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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 29/9. 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

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$ 175WestJet
Find Deal
Fri, 17 Oct - Sun, 19 Oct
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$ 179WestJet
Find Deal
Mon, 29 Sep - Mon, 6 Oct
Air Canada Logo
8:45 a.m. - 3:00 p.m.YVR-ORD
4h 15mdirect
Air Canada Logo
3:45 p.m. - 6:15 p.m.ORD-YVR
4h 30mdirect
C$ 200Air Canada
Find Deal
Fri, 5 Sep - Sun, 14 Sep
Air Canada Logo
8:45 a.m. - 3:00 p.m.YVR-ORD
4h 15mdirect
Air Canada Logo
3:45 p.m. - 6:15 p.m.ORD-YVR
4h 30mdirect
C$ 201Air Canada
Find Deal
Fri, 5 Sep - Sun, 14 Sep
United Airlines Logo
9:00 p.m. - 10:05 p.m.YYZ-ORD
2h 05mdirect
United Airlines Logo
9:20 p.m. - 11:59 p.m.ORD-YYZ
1h 39mdirect
C$ 204United Airlines
Find Deal
Fri, 7 Nov - Mon, 10 Nov
United Airlines Logo
8:55 a.m. - 10:00 a.m.YYZ-ORD
2h 05mdirect
United Airlines Logo
1:19 p.m. - 4:02 p.m.ORD-YYZ
1h 43mdirect
C$ 208United Airlines
Find Deal
Sat, 1 Nov - Sat, 8 Nov
American Airlines Logo
6:29 a.m. - 10:54 a.m.YYC-ORD
3h 25mdirect
American Airlines Logo
9:45 p.m. - 11:59 a.m.ORD-YYC
15h 14m1 stop
C$ 229American Airlines
Find Deal
Tue, 30 Sep - Tue, 21 Oct
American Airlines Logo
3:52 p.m. - 5:52 p.m.YUL-ORD
3h 00mdirect
American Airlines Logo
4:05 p.m. - 10:39 p.m.ORD-YUL
5h 34m1 stop
C$ 238American Airlines
Find Deal
Mon, 10 Nov - Mon, 17 Nov
Porter Airlines Logo
3:35 p.m. - 4:24 p.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 240Porter Airlines
Find Deal
Fri, 5 Sep - Mon, 8 Sep
Porter Airlines Logo
3:35 p.m. - 4:24 p.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 241Porter Airlines
Find Deal
Fri, 26 Sep - Fri, 3 Oct

United Airlines flights from Canada to Chicago

Our best United Airlines deals on Canada to Chicago flight tickets
United Airlines
7 Nov
YYZ9:00 p.m.Toronto Pearson Intl
2h 05m
ORD10:05 p.m.Chicago O'Hare Intl
10 Nov
ORD9:20 p.m.Chicago O'Hare Intl
1h 39m
YYZ11:59 p.m.Toronto Pearson Intl
C$ 204
Find similar
United Airlines
1 Nov
YYZ8:55 a.m.Toronto Pearson Intl
2h 05m
ORD10:00 a.m.Chicago O'Hare Intl
8 Nov
ORD1:19 p.m.Chicago O'Hare Intl
1h 43m
YYZ4:02 p.m.Toronto Pearson Intl
C$ 208
Find similar
United Airlines
24 Sep
YYC6:15 a.m.Calgary
15h 27m
1 stop
ORD10:42 p.m.Chicago O'Hare Intl
7 Oct
ORD8:47 a.m.Chicago O'Hare Intl
3h 51m
YYC11:38 a.m.Calgary
C$ 216
Find similar

Air Canada flights from Canada to Chicago

Our best Air Canada deals on Canada to Chicago flight tickets
Air Canada
5 Sep
YVR8:45 a.m.Vancouver Intl
4h 15m
ORD3:00 p.m.Chicago O'Hare Intl
14 Sep
ORD3:45 p.m.Chicago O'Hare Intl
4h 30m
YVR6:15 p.m.Vancouver Intl
C$ 200
Find similar
Air Canada
5 Sep
YVR8:45 a.m.Vancouver Intl
4h 15m
ORD3:00 p.m.Chicago O'Hare Intl
14 Sep
ORD3:45 p.m.Chicago O'Hare Intl
4h 30m
YVR6:15 p.m.Vancouver Intl
C$ 201
Find similar
Air Canada
6 Nov
YYZ2:15 p.m.Toronto Pearson Intl
1h 55m
ORD3:10 p.m.Chicago O'Hare Intl
10 Nov
ORD3:55 p.m.Chicago O'Hare Intl
1h 39m
YYZ6:34 p.m.Toronto Pearson Intl
C$ 202
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Canada to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 14 August 2025.
Use the filters below to find and compare flights from Canada to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 17/10

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

Chicago O'Hare Intl

Sun 19/10

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

C$ 175

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 29/9

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

Chicago O'Hare Intl

Mon 6/10

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

C$ 179

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 5/9

8:45 a.m.-3:00 p.m.

Nonstop4h 15m

Chicago O'Hare Intl

Sun 14/9

3:45 p.m.-6:15 p.m.

Nonstop4h 30m

C$ 200

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 5/9

8:45 a.m.-3:00 p.m.

Nonstop4h 15m

Chicago O'Hare Intl

Sun 14/9

3:45 p.m.-6:15 p.m.

Nonstop4h 30m

C$ 201

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 7/11

9:00 p.m.-10:05 p.m.

Nonstop2h 05m

Chicago O'Hare Intl

Mon 10/11

9:20 p.m.-11:59 p.m.

Nonstop1h 39m

C$ 204

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 1/11

8:55 a.m.-10:00 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Sat 8/11

1:19 p.m.-4:02 p.m.

Nonstop1h 43m

C$ 208

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 30/9

6:29 a.m.-10:54 a.m.

Nonstop3h 25m

Chicago O'Hare Intl

Tue 21/10

9:45 p.m.-11:59 a.m.

1 stop15h 14m

C$ 229

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Mon 10/11

3:52 p.m.-5:52 p.m.

Nonstop3h 00m

Chicago O'Hare Intl

Mon 17/11

4:05 p.m.-10:39 p.m.

1 stop5h 34m

C$ 238

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 5/9

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Mon 8/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 26/9

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Fri 3/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 241

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 June is another great option to travel to Chicago, with average flight prices from Canada averaging around C$ 308.

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$ 678. 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$ 1,211. 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$ 604. 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$ 1,374 per ticket.

What is the cheapest Canada to Chicago flight route?

Fly from Toronto Island to Chicago Midway 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$ 406 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$ 329 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$ 175.
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)
Search flight deals

  • 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$ 149Free CancellationRating
7.1
9,949 reviews
Search Air Canada flights
WestJetPriceFrom C$ 177Free CancellationRating
7.2
3,013 reviews
Search WestJet flights
DeltaPriceFrom C$ 183Free CancellationRating
8.0
7,980 reviews
Search Delta flights
American AirlinesPriceFrom C$ 185Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Porter AirlinesPriceFrom C$ 201Free CancellationRating
8.0
332 reviews
Search Porter Airlines flights
United AirlinesPriceFrom C$ 241Free CancellationRating
7.4
8,916 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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We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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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
Chicago Midway Airport
Chicago O'Hare Intl Airport