How long does it take to fly to Chicago?

Flight times from Canada to Chicago vary, but if you’re flying out of Toronto and flying into Chicago O'Hare Intl Airport (one of the most popular routes), then the duration is 1h 55m on average. Another popular route from Canada to Chicago is flying from Montreal to Chicago O'Hare Intl Airport, which will take roughly 2h 35m. Keep in mind that layovers or delays could extend your travel time.

What is the most punctual flight time for Canada to Chicago flights?

Generally, flights departing at night tend to experience fewer delays. Flights departing in the evening have, in the past, seen delays more frequently in comparison.

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

The number of flights available between Canada and Chicago is 76 per day as of December 2025. The most frequent departure time is 6:00a.m., with 47% of daily flights leaving at noon.

Which airline has the best punctuality record on Canada to Chicago flights?

According to our data, United Airlines has had the least delays on this route over the last 12 months, with about 6% of their flights experiencing any sort of delay.

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

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

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 54% 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 often are flights from Canada to Chicago delayed?

Historically, on average around 11% of flights between Canada and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 139 minutes.

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

534 flights are operational weekly from Canada to Chicago as of December 2025. The most popular departure day for this route is Mon, with 18% of flights per week taking off on this day.

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week that experiences the fewest delays on this flight route. Saturday has historically seen more delays on average compared to the rest of the week.

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 December 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$ 123 Cheap Flights from Canada to Chicago in 2025/26

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Find the cheapest flights from Canada to Chicago

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Canada to Chicago

Enter your travel dates to find the best prices.

5:35 a.m. - 3:10 p.m.

YYC

ORD

8h 35m1 stop

3:55 p.m. - 12:14 a.m.

ORD

YYC

9h 19m1 stop

C$ 213Air Canada

Wed, 28 Jan - Wed, 4 Feb

5:35 a.m. - 3:10 p.m.

YYC

ORD

8h 35m1 stop

3:55 p.m. - 12:14 a.m.

ORD

YYC

9h 19m1 stop

C$ 219Air Canada

Thu, 15 Jan - Wed, 21 Jan

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$ 246Porter Airlines

Fri, 20 Feb - Mon, 23 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$ 248Porter Airlines

Sun, 18 Jan - Wed, 21 Jan

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$ 249WestJet

Fri, 16 Jan - Mon, 19 Jan

5:30 p.m. - 6:50 p.m.

YYZ

ORD

2h 20mdirect

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

ORD

YYZ

1h 48mdirect

C$ 256United Airlines

Thu, 5 Feb - Sun, 8 Feb

6:15 a.m. - 9:15 p.m.

YYC

ORD

14h 00m1 stop

7:00 a.m. - 9:53 p.m.

ORD

YYC

15h 53m1 stop

C$ 259United Airlines

Fri, 16 Jan - Mon, 19 Jan

7:04 p.m. - 8:04 p.m.

YYZ

ORD

2h 00mdirect

10:10 a.m. - 3:50 p.m.

ORD

YYZ

4h 40m1 stop

C$ 263American Airlines

Thu, 5 Feb - Sun, 8 Feb

3:50 p.m. - 5:50 p.m.

YUL

ORD

3h 00mdirect

6:05 a.m. - 1:45 p.m.

ORD

YUL

6h 40m1 stop

C$ 267American Airlines

Thu, 5 Feb - Sun, 8 Feb

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

YYC

ORD

3h 28mdirect

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

ORD

YYC

3h 49mdirect

C$ 275WestJet

Tue, 26 May - Sat, 30 May

American Airlines flights from Canada to Chicago

Our best American Airlines deals on Canada to Chicago flight tickets

American Airlines

8 Feb

YYZ1:14 p.m.Toronto Pearson Intl

2h 00m

ORD2:14 p.m.Chicago O'Hare Intl

16 Feb

ORD9:47 a.m.Chicago O'Hare Intl

1h 45m

YYZ12:32 p.m.Toronto Pearson Intl

C$ 263

Find similar

American Airlines

5 Feb

YUL3:50 p.m.Montreal Pierre Elliott Trudeau Intl

3h 00m

ORD5:50 p.m.Chicago O'Hare Intl

8 Feb

ORD6:05 a.m.Chicago O'Hare Intl

6h 40m

1 stop

YUL1:45 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 267

Find similar

American Airlines

12 Feb

YYZ11:38 a.m.Toronto Pearson Intl

1h 55m

ORD12:33 p.m.Chicago O'Hare Intl

16 Feb

ORD5:35 a.m.Chicago O'Hare Intl

5h 17m

1 stop

YYZ11:52 a.m.Toronto Pearson Intl

C$ 268

Find similar

WestJet flights from Canada to Chicago

Our best WestJet deals on Canada to Chicago flight tickets

WestJet

16 Jan

YYC9:00 a.m.Calgary

3h 35m

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

19 Jan

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

3h 55m

YYC5:15 p.m.Calgary

C$ 249

Find similar

WestJet

26 May

YYC12:15 p.m.Calgary

3h 28m

ORD4:43 p.m.Chicago O'Hare Intl

30 May

ORD5:30 p.m.Chicago O'Hare Intl

3h 49m

YYC8:19 p.m.Calgary

C$ 275

Find similar

WestJet

26 May

YYC12:15 p.m.Calgary

3h 28m

ORD4:43 p.m.Chicago O'Hare Intl

30 May

ORD5:30 p.m.Chicago O'Hare Intl

3h 49m

YYC8:19 p.m.Calgary

C$ 285

Find similar

Fly from

Fly to

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 28/1

5:35 a.m.-3:10 p.m.

1 stop8h 35m

Chicago O'Hare Intl

Wed 4/2

3:55 p.m.-12:14 a.m.

1 stop9h 19m

C$ 213

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 15/1

5:35 a.m.-3:10 p.m.

1 stop8h 35m

Chicago O'Hare Intl

Wed 21/1

3:55 p.m.-12:14 a.m.

1 stop9h 19m

C$ 219

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 20/2

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

Nonstop1h 50m

Chicago Midway

Mon 23/2

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

Nonstop1h 42m

C$ 246

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 18/1

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

Nonstop1h 50m

Chicago Midway

Wed 21/1

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

Nonstop1h 42m

C$ 248

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 16/1

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

Nonstop3h 35m

Chicago O'Hare Intl

Mon 19/1

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

Nonstop3h 55m

C$ 249

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 5/2

5:30 p.m.-6:50 p.m.

Nonstop2h 20m

Chicago O'Hare Intl

Sun 8/2

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

Nonstop1h 48m

C$ 256

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 16/1

6:15 a.m.-9:15 p.m.

1 stop14h 00m

Chicago O'Hare Intl

Mon 19/1

7:00 a.m.-9:53 p.m.

1 stop15h 53m

C$ 259

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 5/2

7:04 p.m.-8:04 p.m.

Nonstop2h 00m

Chicago O'Hare Intl

Sun 8/2

10:10 a.m.-3:50 p.m.

1 stop4h 40m

C$ 263

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 5/2

3:50 p.m.-5:50 p.m.

Nonstop3h 00m

Chicago O'Hare Intl

Sun 8/2

6:05 a.m.-1:45 p.m.

1 stop6h 40m

C$ 267

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 26/5

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

Nonstop3h 28m

Chicago O'Hare Intl

Sat 30/5

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

Nonstop3h 49m

C$ 275

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

Delays

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$ 310.

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$ 585. 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$ 1,048. 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$ 627. 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$ 1,081 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$ 401 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$ 268 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$ 152
Fastest flight time	1h 49m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Canada in the past 72 hours is C$ 152. The best round-trip flight deal from Canada to Chicago found on momondo in the last 72 hours is C$ 245.

The fastest flight from Canada to Chicago takes 1h 49m

Direct flights go from Canada to Chicago every day.

There are 3 airports in Chicago. From Canada there are direct flights to 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 December 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 15.51% of the total bookings. Other popular models include De Havilland (Bombardier) DHC-8-400 Dash 8Q with 11.00%, Boeing 737-800 with 9.86%, and Embraer 170 with 8.07%.

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$ 149	Free Cancellation	Rating 7.1 10,525 reviews	Search Air Canada flights
WestJet	PriceFrom C$ 176	Free Cancellation	Rating 7.2 3,202 reviews	Search WestJet flights
Delta	PriceFrom C$ 183	Free Cancellation	Rating 7.9 8,008 reviews	Search Delta flights
American Airlines	PriceFrom C$ 185	Free Cancellation	Rating 7.2 11,051 reviews	Search American Airlines flights
United Airlines	PriceFrom C$ 194	Free Cancellation	Rating 7.4 9,092 reviews	Search United Airlines flights
Porter Airlines	PriceFrom C$ 195	Free Cancellation	Rating 8.0 399 reviews	Search Porter 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

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Cheap flights from Canada to Chicago from C$ 123

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 22/5. 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

American Airlines flights from Canada to Chicago

Our best American Airlines deals on Canada to Chicago flight tickets

WestJet flights from Canada to Chicago

Our best WestJet 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

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$ 310.

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?

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

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

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

Which airlines fly to Chicago?

How often are flights from Canada to Chicago delayed?

Historically, on average around 11% of flights between Canada and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 139 minutes.

What is the most punctual flight time for Canada to Chicago flights?

Generally, flights departing at night tend to experience fewer delays. Flights departing in the evening have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week that experiences the fewest delays on this flight route. Saturday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Canada to Chicago flights?

According to our data, United Airlines has had the least delays on this route over the last 12 months, with about 6% of their flights experiencing any sort of delay.

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

The number of flights available between Canada and Chicago is 76 per day as of December 2025. The most frequent departure time is 6:00a.m., with 47% of daily flights leaving at noon.

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

534 flights are operational weekly from Canada to Chicago as of December 2025. The most popular departure day for this route is Mon, with 18% 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