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$77+ 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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
jul. 8 — jul. 151
mar. 7/8
mar. 7/15
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 julio 3, 2025.

Round-trip from

$152
(Kiwi.com)

One-way from

$77
(United Airlines)

Popular in

November

Cheapest in

July

Average price

$266

Good round-trip deal

$192 or less

Good one-way deal

$85 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 ($21 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 July 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 julio 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
mié. 9/105:30 pmORD - YYC
Nonstop3h 49mWestJet
mié. 9/1712:15 pmYYC - ORD
Nonstop3h 28mWestJet
Deal found 7/2$152
This Booking.com deal was found by Cheapflights users on 7/2. 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.
sáb. 8/168:25 pmORD - YYZ
Nonstop1h 45mAir Canada
sáb. 8/234:45 pmYYZ - ORD
Nonstop1h 57mAir Canada
Deal found 7/2$179
This United Airlines deal was found by Cheapflights users on 7/3. 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.
vie. 7/188:05 pmORD - YYC
Nonstop3h 48mUnited Airlines
mié. 7/2312:38 pmYYC - ORD
Nonstop3h 32mUnited Airlines
Deal found 7/3$181
This Cheapflightsfares deal was found by Cheapflights users on 6/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/85:20 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
mié. 7/97:55 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 6/30$181
This United Airlines deal was found by Cheapflights users on 7/2. 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. 8/137:04 amORD - YYZ
Nonstop1h 54mUnited Airlines
mié. 8/1312:45 pmYYZ - ORD
1 stop5h 07mUnited Airlines
Deal found 7/2$181
This FlightHub deal was found by Cheapflights users on 7/3. 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. 8/159:40 amMDW - YTZ
Nonstop1h 40mPorter Airlines
lun. 8/187:55 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 7/3$182
This American Airlines deal was found by Cheapflights users on 7/1. 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.
dom. 10/123:00 pmORD - YYZ
Nonstop1h 40mAmerican Airlines
lun. 10/206:29 pmYYZ - ORD
Nonstop2h 00mAmerican Airlines
Deal found 7/1$185
This Flightnetwork deal was found by Cheapflights users on 7/2. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/245:30 pmORD - YYC
Nonstop3h 49mMultiple Airlines
sáb. 8/301:05 amYYC - ORD
1 stop7h 47mMultiple Airlines
Deal found 7/2$186
This Mytrip deal was found by Cheapflights users on 7/3. 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.
lun. 8/256:20 pmORD - YYC
1 stop7h 55mAir Canada
mié. 9/36:00 amYYC - ORD
1 stop7h 55mAir Canada
Deal found 7/3$211
This FlightHub deal was found by Cheapflights users on 7/1. 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. 7/119:40 amMDW - YTZ
Nonstop1h 40mAir Transat
lun. 7/147:55 amYTZ - MDW
Nonstop1h 50mAir Transat
Deal found 7/1$214
This Delta deal was found by Cheapflights users on 7/1. 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.
mar. 9/99:30 amMDW - YYZ
1 stop6h 53mDelta
sáb. 9/1312:14 pmYYZ - MDW
1 stop7h 21mDelta
Deal found 7/1$234
This oojo deal was found by Cheapflights users on 7/2. 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.
mar. 9/165:30 pmORD - YXX
1 stop8h 33mWestJet
jue. 9/188:55 pmYXX - ORD
1 stop17h 48mWestJet
Deal found 7/2$237

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 julio 3, 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

mié. 9/10

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

mié. 9/17

12:15 pm-4:43 pm

Nonstop3h 28m

$152

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

sáb. 8/16

8:25 pm-11:10 pm

Nonstop1h 45m

Toronto Pearson Intl

sáb. 8/23

4:45 pm-5:42 pm

Nonstop1h 57m

$179

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

vie. 7/18

8:05 pm-10:53 pm

Nonstop3h 48m

Calgary

mié. 7/23

12:38 pm-5:10 pm

Nonstop3h 32m

$181

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

mar. 7/8

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

mié. 7/9

7:55 am-8:45 am

Nonstop1h 50m

$181

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

mié. 8/13

7:04 am-9:58 am

Nonstop1h 54m

Toronto Pearson Intl

mié. 8/13

12:45 pm-4:52 pm

1 stop5h 07m

$181

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

vie. 8/15

9:40 am-12:20 pm

Nonstop1h 40m

Toronto Island

lun. 8/18

7:55 am-8:45 am

Nonstop1h 50m

$182

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

dom. 8/24

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

sáb. 8/30

1:05 am-9:52 am

1 stop7h 47m

$186

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

mié. 8/13

6:00 am-2:44 pm

1 stop7h 44m

Toronto Pearson Intl

mié. 8/13

5:18 pm-11:25 pm

1 stop7h 07m

$197

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

lun. 8/25

6:20 pm-1:15 am

1 stop7h 55m

Calgary

mié. 9/3

6:00 am-2:55 pm

1 stop7h 55m

$211

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

vie. 7/11

9:40 am-12:20 pm

Nonstop1h 40m

Toronto Island

lun. 7/14

7:55 am-8:45 am

Nonstop1h 50m

$214

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

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.

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 julio 3, 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 julio 3, 2025.

The most flights from CHI to CA0 are scheduled on a Wednesday (62 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 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 julio 3, 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

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Porter Airlines
8.0
Very good
298 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Delta
8.0
Very good
7,982 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Air Transat
7.8
Good
407 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Finnair
7.6
Good
1,306 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.

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?

    $77 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 Air Transat and Porter Airlines, with prices starting from $79 and $81, 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 - Calgary, 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%), Japan Airlines (90%) or SkyWest Airlines (90%) 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 $83. While the most popular route (Chicago O'Hare Intl - Vancouver Intl) can be booked for $227 on average our data indicates $1,221 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 julio 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$88Average$476FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$98Average$431FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$109Average$350FlexibilityNo cancel feeOn-time52%
DeltaCheapest$110Average$447FlexibilityNo cancel feeOn-timeN/A
WestJetCheapest$140Average$284FlexibilityNo cancel feeOn-time60%
American AirlinesCheapest$182Average$483FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$464Average$713FlexibilityNo cancel feeOn-time75%

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