How long does it take to fly to Chicago?

Average flight duration from Canada to Chicago depends on which airport you fly into and out of. Flying from Montreal to Chicago O'Hare Intl Airport is 2h 26m on average, while flying from Toronto to Chicago O'Hare Intl Airport is 3h 02m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

What airlines fly to Chicago?

Air Canada, United Airlines and American Airlines 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 49% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 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 90 per day as of August 2025. The most frequent departure time is 6:00AM, with 46% of daily flights leaving at noon.

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

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

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

As of August 2025, there are 635 flights per week flying from Canada to Chicago. The most common day of the week flights depart is Tue, with 20% of flights 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?

As of August 2025, there are 4 operators available to choose from 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.

$99 Cheap Flights from Canada to Chicago in 2025

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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

8:15 am - 9:13 amYYZ-ORD

1h 58mnonstop

2:00 pm - 4:39 pmORD-YYZ

1h 39mnonstop

$147Air Canada

Find Deal

Fri, Nov 7 - Sun, Nov 16

8:20 am - 9:13 amYYZ-ORD

1h 53mnonstop

8:15 pm - 10:54 pmORD-YYZ

1h 39mnonstop

$159Air Canada

Find Deal

Fri, Oct 24 - Mon, Nov 3

4:44 pm - 5:44 pmYYZ-ORD

2h 00mnonstop

5:00 am - 11:03 amORD-YYZ

5h 03m1 stop

$169American Airlines

Find Deal

Fri, Nov 7 - Sun, Nov 16

6:30 am - 7:25 amYYZ-ORD

1h 55mnonstop

11:48 am - 2:31 pmORD-YYZ

1h 43mnonstop

$170American Airlines

Find Deal

Thu, Sep 25 - Sat, Sep 27

7:50 am - 8:39 amYTZ-MDW

1h 49mnonstop

5:20 pm - 8:02 pmMDW-YTZ

1h 42mnonstop

$171Porter Airlines

Find Deal

Thu, Sep 11 - Sun, Sep 14

3:35 pm - 4:24 pmYTZ-MDW

1h 49mnonstop

5:20 pm - 8:02 pmMDW-YTZ

1h 42mnonstop

$172Porter Airlines

Find Deal

Tue, Sep 16 - Mon, Sep 22

10:10 pm - 1:35 pmYVR-ORD

13h 25m1 stop

2:20 pm - 9:00 pmORD-YVR

8h 40m1 stop

$176WestJet

Find Deal

Thu, Oct 30 - Mon, Nov 3

8:55 am - 10:00 amYYZ-ORD

2h 05mnonstop

7:10 am - 9:58 amORD-YYZ

1h 48mnonstop

$178United Airlines

Find Deal

Fri, Nov 7 - Sun, Nov 9

6:00 am - 4:43 pmYVR-ORD

8h 43m2 stops

5:30 pm - 12:11 amORD-YVR

8h 41m1 stop

$179WestJet

Find Deal

Thu, Oct 2 - Mon, Oct 6

6:40 pm - 11:34 pmYYZ-ORD

5h 54m1 stop

1:19 pm - 4:02 pmORD-YYZ

1h 43mnonstop

$184United Airlines

Find Deal

Fri, Nov 7 - Sun, Nov 9

WestJet flights from Canada to Chicago

Our best WestJet deals on Canada to Chicago flight tickets

WestJet

Oct 30

YVR10:10 pmVancouver Intl

13h 25m

1 stop

ORD1:35 pmChicago O'Hare Intl

Nov 3

ORD2:20 pmChicago O'Hare Intl

8h 40m

1 stop

YVR9:00 pmVancouver Intl

$176

Find similar

WestJet

Oct 2

YVR6:00 amVancouver Intl

8h 43m

2 stops

ORD4:43 pmChicago O'Hare Intl

Oct 6

ORD5:30 pmChicago O'Hare Intl

8h 41m

1 stop

YVR12:11 amVancouver Intl

$179

Find similar

WestJet

Oct 29

YVR10:10 pmVancouver Intl

13h 25m

1 stop

ORD1:35 pmChicago O'Hare Intl

Nov 3

ORD2:20 pmChicago O'Hare Intl

8h 40m

1 stop

YVR9:00 pmVancouver Intl

$184

Find similar

United Airlines flights from Canada to Chicago

Our best United Airlines deals on Canada to Chicago flight tickets

United Airlines

Nov 7

YYZ8:55 amToronto Pearson Intl

2h 05m

ORD10:00 amChicago O'Hare Intl

Nov 9

ORD7:10 amChicago O'Hare Intl

1h 48m

YYZ9:58 amToronto Pearson Intl

$178

Find similar

United Airlines

Nov 7

YYZ6:40 pmToronto Pearson Intl

5h 54m

1 stop

ORD11:34 pmChicago O'Hare Intl

Nov 9

ORD1:19 pmChicago O'Hare Intl

1h 43m

YYZ4:02 pmToronto Pearson Intl

$184

Find similar

United Airlines

Sep 19

YYZ9:00 amToronto Pearson Intl

1h 55m

ORD9:55 amChicago O'Hare Intl

Sep 23

ORD1:05 pmChicago O'Hare Intl

1h 41m

YYZ3:46 pmToronto Pearson Intl

$203

Find similar

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 11/7

8:15 am-9:13 am

Nonstop1h 58m

Chicago O'Hare Intl

Sun 11/16

2:00 pm-4:39 pm

Nonstop1h 39m

$147

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 10/24

8:20 am-9:13 am

Nonstop1h 53m

Chicago O'Hare Intl

Mon 11/3

8:15 pm-10:54 pm

Nonstop1h 39m

$159

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 11/7

4:44 pm-5:44 pm

Nonstop2h 00m

Chicago O'Hare Intl

Sun 11/16

5:00 am-11:03 am

1 stop5h 03m

$169

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 9/25

6:30 am-7:25 am

Nonstop1h 55m

Chicago O'Hare Intl

Sat 9/27

11:48 am-2:31 pm

Nonstop1h 43m

$170

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 9/11

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

Sun 9/14

5:20 pm-8:02 pm

Nonstop1h 42m

$171

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 9/16

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

Mon 9/22

5:20 pm-8:02 pm

Nonstop1h 42m

$172

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 10/30

10:10 pm-1:35 pm

1 stop13h 25m

Chicago O'Hare Intl

Mon 11/3

2:20 pm-9:00 pm

1 stop8h 40m

$176

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 11/7

8:55 am-10:00 am

Nonstop2h 05m

Chicago O'Hare Intl

Sun 11/9

7:10 am-9:58 am

Nonstop1h 48m

$178

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Thu 10/2

6:00 am-4:43 pm

2 stops8h 43m

Chicago O'Hare Intl

Mon 10/6

5:30 pm-12:11 am

1 stop8h 41m

$179

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 11/7

6:40 pm-11:34 pm

1 stop5h 54m

Chicago O'Hare Intl

Sun 11/9

1:19 pm-4:02 pm

Nonstop1h 43m

$184

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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, on average, the cheapest month to fly to Chicago from Canada, with most prices found around $224. If you’re not able to fly to Chicago in June, then April is your next best option. Flight prices from Canada to Chicago during April average around $235.

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 $384. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Canada to Chicago for around $628.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Canada to Chicago during this time can be as low as $360. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $557.

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 $295 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 $240 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	$99
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 $99. The best round-trip flight deal from Canada to Chicago found on momondo in the last 72 hours is $147.

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?
As of August 2025, there are 4 operators available to choose from 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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Canada to Chicago is Embraer 175 (Enhanced Winglets) (17.35% of total bookings). The next most popular plane models are De Havilland (Bombardier) DHC-8-400 Dash 8Q (15.72%), Boeing 737-800 (13.85%), and Embraer 175 (8.02%).

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 $109	Free Cancellation	Rating 7.1 9,890 reviews	Search Air Canada flights
United Airlines	PriceFrom $112	Free Cancellation	Rating 7.4 8,916 reviews	Search United Airlines flights
WestJet	PriceFrom $137	Free Cancellation	Rating 7.2 2,997 reviews	Search WestJet flights
Porter Airlines	PriceFrom $158	Free Cancellation	Rating 8.0 322 reviews	Search Porter Airlines flights
American Airlines	PriceFrom $167	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights

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Benton Harbor

Saint Joseph

Lansing

Portage

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

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.

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

Chicago Greater Rockford Airport

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Cheap flights from Canada to Chicago from $99

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 11/1. 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 and deals

Big names and 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

United Airlines flights from Canada to Chicago

Our best United Airlines 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, on average, the cheapest month to fly to Chicago from Canada, with most prices found around $224. If you’re not able to fly to Chicago in June, then April is your next best option. Flight prices from Canada to Chicago during April average around $235.

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?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Canada to Chicago during this time can be as low as $360. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $557.

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?

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

What 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 90 per day as of August 2025. The most frequent departure time is 6:00AM, with 46% of daily flights leaving at noon.

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

As of August 2025, there are 635 flights per week flying from Canada to Chicago. The most common day of the week flights depart is Tue, with 20% of flights 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

Traveling 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 78.5 mi from Chicago