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$55+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YYZ
Jan 28 — Feb 41
Tue 1/28
Tue 2/4
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 January 23, 2025.

Round-trip from

$162
(Kiwi.com)

One-way from

$64
(Trip.com)

Good round-trip deal

$193 or less

Good one-way deal

$120 or less
From Chicago (CHI) to Canada
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One-way flight from Chicago (CHI) to Canada
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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 January 23, 2025.

This Trip.com deal was found by Cheapflights users on 1/22. 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.
Thu 3/64:45 pmORD - YYC
Nonstop3h 51mWestJet
Sun 3/911:30 amYYC - ORD
Nonstop3h 26mWestJet
Deal found 1/22$161
This Flightnetwork deal was found by Cheapflights users on 1/22. 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.
Thu 2/204:45 pmORD - YYC
Nonstop3h 51mMultiple Airlines
Thu 2/276:15 amYYC - ORD
1 stop7h 36mMultiple Airlines
Deal found 1/22$168
This Trip.com deal was found by Cheapflights users on 1/22. 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.
Sat 2/151:05 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 2/2311:20 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 1/22$200
This Air Canada deal was found by Cheapflights users on 1/23. 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 5/307:45 pmORD - YYC
Nonstop3h 44mAir Canada
Wed 6/412:55 amYYC - ORD
1 stop7h 57mAir Canada
Deal found 1/23$200
This Kiwi.com deal was found by Cheapflights users on 1/23. 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 4/28:50 pmMDW - YVR
1 stop27h 40mMultiple Airlines
Wed 4/97:00 amYVR - MDW
2 stops11h 14mMultiple Airlines
Deal found 1/23$206
This Mytrip deal was found by Cheapflights users on 1/23. 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 2/131:05 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
Sun 2/1611:20 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 1/23$219
This United Airlines deal was found by Cheapflights users on 1/23. 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 3/65:00 amORD - YYC
1 stop14h 16mUnited Airlines
Sun 3/97:20 pmYYC - ORD
1 stop14h 59mUnited Airlines
Deal found 1/23$219
This Kiwi.com deal was found by Cheapflights users on 1/22. 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 2/204:45 pmORD - YVR
1 stop9h 16mWestJet
Thu 2/276:30 amYVR - ORD
1 stop7h 26mWestJet
Deal found 1/22$225
This Kiwi.com deal was found by Cheapflights users on 1/22. 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 3/41:32 pmORD - YVR
1 stop10h 58mMultiple Airlines
Tue 3/113:55 pmYVR - ORD
1 stop12h 41mMultiple Airlines
Deal found 1/22$229
This Trip.com deal was found by Cheapflights users on 1/22. 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.
Tue 5/135:30 pmORD - YXX
1 stop8h 31mWestJet
Mon 5/268:55 pmYXX - ORD
1 stop17h 49mWestJet
Deal found 1/22$239
This Flightnetwork deal was found by Cheapflights users on 1/22. 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.
Mon 3/33:35 pmORD - YTZ
1 stop5h 15mAir Canada
Mon 3/108:25 amYTZ - ORD
1 stop7h 20mAir Canada
Deal found 1/22$245
This United Airlines deal was found by Cheapflights users on 1/22. 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.
Sat 2/159:05 pmORD - YYZ
1 stop10h 29mUnited Airlines
Sun 2/1611:00 amYYZ - ORD
Nonstop2h 09mUnited Airlines
Deal found 1/22$247

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 January 23, 2025.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 3/6

4:45 pm-7:36 pm

Nonstop3h 51m

Calgary

Mon 3/10

11:30 am-3:56 pm

Nonstop3h 26m

$162

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 2/20

4:45 pm-7:36 pm

Nonstop3h 51m

Calgary

Thu 2/27

6:15 am-2:51 pm

1 stop7h 36m

$179

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 2/15

1:05 pm-3:47 pm

Nonstop1h 42m

Toronto Island

Sun 2/23

11:20 am-12:10 pm

Nonstop1h 50m

$200

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 4/8

7:20 am-4:37 pm

1 stop10h 17m

Calgary

Tue 4/15

8:30 am-6:54 pm

1 stop9h 24m

$205

ChicagoVancouver

MDW - YVR

MDWYVR

Chicago Midway

Wed 4/2

8:50 pm-10:30 pm

1 stop27h 40m

Vancouver Intl

Wed 4/9

7:00 am-8:14 pm

2 stops11h 14m

$206

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 2/13

1:05 pm-3:47 pm

Nonstop1h 42m

Toronto Island

Sun 2/16

11:20 am-12:10 pm

Nonstop1h 50m

$210

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 3/6

5:00 am-2:21 pm

1 stop10h 21m

Calgary

Sun 3/9

7:20 pm-11:19 am

1 stop14h 59m

$219

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Wed 5/14

5:30 pm-10:35 pm

1 stop7h 05m

Vancouver Intl

Wed 5/21

7:00 am-4:44 pm

1 stop7h 44m

$226

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Thu 2/20

5:10 am-9:50 pm

2 stops18h 40m

Vancouver Intl

Thu 2/27

6:30 am-3:56 pm

1 stop7h 26m

$231

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 3/29

12:55 pm-3:37 pm

Nonstop1h 42m

Toronto Island

Thu 4/3

3:50 pm-4:40 pm

Nonstop1h 50m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/23

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 January 23, 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 January 23, 2025.

The most flights from CH