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 Toronto to Chicago O'Hare Intl Airport is 1h 57m on average, while flying from Montreal to Chicago O'Hare Intl Airport is 2h 35m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

How often are flights from Canada to Chicago delayed?

Historically, on average around 12% 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 138 minutes.

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

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

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

WestJet, Porter Airlines, and Air Canada are the most popular carriers operating from Canada to 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 45% 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.

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

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

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

As of February 2026, there are 577 flights per week flying from Canada to Chicago. The most common day of the week flights depart is Sun, with 17% of flights taking off on this day.

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

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 7% 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 82 per day as of February 2026. The most frequent departure time is 6:00AM, with 48% of daily flights leaving in the afternoon.

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 February 2026, there are 5 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.

$98 Cheap Flights from Canada to Chicago in 2026

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Recent round-trip flight deals from Canada to Chicago

Enter your travel dates to find the best prices.

12:00 pm - 4:40 pm

YYC

ORD

3h 40mnonstop

5:30 pm - 8:25 pm

ORD

YYC

3h 55mnonstop

$163WestJet

Mon, May 4 - Mon, May 11

12:00 pm - 4:40 pm

YYC

ORD

3h 40mnonstop

5:30 pm - 8:25 pm

ORD

YYC

3h 55mnonstop

$165WestJet

Wed, May 20 - Fri, May 29

6:45 am - 10:05 am

YUL

MDW

4h 20m

1 stop

11:00 am - 6:45 pm

MDW

YUL

6h 45m

1 stop

$173Porter Airlines

Fri, Apr 10 - Sun, Apr 12

6:30 pm - 8:08 pm

YUL

ORD

2h 38mnonstop

11:05 am - 2:16 pm

ORD

YUL

2h 11mnonstop

$175Air Canada

Fri, May 1 - Mon, May 4

6:25 pm - 8:10 pm

YUL

ORD

2h 45mnonstop

12:50 pm - 4:05 pm

ORD

YUL

2h 15mnonstop

$176Air Canada

Wed, Mar 25 - Mon, Mar 30

8:55 am - 11:50 am

YUL

MDW

3h 55m

1 stop

11:00 am - 4:30 pm

MDW

YUL

4h 30m

1 stop

$176Porter Airlines

Sat, Apr 25 - Wed, Apr 29

12:30 pm - 2:10 pm

YUL

ORD

2h 40mnonstop

6:40 am - 3:27 pm

ORD

YUL

7h 47m

1 stop

$185American Airlines

Sat, Apr 25 - Sat, May 2

6:00 am - 8:00 am

YUL

ORD

3h 00mnonstop

4:20 pm - 12:13 am

ORD

YUL

6h 53m

1 stop

$186United Airlines

Thu, Mar 26 - Mon, Mar 30

6:35 pm - 11:44 pm

YUL

ORD

6h 09m

1 stop

6:03 pm - 9:26 pm

ORD

YUL

2h 23mnonstop

$191United Airlines

Mon, May 4 - Sat, May 9

3:45 pm - 5:45 pm

YUL

ORD

3h 00mnonstop

6:44 pm - 1:45 pm

ORD

YUL

18h 01m

1 stop

$192American Airlines

Thu, Mar 12 - Mon, Mar 16

American Airlines flights from Canada to Chicago

Our best American Airlines deals on Canada to Chicago flight tickets

American Airlines

Mar 12

YUL3:45 pmMontreal Pierre Elliott Trudeau Intl

3h 00m

ORD5:45 pmChicago O'Hare Intl

Mar 16

ORD6:44 pmChicago O'Hare Intl

18h 01m

1 stop

YUL1:45 pmMontreal Pierre Elliott Trudeau Intl

$192

American Airlines

Mar 18

YYZ11:40 amToronto Pearson Intl

1h 55m

ORD12:35 pmChicago O'Hare Intl

Mar 25

ORD6:00 amChicago O'Hare Intl

8h 00m

1 stop

YYZ3:00 pmToronto Pearson Intl

$209

American Airlines

Feb 26

YYZ4:44 pmToronto Pearson Intl

2h 00m

ORD5:44 pmChicago O'Hare Intl

Mar 1

ORD5:00 amChicago O'Hare Intl

5h 13m

1 stop

YYZ11:13 amToronto Pearson Intl

$211

United Airlines flights from Canada to Chicago

Our best United Airlines deals on Canada to Chicago flight tickets

United Airlines

May 1

YUL9:45 amMontreal Pierre Elliott Trudeau Intl

2h 43m

ORD11:28 amChicago O'Hare Intl

May 4

ORD4:25 pmChicago O'Hare Intl

6h 48m

1 stop

YUL12:13 amMontreal Pierre Elliott Trudeau Intl

$185

United Airlines

Mar 26

YUL6:00 amMontreal Pierre Elliott Trudeau Intl

3h 00m

ORD8:00 amChicago O'Hare Intl

Mar 30

ORD4:20 pmChicago O'Hare Intl

6h 53m

1 stop

YUL12:13 amMontreal Pierre Elliott Trudeau Intl

$186

United Airlines

May 4

YUL6:35 pmMontreal Pierre Elliott Trudeau Intl

6h 09m

1 stop

ORD11:44 pmChicago O'Hare Intl

May 9

ORD6:03 pmChicago O'Hare Intl

2h 23m

YUL9:26 pmMontreal Pierre Elliott Trudeau Intl

$191

Fly from

Fly to

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Mon 5/4

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Mon 5/11

5:30 pm-8:25 pm

Nonstop3h 55m

$163

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Wed 5/20

12:00 pm-4:40 pm

Nonstop3h 40m

Chicago O'Hare Intl

Fri 5/29

5:30 pm-8:25 pm

Nonstop3h 55m

$165

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 4/10

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Sun 4/12

11:00 am-6:45 pm

1 stop6h 45m

$173

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Fri 5/1

6:30 pm-8:08 pm

Nonstop2h 38m

Chicago O'Hare Intl

Mon 5/4

11:05 am-2:16 pm

Nonstop2h 11m

$175

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 3/25

6:25 pm-8:10 pm

Nonstop2h 45m

Chicago O'Hare Intl

Mon 3/30

12:50 pm-4:05 pm

Nonstop2h 15m

$176

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 4/25

8:55 am-11:50 am

1 stop3h 55m

Chicago Midway

Wed 4/29

11:00 am-4:30 pm

1 stop4h 30m

$176

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Sat 4/25

12:30 pm-2:10 pm

Nonstop2h 40m

Chicago O'Hare Intl

Sat 5/2

6:40 am-3:27 pm

1 stop7h 47m

$185

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 3/26

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Mon 3/30

4:20 pm-12:13 am

1 stop6h 53m

$186

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Mon 5/4

6:35 pm-11:44 pm

1 stop6h 09m

Chicago O'Hare Intl

Sat 5/9

6:03 pm-9:26 pm

Nonstop2h 23m

$191

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 3/12

3:45 pm-5:45 pm

Nonstop3h 00m

Chicago O'Hare Intl

Mon 3/16

6:44 pm-1:45 pm

1 stop18h 01m

$192

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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 July is, on average, the cheapest month to fly to Chicago from Canada, with most prices found around $215. If you’re not able to fly to Chicago in July, then June is your next best option. Flight prices from Canada to Chicago during June average around $222.

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 Thursday when prices can be found for as low as $415. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Canada to Chicago for around $691.

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 $375. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $622.

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 $287 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 $195 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 9% 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	$122
Fastest flight time	1h 50m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Canada in the past 72 hours is $122. The best round-trip flight deal from Canada to Chicago found on momondo in the last 72 hours is $195.

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

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?
As of February 2026, there are 5 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) (14.65% of total bookings). The next most popular plane models are De Havilland (Bombardier) DHC-8-400 Dash 8Q (10.75%), Embraer 170 (10.02%), and Embraer 175 (8.64%).

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
Porter Airlines	PriceFrom $80	Free Cancellation	Rating 7.9 414 reviews	Search Porter Airlines flights
Air Canada	PriceFrom $83	Free Cancellation	Rating 7.1 10,698 reviews	Search Air Canada flights
United Airlines	PriceFrom $90	Free Cancellation	Rating 7.4 9,259 reviews	Search United Airlines flights
WestJet	PriceFrom $138	Free Cancellation	Rating 7.2 3,256 reviews	Search WestJet flights
American Airlines	PriceFrom $167	Free Cancellation	Rating 7.2 11,255 reviews	Search American Airlines flights

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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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Cheap flights from Canada to Chicago from $98

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 5/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Find the cheapest flights from Canada to Chicago

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American Airlines flights from Canada to Chicago

Our best American Airlines deals on Canada to Chicago flight tickets

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How to get the cheapest flight ticket from Canada to Chicago

What is the cheapest month to fly to Chicago?

The month of July is, on average, the cheapest month to fly to Chicago from Canada, with most prices found around $215. If you’re not able to fly to Chicago in July, then June is your next best option. Flight prices from Canada to Chicago during June average around $222.

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 $375. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $622.

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 9% 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, Porter Airlines, and Air Canada are the most popular carriers operating from Canada to Chicago

What airlines fly to Chicago?

How often are flights from Canada to Chicago delayed?

Historically, on average around 12% 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 138 minutes.

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

Generally, flights departing at night tend to experience fewer delays. Flights 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 which experiences the fewest number of delays on this flight route. Sunday 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 have had the least number of delays on this route over the last 12 months; with about 7% 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 82 per day as of February 2026. The most frequent departure time is 6:00AM, with 48% of daily flights leaving in the afternoon.

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

As of February 2026, there are 577 flights per week flying from Canada to Chicago. The most common day of the week flights depart is Sun, with 17% 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

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