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 139 minutes.

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

According to our data, United Airlines have had the fewest 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 to Chicago on average per week?

As of December 2025, 377 flights take off from Toronto and land in Chicago each week. The most common flight departure day for this route is Mon, with 16% of weekly flights taking off on this day.

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

The number of flights available between Toronto and Chicago is 53 per day as of December 2025. The most frequent departure time is 11:00, with 47% of daily flights leaving at midday.

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

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

How long does it take to fly to Chicago?

On average, it takes 6h 36m to fly from Toronto to Chicago if you fly out of Toronto (the most popular airport in Toronto) and into Chicago O'Hare Intl Airport (the most popular airport in Chicago). If you’re flying out of Hamilton and into Chicago O'Hare Intl Airport, then the flight time is around 11h 44m.

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

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

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

As of December 2025, there is 1 operator available to choose from for flights from Toronto to Chicago.

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

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Toronto 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.

£82 Cheap Flights from Toronto to Chicago in 2025/26

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Round-trip

One-way

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Cheap return flights

Enter your travel dates to find the best prices.

21:00 - 22:05

YYZ

ORD

2h 05mdirect

11:15 - 14:01

ORD

YYZ

1h 46mdirect

£134United Airlines

Thu, 29 Jan - Sun, 1 Feb

15:30 - 16:40

YYZ

ORD

2h 10mdirect

18:28 - 21:21

ORD

YYZ

1h 53mdirect

£138United Airlines

Mon, 2 Feb - Wed, 18 Feb

11:00 - 12:09

YYZ

ORD

2h 09mdirect

13:02 - 18:57

ORD

YYZ

4h 55m1 stop

£141United Airlines

Fri, 13 Feb - Tue, 17 Feb

08:30 - 14:55

YTZ

ORD

7h 25m1 stop

12:50 - 19:55

ORD

YTZ

6h 05m1 stop

£148Air Canada

Sat, 24 Jan - Sat, 31 Jan

21:00 - 22:05

YYZ

ORD

2h 05mdirect

21:15 - 23:59

ORD

YYZ

1h 44mdirect

£152United Airlines

Fri, 9 Jan - Mon, 12 Jan

06:00 - 09:41

YYZ

ORD

4h 41m1 stop

06:50 - 16:12

ORD

YYZ

8h 22m1 stop

£158Delta

Thu, 5 Feb - Sun, 8 Feb

06:06 - 10:55

YYZ

ORD

5h 49m1 stop

08:50 - 15:59

ORD

YYZ

6h 09m1 stop

£167Delta

Thu, 29 Jan - Sun, 1 Feb

15:30 - 20:10

YTZ

ORD

5h 40m1 stop

07:15 - 18:13

ORD

YTZ

9h 58m2 stops

£195Air Canada

Sat, 24 Jan - Sat, 31 Jan

15:00 - 22:42

YTZ

ORD

8h 42m1 stop

19:21 - 19:50

ORD

YTZ

23h 29m2 stops

£208Multiple Airlines

Sun, 25 Jan - Sun, 1 Feb

15:00 - 22:42

YTZ

ORD

8h 42m1 stop

16:38 - 10:35

ORD

YTZ

16h 57m1 stop

£224Multiple Airlines

Sun, 25 Jan - Sun, 1 Feb

United Airlines flights from Toronto to Chicago

Our best United Airlines deals on Toronto to Chicago flight tickets

United Airlines

29 Jan

YYZ21:00Toronto Pearson Intl

2h 05m

ORD22:05Chicago O'Hare Intl

1 Feb

ORD11:15Chicago O'Hare Intl

1h 46m

YYZ14:01Toronto Pearson Intl

£134

Find similar

United Airlines

2 Feb

YYZ15:30Toronto Pearson Intl

2h 10m

ORD16:40Chicago O'Hare Intl

18 Feb

ORD18:28Chicago O'Hare Intl

1h 53m

YYZ21:21Toronto Pearson Intl

£138

Find similar

United Airlines

13 Feb

YYZ11:00Toronto Pearson Intl

2h 09m

ORD12:09Chicago O'Hare Intl

17 Feb

ORD13:02Chicago O'Hare Intl

4h 55m

1 stop

YYZ18:57Toronto Pearson Intl

£141

Find similar

Air Canada flights from Toronto to Chicago

Our best Air Canada deals on Toronto to Chicago flight tickets

Air Canada

24 Jan

YTZ08:30Toronto Island

7h 25m

1 stop

ORD14:55Chicago O'Hare Intl

31 Jan

ORD12:50Chicago O'Hare Intl

6h 05m

1 stop

YTZ19:55Toronto Island

£148

Find similar

Air Canada

24 Jan

YTZ15:30Toronto Island

5h 40m

1 stop

ORD20:10Chicago O'Hare Intl

31 Jan

ORD07:15Chicago O'Hare Intl

9h 58m

2 stops

YTZ18:13Toronto Island

£195

Find similar

Air Canada

24 Jan

YTZ10:25Toronto Island

9h 12m

2 stops

ORD18:37Chicago O'Hare Intl

31 Jan

ORD07:10Chicago O'Hare Intl

10h 03m

2 stops

YTZ18:13Toronto Island

£211

Find similar

Fly from

Fly to

Route

Depart

Return

Price

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 29/1

21:00-22:05

Nonstop2h 05m

Chicago O'Hare Intl

Sun 1/2

11:15-14:01

Nonstop1h 46m

£134

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Mon 2/2

15:30-16:40

Nonstop2h 10m

Chicago O'Hare Intl

Wed 18/2

18:28-21:21

Nonstop1h 53m

£138

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 13/2

11:00-12:09

Nonstop2h 09m

Chicago O'Hare Intl

Tue 17/2

13:02-18:57

1 stop4h 55m

£141

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 24/1

08:30-14:55

1 stop7h 25m

Chicago O'Hare Intl

Sat 31/1

12:50-19:55

1 stop6h 05m

£148

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 9/1

21:00-22:05

Nonstop2h 05m

Chicago O'Hare Intl

Mon 12/1

21:15-23:59

Nonstop1h 44m

£152

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 5/2

06:00-09:41

1 stop4h 41m

Chicago O'Hare Intl

Sun 8/2

06:50-16:12

1 stop8h 22m

£158

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 29/1

06:06-10:55

1 stop5h 49m

Chicago O'Hare Intl

Sun 1/2

08:50-15:59

1 stop6h 09m

£167

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 24/1

15:30-20:10

1 stop5h 40m

Chicago O'Hare Intl

Sat 31/1

07:15-18:13

2 stops9h 58m

£195

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sun 25/1

15:00-22:42

1 stop8h 42m

Chicago O'Hare Intl

Sun 1/2

19:21-19:50

2 stops23h 29m

£208

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sun 25/1

15:00-22:42

1 stop8h 42m

Chicago O'Hare Intl

Sun 1/2

16:38-10:35

1 stop16h 57m

£224

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How to get the cheapest flight ticket from Toronto 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 cheapest month to fly to Chicago from Toronto is in July. Flight prices, which tend to average around £162, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of July, then book flights to Chicago from Toronto during June instead. Flights to Chicago in June, while not as cheap as those in July, still average around £168.

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 Saturday when prices can be found for as low as £193. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Sunday, with ticket prices averaging around £785.

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

Flying to Chicago from Toronto at midday is the least expensive time of day to depart. momondo users have found prices as low as £248 when looking at flights departing at midday. Flights in the evening are often more expensive, with an average ticket price of £704.

What is the cheapest Toronto to Chicago flight route?

Fly from Toronto Island to Chicago Midway for the best Toronto - 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 when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around £218 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Toronto for as low as £146 on momondo.

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

There are 3 cabin classes available to choose from on Toronto 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 to Chicago flights?

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

How have Toronto to Chicago flight prices changed over time?

As of December 2025, prices for Toronto to Chicago flights are approximately 7% cheaper when compared to flights at the same time last year.

When to book flights from Toronto to Chicago

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

Estimated return price

Cheap Toronto to Chicago (YTO to CHI) flight deals and tips

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

Best price found	£82
Fastest flight time	2h 00m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Toronto in the past 72 hours is £82. The best return flight deal from Toronto to Chicago found on momondo in the last 72 hours is £392.

The fastest flight from Toronto to Chicago takes 2h 00m

Direct flights go from Toronto to Chicago every day.

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

Search flight deals

How far is Toronto to Chicago by plane?
Toronto and Chicago are 435.3 mi apart from one another. 2h 00m is a normal flight duration for this route.
When did momondo last update prices for flights from Toronto to Chicago?
Prices for flights from Toronto to Chicago were last updated today.
How many operators does momondo search for flights from Toronto to Chicago?
As of December 2025, there is 1 operator available to choose from for flights from Toronto to Chicago.
How old do you have to be to fly from Toronto to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Toronto 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 to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Toronto to Chicago is De Havilland (Bombardier) DHC-8-400 Dash 8Q, representing 15.56% of all bookings. The subsequent popular models are Embraer 175 (Enhanced Winglets) at 11.54%, Boeing 737-800 at 10.46%, and Boeing 737 MAX 8 at 9.77%.
What is the most popular airline from Toronto to Chicago?
momondo data reveals that the most frequently booked airline on the route from Toronto to Chicago is Porter Airlines, representing 100% of all bookings.

Best airlines flying from Toronto to Chicago

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

Airline	Rating	Free Cancellation	Price
Air Canada	PriceFrom £137	Free Cancellation	Rating 7.1 10,516 reviews		Search Air Canada flights

Air Canada Flights From Toronto to Chicago
Air Canada flies from Toronto to Chicago around 69 times per week, with 10,516 momondo users rating the airline 7.1/10. The cheapest Air Canada deal from Toronto to Chicago in the last 72 hours was £137 (round-trip), much lower than the average airfare cost of £171 for Air Canada flights on this route.

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Toronto to Chicago. momondo saves you time and could save you money on your trip.

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

Flights from Toronto to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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?

Price alerts on flights to Chicago from Toronto are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Cheap flights from Toronto to Chicago from £95

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Toronto to Chicago departing on 8/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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United Airlines flights from Toronto to Chicago

Our best United Airlines deals on Toronto to Chicago flight tickets

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How to get the cheapest flight ticket from Toronto to Chicago

What is the cheapest month to fly to Chicago?

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 Saturday when prices can be found for as low as £193. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Sunday, with ticket prices averaging around £785.

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

Flying to Chicago from Toronto at midday is the least expensive time of day to depart. momondo users have found prices as low as £248 when looking at flights departing at midday. Flights in the evening are often more expensive, with an average ticket price of £704.

What is the cheapest Toronto to Chicago flight route?

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

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

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

There are 3 cabin classes available to choose from on Toronto 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 to Chicago flights?

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

How have Toronto to Chicago flight prices changed over time?

As of December 2025, prices for Toronto to Chicago flights are approximately 7% cheaper when compared to flights at the same time last year.

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

United Airlines, Delta, and Air Canada are the most popular carriers operating from Toronto 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 139 minutes.

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

According to our data, United Airlines have had the fewest 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 to Chicago on average per day?

The number of flights available between Toronto and Chicago is 53 per day as of December 2025. The most frequent departure time is 11:00, with 47% of daily flights leaving at midday.

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

As of December 2025, 377 flights take off from Toronto and land in Chicago each week. The most common flight departure day for this route is Mon, with 16% of weekly flights taking off on this day.

How long does it take to fly to Chicago?

When to book flights from Toronto to Chicago

Cheap Toronto to Chicago (YTO to CHI) flight deals and tips

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

Best price found

Fastest flight time

Direct flights

Airports in Chicago

How far is Toronto to Chicago by plane?

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

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

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

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

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

What is the most popular airline from Toronto to Chicago?

Best airlines flying from Toronto to Chicago

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

Air Canada Flights From Toronto to 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, organise 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