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 44% 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.

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 has had the lowest 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 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?

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

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

As of November 2025, 586 flights take off from Chicago and land in Canada each week. The most common flight departure day for this route is Mon, with 16% of weekly flights taking off on this day.

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.

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

83 flights are operational daily from Chicago to Canada as of November 2025. The most popular departure time for this route is 1:00p.m., with 41% of flights per day taking off at noon.

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 November 2025.

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$ 83 Cheap Flights from Chicago to Canada in 2025/26

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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$ 212WestJet

Find Deal

lun., 16 feb. - lun., 23 feb.

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$ 213WestJet

Find Deal

lun., 26 ene. - lun., 2 feb.

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

3h 55mdirect

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

8h 35m1 stop

C$ 229Multiple Airlines

Find Deal

vie., 9 ene. - jue., 15 ene.

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

3h 55mdirect

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

8h 35m1 stop

C$ 230Multiple Airlines

Find Deal

lun., 5 ene. - mar., 13 ene.

8:30 p.m. - 11:09 p.m.ORD-YYZ

1h 39mdirect

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

2h 05mdirect

C$ 260Air Canada

Find Deal

jue., 8 ene. - dom., 11 ene.

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

1h 42mdirect

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

1h 50mdirect

C$ 262Porter Airlines

Find Deal

mar., 6 ene. - jue., 8 ene.

8:30 p.m. - 11:09 p.m.ORD-YYZ

1h 39mdirect

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

2h 05mdirect

C$ 264Air Canada

Find Deal

jue., 8 ene. - dom., 11 ene.

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

1h 42mdirect

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

1h 50mdirect

C$ 265Porter Airlines

Find Deal

lun., 26 ene. - lun., 2 feb.

1:00 p.m. - 7:48 p.m.ORD-YUL

5h 48m1 stop

4:45 p.m. - 6:51 p.m.YUL-ORD

3h 06mdirect

C$ 268United Airlines

Find Deal

lun., 26 ene. - sáb., 31 ene.

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

2h 17mdirect

2:13 p.m. - 11:43 p.m.YUL-ORD

10h 30m1 stop

C$ 275United Airlines

Find Deal

dom., 15 feb. - lun., 23 feb.

American Airlines flights from Chicago to Canada

Our best American Airlines deals on Chicago to Canada flight tickets

American Airlines

13 Dec

ORD8:10 a.m.Chicago O'Hare Intl

1h 46m

YYZ10:56 a.m.Toronto Pearson Intl

14 Dec

YYZ6:00 a.m.Toronto Pearson Intl

2h 15m

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

C$ 258

Find similar

American Airlines

16 Jan

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

8h 28m

1 stop

YYZ5:40 p.m.Toronto Pearson Intl

19 Jan

YYZ7:04 p.m.Toronto Pearson Intl

2h 00m

ORD8:04 p.m.Chicago O'Hare Intl

C$ 272

Find similar

American Airlines

7 Jan

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

1h 53m

YYZ12:34 p.m.Toronto Pearson Intl

11 Jan

YYZ7:30 a.m.Toronto Pearson Intl

7h 29m

1 stop

ORD1:59 p.m.Chicago O'Hare Intl

C$ 281

Find similar

Air Canada flights from Chicago to Canada

Our best Air Canada deals on Chicago to Canada flight tickets

Air Canada

8 Jan

ORD8:30 p.m.Chicago O'Hare Intl

1h 39m

YYZ11:09 p.m.Toronto Pearson Intl

11 Jan

YYZ9:00 p.m.Toronto Pearson Intl

2h 05m

ORD10:05 p.m.Chicago O'Hare Intl

C$ 260

Find similar

Air Canada

8 Jan

ORD2:00 p.m.Chicago O'Hare Intl

1h 39m

YYZ4:39 p.m.Toronto Pearson Intl

11 Jan

YYZ9:00 p.m.Toronto Pearson Intl

2h 05m

ORD10:05 p.m.Chicago O'Hare Intl

C$ 261

Find similar

Air Canada

9 Jan

ORD2:00 p.m.Chicago O'Hare Intl

11h 14m

1 stop

YYC12:14 a.m.Calgary

15 Jan

YYC11:40 p.m.Calgary

14h 15m

2 stops

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

C$ 268

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

lun. 16/2

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

Nonstop3h 55m

Calgary

lun. 23/2

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

Nonstop3h 35m

C$ 212

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

lun. 26/1

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

Nonstop3h 55m

Calgary

lun. 2/2

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

Nonstop3h 35m

C$ 213

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

vie. 9/1

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

Nonstop3h 55m

Calgary

jue. 15/1

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

1 stop8h 35m

C$ 229

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

lun. 5/1

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

Nonstop3h 55m

Calgary

mar. 13/1

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

1 stop8h 35m

C$ 230

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

jue. 8/1

8:30 p.m.-11:09 p.m.

Nonstop1h 39m

Toronto Pearson Intl

dom. 11/1

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

Nonstop2h 05m

C$ 260

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

mar. 6/1

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

Nonstop1h 42m

Toronto Island

jue. 8/1

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

Nonstop1h 50m

C$ 262

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

jue. 8/1

8:30 p.m.-11:09 p.m.

Nonstop1h 39m

Toronto Pearson Intl

dom. 11/1

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

Nonstop2h 05m

C$ 264

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

lun. 26/1

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

Nonstop1h 42m

Toronto Island

lun. 2/2

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

Nonstop1h 50m

C$ 265

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

lun. 26/1

1:00 p.m.-7:48 p.m.

1 stop5h 48m

Montreal Pierre Elliott Trudeau Intl

sáb. 31/1

4:45 p.m.-6:51 p.m.

Nonstop3h 06m

C$ 268

ChicagoMontreal

ORD - YUL

ORDYUL

Chicago O'Hare Intl

dom. 15/2

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

Nonstop2h 17m

Montreal Pierre Elliott Trudeau Intl

lun. 23/2

2:13 p.m.-11:43 p.m.

1 stop10h 30m

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 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$ 293. 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$ 328.

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$ 328. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around C$ 517. 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$ 314. 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$ 476 per ticket.

What is the cheapest Chicago to Canada flight route?

Fly from Chicago O'Hare Intl to Toronto Pearson 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 C$ 429 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$ 233 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 63% 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$ 129
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 C$ 129. The best round-trip flight deal from Chicago to Canada found on momondo in the last 72 hours is C$ 125.

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 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 November 2025.
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) (16.17% of total bookings). The next most popular plane models are Boeing 737-800 (10.75%), Embraer 175 (9.24%), and De Havilland (Bombardier) DHC-8-400 Dash 8Q (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
American Airlines	PriceFrom C$ 153	Free Cancellation	Rating 7.2 11,047 reviews	Search American Airlines flights
United Airlines	PriceFrom C$ 173	Free Cancellation	Rating 7.4 9,015 reviews	Search United Airlines flights
Air Canada	PriceFrom C$ 206	Free Cancellation	Rating 7.1 10,459 reviews	Search Air Canada flights
WestJet	PriceFrom C$ 214	Free Cancellation	Rating 7.2 3,163 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.

Start using Trips

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jue. 18/12

jue. 25/12

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Find better results for your trip to Canada

Popular Cities in Canada

Flights to Torontofrom C$ 86

Flights to Vancouverfrom C$ 79

Flights to Montrealfrom C$ 49

Flights to Calgaryfrom C$ 80

Flights to Ottawafrom C$ 195

Flights to Winnipegfrom C$ 133

Flights to Halifaxfrom C$ 86

Flights to Kelownafrom C$ 73

Flights to Saskatoonfrom C$ 135

Flights to Reginafrom C$ 161

Flights to St. John'sfrom C$ 248

Flights to Québec Cityfrom C$ 295

Cheap flights from Chicago to Canada from C$ 79

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 16/2. 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

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Chicago to Canada

Cheap round-trip flights

Cheap one-way flights

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?

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 Toronto Pearson 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?

You could potentially save up to 63% on your flight if you consider stops on a Chicago to Canada flight.

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

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

Which 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 departing 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 has had the lowest 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?

83 flights are operational daily from Chicago to Canada as of November 2025. The most popular departure time for this route is 1:00p.m., with 41% of flights per day taking off at noon.

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

As of November 2025, 586 flights take off from Chicago and land in Canada each week. The most common flight departure day for this route is Mon, with 16% 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