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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 1/20. 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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Find the cheapest flights from Chicago to Canada

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Canada that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Canada.

Cheap last minute flights

Planning a quick getaway from Chicago to Canada? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Canada, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Canada

Find recent round-trip train or bus tickets from Chicago to Canada.

All round-trip flight deals to Canada

The cheapest plane tickets to Canada found on KAYAK recently.
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$135WestJet
Find Deal
Sun, Mar 9 - Thu, Mar 13
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$136WestJet
Find Deal
Mon, Mar 10 - Mon, Mar 17
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
12:05 am - 10:10 amYYC-ORD
9h 05m1 stop
$173Air Canada
Find Deal
Tue, Jan 28 - Sat, Feb 1
6:28 pm - 1:18 amORD-YYC
7h 50m1 stop
12:50 am - 10:54 amYYC-ORD
9h 04m1 stop
$178Air Canada
Find Deal
Tue, Jan 7 - Mon, Jan 13
5:00 am - 6:16 pmORD-YYC
14h 16m1 stop
6:04 am - 10:51 pmYYC-ORD
15h 47m1 stop
$187United Airlines
Find Deal
Thu, Mar 6 - Sat, Mar 15
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$220Porter Airlines
Find Deal
Thu, Jan 16 - Sun, Jan 19
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$221Porter Airlines
Find Deal
Sat, Jan 11 - Fri, Jan 24
10:53 am - 1:42 pmORD-YYZ
1h 49mnonstop
6:45 pm - 7:42 pmYYZ-ORD
1h 57mnonstop
$272United Airlines
Find Deal
Thu, Jan 16 - Sun, Jan 19
8:20 am - 3:00 pmORD-YYZ
5h 40m1 stop
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
$288American Airlines
Find Deal
Mon, Jan 13 - Wed, Jan 15
9:49 am - 12:30 pmORD-YYZ
1h 41mnonstop
11:31 am - 12:31 pmYYZ-ORD
2h 00mnonstop
$291American Airlines
Find Deal
Fri, Jan 17 - Sun, Jan 19
8:50 am - 11:39 amORD-YYC
3h 49mnonstop
$59Air Canada
Find Deal
Mon, Jan 20
3:35 pm - 11:02 pmORD-YYC
8h 27m1 stop
$64Air Canada
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Mon, Jan 20
7:10 am - 9:41 pmORD-YYC
15h 31m1 stop
$68United Airlines
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Sat, Jan 18
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$71WestJet
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Sat, Jun 14
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$98Porter Airlines
Find Deal
Wed, Jan 22
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
$101Porter Airlines
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Thu, Jan 9
12:51 pm - 3:45 pmORD-YYZ
1h 54mnonstop
$112United Airlines
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Sun, Jan 12
4:45 pm - 7:33 amORD-YVR
16h 48m1 stop
$121WestJet
Find Deal
Mon, Apr 21
6:35 pm - 9:20 pmORD-YYZ
1h 45mnonstop
$123American Airlines
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Sun, Jan 12
8:45 pm - 11:53 amORD-YYZ
14h 08m1 stop
$162American Airlines
Find Deal
Sun, Jan 5
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
10:20 am - 11:10 amYTZ-MDW
1h 50mnonstop
$363Porter Airlines
Find Deal
Mon, Dec 23 - Mon, Jan 6
8:20 pm - 10:31 amORD-YVR
16h 11m1 stop
6:30 am - 12:45 pmYVR-ORD
4h 15mnonstop
$385United Airlines
Find Deal
Mon, Dec 23 - Sat, Dec 28
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
$393Porter Airlines
Find Deal
Mon, Dec 23 - Wed, Jan 1
7:26 am - 9:25 pmORD-YVR
15h 59m1 stop
7:00 am - 12:19 amYVR-ORD
15h 19m1 stop
$400American Airlines
Find Deal
Sat, Dec 21 - Fri, Dec 27
2:05 pm - 4:46 pmORD-YYZ
1h 41mnonstop
9:00 am - 10:10 amYYZ-ORD
2h 10mnonstop
$411Air Canada
Find Deal
Mon, Dec 23 - Tue, Jan 7
8:20 pm - 10:31 amORD-YVR
16h 11m1 stop
8:15 pm - 2:51 pmYVR-ORD
16h 36m2 stops
$414United Airlines
Find Deal
Mon, Dec 23 - Mon, Jan 13
9:50 am - 12:31 pmORD-YYZ
1h 41mnonstop
8:00 am - 9:01 amYYZ-ORD
2h 01mnonstop
$452Air Canada
Find Deal
Mon, Dec 23 - Wed, Jan 1
7:26 am - 9:25 pmORD-YVR
15h 59m1 stop
1:30 pm - 11:09 pmYVR-ORD
7h 39m1 stop
$464American Airlines
Find Deal
Sat, Dec 21 - Thu, Dec 26
12:20 pm - 11:53 pmMDW-YYZ
10h 33m1 stop
6:30 am - 12:46 pmYYZ-MDW
7h 16m1 stop
$593WestJet
Find Deal
Fri, Dec 20 - Thu, Jan 30
12:20 pm - 11:53 pmMDW-YYZ
10h 33m1 stop
6:16 pm - 10:12 amYYZ-MDW
16h 56m1 stop
$726WestJet
Find Deal
Fri, Dec 20 - Sun, Jan 5
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$136WestJet
Find Deal
Mon, Mar 10 - Mon, Mar 17
4:45 pm - 7:36 pmORD-YYC
3h 51mnonstop
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$140WestJet
Find Deal
Thu, Mar 20 - Sun, Mar 23
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$216Porter Airlines
Find Deal
Sat, Jan 11 - Fri, Jan 24
1:05 pm - 3:47 pmMDW-YTZ
1h 42mnonstop
11:20 am - 12:10 pmYTZ-MDW
1h 50mnonstop
$220Porter Airlines
Find Deal
Sat, Jan 11 - Fri, Jan 24
3:35 pm - 6:47 pmORD-YUL
2h 12mnonstop
9:15 am - 10:54 amYUL-ORD
2h 39mnonstop
$240Air Canada
Find Deal
Fri, Jan 31 - Fri, Feb 7
9:49 am - 12:30 pmORD-YYZ
1h 41mnonstop
11:31 am - 12:31 pmYYZ-ORD
2h 00mnonstop
$264American Airlines
Find Deal
Mon, Jan 13 - Wed, Jan 15
4:00 pm - 6:41 pmORD-YYZ
1h 41mnonstop
6:40 pm - 7:37 pmYYZ-ORD
1h 57mnonstop
$265Air Canada
Find Deal
Sat, Jan 11 - Fri, Jan 24
10:53 am - 1:42 pmORD-YYZ
1h 49mnonstop
6:45 pm - 7:42 pmYYZ-ORD
1h 57mnonstop
$272United Airlines
Find Deal
Thu, Jan 16 - Sun, Jan 19
9:49 am - 12:30 pmORD-YYZ
1h 41mnonstop
11:31 am - 12:31 pmYYZ-ORD
2h 00mnonstop
$291American Airlines
Find Deal
Fri, Jan 17 - Sun, Jan 19
8:30 pm - 11:11 pmORD-YYZ
1h 41mnonstop
8:00 am - 9:01 amYYZ-ORD
2h 01mnonstop
$324United Airlines
Find Deal
Mon, Jan 6 - Fri, Jan 10

KLM flights from Chicago to Canada

Our best KLM deals on Chicago to Canada flight tickets
KLM
Feb 1
MDW11:19 amChicago Midway
10h 34m
1 stop
YYC8:53 pmCalgary
Feb 8
YYC6:35 amCalgary
10h 08m
1 stop
MDW5:43 pmChicago Midway
KLM
Jan 9
ORD10:30 amChicago O'Hare Intl
7h 39m
1 stop
YYZ7:09 pmToronto Pearson Intl
Jan 12
YYZ6:00 amToronto Pearson Intl
7h 55m
1 stop
ORD12:55 pmChicago O'Hare Intl
KLM
Dec 25
ORD7:30 amChicago O'Hare Intl
11h 43m
1 stop
YYC6:13 pmCalgary
Dec 29
YYC7:00 amCalgary
9h 09m
1 stop
ORD5:09 pmChicago O'Hare Intl

United Airlines flights from Chicago to Canada

Our best United Airlines deals on Chicago to Canada flight tickets
United Airlines
Mar 6
ORD5:00 amChicago O'Hare Intl
14h 16m
1 stop
YYC6:16 pmCalgary
Mar 15
YYC6:04 amCalgary
15h 47m
1 stop
ORD10:51 pmChicago O'Hare Intl
United Airlines
Jan 16
ORD10:53 amChicago O'Hare Intl
1h 49m
YYZ1:42 pmToronto Pearson Intl
Jan 19
YYZ6:45 pmToronto Pearson Intl
1h 57m
ORD7:42 pmChicago O'Hare Intl
United Airlines
Jan 9
ORD12:51 pmChicago O'Hare Intl
5h 29m
1 stop
YYZ7:20 pmToronto Pearson Intl
Jan 12
YYZ9:00 amToronto Pearson Intl
2h 10m
ORD10:10 amChicago 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 February, then book flights to Canada from Chicago during April instead. Flights to Canada in April, while not as cheap as those in February, still average around $279.

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

Our data shows that Tuesday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as $292. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Canada for around $311.

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

In the evening is the cheapest time of day to fly from Chicago to Canada when you can find flight prices for as low as $278. Flying to Canada in the evening 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 $314.

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?

We recommend purchasing flights from Chicago to Canada 50 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to Canada for $299. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $160.

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?

You could potentially save up to 8% on your flight if you consider stops on a Chicago to Canada flight.

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

$59

Fastest flight time

1h 30m

Direct flights

Every day

Airports in Canada

3 airports
The best one-way flight to Canada from Chicago in the past 72 hours is $59. The best round-trip flight deal from Chicago to Canada found on momondo in the last 72 hours is $135.
The fastest flight from Chicago to Canada takes 1h 30m
Direct flights go from Chicago to Canada every day.
There are 3 airports near Canada: Calgary (YYC), 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
Air CanadaPriceFrom $107Free CancellationRating
7.0
8,382 reviews
Search Air Canada flights
Porter AirlinesPriceFrom $122Free CancellationRating
7.9
283 reviews
Search Porter Airlines flights
American AirlinesPriceFrom $122Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
WestJetPriceFrom $124Free CancellationRating
7.2
2,818 reviews
Search WestJet flights
United AirlinesPriceFrom $146Free CancellationRating
7.4
9,055 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom $154Free CancellationRating
8.0
9,554 reviews
Search Alaska Airlines flights
DeltaPriceFrom $154Free CancellationRating
8.0
8,604 reviews
Search Delta 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.


An easier way to manage your Canada trip

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Popular cities in Canada

Popular flights according to clicks in the last 7 days on momondo