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

WestJet, United Airlines, and Porter 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 August 2025, 766 flights take off from Chicago and land in Canada each week. The most common flight departure day for this route is Wed, with 17% of weekly flights taking off on this day.

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

109 flights are operational daily from Chicago to Canada as of August 2025. The most popular departure time for this route is 8:00p.m., with 36% of flights per day taking off in the afternoon.

Which airlines fly to Canada?

Air Canada, United Airlines and WestJet 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 53% of people opting to fly with this airline when travelling to Canada. Keep in mind that there are 3 different airlines that fly to Canada on a routine basis, so you have a few additional options to choose from.

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 3 as of August 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$ 66 Cheap Flights from Chicago to Canada in 2025

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Find the cheapest flights from Chicago to Canada

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

5:30 p.m. - 8:19 p.m.ORD-YYC

3h 49mdirect

12:15 p.m. - 4:43 p.m.YYC-ORD

3h 28mdirect

C$ 179WestJet

Find Deal

Sat, 11 Oct - Fri, 17 Oct

5:30 p.m. - 8:19 p.m.ORD-YYC

3h 49mdirect

12:15 p.m. - 4:43 p.m.YYC-ORD

3h 28mdirect

C$ 182WestJet

Find Deal

Thu, 25 Sep - Mon, 29 Sep

2:00 p.m. - 4:39 p.m.ORD-YYZ

1h 39mdirect

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

1h 58mdirect

C$ 206Air Canada

Find Deal

Fri, 14 Nov - Sun, 16 Nov

3:45 p.m. - 6:15 p.m.ORD-YVR

4h 30mdirect

8:45 a.m. - 3:00 p.m.YVR-ORD

4h 15mdirect

C$ 212Air Canada

Find Deal

Fri, 26 Sep - Fri, 3 Oct

5:20 p.m. - 8:02 p.m.MDW-YTZ

1h 42mdirect

3:35 p.m. - 4:24 p.m.YTZ-MDW

1h 49mdirect

C$ 218Porter Airlines

Find Deal

Wed, 3 Sep - Mon, 8 Sep

1:19 p.m. - 4:02 p.m.ORD-YYZ

1h 43mdirect

7:40 p.m. - 11:43 p.m.YYZ-ORD

5h 03m1 stop

C$ 219United Airlines

Find Deal

Fri, 7 Nov - Fri, 7 Nov

8:45 a.m. - 11:35 a.m.ORD-YYC

3h 50mdirect

12:37 p.m. - 5:10 p.m.YYC-ORD

3h 33mdirect

C$ 223United Airlines

Find Deal

Wed, 5 Nov - Tue, 11 Nov

5:30 p.m. - 12:11 a.m.ORD-YVR

8h 41m1 stop

8:45 a.m. - 3:00 p.m.YVR-ORD

4h 15mdirect

C$ 234

Find Deal

Fri, 5 Sep - Thu, 11 Sep

5:30 p.m. - 10:36 p.m.ORD-YVR

7h 06m1 stop

8:50 a.m. - 8:11 p.m.YVR-ORD

9h 21m1 stop

C$ 237

Find Deal

Fri, 5 Sep - Thu, 11 Sep

9:35 a.m. - 12:17 p.m.MDW-YTZ

1h 42mdirect

7:50 a.m. - 8:39 a.m.YTZ-MDW

1h 49mdirect

C$ 263Porter Airlines

Find Deal

Wed, 3 Sep - Sat, 6 Sep

United Airlines flights from Chicago to Canada

Our best United Airlines deals on Chicago to Canada flight tickets

United Airlines

7 Nov

ORD1:19 p.m.Chicago O'Hare Intl

1h 43m

YYZ4:02 p.m.Toronto Pearson Intl

7 Nov

YYZ7:40 p.m.Toronto Pearson Intl

5h 03m

1 stop

ORD11:43 p.m.Chicago O'Hare Intl

C$ 219

Find similar

United Airlines

5 Nov

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

3h 50m

YYC11:35 a.m.Calgary

11 Nov

YYC12:37 p.m.Calgary

3h 33m

ORD5:10 p.m.Chicago O'Hare Intl

C$ 223

Find similar

United Airlines

7 Nov

ORD4:50 p.m.Chicago O'Hare Intl

1h 55m

YYZ7:45 p.m.Toronto Pearson Intl

10 Nov

YYZ5:30 p.m.Toronto Pearson Intl

2h 09m

ORD6:39 p.m.Chicago O'Hare Intl

C$ 231

Find similar

Air Canada flights from Chicago to Canada

Our best Air Canada deals on Chicago to Canada flight tickets

Air Canada

14 Nov

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

1h 39m

YYZ4:39 p.m.Toronto Pearson Intl

16 Nov

YYZ8:15 a.m.Toronto Pearson Intl

1h 58m

ORD9:13 a.m.Chicago O'Hare Intl

C$ 206

Find similar

Air Canada

26 Sep

ORD3:45 p.m.Chicago O'Hare Intl

4h 30m

YVR6:15 p.m.Vancouver Intl

3 Oct

YVR8:45 a.m.Vancouver Intl

4h 15m

ORD3:00 p.m.Chicago O'Hare Intl

C$ 212

Find similar

Air Canada

5 Sep

ORD3:45 p.m.Chicago O'Hare Intl

4h 30m

YVR6:15 p.m.Vancouver Intl

11 Sep

YVR8:45 a.m.Vancouver Intl

4h 15m

ORD3:00 p.m.Chicago O'Hare Intl

C$ 213

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 11/10

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

Calgary

Fri 17/10

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

C$ 179

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 25/9

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

Calgary

Mon 29/9

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

C$ 182

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Fri 14/11

2:00 p.m.-4:39 p.m.

Nonstop1h 39m

Toronto Pearson Intl

Sun 16/11

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

Nonstop1h 58m

C$ 206

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Fri 26/9

3:45 p.m.-6:15 p.m.

Nonstop4h 30m

Vancouver Intl

Fri 3/10

8:45 a.m.-3:00 p.m.

Nonstop4h 15m

C$ 212

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 3/9

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

Toronto Island

Mon 8/9

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

C$ 218

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Fri 7/11

1:19 p.m.-4:02 p.m.

Nonstop1h 43m

Toronto Pearson Intl

Fri 7/11

7:40 p.m.-11:43 p.m.

1 stop5h 03m

C$ 219

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Wed 5/11

8:45 a.m.-11:35 a.m.

Nonstop3h 50m

Calgary

Tue 11/11

12:37 p.m.-5:10 p.m.

Nonstop3h 33m

C$ 223

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Fri 5/9

5:30 p.m.-12:11 a.m.

1 stop8h 41m

Vancouver Intl

Thu 11/9

8:45 a.m.-3:00 p.m.

Nonstop4h 15m

C$ 234

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Fri 5/9

5:30 p.m.-10:36 p.m.

1 stop7h 06m

Vancouver Intl

Thu 11/9

8:50 a.m.-8:11 p.m.

1 stop9h 21m

C$ 237

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 3/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Sat 6/9

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 263

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

Other information

What is the cheapest month to fly to Canada?

In general, July 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$ 322. If you’re not able to fly to Canada in July, then June is your next best option. Flight prices from Chicago to Canada during June average around C$ 359.

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

Our data shows that Saturday is the least expensive day to fly to Canada. Tickets to fly out on this day can be as low as C$ 338. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around C$ 578. 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$ 321. 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$ 462 per ticket.

What is the cheapest Chicago to Canada flight route?

Fly from Chicago Midway to Toronto Island 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$ 420 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$ 229 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 14% 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$ 66
Fastest flight time	1h 38m
Direct flights	Every day
Airports in Canada	6 airports

The best one-way flight to Canada from Chicago in the past 72 hours is C$ 66. The best round-trip flight deal from Chicago to Canada found on momondo in the last 72 hours is C$ 179.

The fastest flight from Chicago to Canada takes 1h 38m

Direct flights go from Chicago to Canada every day.

There are 6 airports near Canada: Montreal Pierre Elliott Trudeau Intl (YUL), Calgary (YYC), Vancouver Intl (YVR), Toronto Pearson Intl (YYZ), Québec City (YQB), 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 3 as of August 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) (16.58% of total bookings). The next most popular plane models are Embraer 175 (12.22%), De Havilland (Bombardier) DHC-8-400 Dash 8Q (10.14%), and Boeing 737-800 (9.54%).

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
Air Canada	PriceFrom C$ 203	Free Cancellation	Rating 7.1 9,949 reviews	Search Air Canada flights
WestJet	PriceFrom C$ 211	Free Cancellation	Rating 7.2 3,013 reviews	Search WestJet flights
United Airlines	PriceFrom C$ 242	Free Cancellation	Rating 7.4 8,916 reviews	Search United Airlines 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$ 96

Flights to Vancouverfrom C$ 67

Flights to Montrealfrom C$ 227

Flights to Calgaryfrom C$ 72

Flights to Ottawafrom C$ 200

Flights to Winnipegfrom C$ 114

Flights to Halifaxfrom C$ 128

Flights to Kelownafrom C$ 89

Flights to Saskatoonfrom C$ 121

Flights to Reginafrom C$ 112

Flights to St. John'sfrom C$ 251

Flights to Québec Cityfrom C$ 292

Cheap flights from Chicago to Canada from C$ 66

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 29/9. 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

United Airlines flights from Chicago to Canada

Our best United 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 Midway to Toronto Island 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 14% 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 Porter Airlines are the most popular carriers operating from Chicago to Canada

Which airlines fly to Canada?

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

109 flights are operational daily from Chicago to Canada as of August 2025. The most popular departure time for this route is 8:00p.m., with 36% of flights per day taking off in the afternoon.

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

As of August 2025, 766 flights take off from Chicago and land in Canada each week. The most common flight departure day for this route is Wed, with 17% 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