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

The number of flights available between Canada and Chicago is 96 per day as of December 2025. The most frequent departure time is 6:00AM, with 47% of daily flights leaving in the afternoon.

How long does it take to fly to Chicago?

Average flight duration from Canada to Chicago depends on which airport you fly into and out of. Flying from Toronto to Chicago O'Hare Intl Airport is 1h 55m on average, while flying from Montreal to Chicago O'Hare Intl Airport is 2h 35m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

As of December 2025, there are 678 flights per week flying from Canada to Chicago. The most common day of the week flights depart is Fri, with 17% of flights taking off on this day.

What day of the week experiences the fewest flight delays on this route?

Tuesday is statistically the day of the week which experiences the fewest number of 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?

WestJet, Air Canada, and Porter Airlines are the most popular carriers operating from Canada 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.

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

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

What airlines fly to Chicago?

Air Canada, United Airlines and American Airlines 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 45% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

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?

As of December 2025, there are 5 operators available to choose from for flights from Canada to Chicago.

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

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 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.

$93 Cheap Flights from Canada to Chicago in 2025/26

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? 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.

12:15 pm - 4:43 pm

YYC

ORD

3h 28mnonstop

5:30 pm - 8:19 pm

ORD

YYC

3h 49mnonstop

$168WestJet

Thu, May 21 - Sat, May 30

12:15 pm - 4:43 pm

YYC

ORD

3h 28mnonstop

5:30 pm - 8:19 pm

ORD

YYC

3h 49mnonstop

$176WestJet

Fri, May 15 - Mon, May 18

5:35 am - 3:10 pm

YYC

ORD

8h 35m1 stop

3:55 pm - 12:14 am

ORD

YYC

9h 19m1 stop

$179Air Canada

Thu, Jan 22 - Wed, Jan 28

8:15 am - 9:13 am

YYZ

ORD

1h 58mnonstop

3:55 pm - 6:34 pm

ORD

YYZ

1h 39mnonstop

$182Air Canada

Wed, Feb 4 - Wed, Feb 11

9:20 am - 10:10 am

YTZ

MDW

1h 50mnonstop

11:05 am - 1:47 pm

MDW

YTZ

1h 42mnonstop

$182Porter Airlines

Tue, Feb 17 - Mon, Feb 23

9:15 am - 10:05 am

YTZ

MDW

1h 50mnonstop

11:00 am - 1:42 pm

MDW

YTZ

1h 42mnonstop

$183Porter Airlines

Thu, Jan 29 - Wed, Feb 4

10:59 am - 4:09 pm

YYZ

ORD

6h 10m1 stop

6:42 am - 3:30 pm

ORD

YYZ

7h 48m1 stop

$189American Airlines

Thu, Feb 5 - Sun, Feb 8

6:15 am - 11:59 pm

YYC

ORD

16h 44m1 stop

8:45 am - 11:35 am

ORD

YYC

3h 50mnonstop

$190United Airlines

Tue, Feb 3 - Wed, Feb 4

6:00 am - 7:15 am

YYZ

ORD

2h 15mnonstop

1:20 pm - 4:03 pm

ORD

YYZ

1h 43mnonstop

$195American Airlines

Thu, Feb 5 - Sun, Feb 8

2:13 pm - 11:59 pm

YYC

ORD

8h 46m1 stop

8:45 am - 11:35 am

ORD

YYC

3h 50mnonstop

$198United Airlines

Tue, Feb 3 - Wed, Feb 4

WestJet flights from Canada to Chicago

Our best WestJet deals on Canada to Chicago flight tickets

WestJet

May 21

YYC12:15 pmCalgary

3h 28m

ORD4:43 pmChicago O'Hare Intl

May 30

ORD5:30 pmChicago O'Hare Intl

3h 49m

YYC8:19 pmCalgary

$168

Find similar

WestJet

May 15

YYC12:15 pmCalgary

3h 28m

ORD4:43 pmChicago O'Hare Intl

May 18

ORD5:30 pmChicago O'Hare Intl

3h 49m

YYC8:19 pmCalgary

$176

Find similar

WestJet

May 15

YYC12:15 pmCalgary

3h 28m

ORD4:43 pmChicago O'Hare Intl

May 18

ORD5:30 pmChicago O'Hare Intl

3h 49m

YYC8:19 pmCalgary

$187

Find similar

American Airlines flights from Canada to Chicago

Our best American Airlines deals on Canada to Chicago flight tickets

American Airlines

Feb 5

YYZ10:59 amToronto Pearson Intl

6h 10m

1 stop

ORD4:09 pmChicago O'Hare Intl

Feb 8

ORD6:42 amChicago O'Hare Intl

7h 48m

1 stop

YYZ3:30 pmToronto Pearson Intl

$189

Find similar

American Airlines

Feb 7

YUL2:25 pmMontreal Pierre Elliott Trudeau Intl

19h 40m

1 stop

ORD9:05 amChicago O'Hare Intl

Feb 10

ORD9:54 amChicago O'Hare Intl

4h 26m

1 stop

YUL3:20 pmMontreal Pierre Elliott Trudeau Intl

$192

Find similar

American Airlines

Feb 5

YYZ6:00 amToronto Pearson Intl

2h 15m

ORD7:15 amChicago O'Hare Intl

Feb 8

ORD1:20 pmChicago O'Hare Intl

1h 43m

YYZ4:03 pmToronto Pearson Intl

$195

Find similar

Fly from

Fly to

Route

Depart

Return

Price

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 5/21

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

Sat 5/30

5:30 pm-8:19 pm

Nonstop3h 49m

$168

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Fri 5/15

12:15 pm-4:43 pm

Nonstop3h 28m

Chicago O'Hare Intl

Mon 5/18

5:30 pm-8:19 pm

Nonstop3h 49m

$176

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Thu 1/22

5:35 am-3:10 pm

1 stop8h 35m

Chicago O'Hare Intl

Wed 1/28

3:55 pm-12:14 am

1 stop9h 19m

$179

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 2/4

8:15 am-9:13 am

Nonstop1h 58m

Chicago O'Hare Intl

Wed 2/11

3:55 pm-6:34 pm

Nonstop1h 39m

$182

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 2/17

9:20 am-10:10 am

Nonstop1h 50m

Chicago Midway

Mon 2/23

11:05 am-1:47 pm

Nonstop1h 42m

$182

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 1/29

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Wed 2/4

11:00 am-1:42 pm

Nonstop1h 42m

$183

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/5

10:59 am-4:09 pm

1 stop6h 10m

Chicago O'Hare Intl

Sun 2/8

6:42 am-3:30 pm

1 stop7h 48m

$189

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 2/3

6:15 am-11:59 pm

1 stop16h 44m

Chicago O'Hare Intl

Wed 2/4

8:45 am-11:35 am

Nonstop3h 50m

$190

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/5

6:00 am-7:15 am

Nonstop2h 15m

Chicago O'Hare Intl

Sun 2/8

1:20 pm-4:03 pm

Nonstop1h 43m

$195

CalgaryChicago

YYC - ORD

YYCORD

Calgary

Tue 2/3

2:13 pm-11:59 pm

1 stop8h 46m

Chicago O'Hare Intl

Wed 2/4

8:45 am-11:35 am

Nonstop3h 50m

$198

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 July is, on average, the cheapest month to fly to Chicago from Canada, with most prices found around $217. If you’re not able to fly to Chicago in July, then June is your next best option. Flight prices from Canada to Chicago during June average around $225.

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 $415. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Canada to Chicago for around $703.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Canada to Chicago during this time can be as low as $392. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $589.

What is the cheapest Canada to Chicago flight route?

Fly from Calgary 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 $291 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 $195 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	$141
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 $141. The best round-trip flight deal from Canada to Chicago found on momondo in the last 72 hours is $196.

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?
As of December 2025, there are 5 operators available to choose from for flights from Canada to Chicago.
How old do you have to be to fly from Canada to Chicago?
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 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 this flight route, the most popular plane model on flight routes from Canada to Chicago is Embraer 175 (Enhanced Winglets) (15.51% of total bookings). The next most popular plane models are De Havilland (Bombardier) DHC-8-400 Dash 8Q (10.86%), Boeing 737-800 (9.48%), and Embraer 170 (8.73%).

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 $101	Free Cancellation	Rating 7.1 10,551 reviews	Search Air Canada flights
United Airlines	PriceFrom $110	Free Cancellation	Rating 7.4 9,103 reviews	Search United Airlines flights
WestJet	PriceFrom $138	Free Cancellation	Rating 7.2 3,210 reviews	Search WestJet flights
Porter Airlines	PriceFrom $158	Free Cancellation	Rating 8.0 399 reviews	Search Porter Airlines flights
American Airlines	PriceFrom $167	Free Cancellation	Rating 7.2 11,052 reviews	Search American Airlines flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

Finding the right flight to Chicago from Canada is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Yes. All flights to Chicago from Canada on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo helps you find the best flight between Canada and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes. momondo can track prices for Canada to Chicago 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 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

Thu 1/22

Thu 1/29

Email me momondo's favorite 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

Chicago Greater Rockford Airport

Popular cities in the United States

Flights to New Yorkfrom $50

Flights to Los Angelesfrom $49

Flights to Miamifrom $50

Flights to Orlandofrom $50

Flights to San Franciscofrom $53

Flights to Las Vegasfrom $38

Flights to Washington, D.C.from $58

Flights to Bostonfrom $50

Flights to Atlantafrom $47

Flights to Dallasfrom $51

Flights to Seattlefrom $55

Flights to Denverfrom $57

Cheap flights from Canada to Chicago from $93

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 2/23. 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

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

WestJet flights from Canada to Chicago

Our best WestJet deals on Canada to Chicago flight tickets

American Airlines flights from Canada to Chicago

Our best American 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 July is, on average, the cheapest month to fly to Chicago from Canada, with most prices found around $217. If you’re not able to fly to Chicago in July, then June is your next best option. Flight prices from Canada to Chicago during June average around $225.

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?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Canada to Chicago during this time can be as low as $392. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $589.

What is the cheapest Canada to Chicago flight route?

Fly from Calgary 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?

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

What 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 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 which experiences the fewest number of 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 have had the least number of 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 96 per day as of December 2025. The most frequent departure time is 6:00AM, with 47% of daily flights leaving in the afternoon.

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

As of December 2025, there are 678 flights per week flying from Canada to Chicago. The most common day of the week flights depart is Fri, with 17% of flights 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

Traveling 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 78.5 mi from Chicago