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Cheap flights from Chicago to Canada from $59

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Canada departing on 11/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
WestJet Logo
9:00 am - 1:35 pmYYC-ORD
3h 35mnonstop
$145WestJet
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Fri, Oct 24 - Sun, Oct 26
WestJet Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
WestJet Logo
12:15 pm - 4:43 pmYYC-ORD
3h 28mnonstop
$156WestJet
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Thu, Oct 16 - Thu, Oct 23
Air Canada Logo
3:40 pm - 6:15 pmORD-YVR
4h 35mnonstop
Air Canada Logo
8:30 am - 2:41 pmYVR-ORD
4h 11mnonstop
$178Air Canada
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Sat, Nov 15 - Sat, Nov 22
Air Canada Logo
3:40 pm - 6:15 pmORD-YVR
4h 35mnonstop
Air Canada Logo
8:30 am - 2:41 pmYVR-ORD
4h 11mnonstop
$180Air Canada
Find Deal
Fri, Oct 31 - Sun, Nov 2
United Airlines Logo
9:08 pm - 11:02 amORD-YQB
12h 54m1 stop
United Airlines Logo
2:55 pm - 4:57 pmYQB-ORD
3h 02mnonstop
$190United Airlines
Find Deal
Fri, Nov 14 - Fri, Nov 21
United Airlines Logo
8:20 pm - 11:02 amORD-YQB
13h 42m1 stop
United Airlines Logo
2:55 pm - 4:57 pmYQB-ORD
3h 02mnonstop
$193United Airlines
Find Deal
Sat, Nov 15 - Sun, Nov 16
American Airlines Logo
9:49 am - 12:34 pmORD-YYC
3h 45mnonstop
American Airlines Logo
1:29 pm - 5:54 pmYYC-ORD
3h 25mnonstop
$206American Airlines
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Tue, Oct 21 - Fri, Oct 24
American Airlines Logo
9:45 pm - 11:59 amORD-YYC
15h 14m1 stop
American Airlines Logo
1:29 pm - 5:54 pmYYC-ORD
3h 25mnonstop
$216American Airlines
Find Deal
Mon, Oct 20 - Fri, Oct 24
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
$230Porter Airlines
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Thu, Nov 13 - Thu, Nov 20
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
$231Porter Airlines
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Sun, Nov 9 - Thu, Nov 13

Delta flights from Chicago to Canada

Our best Delta deals on Chicago to Canada flight tickets
Delta
Feb 19
ORD7:00 amChicago O'Hare Intl
8h 08m
1 stop
YYZ4:08 pmToronto Pearson Intl
Feb 24
YYZ6:15 amToronto Pearson Intl
8h 06m
1 stop
ORD1:21 pmChicago O'Hare Intl
$233
Find similar
Delta
Feb 12
MDW1:05 pmChicago Midway
9h 49m
1 stop
YUL11:54 pmMontreal Pierre Elliott Trudeau Intl
Feb 15
YUL7:00 amMontreal Pierre Elliott Trudeau Intl
9h 25m
1 stop
MDW3:25 pmChicago Midway
$236
Find similar
Delta
Oct 15
MDW1:48 pmChicago Midway
8h 47m
1 stop
YVR8:35 pmVancouver Intl
Oct 22
YVR6:00 amVancouver Intl
9h 43m
1 stop
MDW5:43 pmChicago Midway
$286
Find similar

Air Canada flights from Chicago to Canada

Our best Air Canada deals on Chicago to Canada flight tickets
Air Canada
Nov 15
ORD3:40 pmChicago O'Hare Intl
4h 35m
YVR6:15 pmVancouver Intl
Nov 22
YVR8:30 amVancouver Intl
4h 11m
ORD2:41 pmChicago O'Hare Intl
$178
Find similar
Air Canada
Oct 31
ORD3:40 pmChicago O'Hare Intl
4h 35m
YVR6:15 pmVancouver Intl
Nov 2
YVR8:30 amVancouver Intl
4h 11m
ORD2:41 pmChicago O'Hare Intl
$180
Find similar
Air Canada
Nov 15
ORD3:40 pmChicago O'Hare Intl
4h 35m
YVR6:15 pmVancouver Intl
Nov 22
YVR8:30 amVancouver Intl
4h 11m
ORD2:41 pmChicago O'Hare Intl
$182
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated October 1, 2025.
Use the filters below to find and compare flights from Chicago to Canada that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 10/24

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

Sun 10/26

9:00 am-1:35 pm

Nonstop3h 35m

$145

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 10/16

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

Thu 10/23

12:15 pm-4:43 pm

Nonstop3h 28m

$156

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Sat 11/15

3:40 pm-6:15 pm

Nonstop4h 35m

Vancouver Intl

Sat 11/22

8:30 am-2:41 pm

Nonstop4h 11m

$178

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Fri 10/31

3:40 pm-6:15 pm

Nonstop4h 35m

Vancouver Intl

Sun 11/2

8:30 am-2:41 pm

Nonstop4h 11m

$180

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Fri 11/14

9:08 pm-11:02 am

1 stop12h 54m

Québec City

Fri 11/21

2:55 pm-4:57 pm

Nonstop3h 02m

$190

ChicagoQuébec City

ORD - YQB

ORDYQB

Chicago O'Hare Intl

Sat 11/15

8:20 pm-11:02 am

1 stop13h 42m

Québec City

Sun 11/16

2:55 pm-4:57 pm

Nonstop3h 02m

$193

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 10/21

9:49 am-12:34 pm

Nonstop3h 45m

Calgary

Fri 10/24

1:29 pm-5:54 pm

Nonstop3h 25m

$206

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 10/20

9:45 pm-11:59 am

1 stop15h 14m

Calgary

Fri 10/24

1:29 pm-5:54 pm

Nonstop3h 25m

$216

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 11/13

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Thu 11/20

2:30 pm-3:20 pm

Nonstop1h 50m

$230

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 11/9

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Thu 11/13

9:15 am-10:05 am

Nonstop1h 50m

$231

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Canada from

How to get the cheapest flight ticket from Chicago to Canada

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Canada?

If you aren’t able to travel during the month of July, then book flights to Canada from Chicago during August instead. Flights to Canada in August, while not as cheap as those in July, still average around $259.

What is the cheapest day to depart on your flight to Canada?

Our data shows that Thursday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as $617. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Canada for around $760.

What is the cheapest time of day to depart on your flight to Canada?

In the morning is the cheapest time of day to fly from Chicago to Canada when you can find flight prices for as low as $583. Flying to Canada in the morning is an ideal time because this is during off-peak travel hours. In contrast, the most expensive time of day to depart to Canada is in the afternoon when prices are around $760.

What is the cheapest Chicago to Canada flight route?

Fly from Chicago O'Hare Intl to Vancouver Intl for the best Chicago - Canada flight prices

How far in advance should I book a flight to Canada?

You are more likely to see cheaper flights to Canada from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Canada for around $306 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Canada from Chicago for as low as $166 on momondo.

What cabin class options are available on Chicago to Canada flights?

There are 4 cabin classes available to choose from on Chicago to Canada flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Canada flights?

No. A direct flight is the cheapest option for a flight between Chicago to Canada.

Cheap Chicago to Canada flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Canada

Best Price Found

$67

Fastest flight time

1h 39m

Direct flights

Every day

Airports in Canada

2 airports
The best one-way flight to Canada from Chicago in the past 72 hours is $67. The best round-trip flight deal from Chicago to Canada found on momondo in the last 72 hours is $163.
The fastest flight from Chicago to Canada takes 1h 39m
Direct flights go from Chicago to Canada every day.
There are 2 airports near Canada: Toronto Pearson Intl (YYZ), Toronto Island (YTZ)
Search flight deals

  • When did momondo last update prices for flights from Chicago to Canada?

    Prices for flights from Chicago to Canada are updated daily.

  • How many operators does momondo search for flights from Chicago to Canada?

  • How old do you have to be to fly from Chicago to Canada?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Canada.

  • What documentation or ID do you need to fly to Canada?

    The necessary travel and health documents for your Canada trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Canada?

Best airlines flying from Chicago to Canada

Compare and see reviews for airlines that fly from Chicago to Canada with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $92Free CancellationRating
7.4
8,929 reviews
Search United Airlines flights
Air CanadaPriceFrom $96Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
DeltaPriceFrom $109Free CancellationRating
7.9
7,961 reviews
Search Delta flights
WestJetPriceFrom $142Free CancellationRating
7.2
3,111 reviews
Search WestJet flights
Porter AirlinesPriceFrom $187Free CancellationRating
7.9
372 reviews
Search Porter Airlines flights
American AirlinesPriceFrom $192Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Alaska AirlinesPriceFrom $464Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Canada?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Canada for you.

Can I find flights from Chicago to Canada with flexible booking policies on momondo?

All flight searches from Chicago to Canada on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Canada?

momondo provides multiple filters to help you find the best flight to Canada from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Canada right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Canada flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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