Which airlines fly to Chicago?

Air Canada, United Airlines and WestJet are the top three most popular airlines that fly to Chicago from Canada according to our data. Air Canada is the first choice among our users, with 56% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from Canada to Chicago on average per day?

The number of flights available between Canada and Chicago is 61 per day as of October 2025. The most frequent departure time is 6:00a.m., with 52% of daily flights leaving in the afternoon.

How long does it take to fly to Chicago?

Flight times from Canada to Chicago vary, but if you’re flying out of Montreal and flying into Chicago O'Hare Intl Airport (one of the most popular routes), then the duration is 2h 32m on average. Another popular route from Canada to Chicago is flying from Toronto to Chicago O'Hare Intl Airport, which will take roughly 2h 56m. Keep in mind that layovers or delays could extend your travel time.

What is the cheapest airline that flies from Canada to Chicago?

WestJet, United Airlines, and Air Canada are the most popular carriers operating from Canada to Chicago

How many flights depart from Canada to Chicago on average per week?

432 flights are operational weekly from Canada to Chicago as of October 2025. The most popular departure day for this route is Thu, with 28% of flights per week taking off on this day.

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?

The number of operators available for flights from Canada to Chicago is 6 as of October 2025.

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.

C$ 139 Cheap Flights from Canada to Chicago in 2025/26

1 adult

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Find the cheapest flights from Canada to Chicago

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One-way

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Recent round-trip flight deals from Canada to Chicago

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9:00 a.m. - 1:35 p.m.YYC-ORD

3h 35mdirect

2:20 p.m. - 5:15 p.m.ORD-YYC

3h 55mdirect

C$ 242WestJet

Find Deal

Fri, 30 Jan - Mon, 2 Mar

7:00 a.m. - 11:18 a.m.YYZ-ORD

5h 18m1 stop

8:15 p.m. - 10:54 p.m.ORD-YYZ

1h 39mdirect

C$ 252Air Canada

Find Deal

Fri, 14 Nov - Mon, 17 Nov

4:07 p.m. - 10:56 p.m.YYZ-ORD

7h 49m1 stop

8:29 a.m. - 5:27 p.m.ORD-YYZ

7h 58m1 stop

C$ 256American Airlines

Find Deal

Wed, 26 Nov - Wed, 3 Dec

9:15 a.m. - 10:05 a.m.YTZ-MDW

1h 50mdirect

11:00 a.m. - 1:42 p.m.MDW-YTZ

1h 42mdirect

C$ 258Porter Airlines

Find Deal

Sun, 23 Nov - Mon, 8 Dec

8:55 a.m. - 10:02 a.m.YYZ-ORD

2h 07mdirect

6:28 p.m. - 9:21 p.m.ORD-YYZ

1h 53mdirect

C$ 258United Airlines

Find Deal

Fri, 13 Feb - Sat, 21 Feb

9:15 a.m. - 10:05 a.m.YTZ-MDW

1h 50mdirect

11:00 a.m. - 1:42 p.m.MDW-YTZ

1h 42mdirect

C$ 261Porter Airlines

Find Deal

Mon, 24 Nov - Mon, 8 Dec

6:00 a.m. - 7:15 a.m.YYZ-ORD

2h 15mdirect

9:39 a.m. - 12:30 p.m.ORD-YYZ

1h 51mdirect

C$ 263American Airlines

Find Deal

Thu, 4 Dec - Sun, 7 Dec

5:30 p.m. - 6:39 p.m.YYZ-ORD

2h 09mdirect

7:10 a.m. - 9:58 a.m.ORD-YYZ

1h 48mdirect

C$ 281United Airlines

Find Deal

Wed, 26 Nov - Sun, 30 Nov

2:30 p.m. - 3:20 p.m.YTZ-MDW

1h 50mdirect

11:00 a.m. - 1:42 p.m.MDW-YTZ

1h 42mdirect

C$ 281Air Transat

Find Deal

Mon, 17 Nov - Wed, 19 Nov

2:30 p.m. - 3:20 p.m.YTZ-MDW

1h 50mdirect

12:45 p.m. - 3:27 p.m.MDW-YTZ

1h 42mdirect

C$ 291Air Transat

Find Deal

Thu, 19 Mar - Sat, 21 Mar

WestJet flights from Canada to Chicago

Our best WestJet deals on Canada to Chicago flight tickets

WestJet

30 Jan

YYC9:00 a.m.Calgary

3h 35m

ORD1:35 p.m.Chicago O'Hare Intl

2 Mar

ORD2:20 p.m.Chicago O'Hare Intl

3h 55m

YYC5:15 p.m.Calgary

C$ 242

Find similar

WestJet

18 Dec

YYZ6:30 a.m.Toronto Pearson Intl

7h 40m

1 stop

MDW1:10 p.m.Chicago Midway

19 Dec

MDW9:59 a.m.Chicago Midway

5h 16m

1 stop

YYZ4:15 p.m.Toronto Pearson Intl

C$ 369

Find similar

WestJet

13 Nov

YYZ6:30 a.m.Toronto Pearson Intl

12h 48m

1 stop

MDW6:18 p.m.Chicago Midway

6 Dec

MDW11:05 a.m.Chicago Midway

4h 57m

1 stop

YYZ5:02 p.m.Toronto Pearson Intl

C$ 468

Find similar

Air Canada flights from Canada to Chicago

Our best Air Canada deals on Canada to Chicago flight tickets

Air Canada

14 Nov

YYZ7:00 a.m.Toronto Pearson Intl

5h 18m

1 stop

ORD11:18 a.m.Chicago O'Hare Intl

17 Nov

ORD8:15 p.m.Chicago O'Hare Intl

1h 39m

YYZ10:54 p.m.Toronto Pearson Intl

C$ 252

Find similar

Air Canada

16 Jan

YYZ12:05 p.m.Toronto Pearson Intl

1h 56m

ORD1:01 p.m.Chicago O'Hare Intl

19 Jan

ORD3:35 p.m.Chicago O'Hare Intl

6h 29m

1 stop

YYZ11:04 p.m.Toronto Pearson Intl

C$ 255

Find similar

Air Canada

27 Nov

YYZ7:00 a.m.Toronto Pearson Intl

5h 18m

1 stop

ORD11:18 a.m.Chicago O'Hare Intl

1 Dec

ORD3:55 p.m.Chicago O'Hare Intl

1h 39m

YYZ6:34 p.m.Toronto Pearson Intl

C$ 272

Find similar

Fly from

Fly to

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 30/1

9:00 a.m.-1:35 p.m.

Nonstop3h 35m

Chicago O'Hare Intl

Mon 2/3

2:20 p.m.-5:15 p.m.

Nonstop3h 55m

C$ 242

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 14/11

7:00 a.m.-11:18 a.m.

1 stop5h 18m

Chicago O'Hare Intl

Mon 17/11

8:15 p.m.-10:54 p.m.

Nonstop1h 39m

C$ 252

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 26/11

4:07 p.m.-10:56 p.m.

1 stop7h 49m

Chicago O'Hare Intl

Wed 3/12

8:29 a.m.-5:27 p.m.

1 stop7h 58m

C$ 256

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 23/11

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Mon 8/12

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 258

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 13/2

8:55 a.m.-10:02 a.m.

Nonstop2h 07m

Chicago O'Hare Intl

Sat 21/2

6:28 p.m.-9:21 p.m.

Nonstop1h 53m

C$ 258

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 24/11

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

Mon 8/12

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 261

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 4/12

6:00 a.m.-7:15 a.m.

Nonstop2h 15m

Chicago O'Hare Intl

Sun 7/12

9:39 a.m.-12:30 p.m.

Nonstop1h 51m

C$ 263

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 26/11

5:30 p.m.-6:39 p.m.

Nonstop2h 09m

Chicago O'Hare Intl

Sun 30/11

7:10 a.m.-9:58 a.m.

Nonstop1h 48m

C$ 281

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 17/11

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Wed 19/11

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 281

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 19/3

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Sat 21/3

12:45 p.m.-3:27 p.m.

Nonstop1h 42m

C$ 291

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

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$ 313.

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$ 629. 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$ 1,078. 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$ 634. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,074 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$ 408 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$ 272 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?

You could potentially save up to 2% on your flight if you consider stops on a Canada to Chicago flight.

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$ 196
Fastest flight time	1h 50m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Canada in the past 72 hours is C$ 196. The best round-trip flight deal from Canada to Chicago found on momondo in the last 72 hours is C$ 347.

The fastest flight from Canada to Chicago takes 1h 50m

Direct flights go from Canada to Chicago every day.

There is 1 airport near Chicago: 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?
The number of operators available for flights from Canada to Chicago is 6 as of October 2025.
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?
Based on momondo bookings for flights between Canada and Chicago, the leading plane model is Embraer 175 (Enhanced Winglets), making up 16.09% of the total bookings. Other popular models include De Havilland (Bombardier) DHC-8-400 Dash 8Q with 12.19%, Boeing 737 MAX 8 with 10.16%, and Boeing 737-800 with 10.04%.

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 Canada	PriceFrom C$ 151	Free Cancellation	Rating 7.1 10,377 reviews	Search Air Canada flights
WestJet	PriceFrom C$ 178	Free Cancellation	Rating 7.2 3,149 reviews	Search WestJet flights
American Airlines	PriceFrom C$ 179	Free Cancellation	Rating 7.2 11,030 reviews	Search American Airlines flights
Delta	PriceFrom C$ 186	Free Cancellation	Rating 7.9 7,993 reviews	Search Delta flights
Porter Airlines	PriceFrom C$ 197	Free Cancellation	Rating 8.0 384 reviews	Search Porter Airlines flights
United Airlines	PriceFrom C$ 207	Free Cancellation	Rating 7.4 8,998 reviews	Search United Airlines flights

Munster

Hammond

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.

An easier way to manage your Chicago trip

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

Chicago Midway Airport

Chicago O'Hare Intl Airport

Popular Cities in the United States

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Cheap flights from Canada to Chicago from C$ 139

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 24/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Canada to Chicago

Recent round-trip flight deals from Canada to Chicago

Recent one-way flight deals from Canada to Chicago

Recent last minute flight deals from Canada to Chicago

Recent direct flight deals from Canada to Chicago

WestJet flights from Canada to Chicago

Our best WestJet deals on Canada to Chicago flight tickets

Air Canada flights from Canada to Chicago

Our best Air Canada deals on Canada to Chicago flight tickets

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Use the filters below to find and compare flights from Canada to Chicago that are best for you.

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$ 313.

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

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

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?

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?

You could potentially save up to 2% on your flight if you consider stops on a Canada to Chicago flight.

What is the cheapest airline that flies from Canada to Chicago?

WestJet, United Airlines, and Air Canada are the most popular carriers operating from Canada to Chicago

Which airlines fly to Chicago?

How many flights depart from Canada to Chicago on average per day?

The number of flights available between Canada and Chicago is 61 per day as of October 2025. The most frequent departure time is 6:00a.m., with 52% of daily flights leaving in the afternoon.

How many flights depart from Canada to Chicago on average per week?

432 flights are operational weekly from Canada to Chicago as of October 2025. The most popular departure day for this route is Thu, with 28% of flights per week taking off on this day.

How long does it take to fly 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

Fastest flight time

Direct flights

Airports in Chicago

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

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?

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

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

Travelling to a place near Chicago?

Why use momondo?

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

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

How can momondo help me find flights 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?

An easier way to manage your Chicago trip

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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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