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

The number of flights available between Canada and Chicago is 125 per day as of September 2025. The most frequent departure time is 6:00a.m., with 49% of daily flights leaving at noon.

How long does it take to fly to Chicago?

Flight times from Canada to Chicago vary, but if you’re flying out of Montreal and flying into Chicago O'Hare Intl Airport (one of the most popular routes), then the duration is 2h 35m on average. Another popular route from Canada to Chicago is flying from Calgary to Chicago O'Hare Intl Airport, which will take roughly 3h 25m. Keep in mind that layovers or delays could extend your travel time.

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

880 flights are operational weekly from Canada to Chicago as of September 2025. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.

Which airlines fly to Chicago?

Air Canada, United Airlines and WestJet are the top three most popular airlines that fly to Chicago from Canada according to our data. Air Canada is the first choice among our users, with 57% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

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

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

Prices for flights from Canada to Chicago were last updated today.

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

The number of operators available for flights from Canada to Chicago is 6 as of September 2025.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Canada to Chicago.

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

The necessary travel and health documents for your Chicago 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$ 136 Cheap Flights from Canada to Chicago in 2025/26

1 adult

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Find the cheapest flights from Canada to Chicago

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Canada to Chicago

7:00 a.m. - 4:43 p.m.YVR-ORD

7h 43m1 stop

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

7h 06m1 stop

C$ 205WestJet

Find Deal

Fri, 17 Oct - Sat, 18 Oct

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

3h 28mdirect

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

3h 49mdirect

C$ 208WestJet

Find Deal

Fri, 17 Oct - Sun, 19 Oct

8:30 a.m. - 2:41 p.m.YVR-ORD

4h 11mdirect

3:40 p.m. - 6:15 p.m.ORD-YVR

4h 35mdirect

C$ 230Air Canada

Find Deal

Sat, 1 Nov - Sat, 8 Nov

1:45 p.m. - 8:04 p.m.YVR-ORD

4h 19mdirect

8:51 a.m. - 11:33 a.m.ORD-YVR

4h 42mdirect

C$ 231United Airlines

Find Deal

Tue, 30 Sep - Sun, 12 Oct

12:35 p.m. - 5:10 p.m.YYC-ORD

3h 35mdirect

7:10 a.m. - 9:53 p.m.ORD-YYC

15h 43m1 stop

C$ 237United Airlines

Find Deal

Thu, 11 Dec - Mon, 15 Dec

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

8h 35m1 stop

2:00 p.m. - 8:39 p.m.ORD-YYC

7h 39m1 stop

C$ 241Air Canada

Find Deal

Sat, 1 Nov - Sat, 8 Nov

1:28 p.m. - 7:43 p.m.YVR-ORD

4h 15mdirect

9:53 a.m. - 12:33 p.m.ORD-YVR

4h 40mdirect

C$ 242American Airlines

Find Deal

Fri, 24 Oct - Mon, 27 Oct

12:54 p.m. - 9:49 a.m.YYC-ORD

19h 55m1 stop

5:00 a.m. - 11:59 a.m.ORD-YYC

7h 59m1 stop

C$ 270American Airlines

Find Deal

Fri, 24 Oct - Wed, 29 Oct

1:10 p.m. - 4:24 p.m.YUL-MDW

4h 14m1 stop

9:35 a.m. - 4:00 p.m.MDW-YUL

5h 25m1 stop

C$ 322Porter Airlines

Find Deal

Fri, 17 Oct - Mon, 20 Oct

6:45 a.m. - 10:05 a.m.YUL-MDW

4h 20m1 stop

4:15 p.m. - 10:45 p.m.MDW-YUL

5h 30m1 stop

C$ 323Porter Airlines

Find Deal

Thu, 30 Oct - Thu, 6 Nov

United Airlines flights from Canada to Chicago

Our best United Airlines deals on Canada to Chicago flight tickets

United Airlines

30 Sep

YVR1:45 p.m.Vancouver Intl

4h 19m

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

12 Oct

ORD8:51 a.m.Chicago O'Hare Intl

4h 42m

YVR11:33 a.m.Vancouver Intl

C$ 231

Find similar

United Airlines

11 Dec

YYC12:35 p.m.Calgary

3h 35m

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

15 Dec

ORD7:10 a.m.Chicago O'Hare Intl

15h 43m

1 stop

YYC9:53 p.m.Calgary

C$ 237

Find similar

United Airlines

1 Oct

YVR1:45 p.m.Vancouver Intl

4h 19m

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

7 Oct

ORD8:51 a.m.Chicago O'Hare Intl

4h 42m

YVR11:33 a.m.Vancouver Intl

C$ 238

Find similar

Lufthansa flights from Canada to Chicago

Our best Lufthansa deals on Canada to Chicago flight tickets

Lufthansa

25 Sep

YVR1:45 p.m.Vancouver Intl

4h 19m

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

1 Oct

ORD8:51 a.m.Chicago O'Hare Intl

4h 42m

YVR11:33 a.m.Vancouver Intl

C$ 243

Find similar

Lufthansa

25 Sep

YVR1:45 p.m.Vancouver Intl

4h 19m

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

1 Oct

ORD2:53 p.m.Chicago O'Hare Intl

8h 56m

1 stop

YVR9:49 p.m.Vancouver Intl

C$ 257

Find similar

Lufthansa

25 Sep

YVR11:00 a.m.Vancouver Intl

7h 18m

1 stop

ORD8:18 p.m.Chicago O'Hare Intl

1 Oct

ORD5:01 a.m.Chicago O'Hare Intl

6h 50m

1 stop

YVR9:51 a.m.Vancouver Intl

C$ 281

Find similar

Fly from

Fly to

Route

Depart

Return

Price

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 17/10

7:00 a.m.-4:43 p.m.

1 stop7h 43m

Chicago O'Hare Intl

Sat 18/10

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

1 stop7h 06m

C$ 205

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 17/10

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

Nonstop3h 28m

Chicago O'Hare Intl

Sun 19/10

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

Nonstop3h 49m

C$ 208

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Sat 1/11

8:30 a.m.-2:41 p.m.

Nonstop4h 11m

Chicago O'Hare Intl

Sat 8/11

3:40 p.m.-6:15 p.m.

Nonstop4h 35m

C$ 230

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Tue 30/9

1:45 p.m.-8:04 p.m.

Nonstop4h 19m

Chicago O'Hare Intl

Sun 12/10

8:51 a.m.-11:33 a.m.

Nonstop4h 42m

C$ 231

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 11/12

12:35 p.m.-5:10 p.m.

Nonstop3h 35m

Chicago O'Hare Intl

Mon 15/12

7:10 a.m.-9:53 p.m.

1 stop15h 43m

C$ 237

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 1/11

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

1 stop8h 35m

Chicago O'Hare Intl

Sat 8/11

2:00 p.m.-8:39 p.m.

1 stop7h 39m

C$ 241

VancouverChicago

YVR - ORD

YVRORD

Vancouver Intl

Fri 24/10

1:28 p.m.-7:43 p.m.

Nonstop4h 15m

Chicago O'Hare Intl

Mon 27/10

9:53 a.m.-12:33 p.m.

Nonstop4h 40m

C$ 242

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 24/10

12:54 p.m.-9:49 a.m.

1 stop19h 55m

Chicago O'Hare Intl

Wed 29/10

5:00 a.m.-11:59 a.m.

1 stop7h 59m

C$ 270

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 17/10

1:10 p.m.-4:24 p.m.

1 stop4h 14m

Chicago Midway

Mon 20/10

9:35 a.m.-4:00 p.m.

1 stop5h 25m

C$ 322

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 30/10

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

Thu 6/11

4:15 p.m.-10:45 p.m.

1 stop5h 30m

C$ 323

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 Canada to Chicago

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 Chicago?

The month of June is another great option to travel to Chicago, with average flight prices from Canada averaging around C$ 310.

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

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 643. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 1,148. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

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

In the evening is the cheapest time of day to fly from Canada to Chicago when you can find flight prices for as low as C$ 620. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,158 per ticket.

What is the cheapest Canada to Chicago flight route?

Fly from Toronto Island to Chicago Midway for the best Canada - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from Canada when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago 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 Chicago from Canada for as low as C$ 297 on momondo.

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

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

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

Cheap Canada to Chicago flight deals and tips

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

Best price found	C$ 210
Fastest flight time	1h 49m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Canada in the past 72 hours is C$ 210. The best round-trip flight deal from Canada to Chicago found on momondo in the last 72 hours is C$ 240.

The fastest flight from Canada to Chicago takes 1h 49m

Direct flights go from Canada to Chicago every day.

There is 1 airport near Chicago: Chicago Midway (MDW)

Search flight deals

When did momondo last update prices for flights from Canada to Chicago?
Prices for flights from Canada to Chicago were last updated today.
How many operators does momondo search for flights from Canada to Chicago?
The number of operators available for flights from Canada to Chicago is 6 as of September 2025.
How old do you have to be to fly from Canada to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Canada to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago 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 Canada to Chicago?
Based on momondo bookings for flights between Canada and Chicago, the leading plane model is Embraer 175 (Enhanced Winglets), making up 16.57% of the total bookings. Other popular models include De Havilland (Bombardier) DHC-8-400 Dash 8Q with 14.40%, Boeing 737-800 with 11.73%, and Boeing 737 MAX 8 with 8.94%.

Best airlines flying from Canada to Chicago

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

Airline	Rating	Free Cancellation	Price
Air Canada	PriceFrom C$ 149	Free Cancellation	Rating 7.1 10,000 reviews	Search Air Canada flights
WestJet	PriceFrom C$ 176	Free Cancellation	Rating 7.2 3,095 reviews	Search WestJet flights
American Airlines	PriceFrom C$ 177	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Delta	PriceFrom C$ 183	Free Cancellation	Rating 7.9 7,961 reviews	Search Delta flights
Porter Airlines	PriceFrom C$ 195	Free Cancellation	Rating 7.9 365 reviews	Search Porter Airlines flights
United Airlines	PriceFrom C$ 208	Free Cancellation	Rating 7.4 8,926 reviews	Search United Airlines flights

Munster

Hammond

Merrillville

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Canada to Chicago . Millions of users trust and use momondo every year so you are in good hands.

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

Yes. momondo enables you to select and highlight flights to Chicago from Canada with this policy.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Canada to Chicago.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Canada and alert you when they change.

An easier way to manage your Chicago 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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Fri 17/10

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

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Cheap flights from Canada to Chicago from C$ 136

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Canada to Chicago departing on 17/10. 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 Canada to Chicago

Recent round-trip flight deals from Canada to Chicago

Recent one-way flight deals from Canada to Chicago

Recent last minute flight deals from Canada to Chicago

Recent direct flight deals from Canada to Chicago

United Airlines flights from Canada to Chicago

Our best United Airlines deals on Canada to Chicago flight tickets

Lufthansa flights from Canada to Chicago

Our best Lufthansa deals on Canada to Chicago flight tickets

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

See travel insights to Chicago from

How to get the cheapest flight ticket from Canada to Chicago

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 Chicago?

The month of June is another great option to travel to Chicago, with average flight prices from Canada averaging around C$ 310.

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

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

What is the cheapest Canada to Chicago flight route?

Fly from Toronto Island to Chicago Midway for the best Canada - Chicago flight prices

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

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

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

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

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

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

Which airlines fly to Chicago?

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

The number of flights available between Canada and Chicago is 125 per day as of September 2025. The most frequent departure time is 6:00a.m., with 49% of daily flights leaving at noon.

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

880 flights are operational weekly from Canada to Chicago as of September 2025. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.

How long does it take to fly to Chicago?

Cheap Canada to Chicago flight deals and tips

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

Best price found

Fastest flight time

Direct flights

Airports in Chicago

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

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

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

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

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

Best airlines flying from Canada to Chicago

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

Travelling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago 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 the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago