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$67+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
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 septiembre 15, 2025.

Round-trip from

$139
(Kiwi.com)

One-way from

$67
(United Airlines)

Popular in

November

Cheapest in

July

Average price

$258

Good round-trip deal

$163 or less

Good one-way deal

$67 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. 6% potential increase in price ($19 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 September 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 septiembre 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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. 10/235:30 pmORD - YYC
Nonstop3h 49mWestJet
lun. 10/279:00 amYYC - ORD
Nonstop3h 35mWestJet
Deal found 9/15$139
This FlightHub deal was found by Cheapflights users on 9/14. 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.
vie. 11/142:20 pmORD - YYC
Nonstop3h 55mWestJet
lun. 11/179:00 amYYC - ORD
Nonstop3h 35mWestJet
Deal found 9/14$151
This Kiwi.com deal was found by Cheapflights users on 9/15. 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. 10/95:30 pmORD - YYC
Nonstop3h 49mWestJet
dom. 10/1212:15 pmYYC - ORD
Nonstop3h 28mWestJet
Deal found 9/15$153
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
dom. 10/125:30 pmORD - YYC
Nonstop3h 49mWestJet
vie. 10/1712:15 pmYYC - ORD
Nonstop3h 28mWestJet
Deal found 9/14$154
This Kiwi.com deal was found by Cheapflights users on 9/13. 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. 10/185:30 pmORD - YYC
Nonstop3h 49mWestJet
vie. 10/2412:15 pmYYC - ORD
Nonstop3h 28mWestJet
Deal found 9/13$155
This United Airlines deal was found by Cheapflights users on 9/15. 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.
mié. 12/108:45 amORD - YYC
Nonstop3h 50mUnited Airlines
sáb. 12/1312:35 pmYYC - ORD
Nonstop3h 35mUnited Airlines
Deal found 9/15$161
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
vie. 10/175:30 pmORD - YVR
1 stop7h 06mWestJet
lun. 10/207:00 amYVR - ORD
1 stop7h 43mWestJet
Deal found 9/13$162
This Kiwi.com deal was found by Cheapflights users on 9/14. 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. 10/115:30 pmORD - YVR
1 stop8h 41mWestJet
sáb. 10/187:00 amYVR - ORD
1 stop7h 43mWestJet
Deal found 9/14$163
This FlightHub deal was found by Cheapflights users on 9/14. 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.
vie. 10/245:30 pmORD - YYC
Nonstop3h 49mWestJet
lun. 10/279:00 amYYC - ORD
Nonstop3h 35mWestJet
Deal found 9/14$163
This Kiwi.com deal was found by Cheapflights users on 9/13. 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. 10/185:30 pmORD - YVR
1 stop7h 06mWestJet
jue. 10/237:00 amYVR - ORD
1 stop7h 43mWestJet
Deal found 9/13$165
This Trip.com deal was found by Cheapflights users on 9/12. 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.
dom. 10/195:30 pmORD - YVR
1 stop8h 41mWestJet
vie. 10/247:00 amYVR - ORD
1 stop7h 43mWestJet
Deal found 9/12$166
This FlightHub deal was found by Cheapflights users on 9/15. 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.
sáb. 10/115:30 pmORD - YYC
Nonstop3h 49mWestJet
sáb. 10/1812:15 pmYYC - ORD
Nonstop3h 28mWestJet
Deal found 9/15$168

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 septiembre 15, 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

mar. 10/28

8:45 am-11:35 am

Nonstop3h 50m

Calgary

mar. 11/4

12:37 pm-5:10 pm

Nonstop3h 33m

$161

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

mié. 12/10

8:45 am-11:35 am

Nonstop3h 50m

Calgary

sáb. 12/13

12:35 pm-5:10 pm

Nonstop3h 35m

$161

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

mié. 2/25

8:45 am-11:41 am

Nonstop3h 56m

Calgary

lun. 3/2

12:37 pm-5:09 pm

Nonstop3h 32m

$161

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

vie. 10/31

7:10 am-2:21 pm

1 stop8h 11m

Calgary

lun. 11/3

12:37 pm-5:10 pm

Nonstop3h 33m

$171

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

sáb. 11/8

8:45 am-11:35 am

Nonstop3h 50m

Calgary

sáb. 11/15

6:15 am-7:40 pm

1 stop12h 25m

$177

ChicagoAbbotsford

ORD - YXX

ORDYXX

Chicago O'Hare Intl

vie. 12/5

2:20 pm-7:45 pm

1 stop7h 25m

Abbotsford

dom. 12/7

9:10 pm-1:35 pm

1 stop14h 25m

$188

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

sáb. 1/10

8:45 am-11:35 am

Nonstop3h 50m

Calgary

sáb. 1/17

12:37 pm-5:08 pm

Nonstop3h 31m

$193

ChicagoAbbotsford

ORD - YXX

ORDYXX

Chicago O'Hare Intl

sáb. 10/4

1:40 pm-8:32 pm

1 stop8h 52m

Abbotsford

sáb. 10/11

5:40 pm-4:43 pm

1 stop21h 03m

$195

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

jue. 9/25

8:51 am-11:33 am

Nonstop4h 42m

Vancouver Intl

sáb. 10/4

1:45 pm-8:04 pm

Nonstop4h 19m

$199

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

dom. 10/19

8:51 am-11:33 am

Nonstop4h 42m

Vancouver Intl

mié. 10/22

10:30 am-4:42 pm

Nonstop4h 12m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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 septiembre 15, 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 septiembre 15, 2025.

The most flights from CHI to CA0 are scheduled on a Friday (64 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (51 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 septiembre 15, 2025.
Peruse reviews from past customers who have flown with Porter Airlines, United Airlines, and American Airlines 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.
Porter Airlines
7.9
Good
363 reviews

Entertainment

7.0

Boarding

8.1

Crew

8.6

Food

7.6

Overall

7.9

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
7.9
Good
363 reviews
Porter Airlines
7.9
Good
363 reviews

Entertainment

7.0

Boarding

8.1

Crew

8.6

Food

7.6

Overall

7.9

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
United Airlines
7.4
Good
8,929 reviews
Porter Airlines
7.9
Good
363 reviews

Entertainment

7.0

Boarding

8.1

Crew

8.6

Food

7.6

Overall

7.9

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
7.9
Good
363 reviews

Entertainment

7.0

Boarding

8.1

Crew

8.6

Food

7.6

Overall

7.9

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
WestJet
7.2
Good
3,091 reviews
Porter Airlines
7.9
Good
363 reviews

Entertainment

7.0

Boarding

8.1

Crew

8.6

Food

7.6

Overall

7.9

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Canada
7.1
Good
10,000 reviews
Porter Airlines
7.9
Good
363 reviews

Entertainment

7.0

Boarding

8.1

Crew

8.6

Food

7.6

Overall

7.9

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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.

  • How long is the flight from Chicago to Canada?

    For as low as $250, United Airlines can have you in Canada from Chicago in 1h 42m. The distance from Chicago to Canada is about 442 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chicago to Canada one-way?

    $67 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on WestJet and Air Canada, with prices starting from $69 and $80, respectively.

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

    While some choose either Chicago O'Hare Intl - Montreal Pierre Elliott Trudeau Intl or Chicago O'Hare Intl - Vancouver Intl, Chicago O'Hare Intl - Toronto Pearson 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 Qatar Airways (85%), Envoy Air (80%) or SkyWest Airlines (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 $74. While the most popular route (Chicago O'Hare Intl - Toronto Pearson Intl) can be booked for $205 on average, our data indicates $762 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.

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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 septiembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$92Average$452FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$96Average$421FlexibilityNo cancel feeOn-time67%
DeltaCheapest$108Average$425FlexibilityNo cancel feeOn-timeN/A
WestJetCheapest$142Average$276FlexibilityNo cancel feeOn-time60%
Porter AirlinesCheapest$187Average$355FlexibilityNo cancel feeOn-time52%
American AirlinesCheapest$192Average$471FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$464Average$709FlexibilityNo cancel feeOn-time75%

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