1 stop6h 15mPorter Airlines
Wed 1/86:55 amYUL - MDW
1 stop6h 15mPorter Airlines
Deal found 12/18$381
This United Airlines deal was found by Cheapflights users on 12/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/238:20 pmORD - YVR
1 stop16h 11mUnited Airlines
Sat 12/286:30 amYVR - ORD
Nonstop4h 15mUnited Airlines
Deal found 12/18$385
This United deal was found by Cheapflights users on 12/18. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/238:20 pmORD - YVR
1 stop16h 11mMultiple Airlines
Mon 1/1310:40 pmYVR - ORD
1 stop8h 17mMultiple Airlines
Deal found 12/18$390
This Air Canada deal was found by Cheapflights users on 12/17. 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.
Sat 12/289:13 pmORD - YYZ
Nonstop1h 46mAir Canada
Sun 1/129:00 amYYZ - ORD
Nonstop2h 10mAir Canada
Deal found 12/17$395
This Air Canada deal was found by Cheapflights users on 12/18. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2911:35 amORD - YTZ
1 stop5h 15mAir Canada
Wed 1/83:25 pmYTZ - ORD
1 stop5h 30mAir Canada
Deal found 12/18$401
This Mytrip deal was found by Cheapflights users on 12/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/249:15 pmORD - YTZ
2 stops18h 43mMultiple Airlines
Wed 1/223:00 pmYTZ - ORD
1 stop8h 55mMultiple Airlines
Deal found 12/18$410
This United Airlines deal was found by Cheapflights users on 12/17. 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 12/259:50 amORD - YYZ
Nonstop1h 41mUnited Airlines
Fri 1/105:30 pmYYZ - ORD
Nonstop2h 13mUnited Airlines
Deal found 12/17$410
This Booking.com deal was found by Cheapflights users on 12/18. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3111:15 amMDW - YTZ
Nonstop1h 42mMultiple Airlines
Thu 1/23:50 pmYTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 12/18$412
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/264:21 pmORD - YYZ
1 stop5h 14mAmerican Airlines
Sat 1/116:20 pmYYZ - ORD
Nonstop2h 00mAmerican Airlines
Deal found 12/17$420
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Wed 12/256:50 amMDW - YYZ
1 stop16h 00mMultiple Airlines
Tue 12/317:10 amYYZ - MDW
1 stop11h 44mMultiple Airlines
Deal found 12/17$442

Find flights from Chicago to Canada within your budget

Customize your flight search to find flights from Chicago to Canada 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 19, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 1/7

4:00 pm-11:18 pm

1 stop8h 18m

Calgary

Wed 1/29

8:30 am-6:38 pm

1 stop9h 08m

$178

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 2/18

7:00 am-9:41 pm

1 stop15h 41m

Calgary

Mon 3/10

6:15 am-2:51 pm

1 stop7h 36m

$182

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 3/6

5:00 am-6:16 pm

1 stop14h 16m

Calgary

Mon 3/10

7:20 pm-11:19 am

1 stop14h 59m

$187

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Mon 1/13

3:25 pm-11:53 pm

1 stop7h 28m

Toronto Pearson Intl

Thu 1/16

7:00 am-1:50 pm

1 stop7h 50m

$201

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 1/11

1:05 pm-3:47 pm

Nonstop1h 42m

Toronto Island

Fri 1/24

11:20 am-12:10 pm

Nonstop1h 50m

$216

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Wed 2/26

1:39 pm-10:30 pm

1 stop10h 51m

Vancouver Intl

Sun 3/2

6:30 am-3:56 pm

1 stop7h 26m

$237

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 2/1

11:19 am-8:53 pm

1 stop10h 34m

Calgary

Sat 2/8

6:35 am-5:43 pm

1 stop10h 08m

$243

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Mon 1/13

11:51 am-5:46 pm

1 stop4h 55m

Toronto Pearson Intl

Mon 1/13

9:00 pm-10:13 pm

Nonstop2h 13m

$247

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Sat 1/11

11:19 am-8:53 pm

1 stop10h 34m

Calgary

Sat 2/1

6:35 am-5:47 pm

1 stop10h 12m

$249

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sun 2/2

1:45 pm-11:18 pm

1 stop10h 33m

Calgary

Sun 2/9

6:35 am-5:29 pm

1 stop9h 54m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Canada

Have a flexible travel schedule? Discover the best time to fly to Canada from Chicago 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 Chicago to Canada

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

What is the cheapest month to book a flight from Chicago to Canada?

Currently, January is the cheapest month in which you can book a flight from Chicago to Canada (average of $243). Flying from Chicago to Canada in July is currently the most expensive (average of $359). 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 CHI to CA?

Find hourly flight availability from Chicago to Canada. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 19, 2024.

When flying from Chicago to Canada, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chicago to Canada

Explore weekly flight availability from Chicago to Canada. 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 19, 2024.

The most flights from CHI to CA0 are scheduled on a Thursday (53 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (29 on average).

Rainfall in Canada by month

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

In terms of precipitation, rainfall in Canada ranges from 2.0 - 3.3 inches per month. June is typically the wettest month, when rainfall can reach 3.3 in. February is typically the driest time to visit Canada when rainfall is around 2.0 in.

Temperature in Canada by month

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

If weather is an important factor for your trip to Canada, 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 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 21.2 F).

Reviews of airlines servicing Canada

Get insights into the airlines that provide service to Canada. 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 Canada. Reviews last updated December 19, 2024.
Read through reviews of airlines operating flights from Chicago to Canada, such as American Airlines, KLM and Air Canada. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,552 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.2

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

Alaska Airlines
8.0
Very good
9,552 reviews
Alaska Airlines
8.0
Very good
9,552 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.2

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

Delta
8.0
Very good
8,600 reviews
Alaska Airlines
8.0
Very good
9,552 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.2

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

Porter Airlines
7.9
Good
283 reviews
Alaska Airlines
8.0
Very good
9,552 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.2

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

KLM
7.8
Good
1,349 reviews
Alaska Airlines
8.0
Very good
9,552 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.2

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

Air Transat
7.8
Good
388 reviews
Alaska Airlines
8.0
Very good
9,552 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.2

Reviews

1 / 10

Things were good, crew was good. It was just the flight itself was very rough. Lots of turbulence, probably one of the shakiest flights I've been on. Kids throwing up, kids crying everywhere because of it.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Canada. 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 Chicago to Canada one-way?

    $64 is the cheapest one-way deal found within the past few days, from Air Canada. You may also be able to find cheap deals on United Airlines and Delta, with prices starting from $68 and $99, respectively.

  • What are the most popular routes from Chicago to Canada?

    While some choose either Chicago O'Hare Intl - Toronto Pearson Intl or Chicago O'Hare Intl - Montreal Pierre Elliott Trudeau Intl, Chicago O'Hare Intl - Vancouver Intl is the most popular route from Chicago to Canada.

  • What are the most reliable airlines from Chicago to Canada?

    No one likes to see their flight delayed. When booking a flight from Chicago to Canada consider choosing Cathay Pacific (100%), Republic Airways (91%) or Copa Airlines (88%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Canada?

    Looking at all options, your cheapest flight can be booked for $127. While the most popular route (Chicago O'Hare Intl - Vancouver Intl) can be booked for $256 on average our data indicates $1,326 when flying from Chicago to Canada.

  • Can I find deals for flights from Chicago to Canada that include hotel bookings?

    Yes. In addition to deals on Chicago to Canada flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Canada?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Canada.

  • Can I find deals for business class flights from Chicago to Canada?

    Yes. Cheapflights offers flight deals from Chicago to Canada 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 Chicago to Canada?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Canada (average of $243). Flying from Chicago to Canada in July is currently the most expensive (average of $359). 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 Chicago to Canada

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Chicago to Canada

Discover the top 7 airlines that operate flights from Chicago to Canada. 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 19, 2024.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$107Average$489FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$122Average$332FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$122Average$470FlexibilityNo cancel feeOn-time71%
WestJetCheapest$124Average$421FlexibilityNo cancel feeOn-time60%
United AirlinesCheapest$146Average$510FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$154Average$474FlexibilityNo cancel feeOn-time75%
DeltaCheapest$154Average$487FlexibilityNo cancel feeOn-timeN/A
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