How often are flights from Toronto to Chicago delayed?

Historically, on average around 11% of flights between Toronto and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 142 minutes.

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.

How many flights depart from Toronto Pearson Intl Airport to Chicago on average per week?

The number of flights available between Toronto Pearson Intl Airport and Chicago is 296 per week as of January 2026. The most frequent departure day is Tue, with 19% of weekly flights leaving on this day.

What airlines fly to Chicago?

Air Canada, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago from Toronto Pearson Intl Airport according to our data. Air Canada is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 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 Toronto 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.

How many flights depart from Toronto Pearson Intl Airport to Chicago on average per day?

The number of flights available between Toronto Pearson Intl Airport and Chicago is 42 per day as of January 2026. The most frequent departure time is 6:00AM, with 48% of daily flights leaving at noon.

Which airline has the best punctuality record on Toronto 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 is the cheapest airline that flies from Toronto Pearson Intl to Chicago?

United Airlines and Delta are the most popular carriers operating from Toronto Pearson Intl to Chicago

How many operators does momondo search for flights from Toronto Pearson Intl Airport to Chicago?

There are 4 operators available for flights from Toronto Pearson Intl Airport to Chicago as of January 2026.

How old do you have to be to fly from Toronto Pearson Intl Airport 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 Toronto Pearson Intl Airport 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.

$114 Cheap Flights from Toronto Pearson Intl Airport to Chicago in 2026

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 Toronto Pearson Intl Airport to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:00 pm - 10:05 pm

YYZ

ORD

2h 05mnonstop

11:15 am - 2:01 pm

ORD

YYZ

1h 46mnonstop

$182Lufthansa

Thu, Feb 5 - Sun, Feb 8

7:04 pm - 8:04 pm

YYZ

ORD

2h 00mnonstop

11:50 am - 5:40 pm

ORD

YYZ

4h 50m1 stop

$184American Airlines

Tue, Feb 3 - Wed, Feb 11

10:59 am - 4:45 pm

YYZ

ORD

6h 46m1 stop

9:46 am - 12:30 pm

ORD

YYZ

1h 44mnonstop

$190American Airlines

Fri, Feb 13 - Mon, Feb 16

6:40 pm - 7:45 pm

YYZ

ORD

2h 05mnonstop

10:00 am - 12:40 pm

ORD

YYZ

1h 40mnonstop

$192Air Canada

Wed, Feb 18 - Wed, Feb 25

6:40 pm - 7:40 pm

YYZ

ORD

2h 00mnonstop

8:40 pm - 11:15 pm

ORD

YYZ

1h 35mnonstop

$193Air Canada

Fri, Jan 30 - Mon, Feb 2

6:15 am - 11:06 am

YYZ

ORD

5h 51m1 stop

2:00 pm - 4:39 pm

ORD

YYZ

1h 39mnonstop

$194Air Canada

Thu, Feb 5 - Sun, Feb 8

6:00 am - 8:52 am

YYZ

MDW

3h 52m1 stop

6:35 pm - 10:42 pm

MDW

YYZ

3h 07m1 stop

$207Delta

Tue, Feb 3 - Tue, Feb 10

6:00 am - 8:52 am

YYZ

MDW

3h 52m1 stop

1:26 pm - 7:08 pm

MDW

YYZ

4h 42m1 stop

$216Delta

Thu, Feb 5 - Sun, Feb 8

7:15 am - 7:58 pm

YYZ

MDW

13h 43m1 stop

1:00 pm - 12:14 am

MDW

YYZ

10h 14m1 stop

$249Multiple Airlines

Mon, Feb 2 - Mon, Feb 9

6:00 am - 8:52 am

YYZ

MDW

3h 52m1 stop

9:33 am - 4:12 pm

MDW

YYZ

5h 39m1 stop

$275KLM

Thu, Feb 5 - Sun, Feb 8

American Airlines flights from Toronto Pearson Intl Airport to Chicago

Our best American Airlines deals on Toronto Pearson Intl Airport to Chicago flight tickets

American Airlines

Feb 3

YYZ7:04 pmToronto Pearson Intl

2h 00m

ORD8:04 pmChicago O'Hare Intl

Feb 11

ORD11:50 amChicago O'Hare Intl

4h 50m

1 stop

YYZ5:40 pmToronto Pearson Intl

$184

Find similar

American Airlines

Feb 13

YYZ10:59 amToronto Pearson Intl

6h 46m

1 stop

ORD4:45 pmChicago O'Hare Intl

Feb 16

ORD9:46 amChicago O'Hare Intl

1h 44m

YYZ12:30 pmToronto Pearson Intl

$190

Find similar

American Airlines

Jan 31

YYZ4:44 pmToronto Pearson Intl

2h 00m

ORD5:44 pmChicago O'Hare Intl

Feb 2

ORD6:31 pmChicago O'Hare Intl

1h 52m

YYZ9:23 pmToronto Pearson Intl

$196

Find similar

Air Canada flights from Toronto Pearson Intl Airport to Chicago

Our best Air Canada deals on Toronto Pearson Intl Airport to Chicago flight tickets

Air Canada

Feb 18

YYZ6:40 pmToronto Pearson Intl

2h 05m

ORD7:45 pmChicago O'Hare Intl

Feb 25

ORD10:00 amChicago O'Hare Intl

1h 40m

YYZ12:40 pmToronto Pearson Intl

$192

Find similar

Air Canada

Jan 30

YYZ6:40 pmToronto Pearson Intl

2h 00m

ORD7:40 pmChicago O'Hare Intl

Feb 2

ORD8:40 pmChicago O'Hare Intl

1h 35m

YYZ11:15 pmToronto Pearson Intl

$193

Find similar

Air Canada

Feb 5

YYZ6:15 amToronto Pearson Intl

5h 51m

1 stop

ORD11:06 amChicago O'Hare Intl

Feb 8

ORD2:00 pmChicago O'Hare Intl

1h 39m

YYZ4:39 pmToronto Pearson Intl

$194

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/5

9:00 pm-10:05 pm

Nonstop2h 05m

Chicago O'Hare Intl

Sun 2/8

11:15 am-2:01 pm

Nonstop1h 46m

$182

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 2/3

7:04 pm-8:04 pm

Nonstop2h 00m

Chicago O'Hare Intl

Wed 2/11

11:50 am-5:40 pm

1 stop4h 50m

$184

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 2/13

10:59 am-4:45 pm

1 stop6h 46m

Chicago O'Hare Intl

Mon 2/16

9:46 am-12:30 pm

Nonstop1h 44m

$190

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 2/18

6:40 pm-7:45 pm

Nonstop2h 05m

Chicago O'Hare Intl

Wed 2/25

10:00 am-12:40 pm

Nonstop1h 40m

$192

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 1/30

6:40 pm-7:40 pm

Nonstop2h 00m

Chicago O'Hare Intl

Mon 2/2

8:40 pm-11:15 pm

Nonstop1h 35m

$193

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 2/5

6:15 am-11:06 am

1 stop5h 51m

Chicago O'Hare Intl

Sun 2/8

2:00 pm-4:39 pm

Nonstop1h 39m

$194

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Tue 2/3

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Tue 2/10

6:35 pm-10:42 pm

1 stop3h 07m

$207

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 2/5

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Sun 2/8

1:26 pm-7:08 pm

1 stop4h 42m

$216

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Mon 2/2

7:15 am-7:58 pm

1 stop13h 43m

Chicago Midway

Mon 2/9

1:00 pm-12:14 am

1 stop10h 14m

$249

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Thu 2/5

6:00 am-8:52 am

1 stop3h 52m

Chicago Midway

Sun 2/8

9:33 am-4:12 pm

1 stop5h 39m

$275

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 Toronto Pearson Intl Airport 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 September is, on average, the cheapest month to fly to Chicago from Toronto Pearson Intl Airport, with most prices found around $231. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Toronto Pearson Intl Airport to Chicago during August average around $238.

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 $410. 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 Toronto Pearson Intl Airport to Chicago for around $696.

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 Toronto Pearson Intl Airport to Chicago during this time can be as low as $375. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $601.

What is the cheapest Toronto Pearson Intl to Chicago flight route?

Fly from Toronto Pearson Intl to Chicago O'Hare Intl for the best Toronto Pearson Intl - 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 Toronto Pearson Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $287 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Toronto Pearson Intl Airport for as low as $195 on momondo.

What cabin class options are available on Toronto Pearson Intl to Chicago flights?

There are 4 cabin classes available to choose from on Toronto Pearson Intl 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 Toronto Pearson Intl Airport to Chicago flights?

No. A direct flight is the cheapest option for a flight between Toronto Pearson Intl Airport to Chicago.

How have Toronto Pearson Intl Airport to Chicago flight prices changed over time?

As of January 2026, prices for Toronto Pearson Intl Airport to Chicago flights are approximately 48% cheaper when compared to flights at the same time last year.

When to book flights from Toronto Pearson Intl Airport to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Toronto Pearson Intl Airport to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Toronto Pearson Intl Airport to Chicago (YYZ to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto Pearson Intl Airport to Chicago

Best Price Found	$252
Fastest flight time	1h 55m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Toronto Pearson Intl Airport in the past 72 hours is $252. The best round-trip flight deal from Toronto Pearson Intl Airport to Chicago found on momondo in the last 72 hours is $381.

The fastest flight from Toronto Pearson Intl Airport to Chicago takes 1h 55m

Direct flights go from Toronto Pearson Intl Airport to Chicago every day.

There are 3 airports in Chicago. From Toronto Pearson Intl Airport there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

How far is Toronto Pearson Intl to Chicago by plane?
The straight-line distance from Toronto Pearson Intl to Chicago is 424.4 mi. Typically, this will take 1h 55m by plane in normal conditions.
When did momondo last update prices for flights from Toronto Pearson Intl Airport to Chicago?
Prices for flights from Toronto Pearson Intl Airport to Chicago refresh daily.
How many operators does momondo search for flights from Toronto Pearson Intl Airport to Chicago?
There are 4 operators available for flights from Toronto Pearson Intl Airport to Chicago as of January 2026.
How old do you have to be to fly from Toronto Pearson Intl Airport 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 Toronto Pearson Intl Airport 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 Toronto Pearson Intl Airport to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Toronto Pearson Intl Airport to Chicago is Embraer 195 E2 (12.70% of total bookings). The next most popular plane models are De Havilland (Bombardier) DHC-8-400 Dash 8Q (11.02%), Embraer 175 (Enhanced Winglets) (10.99%), and Embraer 170 (8.22%).
What is the most popular airline from Toronto Pearson Intl Airport to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Toronto Pearson Intl Airport to Chicago is Air Canada (66% of total bookings). The next most popular airlines are United Airlines (21%) and American Airlines (13%).

Best airlines flying from Toronto Pearson Intl Airport to Chicago

Compare and see reviews for airlines that fly from Toronto Pearson Intl Airport to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Air Canada	PriceFrom $149	Free Cancellation	Rating 7.1 10,597 reviews	Search Air Canada flights
United Airlines	PriceFrom $165	Free Cancellation	Rating 7.4 9,134 reviews	Search United Airlines flights
Porter Airlines	PriceFrom $180	Free Cancellation	Rating 8.0 405 reviews	Search Porter Airlines flights
American Airlines	PriceFrom $193	Free Cancellation	Rating 7.2 11,083 reviews	Search American Airlines flights

Porter Airlines Flights From Toronto Pearson Intl Airport to Chicago
The lowest priced Porter Airlines flight from Toronto Pearson Intl Airport to Chicago from the last 72 hours was $180. Generally, Porter Airlines has 20 flights on this route every week with an average price of $423. Porter Airlines is rated 8.0/10 by our users.
United Airlines Flights From Toronto Pearson Intl Airport to Chicago
United Airlines (7.4/10 from 9,134 reviews) operates around 58 flights from Toronto Pearson Intl Airport to Chicago in any given week. The average United Airlines airfare for this route is around $281, with deals from around $165 rare but found on momondo. Referenced prices are for round-trip Toronto Pearson Intl Airport to Chicago flight searches in the last 72 hours.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

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 Toronto to Chicago for you.

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

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

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

momondo helps you find the best flight between Toronto 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 Toronto to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Toronto. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when 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.

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 2/5

Thu 2/12

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

Cheap flights from Toronto Pearson Intl Airport to Chicago from $114

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 Toronto Pearson Intl Airport to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

American Airlines flights from Toronto Pearson Intl Airport to Chicago

Our best American Airlines deals on Toronto Pearson Intl Airport to Chicago flight tickets

Air Canada flights from Toronto Pearson Intl Airport to Chicago

Our best Air Canada deals on Toronto Pearson Intl Airport to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Toronto Pearson Intl Airport to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Toronto Pearson Intl Airport to Chicago

What is the cheapest month to fly to Chicago?

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 Toronto Pearson Intl Airport to Chicago during this time can be as low as $375. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $601.

What is the cheapest Toronto Pearson Intl to Chicago flight route?

Fly from Toronto Pearson Intl to Chicago O'Hare Intl for the best Toronto Pearson Intl - Chicago flight prices

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

What cabin class options are available on Toronto Pearson Intl to Chicago flights?

There are 4 cabin classes available to choose from on Toronto Pearson Intl 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 Toronto Pearson Intl Airport to Chicago flights?

No. A direct flight is the cheapest option for a flight between Toronto Pearson Intl Airport to Chicago.

How have Toronto Pearson Intl Airport to Chicago flight prices changed over time?

As of January 2026, prices for Toronto Pearson Intl Airport to Chicago flights are approximately 48% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from Toronto Pearson Intl to Chicago?

United Airlines and Delta are the most popular carriers operating from Toronto Pearson Intl to Chicago

What airlines fly to Chicago?

How often are flights from Toronto to Chicago delayed?

Historically, on average around 11% of flights between Toronto and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 142 minutes.

What is the most punctual flight time for Toronto 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 Toronto 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 Toronto Pearson Intl Airport to Chicago on average per day?

The number of flights available between Toronto Pearson Intl Airport and Chicago is 42 per day as of January 2026. The most frequent departure time is 6:00AM, with 48% of daily flights leaving at noon.

How many flights depart from Toronto Pearson Intl Airport to Chicago on average per week?

The number of flights available between Toronto Pearson Intl Airport and Chicago is 296 per week as of January 2026. The most frequent departure day is Tue, with 19% of weekly flights leaving on this day.

When to book flights from Toronto Pearson Intl Airport to Chicago

Cheap Toronto Pearson Intl Airport to Chicago (YYZ to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Toronto Pearson Intl Airport to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is Toronto Pearson Intl to Chicago by plane?

When did momondo last update prices for flights from Toronto Pearson Intl Airport to Chicago?

How many operators does momondo search for flights from Toronto Pearson Intl Airport to Chicago?

How old do you have to be to fly from Toronto Pearson Intl Airport to Chicago?

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

What is the most popular plane model from Toronto Pearson Intl Airport to Chicago?

What is the most popular airline from Toronto Pearson Intl Airport to Chicago?

Best airlines flying from Toronto Pearson Intl Airport to Chicago

Compare and see reviews for airlines that fly from Toronto Pearson Intl Airport to Chicago with momondo

Porter Airlines Flights From Toronto Pearson Intl Airport to Chicago

United Airlines Flights From Toronto Pearson Intl Airport to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

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

I’m not ready to book a flight from Toronto 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