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Cheap flights from Chicago to Canada from C$ 92

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 20/4. 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 from Chicago to Canada

The cheapest plane tickets from Chicago to Canada found on KAYAK recently.
4:45 p.m. - 7:36 p.m.ORD-YYC
3h 51mdirect
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
C$ 227WestJet
Find Deal
Mon, 10 Mar - Mon, 24 Mar
4:45 p.m. - 7:36 p.m.ORD-YYC
3h 51mdirect
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
C$ 232WestJet
Find Deal
Thu, 10 Apr - Thu, 17 Apr
4:45 p.m. - 7:36 p.m.ORD-YYC
3h 51mdirect
6:15 a.m. - 2:51 p.m.YYC-ORD
7h 36m1 stop
C$ 258
Find Deal
Thu, 20 Feb - Thu, 27 Feb
4:45 p.m. - 7:36 p.m.ORD-YYC
3h 51mdirect
8:30 a.m. - 6:41 p.m.YYC-ORD
9h 11m1 stop
C$ 265
Find Deal
Thu, 6 Mar - Thu, 13 Mar
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
C$ 284Porter Airlines
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Thu, 13 Feb - Sun, 16 Feb
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
C$ 288Porter Airlines
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Tue, 25 Feb - Thu, 27 Feb
7:10 a.m. - 9:48 p.m.ORD-YYC
15h 38m1 stop
8:30 a.m. - 12:49 p.m.YYC-ORD
3h 19mdirect
C$ 294United Airlines
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Sat, 17 May - Sat, 24 May
8:47 a.m. - 11:39 a.m.ORD-YYC
3h 52mdirect
2:09 p.m. - 12:23 a.m.YYC-ORD
9h 14m1 stop
C$ 302United Airlines
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Tue, 11 Mar - Wed, 12 Mar
2:05 p.m. - 9:18 p.m.ORD-YYC
8h 13m1 stop
8:30 a.m. - 6:38 p.m.YYC-ORD
9h 08m1 stop
C$ 338Air Canada
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Sat, 8 Feb - Tue, 11 Feb
2:40 p.m. - 11:03 p.m.ORD-YYC
9h 23m1 stop
6:00 a.m. - 2:54 p.m.YYC-ORD
7h 54m1 stop
C$ 350Air Canada
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Mon, 14 Jul - Sat, 19 Jul
4:45 p.m. - 7:36 p.m.ORD-YYC
3h 51mdirect
C$ 92WestJet
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Sun, 20 Apr
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 94WestJet
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Wed, 14 May
1:05 p.m. - 9:41 p.m.ORD-YYC
9h 36m1 stop
C$ 122United Airlines
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Tue, 11 Mar
7:26 a.m. - 11:53 p.m.ORD-YYZ
15h 27m1 stop
C$ 127
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Thu, 30 Jan
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 128Porter Airlines
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Tue, 4 Mar
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 130Porter Airlines
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Thu, 6 Mar
1:32 p.m. - 10:55 p.m.ORD-YYC
10h 23m1 stop
C$ 131
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Wed, 26 Feb
2:40 p.m. - 11:03 p.m.ORD-YYC
9h 23m1 stop
C$ 138Air Canada
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Sun, 20 Jul
6:39 p.m. - 1:18 a.m.ORD-YYC
7h 39m1 stop
C$ 157Air Canada
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Sun, 23 Mar
10:53 a.m. - 1:42 p.m.ORD-YYZ
1h 49mdirect
C$ 190United Airlines
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Wed, 12 Feb
8:50 a.m. - 11:39 a.m.ORD-YYC
3h 49mdirect
6:19 a.m. - 7:31 p.m.YYC-ORD
12h 12m1 stop
C$ 394United Airlines
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Thu, 23 Jan - Thu, 30 Jan
5:35 a.m. - 12:11 a.m.ORD-YYZ
17h 36m1 stop
7:50 p.m. - 9:39 a.m.YYZ-ORD
14h 49m1 stop
C$ 402
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Sat, 25 Jan - Sun, 26 Jan
1:26 p.m. - 8:53 p.m.MDW-YYC
8h 27m1 stop
6:35 a.m. - 5:47 p.m.YYC-MDW
10h 12m1 stop
C$ 409Delta
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Thu, 23 Jan - Thu, 30 Jan
4:15 p.m. - 8:53 p.m.ORD-YYC
5h 38m1 stop
6:35 a.m. - 5:29 p.m.YYC-ORD
9h 54m1 stop
C$ 409Delta
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Sun, 26 Jan - Fri, 31 Jan
2:05 p.m. - 9:18 p.m.ORD-YYC
8h 13m1 stop
12:50 a.m. - 10:10 a.m.YYC-ORD
8h 20m1 stop
C$ 445Air Canada
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Sun, 26 Jan - Thu, 30 Jan
2:05 p.m. - 9:18 p.m.ORD-YYC
8h 13m1 stop
8:30 a.m. - 6:38 p.m.YYC-ORD
9h 08m1 stop
C$ 520Air Canada
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Sat, 25 Jan - Sun, 26 Jan
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
C$ 641Porter Airlines
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Thu, 23 Jan - Sun, 2 Feb
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
C$ 642Porter Airlines
Find Deal
Fri, 24 Jan - Wed, 29 Jan
6:45 a.m. - 11:59 a.m.ORD-YYZ
4h 14m1 stop
6:00 a.m. - 9:16 a.m.YYZ-ORD
4h 16m1 stop
C$ 739WestJet
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Fri, 24 Jan - Tue, 28 Jan
6:45 a.m. - 11:59 a.m.ORD-YYZ
4h 14m1 stop
6:00 a.m. - 9:28 p.m.YYZ-ORD
16h 28m1 stop
C$ 746WestJet
Find Deal
Fri, 24 Jan - Tue, 28 Jan
4:45 p.m. - 7:36 p.m.ORD-YYC
3h 51mdirect
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
C$ 227WestJet
Find Deal
Mon, 10 Mar - Mon, 24 Mar
4:45 p.m. - 7:36 p.m.ORD-YYC
3h 51mdirect
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
C$ 232WestJet
Find Deal
Thu, 10 Apr - Thu, 17 Apr
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
C$ 284Porter Airlines
Find Deal
Thu, 13 Feb - Sun, 16 Feb
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
C$ 288Porter Airlines
Find Deal
Tue, 25 Feb - Thu, 27 Feb
1:05 p.m. - 3:47 p.m.MDW-YTZ
1h 42mdirect
11:20 a.m. - 12:10 p.m.YTZ-MDW
1h 50mdirect
C$ 314
Find Deal
Thu, 13 Feb - Sun, 16 Feb
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
C$ 384
Find Deal
Fri, 25 Apr - Mon, 28 Apr
2:05 p.m. - 4:46 p.m.ORD-YYZ
1h 41mdirect
2:00 p.m. - 2:51 p.m.YYZ-ORD
1h 51mdirect
C$ 405Air Canada
Find Deal
Tue, 18 Mar - Wed, 19 Mar
7:12 a.m. - 9:58 a.m.ORD-YYZ
1h 46mdirect
9:00 p.m. - 10:06 p.m.YYZ-ORD
2h 06mdirect
C$ 407Air Canada
Find Deal
Mon, 3 Mar - Mon, 10 Mar
8:47 a.m. - 11:39 a.m.ORD-YYC
3h 52mdirect
12:41 p.m. - 5:10 p.m.YYC-ORD
3h 29mdirect
C$ 452United Airlines
Find Deal
Tue, 11 Mar - Wed, 12 Mar
9:50 a.m. - 12:25 p.m.ORD-YYZ
1h 35mdirect
11:00 a.m. - 12:09 p.m.YYZ-ORD
2h 09mdirect
C$ 474United Airlines
Find Deal
Tue, 11 Feb - Sun, 16 Feb

WestJet flights from Chicago to Canada

Our best WestJet deals on Chicago to Canada flight tickets
WestJet
10 Mar
ORD4:45 p.m.Chicago O'Hare Intl
3h 51m
YYC7:36 p.m.Calgary
24 Mar
YYC11:30 a.m.Calgary
3h 26m
ORD3:56 p.m.Chicago O'Hare Intl
WestJet
10 Apr
ORD4:45 p.m.Chicago O'Hare Intl
3h 51m
YYC7:36 p.m.Calgary
17 Apr
YYC11:30 a.m.Calgary
3h 26m
ORD3:56 p.m.Chicago O'Hare Intl
WestJet
27 Feb
ORD4:45 p.m.Chicago O'Hare Intl
3h 51m
YYC7:36 p.m.Calgary
6 Mar
YYC11:30 a.m.Calgary
3h 26m
ORD3:56 p.m.Chicago O'Hare Intl

American Airlines flights from Chicago to Canada

Our best American Airlines deals on Chicago to Canada flight tickets
American Airlines
14 Feb
ORD3:00 p.m.Chicago O'Hare Intl
1h 30m
YYZ5:30 p.m.Toronto Pearson Intl
18 Feb
YYZ6:15 a.m.Toronto Pearson Intl
2h 15m
ORD7:30 a.m.Chicago O'Hare Intl
American Airlines
13 Feb
ORD8:11 a.m.Chicago O'Hare Intl
1h 40m
YYZ10:51 a.m.Toronto Pearson Intl
18 Feb
YYZ6:15 a.m.Toronto Pearson Intl
2h 15m
ORD7:30 a.m.Chicago O'Hare Intl
American Airlines
31 Jan
ORD8:11 a.m.Chicago O'Hare Intl
1h 40m
YYZ10:51 a.m.Toronto Pearson Intl
21 Feb
YYZ6:15 a.m.Toronto Pearson Intl
2h 15m
ORD7:30 a.m.Chicago 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?

In general, April is the cheapest month to fly from Chicago to Canada. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 394. If you’re not able to fly to Canada in April, then February is your next best option. Flight prices from Chicago to Canada during February average around C$ 399.

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 C$ 409. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around C$ 512. These prices are subject to change though, so be sure to set up a Price Alert for flights to Canada.

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

According to our data, the cheapest time of day to fly to Canada is at noon. momondo users have found flights departing from Chicago to Canada at noon for as low as C$ 403. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the evening is when there is more demand to fly to Canada, so prices are often more expensive at around C$ 512 per ticket.

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 21 weeks ahead of your departure date. In general, you can expect to find flights to Canada for around C$ 442 when searching 21 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 C$ 284 on momondo.

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

There are 3 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

C$ 92

Fastest flight time

1h 30m

Direct flights

Every day

Airports in Canada

4 airports
The best one-way flight to Canada from Chicago in the past 72 hours is C$ 92. The best round-trip flight deal from Chicago to Canada found on momondo in the last 72 hours is C$ 227.
The fastest flight from Chicago to Canada takes 1h 30m
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 refresh 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?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, 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
WestJetPriceFrom C$ 143Free CancellationRating
7.2
2,829 reviews
Search WestJet flights
United AirlinesPriceFrom C$ 189Free CancellationRating
7.4
8,985 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 192Free CancellationRating
7.0
8,635 reviews
Search Air Canada flights
Porter AirlinesPriceFrom C$ 314Free CancellationRating
7.9
277 reviews
Search Porter Airlines flights

Why use momondo?

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

It is quick and easy to find Chicago to Canada flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Canada that suits you.

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

momondo does allow users to show only those flights to Canada from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Canada from Chicago.

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

Yes. momondo can track prices for Chicago to Canada flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.


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