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

As of January 2026, 618 flights take off from Chicago and land in Canada each week. The most common flight departure day for this route is Thu, with 15% of weekly flights taking off on this day.

Which airlines fly to Canada?

United Airlines, Air Canada and WestJet are the top three most popular airlines that fly to Canada from Chicago according to our data. United Airlines is the first choice among our users, with 45% of people opting to fly with this airline when travelling to Canada. Keep in mind that there are 4 different airlines that fly to Canada on a routine basis, so you have a few additional options to choose from.

How often are flights from Chicago to Canada delayed?

Historically, on average around 18% of flights between Chicago and Canada have experienced a delay on any given week. The average delay length over the past 12 months has been 136 minutes.

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. Friday has historically seen more delays on average compared to the rest of the week.

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

88 flights are operational daily from Chicago to Canada as of January 2026. The most popular departure time for this route is 6:00p.m., with 45% of flights per day taking off at noon.

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

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

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

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

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

According to our data, Korean Air has had the least delays on this route over the last 12 months, with about 11% of their flights experiencing any sort of delay.

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

Prices for flights from Chicago to Canada refresh daily.

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

The number of operators available for flights from Chicago to Canada is 4 as of January 2026.

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

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 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.

C$ 88 Cheap Flights from Chicago to Canada in 2026

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Find the cheapest flights from Chicago to Canada

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

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

ORD

YYC

3h 55mdirect

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

YYC

ORD

3h 35mdirect

C$ 229WestJet

Mon, 9 Mar - Mon, 16 Mar

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

ORD

YYC

3h 55mdirect

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

YYC

ORD

3h 35mdirect

C$ 232WestJet

Fri, 20 Feb - Fri, 27 Feb

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

ORD

YYC

9h 19m1 stop

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

YYC

ORD

8h 35m1 stop

C$ 241Air Canada

Thu, 22 Jan - Wed, 28 Jan

11:05 a.m. - 1:47 p.m.

MDW

YTZ

1h 42mdirect

9:20 a.m. - 10:10 a.m.

YTZ

MDW

1h 50mdirect

C$ 261Porter Airlines

Tue, 27 Jan - Tue, 3 Feb

11:05 a.m. - 1:47 p.m.

MDW

YTZ

1h 42mdirect

9:20 a.m. - 10:10 a.m.

YTZ

MDW

1h 50mdirect

C$ 264Porter Airlines

Thu, 5 Feb - Tue, 10 Feb

11:15 a.m. - 2:01 p.m.

ORD

YYZ

1h 46mdirect

9:00 p.m. - 10:05 p.m.

YYZ

ORD

2h 05mdirect

C$ 281United Airlines

Thu, 5 Feb - Sun, 8 Feb

8:40 p.m. - 11:19 p.m.

ORD

YYZ

1h 39mdirect

6:15 a.m. - 11:06 a.m.

YYZ

ORD

5h 51m1 stop

C$ 283Air Canada

Tue, 3 Feb - Thu, 5 Feb

5:15 a.m. - 11:20 p.m.

ORD

YYZ

17h 05m1 stop

8:15 a.m. - 9:13 a.m.

YYZ

ORD

1h 58mdirect

C$ 285Multiple Airlines

Wed, 4 Feb - Wed, 11 Feb

5:32 p.m. - 11:20 p.m.

ORD

YYZ

28h 48m1 stop

7:35 a.m. - 10:08 p.m.

YYZ

ORD

15h 33m1 stop

C$ 288Multiple Airlines

Tue, 3 Feb - Tue, 10 Feb

6:00 p.m. - 9:17 p.m.

ORD

YUL

2h 17mdirect

6:00 a.m. - 8:00 a.m.

YUL

ORD

3h 00mdirect

C$ 293United Airlines

Sat, 14 Feb - Sun, 15 Feb

Air Canada flights from Chicago to Canada

Our best Air Canada deals on Chicago to Canada flight tickets

Air Canada

22 Jan

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

9h 19m

1 stop

YYC12:14 a.m.Calgary

28 Jan

YYC8:00 a.m.Calgary

8h 48m

1 stop

ORD5:48 p.m.Chicago O'Hare Intl

C$ 241

Air Canada

10 Feb

ORD7:15 a.m.Chicago O'Hare Intl

9h 54m

1 stop

YYC4:09 p.m.Calgary

18 Feb

YYC5:35 a.m.Calgary

8h 20m

1 stop

ORD2:55 p.m.Chicago O'Hare Intl

C$ 271

Air Canada

2 Jun

ORD8:45 a.m.Chicago O'Hare Intl

8h 14m

1 stop

YYC3:59 p.m.Calgary

10 Jun

YYC6:30 a.m.Calgary

9h 29m

1 stop

ORD4:59 p.m.Chicago O'Hare Intl

C$ 278

American Airlines flights from Chicago to Canada

Our best American Airlines deals on Chicago to Canada flight tickets

American Airlines

3 Feb

ORD10:10 a.m.Chicago O'Hare Intl

6h 30m

1 stop

YYZ5:40 p.m.Toronto Pearson Intl

7 Feb

YYZ4:44 p.m.Toronto Pearson Intl

2h 00m

ORD5:44 p.m.Chicago O'Hare Intl

C$ 294

American Airlines

4 Feb

ORD8:12 a.m.Chicago O'Hare Intl

13h 32m

1 stop

YUL10:44 p.m.Montreal Pierre Elliott Trudeau Intl

9 Feb

YUL7:30 a.m.Montreal Pierre Elliott Trudeau Intl

12h 04m

1 stop

ORD6:34 p.m.Chicago O'Hare Intl

C$ 296

American Airlines

5 Feb

ORD9:41 a.m.Chicago O'Hare Intl

1h 53m

YYZ12:34 p.m.Toronto Pearson Intl

8 Feb

YYZ4:30 p.m.Toronto Pearson Intl

7h 57m

1 stop

ORD11:27 p.m.Chicago O'Hare Intl

C$ 301

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 9/3

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

Nonstop3h 55m

Calgary

Mon 16/3

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

Nonstop3h 35m

C$ 229

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 20/2

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

Nonstop3h 55m

Calgary

Fri 27/2

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

Nonstop3h 35m

C$ 232

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 22/1

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

1 stop9h 19m

Calgary

Wed 28/1

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

1 stop8h 35m

C$ 241

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 27/1

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

Toronto Island

Tue 3/2

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

C$ 261

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 5/2

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

Toronto Island

Tue 10/2

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

C$ 264

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 5/2

11:15 a.m.-2:01 p.m.

Nonstop1h 46m

Toronto Pearson Intl

Sun 8/2

9:00 p.m.-10:05 p.m.

Nonstop2h 05m

C$ 281

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 3/2

8:40 p.m.-11:19 p.m.

Nonstop1h 39m

Toronto Pearson Intl

Thu 5/2

6:15 a.m.-11:06 a.m.

1 stop5h 51m

C$ 283

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Wed 4/2

5:15 a.m.-11:20 p.m.

1 stop17h 05m

Toronto Pearson Intl

Wed 11/2

8:15 a.m.-9:13 a.m.

Nonstop1h 58m

C$ 285

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Tue 3/2

5:32 p.m.-11:20 p.m.

1 stop28h 48m

Toronto Pearson Intl

Tue 10/2

7:35 a.m.-10:08 p.m.

1 stop15h 33m

C$ 288

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

Sat 14/2

6:00 p.m.-9:17 p.m.

Nonstop2h 17m

Montreal Pierre Elliott Trudeau Intl

Sun 15/2

6:00 a.m.-8:00 a.m.

Nonstop3h 00m

C$ 293

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 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?

In general, September is the cheapest month to fly from Chicago to Canada. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 289. If you’re not able to fly to Canada in September, then July is your next best option. Flight prices from Chicago to Canada during July average around C$ 323.

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 C$ 332. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around C$ 485. These prices are subject to change though, so be sure to set up a Price Alert for flights to Canada.

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

According to our data, the cheapest time of day to fly to Canada is in the evening. momondo users have found flights departing from Chicago to Canada in the evening for as low as C$ 288. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the morning is when there is more demand to fly to Canada, so prices are often more expensive at around C$ 468 per ticket.

What is the cheapest Chicago to Canada flight route?

Fly from Chicago O'Hare Intl to Calgary 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 C$ 401 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 C$ 210 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?

You could potentially save up to 40% on your flight if you consider stops on a Chicago to Canada flight.

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	C$ 84
Fastest flight time	1h 39m
Direct flights	Every day
Airports in Canada	513 airports

The best one-way flight to Canada from Chicago in the past 72 hours is C$ 84. The best round-trip flight deal from Chicago to Canada found on momondo in the last 72 hours is C$ 172.

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

Direct flights go from Chicago to Canada every day.

There are 513 airports in Canada. From Chicago there are direct flights to 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 refresh daily.
How many operators does momondo search for flights from Chicago to Canada?
The number of operators available for flights from Chicago to Canada is 4 as of January 2026.
How old do you have to be to fly from Chicago to Canada?
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 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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Canada is Embraer 175 (Enhanced Winglets) (15.42% of total bookings). The next most popular plane models are Embraer 170 (10.15%), De Havilland (Bombardier) DHC-8-400 Dash 8Q (8.36%), and Embraer 175 (7.76%).

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
American Airlines	PriceFrom C$ 151	Free Cancellation	Rating 7.2 11,095 reviews	Search American Airlines flights
United Airlines	PriceFrom C$ 170	Free Cancellation	Rating 7.4 9,141 reviews	Search United Airlines flights
Air Canada	PriceFrom C$ 203	Free Cancellation	Rating 7.1 10,603 reviews	Search Air Canada flights
WestJet	PriceFrom C$ 211	Free Cancellation	Rating 7.2 3,235 reviews	Search WestJet flights

Why use momondo?

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

It is quick and easy to find Chicago to Canada flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Canada that suits you.

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

momondo does allow users to show only those flights to Canada from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Canada from Chicago.

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

Yes. momondo can track prices for Chicago to Canada 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 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 C$ 109

Flights to Vancouverfrom C$ 75

Flights to Montrealfrom C$ 58

Flights to Calgaryfrom C$ 79

Flights to Ottawafrom C$ 101

Flights to Winnipegfrom C$ 119

Flights to Halifaxfrom C$ 58

Flights to Kelownafrom C$ 86

Flights to Saskatoonfrom C$ 149

Flights to Reginafrom C$ 173

Flights to St. John'sfrom C$ 209

Flights to Québec Cityfrom C$ 317

Cheap flights from Chicago to Canada from C$ 88

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 4/2. 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

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Find the cheapest flights from Chicago to Canada

Cheap round-trip flights

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Cheap last-minute flights

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Air Canada flights from Chicago to Canada

Our best Air Canada deals on Chicago to Canada flight tickets

American Airlines flights from Chicago to Canada

Our best American Airlines 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

What is the cheapest month to fly to Canada?

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

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 Calgary 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?

You could potentially save up to 40% on your flight if you consider stops on a Chicago to Canada flight.

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

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

Which airlines fly to Canada?

How often are flights from Chicago to Canada delayed?

Historically, on average around 18% of flights between Chicago and Canada 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 Chicago to Canada flights?

Generally, flights departing in the morning 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. Friday has historically seen more delays on average compared to the rest of the week.

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

According to our data, Korean Air has had the least delays on this route over the last 12 months, with about 11% of their flights experiencing any sort of delay.

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

88 flights are operational daily from Chicago to Canada as of January 2026. The most popular departure time for this route is 6:00p.m., with 45% of flights per day taking off at noon.

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

As of January 2026, 618 flights take off from Chicago and land in Canada each week. The most common flight departure day for this route is Thu, with 15% of weekly flights taking off 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