How often are flights $[0, preposition:'from ']$[0, article:'from ']$[0, place:'from'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] delayed?

Historically, on average around 18% of flights between $[0, place:'genitive'] and $[1, place:'genitive'] have experienced a delay on any given week. The average delay length over the past 12 months has been 136 minutes.

Which airline has the best punctuality record on $[0,article:'genitive ']$[0,place:'genitive'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] flights?

According to our data, Air Antilles have had the least number of delays on this route over the last 12 months; with no flights being classified as delayed.

What is the most punctual flight time for $[0,article:'genitive ']$[0,place:'genitive'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] flights?

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

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

As of November 2025, there are 85 flights per day flying from Chicago to Canada. The most common time of day flights depart is 1:00PM, with 41% of flights taking off at noon.

What airlines fly to Canada?

Air Canada, United Airlines and American Airlines are the top three most popular airlines that fly to Canada from Chicago according to our data. Air Canada is the first choice among our users, with 30% of people opting to fly with this airline when traveling to Canada. Keep in mind that there are 7 different airlines that fly to Canada on a routine basis, so you have a few additional options to choose from.

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

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

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

The number of flights available between Chicago and Canada is 596 per week as of November 2025. The most frequent departure day is Fri, with 16% of weekly flights leaving on this day.

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

Prices for flights from Chicago to Canada are updated daily.

How many operators does momondo search for flights from Chicago to Canada?

There are 7 operators available for flights from Chicago to Canada as of November 2025.

How old do you have to be to fly from Chicago to Canada?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Canada.

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

The necessary travel and health documents for your Canada 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.

$59 Cheap Flights from Chicago to Canada in 2025/26

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

2:20 pm - 5:15 pmORD-YYC

3h 55mnonstop

9:00 am - 1:35 pmYYC-ORD

3h 35mnonstop

$151WestJet

Find Deal

Mon, Feb 16 - Mon, Feb 23

2:20 pm - 5:15 pmORD-YYC

3h 55mnonstop

9:00 am - 1:35 pmYYC-ORD

3h 35mnonstop

$152WestJet

Find Deal

Mon, Jan 26 - Mon, Feb 2

8:10 am - 10:56 amORD-YYZ

1h 46mnonstop

6:00 am - 7:15 amYYZ-ORD

2h 15mnonstop

$184American Airlines

Find Deal

Sat, Dec 13 - Sun, Dec 14

8:30 pm - 11:09 pmORD-YYZ

1h 39mnonstop

9:00 pm - 10:05 pmYYZ-ORD

2h 05mnonstop

$185Air Canada

Find Deal

Thu, Jan 8 - Sun, Jan 11

2:00 pm - 4:39 pmORD-YYZ

1h 39mnonstop

9:00 pm - 10:05 pmYYZ-ORD

2h 05mnonstop

$186Air Canada

Find Deal

Thu, Jan 8 - Sun, Jan 11

11:00 am - 1:42 pmMDW-YTZ

1h 42mnonstop

9:15 am - 10:05 amYTZ-MDW

1h 50mnonstop

$187Porter Airlines

Find Deal

Tue, Jan 6 - Thu, Jan 8

11:00 am - 1:42 pmMDW-YTZ

1h 42mnonstop

9:15 am - 10:05 amYTZ-MDW

1h 50mnonstop

$189Porter Airlines

Find Deal

Mon, Jan 26 - Fri, Jan 30

1:00 pm - 7:48 pmORD-YUL

5h 48m1 stop

4:45 pm - 6:51 pmYUL-ORD

3h 06mnonstop

$191United Airlines

Find Deal

Mon, Jan 26 - Sat, Jan 31

7:22 am - 1:00 pmORD-YYZ

4h 38m1 stop

6:15 am - 7:30 amYYZ-ORD

2h 15mnonstop

$194American Airlines

Find Deal

Tue, Mar 31 - Sun, Apr 5

6:00 pm - 9:17 pmORD-YUL

2h 17mnonstop

2:13 pm - 11:43 pmYUL-ORD

10h 30m1 stop

$196United Airlines

Find Deal

Sun, Feb 15 - Mon, Feb 23

American Airlines flights from Chicago to Canada

Our best American Airlines deals on Chicago to Canada flight tickets

American Airlines

Dec 13

ORD8:10 amChicago O'Hare Intl

1h 46m

YYZ10:56 amToronto Pearson Intl

Dec 14

YYZ6:00 amToronto Pearson Intl

2h 15m

ORD7:15 amChicago O'Hare Intl

$184

Find similar

American Airlines

Mar 31

ORD7:22 amChicago O'Hare Intl

4h 38m

1 stop

YYZ1:00 pmToronto Pearson Intl

Apr 5

YYZ6:15 amToronto Pearson Intl

2h 15m

ORD7:30 amChicago O'Hare Intl

$194

Find similar

American Airlines

Jan 7

ORD9:41 amChicago O'Hare Intl

1h 53m

YYZ12:34 pmToronto Pearson Intl

Jan 11

YYZ7:30 amToronto Pearson Intl

7h 29m

1 stop

ORD1:59 pmChicago O'Hare Intl

$200

Find similar

Air Canada flights from Chicago to Canada

Our best Air Canada deals on Chicago to Canada flight tickets

Air Canada

Jan 8

ORD8:30 pmChicago O'Hare Intl

1h 39m

YYZ11:09 pmToronto Pearson Intl

Jan 11

YYZ9:00 pmToronto Pearson Intl

2h 05m

ORD10:05 pmChicago O'Hare Intl

$185

Find similar

Air Canada

Jan 8

ORD2:00 pmChicago O'Hare Intl

1h 39m

YYZ4:39 pmToronto Pearson Intl

Jan 11

YYZ9:00 pmToronto Pearson Intl

2h 05m

ORD10:05 pmChicago O'Hare Intl

$186

Find similar

Air Canada

Jan 8

ORD8:30 pmChicago O'Hare Intl

1h 39m

YYZ11:09 pmToronto Pearson Intl

Jan 11

YYZ9:00 pmToronto Pearson Intl

2h 05m

ORD10:05 pmChicago O'Hare Intl

$188

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 2/16

2:20 pm-5:15 pm

Nonstop3h 55m

Calgary

Mon 2/23

9:00 am-1:35 pm

Nonstop3h 35m

$151

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 1/26

2:20 pm-5:15 pm

Nonstop3h 55m

Calgary

Mon 2/2

9:00 am-1:35 pm

Nonstop3h 35m

$152

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 12/13

8:10 am-10:56 am

Nonstop1h 46m

Toronto Pearson Intl

Sun 12/14

6:00 am-7:15 am

Nonstop2h 15m

$184

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 1/8

8:30 pm-11:09 pm

Nonstop1h 39m

Toronto Pearson Intl

Sun 1/11

9:00 pm-10:05 pm

Nonstop2h 05m

$185

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 1/8

2:00 pm-4:39 pm

Nonstop1h 39m

Toronto Pearson Intl

Sun 1/11

9:00 pm-10:05 pm

Nonstop2h 05m

$186

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 1/6

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Thu 1/8

9:15 am-10:05 am

Nonstop1h 50m

$187

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 1/26

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Fri 1/30

9:15 am-10:05 am

Nonstop1h 50m

$189

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Mon 1/26

1:00 pm-7:48 pm

1 stop5h 48m

Montreal Pierre Elliott Trudeau Intl

Sat 1/31

4:45 pm-6:51 pm

Nonstop3h 06m

$191

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 3/31

7:22 am-1:00 pm

1 stop4h 38m

Toronto Pearson Intl

Sun 4/5

6:15 am-7:30 am

Nonstop2h 15m

$194

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Sun 2/15

6:00 pm-9:17 pm

Nonstop2h 17m

Montreal Pierre Elliott Trudeau Intl

Mon 2/23

2:13 pm-11:43 pm

1 stop10h 30m

$196

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How to get the cheapest flight ticket from Chicago to Canada

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 Canada?

If you aren’t able to travel during the month of September, then book flights to Canada from Chicago during July instead. Flights to Canada in July, while not as cheap as those in September, still average around $234.

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

Our data shows that Thursday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as $602. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Canada for around $767.

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

In the morning is the cheapest time of day to fly from Chicago to Canada when you can find flight prices for as low as $591. Flying to Canada in the morning is an ideal time because this is during off-peak travel hours. In contrast, the most expensive time of day to depart to Canada is in the afternoon when prices are around $760.

What is the cheapest Chicago to Canada flight route?

Fly from Chicago O'Hare Intl to Halifax Intl for the best Chicago - Canada flight prices

How far in advance should I book a flight to Canada?

You are more likely to see cheaper flights to Canada from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Canada for around $306 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Canada from Chicago for as low as $166 on momondo.

What cabin class options are available on Chicago to Canada flights?

There are 4 cabin classes available to choose from on Chicago to Canada 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 Chicago to Canada flights?

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

Cheap Chicago to Canada flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Canada

Best Price Found	$72
Fastest flight time	1h 39m
Direct flights	Every day
Airports in Canada	2 airports

The best one-way flight to Canada from Chicago in the past 72 hours is $72. The best round-trip flight deal from Chicago to Canada found on momondo in the last 72 hours is $198.

The fastest flight from Chicago to Canada takes 1h 39m

Direct flights go from Chicago to Canada every day.

There are 2 airports near Canada: Toronto Pearson Intl (YYZ), Toronto Island (YTZ)

Search flight deals

When did momondo last update prices for flights from Chicago to Canada?
Prices for flights from Chicago to Canada are updated daily.
How many operators does momondo search for flights from Chicago to Canada?
There are 7 operators available for flights from Chicago to Canada as of November 2025.
How old do you have to be to fly from Chicago to Canada?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Canada.
What documentation or ID do you need to fly to Canada?
The necessary travel and health documents for your Canada 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 Chicago to Canada?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Canada is Embraer 175 (Enhanced Winglets), representing 16.17% of all bookings. The subsequent popular models are Boeing 737-800 at 10.75%, Embraer 175 at 9.24%, and De Havilland (Bombardier) DHC-8-400 Dash 8Q at 8.69%.

Best airlines flying from Chicago to Canada

Compare and see reviews for airlines that fly from Chicago to Canada with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $88	Free Cancellation	Rating 7.4 9,020 reviews	Search United Airlines flights
Air Canada	PriceFrom $91	Free Cancellation	Rating 7.1 10,462 reviews	Search Air Canada flights
Delta	PriceFrom $109	Free Cancellation	Rating 7.9 8,003 reviews	Search Delta flights
WestJet	PriceFrom $142	Free Cancellation	Rating 7.2 3,163 reviews	Search WestJet flights
Porter Airlines	PriceFrom $185	Free Cancellation	Rating 8.0 392 reviews	Search Porter Airlines flights
American Airlines	PriceFrom $192	Free Cancellation	Rating 7.2 11,045 reviews	Search American Airlines flights
Alaska Airlines	PriceFrom $464	Free Cancellation	Rating 8.0 11,317 reviews	Search Alaska Airlines flights

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Canada for you.

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

All flight searches from Chicago to Canada on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Canada?

momondo provides multiple filters to help you find the best flight to Canada from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Canada right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Canada flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Canada 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 Canada

Popular cities in Canada

Flights to Torontofrom $61

Flights to Vancouverfrom $79

Flights to Montrealfrom $158

Flights to Calgaryfrom $144

Flights to Ottawafrom $158

Flights to Halifaxfrom $232

Flights to Winnipegfrom $135

Flights to Québec Cityfrom $274

Flights to Saskatoonfrom $167

Flights to Vancouverfrom $78

Flights to Kelownafrom $144

Flights to St. John'sfrom $340

Cheap flights from Chicago to Canada from $59

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Canada departing on 1/16. 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

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Price Alerts

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Find the cheapest flights from Chicago to Canada

Cheap round-trip flights

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Cheap last minute flights

Cheap direct flights

American Airlines flights from Chicago to Canada

Our best American Airlines deals on Chicago to Canada flight tickets

Air Canada flights from Chicago to Canada

Our best Air Canada deals on Chicago to Canada flight tickets

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

See travel insights to Canada from

How to get the cheapest flight ticket from Chicago to Canada

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 Canada?

If you aren’t able to travel during the month of September, then book flights to Canada from Chicago during July instead. Flights to Canada in July, while not as cheap as those in September, still average around $234.

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

Our data shows that Thursday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as $602. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Canada for around $767.

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

What is the cheapest Chicago to Canada flight route?

Fly from Chicago O'Hare Intl to Halifax Intl for the best Chicago - Canada flight prices

How far in advance should I book a flight to Canada?

What cabin class options are available on Chicago to Canada flights?

There are 4 cabin classes available to choose from on Chicago to Canada 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 Chicago to Canada flights?

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

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

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

What airlines fly to Canada?

How often are flights $[0, preposition:'from ']$[0, article:'from ']$[0, place:'from'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] delayed?

Historically, on average around 18% of flights between $[0, place:'genitive'] and $[1, place:'genitive'] have experienced a delay on any given week. The average delay length over the past 12 months has been 136 minutes.

What is the most punctual flight time for $[0,article:'genitive ']$[0,place:'genitive'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] flights?

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

Which airline has the best punctuality record on $[0,article:'genitive ']$[0,place:'genitive'] $[1, preposition:'to ']$[1, article:'to ']$[1, place:'to'] flights?

According to our data, Air Antilles have had the least number of delays on this route over the last 12 months; with no flights being classified as delayed.

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

As of November 2025, there are 85 flights per day flying from Chicago to Canada. The most common time of day flights depart is 1:00PM, with 41% of flights taking off at noon.

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

The number of flights available between Chicago and Canada is 596 per week as of November 2025. The most frequent departure day is Fri, with 16% of weekly flights leaving on this day.

Cheap Chicago to Canada flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Canada

Best Price Found

Fastest flight time

Direct flights

Airports in Canada

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

How many operators does momondo search for flights from Chicago to Canada?

How old do you have to be to fly from Chicago to Canada?

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

What is the most popular plane model from Chicago to Canada?

Best airlines flying from Chicago to Canada

Compare and see reviews for airlines that fly from Chicago to Canada with momondo

Why use momondo?

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

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

How can momondo help me find flights from Chicago to Canada?

I’m not ready to book a flight from Chicago to Canada right now. Can momondo alert me if prices change?

An easier way to manage your Canada 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 Canada

Popular cities in Canada

Popular flights according to clicks in the last 7 days on momondo