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Cheap flights from Canada to Chicago from C$ 148

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 7/4. 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 Canada to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Canada to Chicago 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 Canada to Chicago.

Cheap last-minute flights

Planning a quick getaway from Canada to Chicago? 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 Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
4:45 p.m. - 7:36 p.m.ORD-YYC
3h 51mdirect
C$ 235WestJet
Find Deal
Thu, 20 Feb - Mon, 24 Feb
12:20 p.m. - 1:11 p.m.YYZ-ORD
1h 51mdirect
4:00 p.m. - 6:41 p.m.ORD-YYZ
1h 41mdirect
C$ 249Air Canada
Find Deal
Fri, 10 Jan - Mon, 13 Jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 307Porter Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
7:00 a.m. - 2:39 p.m.YYC-ORD
6h 39m1 stop
12:35 p.m. - 11:16 p.m.ORD-YYC
11h 41m2 stops
C$ 307Delta
Find Deal
Sat, 7 Dec - Tue, 10 Dec
7:00 a.m. - 4:58 p.m.YYC-ORD
8h 58m1 stop
12:35 p.m. - 11:16 p.m.ORD-YYC
11h 41m2 stops
C$ 309Delta
Find Deal
Sat, 7 Dec - Tue, 10 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 312Porter Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
11:00 a.m. - 11:59 a.m.YYZ-ORD
1h 59mdirect
7:19 a.m. - 9:58 a.m.ORD-YYZ
1h 39mdirect
C$ 343United Airlines
Find Deal
Wed, 11 Dec - Thu, 12 Dec
2:45 p.m. - 11:20 p.m.YYZ-ORD
9h 35m1 stop
7:19 a.m. - 9:58 a.m.ORD-YYZ
1h 39mdirect
C$ 364United Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
12:57 p.m. - 10:45 p.m.YUL-ORD
10h 48m1 stop
7:00 a.m. - 1:44 p.m.ORD-YUL
5h 44m1 stop
C$ 385American Airlines
Find Deal
Fri, 13 Dec - Sun, 15 Dec
5:30 p.m. - 7:46 a.m.YUL-ORD
15h 16m1 stop
4:21 p.m. - 10:57 p.m.ORD-YUL
5h 36m1 stop
C$ 388American Airlines
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Thu, 12 Dec - Mon, 16 Dec
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
C$ 148WestJet
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Mon, 7 Apr
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
C$ 151WestJet
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Mon, 3 Mar
2:00 p.m. - 2:51 p.m.YYZ-ORD
1h 51mdirect
C$ 160Air Canada
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Wed, 12 Feb
8:30 a.m. - 6:36 p.m.YYC-ORD
9h 06m1 stop
C$ 164Air Canada
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Sat, 7 Dec
6:19 a.m. - 11:59 p.m.YYC-ORD
16h 40m1 stop
C$ 179United Airlines
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Tue, 21 Jan
1:32 p.m. - 6:03 p.m.YYC-ORD
3h 31mdirect
C$ 186American Airlines
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Wed, 19 Feb
10:20 a.m. - 11:10 a.m.YTZ-MDW
1h 50mdirect
C$ 189Porter Airlines
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Mon, 16 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
C$ 190Porter Airlines
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Thu, 19 Dec
12:20 p.m. - 1:11 p.m.YYZ-ORD
1h 51mdirect
C$ 206United Airlines
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Sat, 14 Dec
6:15 a.m. - 7:30 a.m.YYZ-ORD
2h 15mdirect
C$ 221American Airlines
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Sat, 18 Jan
12:50 a.m. - 10:05 a.m.YYC-ORD
8h 15m1 stop
2:05 p.m. - 9:18 p.m.ORD-YYC
8h 13m1 stop
C$ 315Air Canada
Find Deal
Mon, 25 Nov - Sat, 30 Nov
8:30 a.m. - 6:36 p.m.YYC-ORD
9h 06m1 stop
2:05 p.m. - 9:18 p.m.ORD-YYC
8h 13m1 stop
C$ 330Air Canada
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Sat, 23 Nov - Sat, 30 Nov
12:41 p.m. - 5:09 p.m.YYC-ORD
3h 28mdirect
8:45 a.m. - 11:39 a.m.ORD-YYC
3h 54mdirect
C$ 438United Airlines
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Thu, 21 Nov - Fri, 29 Nov
2:09 p.m. - 11:57 p.m.YYC-ORD
8h 48m1 stop
8:45 a.m. - 11:39 a.m.ORD-YYC
3h 54mdirect
C$ 445United Airlines
Find Deal
Thu, 21 Nov - Fri, 29 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 538Porter Airlines
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Fri, 22 Nov - Tue, 3 Dec
1:10 p.m. - 2:10 p.m.YYZ-ORD
2h 00mdirect
1:25 p.m. - 4:00 p.m.ORD-YYZ
1h 35mdirect
C$ 545American Airlines
Find Deal
Fri, 22 Nov - Tue, 3 Dec
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 550Porter Airlines
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Sun, 24 Nov - Tue, 3 Dec
6:20 p.m. - 7:20 p.m.YYZ-ORD
2h 00mdirect
5:00 a.m. - 11:00 a.m.ORD-YYZ
5h 00m1 stop
C$ 557American Airlines
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Fri, 22 Nov - Tue, 3 Dec
6:00 a.m. - 6:32 p.m.YUL-MDW
13h 32m1 stop
2:17 p.m. - 11:33 p.m.MDW-YUL
8h 16m1 stop
C$ 568WestJet
Find Deal
Sun, 24 Nov - Wed, 27 Nov
10:05 a.m. - 12:50 p.m.YYZ-ORD
3h 45m1 stop
5:55 p.m. - 11:24 a.m.ORD-YYZ
16h 29m1 stop
C$ 616WestJet
Find Deal
Mon, 25 Nov - Mon, 2 Dec
11:30 a.m. - 3:56 p.m.YYC-ORD
3h 26mdirect
4:45 p.m. - 7:36 p.m.ORD-YYC
3h 51mdirect
C$ 235WestJet
Find Deal
Thu, 20 Feb - Mon, 24 Feb
12:20 p.m. - 1:11 p.m.YYZ-ORD
1h 51mdirect
4:00 p.m. - 6:41 p.m.ORD-YYZ
1h 41mdirect
C$ 249Air Canada
Find Deal
Fri, 10 Jan - Mon, 13 Jan
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 307Porter Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 312Porter Airlines
Find Deal
Thu, 12 Dec - Sun, 15 Dec
11:00 a.m. - 11:59 a.m.YYZ-ORD
1h 59mdirect
7:19 a.m. - 9:58 a.m.ORD-YYZ
1h 39mdirect
C$ 343United Airlines
Find Deal
Wed, 11 Dec - Thu, 12 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 364Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 Dec
9:40 a.m. - 10:30 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 365Air Transat
Find Deal
Thu, 12 Dec - Sun, 15 Dec
12:20 p.m. - 1:11 p.m.YYZ-ORD
1h 51mdirect
7:19 a.m. - 9:58 a.m.ORD-YYZ
1h 39mdirect
C$ 375United Airlines
Find Deal
Wed, 11 Dec - Thu, 12 Dec
1:20 p.m. - 5:45 p.m.YYC-ORD
3h 25mdirect
9:45 a.m. - 12:30 p.m.ORD-YYC
3h 45mdirect
C$ 531American Airlines
Find Deal
Wed, 30 Apr - Mon, 5 May
6:15 a.m. - 7:30 a.m.YYZ-ORD
2h 15mdirect
6:30 p.m. - 9:20 p.m.ORD-YYZ
1h 50mdirect
C$ 581American Airlines
Find Deal
Sat, 30 Nov - Sat, 7 Dec

Delta flights from Canada to Chicago

Our best Delta deals on Canada to Chicago flight tickets
Delta
7 Dec
YYC7:00 a.m.Calgary
6h 39m
1 stop
ORD2:39 p.m.Chicago O'Hare Intl
10 Dec
ORD12:35 p.m.Chicago O'Hare Intl
11h 41m
2 stops
YYC11:16 p.m.Calgary
Delta
7 Dec
YYC7:00 a.m.Calgary
8h 58m
1 stop
ORD4:58 p.m.Chicago O'Hare Intl
10 Dec
ORD12:35 p.m.Chicago O'Hare Intl
11h 41m
2 stops
YYC11:16 p.m.Calgary
Delta
9 Jan
YYC6:35 a.m.Calgary
13h 18m
2 stops
ORD8:53 p.m.Chicago O'Hare Intl
12 Jan
ORD6:55 a.m.Chicago O'Hare Intl
14h 58m
2 stops
YYC8:53 p.m.Calgary

American Airlines flights from Canada to Chicago

Our best American Airlines deals on Canada to Chicago flight tickets
American Airlines
13 Dec
YUL12:57 p.m.Montreal Pierre Elliott Trudeau Intl
10h 48m
1 stop
ORD10:45 p.m.Chicago O'Hare Intl
15 Dec
ORD7:00 a.m.Chicago O'Hare Intl
5h 44m
1 stop
YUL1:44 p.m.Montreal Pierre Elliott Trudeau Intl
American Airlines
12 Dec
YUL5:30 p.m.Montreal Pierre Elliott Trudeau Intl
15h 16m
1 stop
ORD7:46 a.m.Chicago O'Hare Intl
16 Dec
ORD4:21 p.m.Chicago O'Hare Intl
5h 36m
1 stop
YUL10:57 p.m.Montreal Pierre Elliott Trudeau Intl
American Airlines
12 Dec
YUL5:30 p.m.Montreal Pierre Elliott Trudeau Intl
15h 16m
1 stop
ORD7:46 a.m.Chicago O'Hare Intl
15 Dec
ORD7:00 a.m.Chicago O'Hare Intl
5h 44m
1 stop
YUL1:44 p.m.Montreal Pierre Elliott Trudeau 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 Canada to Chicago flight route?

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

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$ 148

Fastest flight time

1h 50m

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$ 148. The best round-trip flight deal from Canada to Chicago found on momondo in the last 72 hours is C$ 235.
The fastest flight from Canada to Chicago takes 1h 50m
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
American AirlinesPriceFrom C$ 198Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
WestJetPriceFrom C$ 234Free CancellationRating
7.3
2,811 reviews
Search WestJet flights
Porter AirlinesPriceFrom C$ 271Free CancellationRating
7.8
288 reviews
Search Porter Airlines flights
Air CanadaPriceFrom C$ 284Free CancellationRating
7.0
8,237 reviews
Search Air Canada flights
DeltaPriceFrom C$ 310Free CancellationRating
8.0
8,756 reviews
Search Delta flights
United AirlinesPriceFrom C$ 322Free CancellationRating
7.4
9,171 reviews
Search United Airlines flights
Alaska AirlinesPriceFrom C$ 364Free CancellationRating
8.0
9,461 reviews
Search Alaska Airlines flights
WestJet EncorePriceFrom C$ 564Free CancellationRating
8.6
10 reviews
Search WestJet Encore flights

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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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago