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

The number of flights available between Canada and Chicago is 95 per day as of January 2026. The most frequent departure time is 6:00a.m., with 47% of daily flights leaving in the afternoon.

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 54% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

According to our data, United Airlines has had the least delays on this route over the last 12 months, with about 6% of their flights experiencing any sort of delay.

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

665 flights are operational weekly from Canada to Chicago as of January 2026. The most popular departure day for this route is Mon, with 16% of flights per week taking off on this day.

How often are flights from Canada to Chicago delayed?

Historically, on average around 11% of flights between Canada and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 139 minutes.

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

Generally, flights departing at night 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. Saturday has historically seen more delays on average compared to the rest of the week.

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

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

How long does it take to fly to Chicago?

Flight times from Canada to Chicago vary, but if you’re flying out of Toronto and flying into Chicago O'Hare Intl Airport (one of the most popular routes), then the duration is 1h 55m on average. Another popular route from Canada to Chicago is flying from Montreal to Chicago O'Hare Intl Airport, which will take roughly 2h 35m. Keep in mind that layovers or delays could extend your travel time.

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 7 as of January 2026.

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$ 139 Cheap Flights from Canada to Chicago in 2026

1 adult

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Canada to Chicago

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Canada to Chicago

Enter your travel dates to find the best prices.

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

YYC

ORD

3h 35mdirect

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

ORD

YYC

3h 55mdirect

C$ 205WestJet

Fri, 27 Feb - Fri, 6 Mar

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

YYC

ORD

3h 35mdirect

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

ORD

YYC

3h 55mdirect

C$ 229WestJet

Fri, 30 Jan - Mon, 2 Feb

5:30 a.m. - 3:10 p.m.

YYC

ORD

8h 40m

1 stop

3:55 p.m. - 11:59 p.m.

ORD

YYC

9h 04m

1 stop

C$ 251Air Canada

Sat, 28 Feb - Sat, 7 Mar

9:15 a.m. - 2:25 p.m.

YUL

ORD

6h 10m

1 stop

7:10 a.m. - 1:28 p.m.

ORD

YUL

5h 18m

1 stop

C$ 254United Airlines

Wed, 11 Feb - Wed, 18 Feb

9:25 a.m. - 11:06 a.m.

YUL

ORD

2h 41mdirect

3:35 p.m. - 6:40 p.m.

ORD

YUL

2h 05mdirect

C$ 255Air Canada

Thu, 5 Feb - Sun, 8 Feb

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

YUL

MDW

4h 20m

1 stop

11:00 a.m. - 4:30 p.m.

MDW

YUL

4h 30m

1 stop

C$ 255Porter Airlines

Thu, 26 Feb - Thu, 5 Mar

2:30 p.m. - 3:20 p.m.

YTZ

MDW

1h 50mdirect

4:15 p.m. - 6:57 p.m.

MDW

YTZ

1h 42mdirect

C$ 257Porter Airlines

Sun, 15 Feb - Wed, 18 Mar

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

YYC

ORD

14h 17m

1 stop

12:55 p.m. - 9:48 p.m.

ORD

YYC

9h 53m

1 stop

C$ 257United Airlines

Tue, 31 Mar - Wed, 8 Apr

7:00 a.m. - 1:50 p.m.

YYZ

ORD

7h 50m

1 stop

6:31 p.m. - 9:23 p.m.

ORD

YYZ

1h 52mdirect

C$ 261American Airlines

Thu, 5 Feb - Tue, 10 Feb

6:00 a.m. - 7:15 a.m.

YYZ

ORD

2h 15mdirect

6:40 a.m. - 3:30 p.m.

ORD

YYZ

7h 50m

1 stop

C$ 265American Airlines

Wed, 18 Feb - Fri, 20 Feb

American Airlines flights from Canada to Chicago

Our best American Airlines deals on Canada to Chicago flight tickets

American Airlines

12 Feb

YUL2:25 p.m.Montreal Pierre Elliott Trudeau Intl

10h 51m

1 stop

ORD12:16 a.m.Chicago O'Hare Intl

17 Feb

ORD8:23 a.m.Chicago O'Hare Intl

5h 59m

1 stop

YUL3:22 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 261

American Airlines

18 Feb

YYZ6:00 a.m.Toronto Pearson Intl

2h 15m

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

20 Feb

ORD6:40 a.m.Chicago O'Hare Intl

7h 50m

1 stop

YYZ3:30 p.m.Toronto Pearson Intl

C$ 265

American Airlines

5 Feb

YYZ5:15 p.m.Toronto Pearson Intl

6h 19m

1 stop

ORD10:34 p.m.Chicago O'Hare Intl

10 Feb

ORD9:00 a.m.Chicago O'Hare Intl

5h 30m

1 stop

YYZ3:30 p.m.Toronto Pearson Intl

C$ 275

United Airlines flights from Canada to Chicago

Our best United Airlines deals on Canada to Chicago flight tickets

United Airlines

11 Feb

YUL9:15 a.m.Montreal Pierre Elliott Trudeau Intl

6h 10m

1 stop

ORD2:25 p.m.Chicago O'Hare Intl

18 Feb

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

5h 18m

1 stop

YUL1:28 p.m.Montreal Pierre Elliott Trudeau Intl

C$ 254

United Airlines

31 Mar

YYC6:00 a.m.Calgary

14h 17m

1 stop

ORD9:17 p.m.Chicago O'Hare Intl

8 Apr

ORD12:55 p.m.Chicago O'Hare Intl

9h 53m

1 stop

YYC9:48 p.m.Calgary

C$ 257

United Airlines

4 Feb

YYZ3:30 p.m.Toronto Pearson Intl

1h 58m

ORD4:28 p.m.Chicago O'Hare Intl

12 Feb

ORD7:07 a.m.Chicago O'Hare Intl

1h 51m

YYZ9:58 a.m.Toronto Pearson Intl

C$ 262

Fly from

Fly to

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 27/2

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

Nonstop3h 35m

Chicago O'Hare Intl

Fri 6/3

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

Nonstop3h 55m

C$ 205

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 30/1

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

Nonstop3h 35m

Chicago O'Hare Intl

Mon 2/2

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

Nonstop3h 55m

C$ 229

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Sat 28/2

5:30 a.m.-3:10 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Sat 7/3

3:55 p.m.-11:59 p.m.

1 stop9h 04m

C$ 251

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Wed 11/2

9:15 a.m.-2:25 p.m.

1 stop6h 10m

Chicago O'Hare Intl

Wed 18/2

7:10 a.m.-1:28 p.m.

1 stop5h 18m

C$ 254

MontrealChicago

YUL - ORD

YULORD

Montreal Pierre Elliott Trudeau Intl

Thu 5/2

9:25 a.m.-11:06 a.m.

Nonstop2h 41m

Chicago O'Hare Intl

Sun 8/2

3:35 p.m.-6:40 p.m.

Nonstop2h 05m

C$ 255

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 26/2

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

1 stop4h 20m

Chicago Midway

Thu 5/3

11:00 a.m.-4:30 p.m.

1 stop4h 30m

C$ 255

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 15/2

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Wed 18/3

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 257

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 31/3

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

1 stop14h 17m

Chicago O'Hare Intl

Wed 8/4

12:55 p.m.-9:48 p.m.

1 stop9h 53m

C$ 257

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 5/2

7:00 a.m.-1:50 p.m.

1 stop7h 50m

Chicago O'Hare Intl

Tue 10/2

6:31 p.m.-9:23 p.m.

Nonstop1h 52m

C$ 261

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 18/2

6:00 a.m.-7:15 a.m.

Nonstop2h 15m

Chicago O'Hare Intl

Fri 20/2

6:40 a.m.-3:30 p.m.

1 stop7h 50m

C$ 265

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

Delays

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$ 312.

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$ 583. 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$ 1,039. 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$ 646. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,084 per ticket.

What is the cheapest Canada to Chicago flight route?

Fly from Vancouver Intl to Chicago O'Hare Intl 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$ 398 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$ 271 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$ 199
Fastest flight time	1h 49m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Canada in the past 72 hours is C$ 199. The best round-trip flight deal from Canada to Chicago found on momondo in the last 72 hours is C$ 320.

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

Direct flights go from Canada to Chicago every day.

There are 3 airports in Chicago. From Canada there are direct flights to 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 7 as of January 2026.
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 15.07% of the total bookings. Other popular models include De Havilland (Bombardier) DHC-8-400 Dash 8Q with 10.46%, Embraer 170 with 9.65%, and Embraer 195 E2 with 7.94%.

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$ 150	Free Cancellation	Rating 7.1 10,619 reviews	Search Air Canada flights
Delta	PriceFrom C$ 177	Free Cancellation	Rating 7.9 8,040 reviews	Search Delta flights
WestJet	PriceFrom C$ 177	Free Cancellation	Rating 7.2 3,240 reviews	Search WestJet flights
American Airlines	PriceFrom C$ 186	Free Cancellation	Rating 7.2 11,119 reviews	Search American Airlines flights
United Airlines	PriceFrom C$ 188	Free Cancellation	Rating 7.4 9,156 reviews	Search United Airlines flights
Porter Airlines	PriceFrom C$ 190	Free Cancellation	Rating 8.0 407 reviews	Search Porter Airlines flights
Alaska Airlines	PriceFrom C$ 389	Free Cancellation	Rating 7.9 11,701 reviews	Search Alaska 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.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Fri 13/2

Fri 20/2

Email me momondo's favourite deals

By creating a price alert you accept our terms of use and privacy policy.

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

Popular Cities in the United States

Flights to Fort Lauderdalefrom C$ 147

Flights to Orlandofrom C$ 174

Flights to New Yorkfrom C$ 205

Flights to Las Vegasfrom C$ 129

Flights to Los Angelesfrom C$ 142

Flights to Miamifrom C$ 260

Flights to San Franciscofrom C$ 133

Flights to Honolulufrom C$ 286

Flights to Phoenixfrom C$ 147

Flights to Tampafrom C$ 180

Flights to Houstonfrom C$ 247

Flights to Seattlefrom C$ 151

Cheap flights from Canada to Chicago from C$ 139

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 9/3. 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

American Airlines flights from Canada to Chicago

Our best American Airlines deals on Canada to Chicago flight tickets

United Airlines flights from Canada to Chicago

Our best United Airlines deals on Canada to Chicago flight tickets

momondo Fare Finder

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

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$ 312.

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 Vancouver Intl to Chicago O'Hare Intl 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?

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

Which airlines fly to Chicago?

How often are flights from Canada to Chicago delayed?

Historically, on average around 11% of flights between Canada and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 139 minutes.

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

Generally, flights departing at night 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. Saturday has historically seen more delays on average compared to the rest of the week.

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

According to our data, United Airlines has had the least delays on this route over the last 12 months, with about 6% of their flights experiencing any sort of delay.

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

The number of flights available between Canada and Chicago is 95 per day as of January 2026. The most frequent departure time is 6:00a.m., with 47% of daily flights leaving in the afternoon.

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

665 flights are operational weekly from Canada to Chicago as of January 2026. The most popular departure day for this route is Mon, with 16% 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