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 32% 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.

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

The number of flights available between Chicago and Canada is 766 per week as of August 2025. The most frequent departure day is Wed, with 17% of weekly flights leaving on this day.

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

As of August 2025, there are 109 flights per day flying from Chicago to Canada. The most common time of day flights depart is 8:00PM, with 36% of flights taking off in the afternoon.

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

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 August 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.

$48 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 pm - 8:19 pmORD-YYC

3h 49mnonstop

12:15 pm - 4:43 pmYYC-ORD

3h 28mnonstop

$130WestJet

Find Deal

Sat, Oct 11 - Fri, Oct 17

5:30 pm - 8:19 pmORD-YYC

3h 49mnonstop

12:15 pm - 4:43 pmYYC-ORD

3h 28mnonstop

$132WestJet

Find Deal

Thu, Sep 25 - Mon, Sep 29

2:00 pm - 4:39 pmORD-YYZ

1h 39mnonstop

8:15 am - 9:13 amYYZ-ORD

1h 58mnonstop

$150Air Canada

Find Deal

Fri, Nov 14 - Sun, Nov 16

8:48 am - 2:14 pmORD-YYZ

4h 26m1 stop

5:30 pm - 6:39 pmYYZ-ORD

2h 09mnonstop

$153United Airlines

Find Deal

Sat, Nov 1 - Sat, Nov 1

3:45 pm - 6:15 pmORD-YVR

4h 30mnonstop

8:45 am - 3:00 pmYVR-ORD

4h 15mnonstop

$154Air Canada

Find Deal

Fri, Sep 26 - Fri, Oct 3

5:20 pm - 8:02 pmMDW-YTZ

1h 42mnonstop

3:35 pm - 4:24 pmYTZ-MDW

1h 49mnonstop

$158Porter Airlines

Find Deal

Wed, Sep 3 - Mon, Sep 8

1:19 pm - 4:02 pmORD-YYZ

1h 43mnonstop

6:40 pm - 11:34 pmYYZ-ORD

5h 54m1 stop

$159United Airlines

Find Deal

Sun, Nov 2 - Sun, Nov 2

6:10 am - 11:59 amORD-YYZ

4h 49m1 stop

3:11 pm - 4:05 pmYYZ-ORD

1h 54mnonstop

$173American Airlines

Find Deal

Sat, Oct 4 - Sat, Oct 4

8:30 pm - 11:19 pmORD-YYC

3h 49mnonstop

6:29 am - 10:54 amYYC-ORD

3h 25mnonstop

$181American Airlines

Find Deal

Fri, Sep 26 - Tue, Sep 30

9:35 am - 12:17 pmMDW-YTZ

1h 42mnonstop

7:50 am - 8:39 amYTZ-MDW

1h 49mnonstop

$191Porter Airlines

Find Deal

Wed, Sep 3 - Sat, Sep 6

United Airlines flights from Chicago to Canada

Our best United Airlines deals on Chicago to Canada flight tickets

United Airlines

Nov 1

ORD8:48 amChicago O'Hare Intl

4h 26m

1 stop

YYZ2:14 pmToronto Pearson Intl

Nov 1

YYZ5:30 pmToronto Pearson Intl

2h 09m

ORD6:39 pmChicago O'Hare Intl

$153

Find similar

United Airlines

Nov 2

ORD1:19 pmChicago O'Hare Intl

1h 43m

YYZ4:02 pmToronto Pearson Intl

Nov 2

YYZ6:40 pmToronto Pearson Intl

5h 54m

1 stop

ORD11:34 pmChicago O'Hare Intl

$159

Find similar

United Airlines

Nov 25

ORD8:45 amChicago O'Hare Intl

3h 50m

YYC11:35 amCalgary

Dec 2

YYC12:35 pmCalgary

3h 35m

ORD5:10 pmChicago O'Hare Intl

$162

Find similar

Air Canada flights from Chicago to Canada

Our best Air Canada deals on Chicago to Canada flight tickets

Air Canada

Nov 14

ORD2:00 pmChicago O'Hare Intl

1h 39m

YYZ4:39 pmToronto Pearson Intl

Nov 16

YYZ8:15 amToronto Pearson Intl

1h 58m

ORD9:13 amChicago O'Hare Intl

$150

Find similar

Air Canada

Sep 26

ORD3:45 pmChicago O'Hare Intl

4h 30m

YVR6:15 pmVancouver Intl

Oct 3

YVR8:45 amVancouver Intl

4h 15m

ORD3:00 pmChicago O'Hare Intl

$154

Find similar

Air Canada

Sep 5

ORD3:45 pmChicago O'Hare Intl

4h 30m

YVR6:15 pmVancouver Intl

Sep 11

YVR8:45 amVancouver Intl

4h 15m

ORD3:00 pmChicago O'Hare Intl

$155

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 10/11

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

Fri 10/17

12:15 pm-4:43 pm

Nonstop3h 28m

$130

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 9/25

5:30 pm-8:19 pm

Nonstop3h 49m

Calgary

Mon 9/29

12:15 pm-4:43 pm

Nonstop3h 28m

$132

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Fri 11/14

2:00 pm-4:39 pm

Nonstop1h 39m

Toronto Pearson Intl

Sun 11/16

8:15 am-9:13 am

Nonstop1h 58m

$150

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 11/1

8:48 am-2:14 pm

1 stop4h 26m

Toronto Pearson Intl

Sat 11/1

5:30 pm-6:39 pm

Nonstop2h 09m

$153

ChicagoVancouver

ORD - YVR

ORDYVR

Chicago O'Hare Intl

Fri 9/26

3:45 pm-6:15 pm

Nonstop4h 30m

Vancouver Intl

Fri 10/3

8:45 am-3:00 pm

Nonstop4h 15m

$154

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 9/3

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

Mon 9/8

3:35 pm-4:24 pm

Nonstop1h 49m

$158

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sun 11/2

1:19 pm-4:02 pm

Nonstop1h 43m

Toronto Pearson Intl

Sun 11/2

6:40 pm-11:34 pm

1 stop5h 54m

$159

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 10/4

6:10 am-11:59 am

1 stop4h 49m

Toronto Pearson Intl

Sat 10/4

3:11 pm-4:05 pm

Nonstop1h 54m

$173

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Fri 9/26

8:30 pm-11:19 pm

Nonstop3h 49m

Calgary

Tue 9/30

6:29 am-10:54 am

Nonstop3h 25m

$181

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 9/3

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sat 9/6

7:50 am-8:39 am

Nonstop1h 49m

$191

Flights are sorted by cheapest round-trip flights first.

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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

Other information

What is the cheapest month to fly to Canada?

If you aren’t able to travel during the month of July, then book flights to Canada from Chicago during June instead. Flights to Canada in June, while not as cheap as those in July, still average around $261.

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 $622. 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 $562. 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 $762.

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 $305 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	$48
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 $48. The best round-trip flight deal from Chicago to Canada found on momondo in the last 72 hours is $130.

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 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 August 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 16.58% of all bookings. The subsequent popular models are Embraer 175 at 12.22%, De Havilland (Bombardier) DHC-8-400 Dash 8Q at 10.14%, and Boeing 737-800 at 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
United Airlines	PriceFrom $92	Free Cancellation	Rating 7.4 8,916 reviews	Search United Airlines flights
Air Canada	PriceFrom $97	Free Cancellation	Rating 7.1 9,949 reviews	Search Air Canada flights
Delta	PriceFrom $108	Free Cancellation	Rating 8.0 7,980 reviews	Search Delta flights
WestJet	PriceFrom $143	Free Cancellation	Rating 7.2 3,013 reviews	Search WestJet flights
Porter Airlines	PriceFrom $187	Free Cancellation	Rating 8.0 332 reviews	Search Porter Airlines flights
American Airlines	PriceFrom $192	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Alaska Airlines	PriceFrom $464	Free Cancellation	Rating 8.0 10,000 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 $93

Flights to Vancouverfrom $81

Flights to Montrealfrom $175

Flights to Calgaryfrom $136

Flights to Ottawafrom $198

Flights to Halifaxfrom $170

Flights to Winnipegfrom $180

Flights to Québec Cityfrom $153

Flights to Saskatoonfrom $129

Flights to Kelownafrom $190

Flights to St. John'sfrom $267

Flights to Reginafrom $242

Cheap flights from Chicago to Canada from $48

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 9/29. 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

Trusted and free

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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?

If you aren’t able to travel during the month of July, then book flights to Canada from Chicago during June instead. Flights to Canada in June, while not as cheap as those in July, still average around $261.

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 $622. 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 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?

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?

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

What airlines fly to Canada?

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

As of August 2025, there are 109 flights per day flying from Chicago to Canada. The most common time of day flights depart is 8:00PM, with 36% of flights taking off in the afternoon.

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

The number of flights available between Chicago and Canada is 766 per week as of August 2025. The most frequent departure day is Wed, with 17% 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