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 54% 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.

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 55 per day as of October 2025. The most frequent departure time is 1:00PM, with 47% of daily flights leaving in the afternoon.

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

American Airlines, Air Canada, and Delta are the most popular carriers operating from Toronto Pearson Intl to Chicago

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 385 per week as of October 2025. The most frequent departure day is Thu, with 16% of weekly flights leaving on this day.

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

There are 5 operators available for flights from Toronto Pearson Intl Airport to Chicago as of October 2025.

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.

$119 Cheap Flights from Toronto Pearson Intl Airport to Chicago in 2025/26

Q: What is the typical price of a round-trip flight between Toronto Pearson Intl Airport and Chicago?

Prices are currently low for flights on this route. Typical prices usually range from $214 to $405. The lowest price recently found on this route was $174.

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One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 am - 10:42 amYYZ-ORD

5h 42m1 stop

8:11 am - 10:52 amORD-YYZ

1h 41mnonstop

$174American Airlines

Find Deal

Fri, Nov 21 - Tue, Nov 25

10:57 am - 4:53 pmYYZ-ORD

6h 56m1 stop

8:20 am - 3:57 pmORD-YYZ

6h 37m1 stop

$182American Airlines

Find Deal

Thu, Nov 20 - Sun, Nov 23

9:00 pm - 10:05 pmYYZ-ORD

2h 05mnonstop

3:55 pm - 6:34 pmORD-YYZ

1h 39mnonstop

$200Multiple Airlines

Find Deal

Tue, Dec 23 - Mon, Jan 12

6:05 am - 10:01 amYYZ-ORD

4h 56m1 stop

8:55 am - 2:48 pmORD-YYZ

4h 53m1 stop

$201Delta

Find Deal

Mon, Nov 24 - Fri, Dec 5

11:00 am - 12:05 pmYYZ-ORD

2h 05mnonstop

8:15 pm - 10:54 pmORD-YYZ

1h 39mnonstop

$205Multiple Airlines

Find Deal

Wed, Dec 17 - Mon, Jan 5

6:05 am - 8:57 amYYZ-ORD

3h 52m1 stop

10:46 am - 5:15 pmORD-YYZ

5h 29m1 stop

$210Delta

Find Deal

Thu, Nov 27 - Sat, Nov 29

9:00 pm - 10:05 pmYYZ-ORD

2h 05mnonstop

9:15 pm - 11:59 pmORD-YYZ

1h 44mnonstop

$231United Airlines

Find Deal

Sun, Dec 21 - Tue, Jan 6

7:40 pm - 11:44 pmYYZ-ORD

5h 04m1 stop

9:20 pm - 11:59 pmORD-YYZ

1h 39mnonstop

$237United Airlines

Find Deal

Mon, Dec 22 - Mon, Jan 5

4:50 pm - 5:48 pmYYZ-ORD

1h 58mnonstop

8:00 am - 10:40 amORD-YYZ

1h 40mnonstop

$248Air Canada

Find Deal

Sat, Nov 8 - Sun, Nov 9

7:00 am - 11:18 amYYZ-ORD

5h 18m1 stop

8:00 am - 10:40 amORD-YYZ

1h 40mnonstop

$252Air Canada

Find Deal

Sat, Nov 8 - Sun, Nov 9

Delta flights from Toronto Pearson Intl Airport to Chicago

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

Delta

Nov 24

YYZ6:05 amToronto Pearson Intl

4h 56m

1 stop

ORD10:01 amChicago O'Hare Intl

Dec 5

ORD8:55 amChicago O'Hare Intl

4h 53m

1 stop

YYZ2:48 pmToronto Pearson Intl

$201

Find similar

Delta

Nov 27

YYZ6:05 amToronto Pearson Intl

3h 52m

1 stop

ORD8:57 amChicago O'Hare Intl

Nov 29

ORD10:46 amChicago O'Hare Intl

5h 29m

1 stop

YYZ5:15 pmToronto Pearson Intl

$210

Find similar

Delta

Nov 20

YYZ12:08 pmToronto Pearson Intl

7h 18m

1 stop

ORD6:26 pmChicago O'Hare Intl

Nov 24

ORD6:00 amChicago O'Hare Intl

9h 02m

1 stop

YYZ4:02 pmToronto Pearson Intl

$211

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

Nov 8

YYZ4:50 pmToronto Pearson Intl

1h 58m

ORD5:48 pmChicago O'Hare Intl

Nov 9

ORD8:00 amChicago O'Hare Intl

1h 40m

YYZ10:40 amToronto Pearson Intl

$248

Find similar

Air Canada

Nov 8

YYZ7:00 amToronto Pearson Intl

5h 18m

1 stop

ORD11:18 amChicago O'Hare Intl

Nov 9

ORD8:00 amChicago O'Hare Intl

1h 40m

YYZ10:40 amToronto Pearson Intl

$252

Find similar

Air Canada

Nov 24

YYZ7:00 amToronto Pearson Intl

5h 18m

1 stop

ORD11:18 amChicago O'Hare Intl

Nov 27

ORD8:15 pmChicago O'Hare Intl

1h 39m

YYZ10:54 pmToronto Pearson Intl

$253

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

Fri 11/21

6:00 am-10:42 am

1 stop5h 42m

Chicago O'Hare Intl

Tue 11/25

8:11 am-10:52 am

Nonstop1h 41m

$174

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 11/20

10:57 am-4:53 pm

1 stop6h 56m

Chicago O'Hare Intl

Sun 11/23

8:20 am-3:57 pm

1 stop6h 37m

$182

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Tue 12/23

9:00 pm-10:05 pm

Nonstop2h 05m

Chicago O'Hare Intl

Mon 1/12

3:55 pm-6:34 pm

Nonstop1h 39m

$200

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 11/24

6:05 am-10:01 am

1 stop4h 56m

Chicago O'Hare Intl

Fri 12/5

8:55 am-2:48 pm

1 stop4h 53m

$201

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 12/17

11:00 am-12:05 pm

Nonstop2h 05m

Chicago O'Hare Intl

Mon 1/5

8:15 pm-10:54 pm

Nonstop1h 39m

$205

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 11/27

6:05 am-8:57 am

1 stop3h 52m

Chicago O'Hare Intl

Sat 11/29

10:46 am-5:15 pm

1 stop5h 29m

$210

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sun 12/21

9:00 pm-10:05 pm

Nonstop2h 05m

Chicago O'Hare Intl

Tue 1/6

9:15 pm-11:59 pm

Nonstop1h 44m

$231

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 12/22

7:40 pm-11:44 pm

1 stop5h 04m

Chicago O'Hare Intl

Mon 1/5

9:20 pm-11:59 pm

Nonstop1h 39m

$237

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 11/8

4:50 pm-5:48 pm

Nonstop1h 58m

Chicago O'Hare Intl

Sun 11/9

8:00 am-10:40 am

Nonstop1h 40m

$248

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Sat 11/8

7:00 am-11:18 am

1 stop5h 18m

Chicago O'Hare Intl

Sun 11/9

8:00 am-10:40 am

Nonstop1h 40m

$252

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

Other information

What is the typical price of a round-trip flight between Toronto Pearson Intl Airport and Chicago?

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 $240.

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 $405. 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 $634.

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 morning. Flights from Toronto Pearson Intl Airport to Chicago during this time can be as low as $429. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $569.

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 $292 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 October 2025, prices for Toronto Pearson Intl Airport to Chicago flights are approximately 35% 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	$219
Fastest flight time	1h 53m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Toronto Pearson Intl Airport in the past 72 hours is $219. The best round-trip flight deal from Toronto Pearson Intl Airport to Chicago found on momondo in the last 72 hours is $392.

The fastest flight from Toronto Pearson Intl Airport to Chicago takes 1h 53m

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

There is 1 airport near Chicago: 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 5 operators available for flights from Toronto Pearson Intl Airport to Chicago as of October 2025.
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 De Havilland (Bombardier) DHC-8-400 Dash 8Q (12.70% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (11.48%), Boeing 737 MAX 8 (9.95%), and Boeing 737-800 (8.64%).
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 (18%) and American Airlines (16%).

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 $144	Free Cancellation	Rating 7.1 10,307 reviews	Search Air Canada flights
United Airlines	PriceFrom $165	Free Cancellation	Rating 7.4 8,982 reviews	Search United Airlines flights
Porter Airlines	PriceFrom $180	Free Cancellation	Rating 8.0 381 reviews	Search Porter Airlines flights
American Airlines	PriceFrom $196	Free Cancellation	Rating 7.2 11,040 reviews	Search American Airlines flights
WestJet	PriceFrom $208	Free Cancellation	Rating 7.2 3,127 reviews	Search WestJet 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 7 flights on this route every week with an average price of $420. 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 8,982 reviews) operates around 74 flights from Toronto Pearson Intl Airport to Chicago in any given week. The average United Airlines airfare for this route is around $287, 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

Crown Point

Munster

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.

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Sat 11/22

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Cheap flights from Toronto Pearson Intl Airport to Chicago from $119

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Filter for what you want

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Find the cheapest flights from Toronto Pearson Intl Airport to Chicago

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Delta flights from Toronto Pearson Intl Airport to Chicago

Our best Delta 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

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 typical price of a round-trip flight between Toronto Pearson Intl Airport and 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 morning. Flights from Toronto Pearson Intl Airport to Chicago during this time can be as low as $429. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $569.

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 October 2025, prices for Toronto Pearson Intl Airport to Chicago flights are approximately 35% cheaper when compared to flights at the same time last year.

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

American Airlines, Air Canada, and Delta are the most popular carriers operating from Toronto Pearson Intl to Chicago

What airlines fly to Chicago?

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 55 per day as of October 2025. The most frequent departure time is 1:00PM, with 47% of daily flights leaving in the afternoon.

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 385 per week as of October 2025. The most frequent departure day is Thu, with 16% 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

Airports listed have a maximum distance of 78.5 mi from Chicago