Question 1

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

Accepted Answer

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 £208 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 £142 on momondo.

Question 2

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

Accepted Answer

The number of flights available between Toronto and Chicago is 49 per day as of January 2026. The most frequent departure time is 11:00, with 43% of daily flights leaving at midday.

Question 3

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

Accepted Answer

As of January 2026, 347 flights take off from Toronto and land in Chicago each week. The most common flight departure day for this route is Fri, with 17% of weekly flights taking off on this day.

Question 4

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

Accepted Answer

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

Question 5

What is the cheapest Toronto to Chicago flight route?

Accepted Answer

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

Question 6

How often are flights from Toronto to Chicago delayed?

Accepted Answer

Historically, on average around 12% 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 138 minutes.

Question 7

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

Accepted Answer

Flying to Chicago from Toronto at midday is the least expensive time of day to depart. momondo users have found prices as low as £241 when looking at flights departing at midday. Flights in the afternoon are often more expensive, with an average ticket price of £519.

Question 8

How long does it take to fly to Chicago?

Accepted Answer

On average, it takes 3h 41m 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.

Question 9

What is the cheapest month to fly to Chicago?

Accepted Answer

The cheapest month to fly to Chicago from Toronto is in July. Flight prices, which tend to average around £158, 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 £164.

Question 10

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

Accepted Answer

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.

Question 11

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

Accepted Answer

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as £194. 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 £765.

Question 12

How have Toronto to Chicago flight prices changed over time?

Accepted Answer

As of January 2026, prices for Toronto to Chicago flights are approximately 18% cheaper when compared to flights at the same time last year.

Question 13

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

Accepted Answer

Tuesday is statistically the day of the week that experiences the fewest delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

Question 14

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

Accepted Answer

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.

Question 15

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

Accepted Answer

Prices are currently low for flights on this route.Typical prices usually range from £161 to £237.
The lowest price recently found on this route was £139.

Question 16

Can stopping save me money on Toronto to Chicago flights?

Accepted Answer

You could potentially save up to 11% on your flight if you consider stops on a Toronto to Chicago flight.

Question 17

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

Accepted Answer

According to our data, United Airlines have had the fewest delays on this route over the last 12 months, with about 7% of their flights experiencing any sort of delay.

Question 18

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

Accepted Answer

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

Question 19

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

Accepted Answer

As of January 2026, there is 1 operator available to choose from for flights from Toronto to Chicago.

Question 20

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

Accepted Answer

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.

Question 21

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

Accepted Answer

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.

Best price found	£179
Fastest flight time	1h 58m
Direct flights	Every day
Airports in Chicago	3 airports

Cheap flights from Toronto to Chicago from £89

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 25/2. 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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How to get the cheapest flight ticket from Toronto to Chicago

What is the typical price of a round-trip flight between Toronto and 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 Friday when prices can be found for as low as £194. 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 £765.

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 £241 when looking at flights departing at midday. Flights in the afternoon are often more expensive, with an average ticket price of £519.

What is the cheapest Toronto to Chicago flight route?

Fly from Toronto Island to Chicago O'Hare Intl 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?

You could potentially save up to 11% on your flight if you consider stops on a Toronto to Chicago flight.

How have Toronto to Chicago flight prices changed over time?

As of January 2026, prices for Toronto to Chicago flights are approximately 18% cheaper when compared to flights at the same time last year.

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

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

How often are flights from Toronto to Chicago delayed?

Historically, on average around 12% 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 138 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. Sunday 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 7% 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 49 per day as of January 2026. The most frequent departure time is 11:00, with 43% of daily flights leaving at midday.

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

As of January 2026, 347 flights take off from Toronto and land in Chicago each week. The most common flight departure day for this route is Fri, with 17% 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

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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?

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