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$57+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
Aug 16 — Aug 231
Sat 8/16
Sat 8/23
1 adult, Economy
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Cheap flight deals from Chicago to Canada

Keep the following information in mind while searching for Chicago to Canada flight deals. Data was last updated August 11, 2025.

Round-trip from

$150
(FlightHub)

One-way from

$57
(FlightHub)

Popular in

November

Cheapest in

July

Average price

$274

Good round-trip deal

$150 or less

Good one-way deal

$86 or less
From Chicago (CHI) to Canada
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One-way flight from Chicago (CHI) to Canada
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Highest demand for flights based on searches. 8% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Canada.
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Price to beat on a 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 August 11, 2025.

This FlightHub deal was found by Cheapflights users on 8/9. 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.
Tue 9/165:30 pmORD - YYC
Nonstop3h 49mWestJet
Tue 9/2312:15 pmYYC - ORD
Nonstop3h 28mWestJet
Deal found 8/9$150
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Thu 9/45:30 pmORD - YYC
Nonstop3h 49mWestJet
Mon 9/812:15 pmYYC - ORD
Nonstop3h 28mWestJet
Deal found 8/11$151
This FlightHub deal was found by Cheapflights users on 8/10. 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 9/255:30 pmORD - YYC
Nonstop3h 49mWestJet
Tue 9/3012:15 pmYYC - ORD
Nonstop3h 28mWestJet
Deal found 8/10$152
This Mytrip deal was found by Cheapflights users on 8/9. 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.
Wed 9/242:00 pmORD - YQB
1 stop7h 10mAir Canada
Wed 10/16:15 amYQB - ORD
1 stop4h 36mAir Canada
Deal found 8/9$156
This FlightHub deal was found by Cheapflights users on 8/8. 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.
Wed 9/35:30 pmORD - YYC
Nonstop3h 49mWestJet
Tue 9/912:15 pmYYC - ORD
Nonstop3h 28mWestJet
Deal found 8/8$157
This Kiwi.com deal was found by Cheapflights users on 8/10. 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 10/41:40 pmORD - YYC
1 stop6h 00mWestJet
Sun 10/1212:15 pmYYC - ORD
Nonstop3h 28mWestJet
Deal found 8/10$160
This Mytrip deal was found by Cheapflights users on 8/10. 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.
Wed 10/2210:40 amORD - YQB
1 stop5h 50mAir Canada
Sat 10/2511:20 amYQB - ORD
1 stop4h 44mAir Canada
Deal found 8/10$160
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Thu 10/25:30 pmORD - YYC
Nonstop3h 49mWestJet
Sat 10/1112:15 pmYYC - ORD
Nonstop3h 28mWestJet
Deal found 8/10$163
This FlightHub deal was found by Cheapflights users on 8/9. 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.
Sat 9/201:40 pmORD - YYC
1 stop6h 00mWestJet
Mon 9/2212:15 pmYYC - ORD
Nonstop3h 28mWestJet
Deal found 8/9$164
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 9/235:30 pmORD - YYC
Nonstop3h 49mWestJet
Fri 10/312:15 pmYYC - ORD
Nonstop3h 28mWestJet
Deal found 8/9$166
This FlightHub deal was found by Cheapflights users on 8/10. 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 10/235:30 pmORD - YYC
Nonstop3h 49mWestJet
Sun 10/269:00 amYYC - ORD
Nonstop3h 35mWestJet
Deal found 8/10$167
This United Airlines deal was found by Cheapflights users on 8/9. 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 9/1510:40 amORD - YQB
Nonstop2h 36mUnited Airlines
Mon 9/154:55 pmYQB - ORD
1 stop7h 30mUnited Airlines
Deal found 8/9$170

Cheapflights Fare Finder

 
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 August 11, 2025.
Use the filters below to find and compare flights from Chicago to Canada that are best for you.

Fly from

Chicago

Fly to

Canada

Route

Depart

Return

Price

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 9/16

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

Tue 9/23

12:15 pm-4:43 pm

Nonstop3h 28m

$150

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 9/4

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

Mon 9/8

12:15 pm-4:43 pm

Nonstop3h 28m

$151

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 9/25

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

Tue 9/30

12:15 pm-4:43 pm

Nonstop3h 28m

$152

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Wed 9/24

2:00 pm-10:10 pm

1 stop7h 10m

Québec City

Wed 10/1

6:15 am-9:51 am

1 stop4h 36m

$156

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 9/3

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

Tue 9/9

12:15 pm-4:43 pm

Nonstop3h 28m

$157

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Wed 10/22

10:40 am-5:30 pm

1 stop5h 50m

Québec City

Sat 10/25

11:20 am-3:04 pm

1 stop4h 44m

$160

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 10/4

1:40 pm-6:40 pm

1 stop6h 00m

Calgary

Sun 10/12

12:15 pm-4:43 pm

Nonstop3h 28m

$160

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 10/2

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

Sat 10/11

12:15 pm-4:43 pm

Nonstop3h 28m

$163

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 9/20

1:40 pm-6:40 pm

1 stop6h 00m

Calgary

Mon 9/22

12:15 pm-4:43 pm

Nonstop3h 28m

$164

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Mon 9/15

10:40 am-2:16 pm

Nonstop2h 36m

Québec City

Mon 9/15

4:55 pm-11:25 pm

1 stop7h 30m

$170

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/8

Showing 1-10 of 60 results
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6

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Canada

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 August is currently the most expensive (average of $348). 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 August 11, 2025.

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 August 11, 2025.

The most flights from CHI to CA0 are scheduled on a Monday (64 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (48 on average).

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 August 11, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Porter Airlines, and Delta from Chicago to Canada to help guide your decision. 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
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Comfort

7.8

Entertainment

7.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Comfort

7.8

Entertainment

7.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Porter Airlines
8.0
Very good
330 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Comfort

7.8

Entertainment

7.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Delta
8.0
Very good
7,978 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Comfort

7.8

Entertainment

7.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Air Transat
7.7
Good
425 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Comfort

7.8

Entertainment

7.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)
Finnair
7.6
Good
1,321 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Crew

8.5

Overall

8.0

Comfort

7.8

Entertainment

7.0

Food

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Aug 2025

BOI - LAX

flying in first class, my husband froze the entire flight and was miserable. first class does not offer blankets or any entertainment. (TV etc)

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?

    $57 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on Air Canada and United Airlines, with prices starting from $64 and $67, 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 SkyWest Airlines (89%), Envoy Air (82%) or Royal Jordanian (80%) 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 $69. While the most popular route (Chicago O'Hare Intl - Vancouver Intl) can be booked for $189 on average our data indicates $791 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 August is currently the most expensive (average of $348). 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 August 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$92Average$466FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$97Average$430FlexibilityNo cancel feeOn-time67%
DeltaCheapest$108Average$444FlexibilityNo cancel feeOn-timeN/A
WestJetCheapest$143Average$279FlexibilityNo cancel feeOn-time60%
Porter AirlinesCheapest$187Average$326FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$192Average$482FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$464Average$707FlexibilityNo cancel feeOn-time75%

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