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Cheap flights from Chicago to Canada from $64

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 5/1. 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

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Canada.
 Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
 Logo
5:50 am - 2:47 pmYYC-ORD
7h 57m1 stop
Sat, May 3 - Sat, May 10
Air Canada Logo
3:35 pm - 11:06 pmORD-YYC
8h 31m1 stop
Air Canada Logo
5:50 am - 2:47 pmYYC-ORD
7h 57m1 stop
$144Air Canada
Find Deal
Sat, May 3 - Sat, May 10
WestJet Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
WestJet Logo
12:15 pm - 4:44 pmYYC-ORD
3h 29mnonstop
$145WestJet
Find Deal
Thu, May 1 - Sat, May 10
WestJet Logo
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
WestJet Logo
12:15 pm - 4:44 pmYYC-ORD
3h 29mnonstop
$148WestJet
Find Deal
Fri, May 16 - Sat, May 24
American Airlines Logo
8:30 pm - 11:29 pmORD-YYC
3h 59mnonstop
American Airlines Logo
6:29 am - 10:54 amYYC-ORD
3h 25mnonstop
$180American Airlines
Find Deal
Sun, Jun 15 - Fri, Jun 20
Porter Airlines Logo
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
$190Porter Airlines
Find Deal
Wed, Apr 23 - Tue, Apr 29
Porter Airlines Logo
9:40 am - 12:22 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
$191Porter Airlines
Find Deal
Tue, May 13 - Tue, May 20
United Airlines Logo
7:10 am - 9:48 pmORD-YYC
15h 38m1 stop
United Airlines Logo
1:30 pm - 12:29 amYYC-ORD
9h 59m1 stop
$205United Airlines
Find Deal
Tue, May 6 - Thu, May 8
American Airlines Logo
8:25 pm - 11:29 pmORD-YYC
4h 04mnonstop
American Airlines Logo
6:29 am - 10:54 amYYC-ORD
3h 25mnonstop
$225American Airlines
Find Deal
Sun, Aug 3 - Tue, Aug 12
United Airlines Logo
9:31 pm - 12:01 pmORD-YYZ
13h 30m1 stop
United Airlines Logo
2:20 pm - 3:14 pmYYZ-ORD
1h 54mnonstop
$269United Airlines
Find Deal
Sat, Aug 9 - Sun, Aug 10

United Airlines flights from Chicago to Canada

Our best United Airlines deals on Chicago to Canada flight tickets
United Airlines
May 6
ORD7:10 amChicago O'Hare Intl
15h 38m
1 stop
YYC9:48 pmCalgary
May 8
YYC1:30 pmCalgary
9h 59m
1 stop
ORD12:29 amChicago O'Hare Intl
United Airlines
Aug 9
ORD9:31 pmChicago O'Hare Intl
13h 30m
1 stop
YYZ12:01 pmToronto Pearson Intl
Aug 10
YYZ2:20 pmToronto Pearson Intl
1h 54m
ORD3:14 pmChicago O'Hare Intl
United Airlines
Apr 2
ORD8:52 amChicago O'Hare Intl
3h 49m
YYC11:41 amCalgary
Apr 6
YYC6:15 amCalgary
7h 40m
1 stop
ORD2:55 pmChicago O'Hare Intl

American Airlines flights from Chicago to Canada

Our best American Airlines deals on Chicago to Canada flight tickets
American Airlines
Jun 15
ORD8:30 pmChicago O'Hare Intl
3h 59m
YYC11:29 pmCalgary
Jun 20
YYC6:29 amCalgary
3h 25m
ORD10:54 amChicago O'Hare Intl
American Airlines
Aug 3
ORD8:25 pmChicago O'Hare Intl
4h 04m
YYC11:29 pmCalgary
Aug 12
YYC6:29 amCalgary
3h 25m
ORD10:54 amChicago O'Hare Intl
American Airlines
Apr 22
ORD8:30 pmChicago O'Hare Intl
12h 20m
1 stop
YUL9:50 amMontreal Pierre Elliott Trudeau Intl
Apr 23
YUL12:30 pmMontreal Pierre Elliott Trudeau Intl
2h 35m
ORD2:05 pmChicago O'Hare Intl

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 April, then book flights to Canada from Chicago during September instead. Flights to Canada in September, while not as cheap as those in April, still average around $284.

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

Our data shows that Friday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as $623. 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 $772.

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 $569. 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 $762.

What is the cheapest Chicago to Canada flight route?

Fly from Chicago O'Hare Intl to Calgary 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 15 weeks ahead of your departure date. In general, you can expect to find flights to Canada for around $321 when searching 15 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 $241 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.

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

$64

Fastest flight time

1h 35m

Direct flights

Every day

Airports in Canada

4 airports
The best one-way flight to Canada from Chicago in the past 72 hours is $64. The best round-trip flight deal from Chicago to Canada found on momondo in the last 72 hours is $136.
The fastest flight from Chicago to Canada takes 1h 35m
Direct flights go from Chicago to Canada every day.
There are 4 airports near Canada: Calgary (YYC), Vancouver Intl (YVR), Toronto Pearson Intl (YYZ), Toronto Island (YTZ)

  • 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
8,615 reviews
Search United Airlines flights
Air CanadaPriceFrom $116Free CancellationRating
7.0
9,022 reviews
Search Air Canada flights
Porter AirlinesPriceFrom $122Free CancellationRating
7.9
278 reviews
Search Porter Airlines flights
American AirlinesPriceFrom $122Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
WestJetPriceFrom $131Free CancellationRating
7.2
2,789 reviews
Search WestJet flights
DeltaPriceFrom $137Free CancellationRating
8.0
7,898 reviews
Search Delta flights
Alaska AirlinesPriceFrom $154Free CancellationRating
8.0
9,820 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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