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Cheap flights from Canada to Chicago from $108

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 3/3. 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.
12:20 pm - 1:11 pmYYZ-ORD
1h 51mnonstop
4:00 pm - 6:41 pmORD-YYZ
1h 41mnonstop
$178Air Canada
Find Deal
Fri, Jan 10 - Mon, Jan 13
12:50 am - 9:55 amYYC-ORD
8h 05m1 stop
9:03 am - 4:52 pmORD-YYC
8h 49m1 stop
$196Air Canada
Find Deal
Mon, Mar 31 - Tue, Apr 8
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$219Porter Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
10:20 am - 11:10 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$223Porter Airlines
Find Deal
Fri, Dec 13 - Tue, Dec 17
2:00 pm - 2:51 pmYYZ-ORD
1h 51mnonstop
8:25 pm - 11:06 pmORD-YYZ
1h 41mnonstop
$245United Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
2:45 pm - 11:20 pmYYZ-ORD
9h 35m1 stop
7:19 am - 9:58 amORD-YYZ
1h 39mnonstop
$260United Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
6:30 am - 6:32 pmYYZ-MDW
13h 02m1 stop
9:38 am - 11:34 pmMDW-YYZ
12h 56m1 stop
$267WestJet
Find Deal
Thu, Dec 12 - Mon, Dec 16
6:00 am - 12:30 pmYYZ-ORD
7h 30m1 stop
5:09 pm - 10:55 pmORD-YYZ
4h 46m1 stop
$270American Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
6:30 am - 12:46 pmYYZ-MDW
7h 16m1 stop
11:19 am - 11:11 pmMDW-YYZ
10h 52m1 stop
$271WestJet
Find Deal
Tue, Jan 7 - Sat, Jan 11
7:30 am - 10:45 pmYUL-ORD
16h 15m1 stop
2:55 pm - 10:05 amORD-YUL
18h 10m1 stop
$281American Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
$108WestJet
Find Deal
Mon, Mar 3
12:15 pm - 4:44 pmYYC-ORD
3h 29mnonstop
$110WestJet
Find Deal
Thu, May 1
2:00 pm - 2:51 pmYYZ-ORD
1h 51mnonstop
$114Air Canada
Find Deal
Wed, Feb 12
8:30 am - 6:38 pmYYC-ORD
9h 08m1 stop
$118Air Canada
Find Deal
Sat, Jan 18
11:10 am - 12:00 pmYTZ-MDW
1h 50mnonstop
$133Porter Airlines
Find Deal
Sat, Dec 14
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
$136Porter Airlines
Find Deal
Thu, Dec 19
6:35 pm - 7:32 pmYYZ-ORD
1h 57mnonstop
$147United Airlines
Find Deal
Tue, Dec 17
12:20 pm - 6:36 pmYYZ-ORD
7h 16m1 stop
$152United Airlines
Find Deal
Fri, Dec 13
7:30 am - 12:20 pmYUL-ORD
5h 50m1 stop
$167American Airlines
Find Deal
Tue, Dec 10
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
$177American Airlines
Find Deal
Thu, Dec 5
12:41 pm - 5:09 pmYYC-ORD
3h 28mnonstop
8:45 am - 11:39 amORD-YYC
3h 54mnonstop
$313United Airlines
Find Deal
Thu, Nov 21 - Fri, Nov 29
2:09 pm - 11:57 pmYYC-ORD
8h 48m1 stop
8:45 am - 11:39 amORD-YYC
3h 54mnonstop
$318United Airlines
Find Deal
Thu, Nov 21 - Fri, Nov 29
8:30 am - 6:36 pmYYC-ORD
9h 06m1 stop
7:28 am - 8:44 pmORD-YYC
14h 16m1 stop
$354Air Canada
Find Deal
Thu, Nov 21 - Sun, Nov 24
6:00 am - 6:32 pmYUL-MDW
13h 32m1 stop
2:17 pm - 11:33 pmMDW-YUL
8h 16m1 stop
$406WestJet
Find Deal
Sun, Nov 24 - Wed, Nov 27
6:20 pm - 7:55 pmYUL-ORD
2h 35mnonstop
2:00 pm - 9:48 pmORD-YUL
6h 48m1 stop
$408Air Canada
Find Deal
Mon, Nov 25 - Wed, Dec 4
11:50 am - 4:40 pmYUL-MDW
5h 50m1 stop
12:05 pm - 7:20 pmMDW-YUL
6h 15m1 stop
$430Porter Airlines
Find Deal
Mon, Nov 25 - Mon, Dec 2
2:55 pm - 6:32 pmYYZ-MDW
4h 37m1 stop
9:30 am - 11:50 pmMDW-YYZ
13h 20m1 stop
$436WestJet
Find Deal
Mon, Nov 25 - Sat, Nov 30
11:10 am - 12:00 pmYTZ-MDW
1h 50mnonstop
12:55 pm - 3:37 pmMDW-YTZ
1h 42mnonstop
$438Porter Airlines
Find Deal
Sat, Nov 23 - Sat, Nov 30
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
8:11 am - 10:51 amORD-YYZ
1h 40mnonstop
$443American Airlines
Find Deal
Sat, Nov 23 - Sat, Nov 30
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
5:00 am - 11:00 amORD-YYZ
5h 00m1 stop
$453American Airlines
Find Deal
Sat, Nov 23 - Sat, Nov 30
11:30 am - 3:56 pmYYC-ORD
3h 26mnonstop
5:30 pm - 8:19 pmORD-YYC
3h 49mnonstop
$170WestJet
Find Deal
Mon, Apr 21 - Mon, Apr 28
12:20 pm - 1:11 pmYYZ-ORD
1h 51mnonstop
4:00 pm - 6:41 pmORD-YYZ
1h 41mnonstop
$178Air Canada
Find Deal
Fri, Jan 10 - Mon, Jan 13
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$219Porter Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
10:20 am - 11:10 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$223Porter Airlines
Find Deal
Fri, Dec 13 - Tue, Dec 17
2:00 pm - 2:51 pmYYZ-ORD
1h 51mnonstop
8:25 pm - 11:06 pmORD-YYZ
1h 41mnonstop
$245United Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$262Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
9:00 am - 10:05 amYYZ-ORD
2h 05mnonstop
7:19 am - 9:58 amORD-YYZ
1h 39mnonstop
$269United Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$271Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
1:20 pm - 5:45 pmYYC-ORD
3h 25mnonstop
9:45 am - 12:30 pmORD-YYC
3h 45mnonstop
$379American Airlines
Find Deal
Wed, Apr 30 - Mon, May 5
6:15 am - 7:30 amYYZ-ORD
2h 15mnonstop
1:25 pm - 4:00 pmORD-YYZ
1h 35mnonstop
$455American Airlines
Find Deal
Sun, Dec 1 - Wed, Dec 4

Air Canada flights from Canada to Chicago

Our best Air Canada deals on Canada to Chicago flight tickets
Air Canada
Jan 10
YYZ12:20 pmToronto Pearson Intl
1h 51m
ORD1:11 pmChicago O'Hare Intl
Jan 13
ORD4:00 pmChicago O'Hare Intl
1h 41m
YYZ6:41 pmToronto Pearson Intl
Air Canada
Mar 31
YYC12:50 amCalgary
8h 05m
1 stop
ORD9:55 amChicago O'Hare Intl
Apr 8
ORD9:03 amChicago O'Hare Intl
8h 49m
1 stop
YYC4:52 pmCalgary
Air Canada
Jan 9
YYC8:30 amCalgary
9h 08m
1 stop
ORD6:38 pmChicago O'Hare Intl
Jan 18
ORD2:05 pmChicago O'Hare Intl
8h 13m
1 stop
YYC9:18 pmCalgary

American Airlines flights from Canada to Chicago

Our best American Airlines deals on Canada to Chicago flight tickets
American Airlines
Dec 12
YYZ6:00 amToronto Pearson Intl
7h 30m
1 stop
ORD12:30 pmChicago O'Hare Intl
Dec 16
ORD5:09 pmChicago O'Hare Intl
4h 46m
1 stop
YYZ10:55 pmToronto Pearson Intl
American Airlines
Dec 12
YUL7:30 amMontreal Pierre Elliott Trudeau Intl
16h 15m
1 stop
ORD10:45 pmChicago O'Hare Intl
Dec 16
ORD2:55 pmChicago O'Hare Intl
18h 10m
1 stop
YUL10:05 amMontreal Pierre Elliott Trudeau Intl
American Airlines
Dec 3
YYZ6:15 amToronto Pearson Intl
2h 15m
ORD7:30 amChicago O'Hare Intl
Dec 4
ORD8:11 amChicago O'Hare Intl
1h 40m
YYZ10:51 amToronto 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 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

$108

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 $108. The best round-trip flight deal from Canada to Chicago found on momondo in the last 72 hours is $178.
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?

    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 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
United AirlinesPriceFrom $112Free CancellationRating
7.4
9,172 reviews
Search United Airlines flights
Air CanadaPriceFrom $157Free CancellationRating
7.0
8,238 reviews
Search Air Canada flights
American AirlinesPriceFrom $166Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
WestJetPriceFrom $186Free CancellationRating
7.3
2,810 reviews
Search WestJet flights
Porter AirlinesPriceFrom $205Free CancellationRating
7.8
286 reviews
Search Porter Airlines flights
DeltaPriceFrom $370Free CancellationRating
8.0
8,758 reviews
Search Delta flights

Why use momondo?

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

Finding the right flight to Chicago from Canada is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Yes. All flights to Chicago from Canada on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo helps you find the best flight between Canada and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes. momondo can track prices for Canada to Chicago 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.


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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 78.5 mi from Chicago