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Cheap flights from Canada to Chicago from C$ 120

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Canada to Chicago departing on 4/10. 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 Canada to Chicago

Recent round-trip flight deals from Canada to Chicago

Porter Airlines Logo
7:30 a.m. - 8:19 a.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
9:15 a.m. - 11:57 a.m.MDW-YTZ
1h 42mdirect
C$ 177Porter Airlines
Find Deal
Fri, 5 Sep - Mon, 8 Sep
Porter Airlines Logo
10:45 a.m. - 4:24 p.m.YUL-MDW
6h 39m1 stop
Porter Airlines Logo
9:15 a.m. - 4:00 p.m.MDW-YUL
5h 45m1 stop
C$ 177Porter Airlines
Find Deal
Mon, 15 Sep - Mon, 22 Sep
Air Canada Logo
8:20 a.m. - 9:51 a.m.YUL-ORD
2h 31mdirect
Air Canada Logo
3:35 p.m. - 6:50 p.m.ORD-YUL
2h 15mdirect
C$ 180Air Canada
Find Deal
Tue, 9 Sep - Sun, 14 Sep
Air Canada Logo
8:20 a.m. - 9:51 a.m.YUL-ORD
2h 31mdirect
Air Canada Logo
9:55 a.m. - 5:50 p.m.ORD-YUL
6h 55m1 stop
C$ 181Air Canada
Find Deal
Tue, 9 Sep - Sun, 14 Sep
WestJet Logo
12:15 p.m. - 4:43 p.m.YYC-ORD
3h 28mdirect
WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 195WestJet
Find Deal
Mon, 8 Sep - Thu, 11 Sep
WestJet Logo
12:15 p.m. - 4:43 p.m.YYC-ORD
3h 28mdirect
WestJet Logo
5:30 p.m. - 8:19 p.m.ORD-YYC
3h 49mdirect
C$ 199WestJet
Find Deal
Wed, 17 Sep - Fri, 19 Sep
American Airlines Logo
6:30 a.m. - 7:26 a.m.YYZ-ORD
1h 56mdirect
American Airlines Logo
3:05 p.m. - 5:47 p.m.ORD-YYZ
1h 42mdirect
C$ 219American Airlines
Find Deal
Mon, 1 Sep - Fri, 5 Sep
United Airlines Logo
7:40 p.m. - 11:43 p.m.YYZ-ORD
5h 03m1 stop
United Airlines Logo
4:20 p.m. - 11:29 p.m.ORD-YYZ
6h 09m1 stop
C$ 233United Airlines
Find Deal
Fri, 31 Oct - Mon, 3 Nov
American Airlines Logo
7:35 a.m. - 8:11 p.m.YYZ-ORD
13h 36m1 stop
American Airlines Logo
3:05 p.m. - 5:47 p.m.ORD-YYZ
1h 42mdirect
C$ 243American Airlines
Find Deal
Sat, 30 Aug - Fri, 5 Sep
United Airlines Logo
11:00 a.m. - 11:59 a.m.YYZ-ORD
1h 59mdirect
United Airlines Logo
9:20 p.m. - 11:59 p.m.ORD-YYZ
1h 39mdirect
C$ 248United Airlines
Find Deal
Thu, 30 Oct - Sun, 2 Nov

WestJet flights from Canada to Chicago

Our best WestJet deals on Canada to Chicago flight tickets
WestJet
8 Sep
YYC12:15 p.m.Calgary
3h 28m
ORD4:43 p.m.Chicago O'Hare Intl
11 Sep
ORD5:30 p.m.Chicago O'Hare Intl
3h 49m
YYC8:19 p.m.Calgary
WestJet
17 Sep
YYC12:15 p.m.Calgary
3h 28m
ORD4:43 p.m.Chicago O'Hare Intl
19 Sep
ORD5:30 p.m.Chicago O'Hare Intl
3h 49m
YYC8:19 p.m.Calgary
WestJet
29 Aug
YYC12:15 p.m.Calgary
3h 29m
ORD4:44 p.m.Chicago O'Hare Intl
3 Sep
ORD5:30 p.m.Chicago O'Hare Intl
3h 49m
YYC8:19 p.m.Calgary

American Airlines flights from Canada to Chicago

Our best American Airlines deals on Canada to Chicago flight tickets
American Airlines
1 Sep
YYZ6:30 a.m.Toronto Pearson Intl
1h 56m
ORD7:26 a.m.Chicago O'Hare Intl
5 Sep
ORD3:05 p.m.Chicago O'Hare Intl
1h 42m
YYZ5:47 p.m.Toronto Pearson Intl
American Airlines
30 Aug
YYZ7:35 a.m.Toronto Pearson Intl
13h 36m
1 stop
ORD8:11 p.m.Chicago O'Hare Intl
5 Sep
ORD3:05 p.m.Chicago O'Hare Intl
1h 42m
YYZ5:47 p.m.Toronto Pearson Intl
American Airlines
11 Jul
YYZ7:25 p.m.Toronto Pearson Intl
5h 32m
1 stop
ORD11:57 p.m.Chicago O'Hare Intl
12 Jul
ORD8:24 p.m.Chicago O'Hare Intl
2h 05m
YYZ11:29 p.m.Toronto Pearson Intl

See travel insights to Chicago from

How to get the cheapest flight ticket from Canada to Chicago

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 Chicago?

The month of May is another great option to travel to Chicago, with average flight prices from Canada averaging around C$ 333.

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

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 680. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 1,259. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

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

In the evening is the cheapest time of day to fly from Canada to Chicago when you can find flight prices for as low as C$ 560. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,440 per ticket.

What is the cheapest Canada to Chicago flight route?

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

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

You are more likely to see cheaper flights to Chicago from Canada when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 403 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Canada for as low as C$ 335 on momondo.

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

There are 4 cabin classes available to choose from on Canada to Chicago 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 Canada to Chicago flights?

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

Cheap Canada to Chicago flight deals and tips

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

Best price found

C$ 120

Fastest flight time

1h 49m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Canada in the past 72 hours is C$ 120. The best round-trip flight deal from Canada to Chicago found on momondo in the last 72 hours is C$ 177.
The fastest flight from Canada to Chicago takes 1h 49m
Direct flights go from Canada to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

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

    Prices for flights from Canada to Chicago were last updated today.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Canada to Chicago.

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

    The necessary travel and health documents for your Chicago 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 Canada to Chicago?


Best airlines flying from Canada to Chicago

Compare and see reviews for airlines that fly from Canada to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom C$ 147Free CancellationRating
7.1
9,681 reviews
Search Air Canada flights
American AirlinesPriceFrom C$ 168Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
WestJetPriceFrom C$ 175Free CancellationRating
7.2
2,917 reviews
Search WestJet flights
DeltaPriceFrom C$ 183Free CancellationRating
8.0
7,982 reviews
Search Delta flights
Porter AirlinesPriceFrom C$ 230Free CancellationRating
8.0
298 reviews
Search Porter Airlines flights
United AirlinesPriceFrom C$ 239Free CancellationRating
7.4
8,861 reviews
Search United Airlines flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Hammond
Munster
Benton Harbor
Merrillville

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Canada to Chicago . Millions of users trust and use momondo every year so you are in good hands.

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

Yes. momondo enables you to select and highlight flights to Chicago from Canada with this policy.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Canada to Chicago.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Canada and alert you when they change.


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Tue 8/7
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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago