How long does a flight from Toronto to Chicago take?

A direct flight to Chicago will take on average 1h 54m to travel the 436 miles flying distance from Toronto. Visit our flight page for the latest deals!>/a>

How many flights are there between Toronto Pearson Intl Airport and Chicago O'Hare Intl Airport per day?

Each day, there are between 15 and 18 direct flights that take off from Toronto Pearson Intl Airport and land in Chicago O'Hare Intl Airport, with an average flight time of 1h 58m. The most common departure time is 11:00 and most flights take off in the morning. Each week, there are 123 flights. The most frequent day of departure is Monday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday. Visit our flight page for the latest deals!>/a>

Which airlines fly most frequently between Toronto and Chicago?

Toronto and Chicago are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (47 flights per week), Air Canada (41 flights per week), and American Airlines (35 flights per week). Visit our flight page for the latest deals!>/a>

Which airports will I be using when flying from Toronto to Chicago?

Toronto airport is called Toronto Pearson Intl and the only airport in Chicago is Chicago O'Hare Intl. Visit our flight page for the latest deals!>/a>

What’s the earliest departure time from Toronto to Chicago?

Early birds can take the earliest flight from Toronto Pearson Intl Airport at 06:30 and will be landing in Chicago O'Hare Intl Airport at 07:25.

Which airlines fly direct between Toronto Pearson Intl Airport and Chicago O'Hare Intl Airport?

There are 3 airlines that fly direct from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport. They are: Air Canada, American Airlines and United Airlines . The cheapest price of all airlines flying this route was found with Air Canada at £160 for a return flight. On average, the best prices for this route can be found at Air Canada.

Which airlines offer Wi-Fi service onboard planes from Toronto to Chicago?

Air Canada, and United Airlines offer inflight Wi-Fi service on the Toronto to Chicago flight route.

Which aircraft models fly most regularly from Toronto to Chicago?

The De Havilland (Bombardier) DHC-8-400 Dash 8Q is the aircraft model that flies most regularly on the Toronto to Chicago flight route.

Which airline alliances offer flights from Toronto to Chicago?

oneworld, and Star Alliance are the airline alliances operating flights between Toronto and Chicago, with oneworld being the most commonly used for this route.

On which days can I fly direct from Toronto to Chicago?

There are direct flights from Toronto to Chicago on a daily basis.

How does KAYAK find such low prices on flights from Toronto to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Toronto to Chicago. Visit our flight page for the latest deals!>/a>

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Toronto to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Toronto is likely to change within 7 days, so travellers know whether to wait or book now. Visit our flight page for the latest deals!>/a>

What is the Hacker Fare option on flights from Toronto to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to Chicago with an airline and back to Toronto with another airline. Visit our flight page for the latest deals!>/a>

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Toronto to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Toronto up to 3 days before/after your preferred dates. You can then pick the flights that suit you best. Visit our flight page for the latest deals!>/a>

Which cabin class options are there for flights between Toronto Pearson Intl Airport and Chicago O'Hare Intl Airport?

There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy . Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Which airlines provide the cheapest flights from Toronto to Chicago?

In the past 3 days, the cheapest return tickets from Toronto to Chicago were found on Air Canada (£167) and Delta (£194).

£89 CHEAP FLIGHTS from Toronto to Chicago (YYZ - ORD)

YYZ - ORD

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

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Flights Deals

Cheap Flight Deals from Toronto to Chicago (YYZ-ORD)

Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Toronto to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Round-trip

One-way

Last minute

Direct

Recent return flight deals from Toronto to Chicago

KAYAK's recommended return flight deals from the most popular airlines that fly from Toronto to Chicago.

Discover the best prices for you by selecting your travel dates on KAYAK.

06:15 - 09:51YYZ-ORD

4h 36m1 stop

08:50 - 15:57ORD-YYZ

6h 07m1 stop

£167Air Canada

Find Deal

Fri, 3 Oct - Mon, 6 Oct

07:20 - 16:46YYZ-ORD

10h 26m1 stop

13:56 - 21:04ORD-YYZ

6h 08m1 stop

£187

Find Deal

Wed, 25 Jun - Wed, 2 Jul

14:45 - 15:50YYZ-ORD

2h 05mdirect

14:16 - 21:07ORD-YYZ

5h 51m1 stop

£191

Find Deal

Thu, 12 Jun - Tue, 17 Jun

15:50 - 18:37YYZ-ORD

3h 47m1 stop

06:24 - 11:40ORD-YYZ

4h 16m1 stop

£194Delta

Find Deal

Tue, 27 May - Tue, 3 Jun

14:30 - 20:46YYZ-ORD

7h 16m1 stop

06:24 - 11:40ORD-YYZ

4h 16m1 stop

£197Delta

Find Deal

Wed, 21 May - Mon, 26 May

13:00 - 14:01YYZ-ORD

2h 01mdirect

21:31 - 10:04ORD-YYZ

11h 33m1 stop

£216United Airlines

Find Deal

Fri, 20 Jun - Mon, 23 Jun

06:15 - 09:51YYZ-ORD

4h 36m1 stop

15:35 - 21:39ORD-YYZ

5h 04m1 stop

£216Air Canada

Find Deal

Sun, 12 Oct - Sat, 18 Oct

19:47 - 23:15YYZ-ORD

4h 28m1 stop

08:52 - 14:19ORD-YYZ

4h 27m1 stop

£229United Airlines

Find Deal

Wed, 21 May - Sun, 25 May

09:49 - 20:21YYZ-ORD

11h 32m1 stop

06:24 - 18:04ORD-YYZ

10h 40m2 stops

£260WestJet

Find Deal

Wed, 21 May - Mon, 26 May

15:59 - 20:34YYZ-ORD

5h 35m1 stop

06:00 - 18:03ORD-YYZ

11h 03m2 stops

£264WestJet

Find Deal

Fri, 29 Aug - Wed, 3 Sep

Expert advice

Expert advice for your flight from Toronto to Chicago

Snippets provided in this section are AI-generated based on a summarisation of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are specific to the author and reflect their authentic experience, which may vary significantly from the experience of others.

KAYAK teamed up with top travel experts to share the best tips for your journey.

Airlines

American Airlines

Basic Economy offers late boarding and no free checked bags, ideal for light travelers.

Main Cabin Extra provides early boarding and complimentary drinks, enhancing short flight comfort.

Read more about American Airlinesby Harriet Baskas

United Airlines

Economy Plus offers extra legroom, ideal for added comfort on short flights.

Priority Boarding places you in Zone 2, ensuring cabin bag space.

Read more about United Airlinesby Stefanie Waldek

British Airways

Economy fares include a cabin bag, avoiding surprise fees common with budget carriers.

BA's professional cabin crew enhance the overall flight experience.

Read more about British Airwaysby Duncan Madden

Air Canada

Preferred Economy seats offer extra legroom for a fee, enhancing comfort on short-haul flights.

Priority check-in available for higher fare classes, streamlining the airport experience.

Read more about Air Canadaby Stefanie Waldek

Airports

YYZ

Pearson's security queues can be long. Arrive early: 2 hours for domestic, 3 for international. Check wait times online.

ORD

Take the CTA Blue Line train from ORD to downtown Chicago in about 45 minutes, avoiding traffic delays.

Our travel experts

Harriet Baskas

Expert on American Airlines

Stefanie Waldek

Expert on United Airlines, Air Canada, ORD and YYZ

Duncan Madden

Expert on British Airways

Useful Info

KAYAK's insights & trends for Toronto to Chicago flights

Get data-powered insights and trends into flights from Toronto to Chicago to help you find the cheapest flights, the best time to fly and much more.

Prices

Airlines

If your flying dates are flexible, you should consider flying to Chicago on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Toronto to Chicago. For your return ticket, we recommend flying on a Sunday and avoiding Tuesdays for the best deals.

What is the cheapest month to fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

The cheapest month for flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport is May, where tickets cost £207 (return) on average. On the other hand, the most expensive months are January and December, where the average cost of round-trip tickets is £263 and £248 respectively.

Can I save money by flying with a stopover from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

No, with an average price for the route of £267, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?

To get a below average price on the flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Find deals

Low season	January
High season	August
Cheapest flight	£89

Best time to beat the crowds but there is an average 16% increase in price.

Most popular time to fly (3% more expensive on average)

Flight from Toronto to Chicago

When to book flights from Toronto to Chicago

Are your dates flexible? Find out the best times to travel from Toronto to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.

Estimated return price

KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

BrianFlew with Air CanadaOct 2024

Be prepared for a labyrinthine experience traversing the various levels and passages of the Toronto airport. Bring quality walking shoes, as it is likely well over a km in total walking time.

Jo AnnFlew with Air CanadaJun 2024

It seemed that anyone who checked a bag was able to retrieve it quickly.

Verified travelerFlew with United AirlinesMar 2024

Carry-on baggage sizing for United US bound flights appears to be much smaller than for Canadian flights, which forced me to check my bag at the last minute. So check online ahead of time

Verified travelerFlew with Air CanadaFeb 2024

I would definitely choose Air Canada over dirty old United airplanes any day.

Verified travelerFlew with United AirlinesDec 2023

The departure time was very convenient with the United.

What is the cheapest flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?
In the last 3 days, the lowest price for a flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport was £119 for a one-way ticket and £224 for a return.
Which airports will I be using when flying from Toronto to Chicago?
Toronto airport is called Toronto Pearson Intl and the only airport in Chicago is Chicago O'Hare Intl.
Which airlines offer Wi-Fi service onboard planes from Toronto to Chicago?
Air Canada, and United Airlines offer inflight Wi-Fi service on the Toronto to Chicago flight route.
Which aircraft models fly most regularly from Toronto to Chicago?
The De Havilland (Bombardier) DHC-8-400 Dash 8Q is the aircraft model that flies most regularly on the Toronto to Chicago flight route.
Which airline alliances offer flights from Toronto to Chicago?
oneworld, and Star Alliance are the airline alliances operating flights between Toronto and Chicago, with oneworld being the most commonly used for this route.
On which days can I fly direct from Toronto to Chicago?
There are direct flights from Toronto to Chicago on a daily basis.
How does KAYAK find such low prices on flights from Toronto to Chicago?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Toronto to Chicago.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Toronto to Chicago?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Toronto is likely to change within 7 days, so travellers know whether to wait or book now.
What is the Hacker Fare option on flights from Toronto to Chicago?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to Chicago with an airline and back to Toronto with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Toronto to Chicago?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Toronto up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Looking for a cheap flight from Chicago to Toronto? 25% of our users found flights on this route for £232 or less one-way and £177 or less round-trip.

Direct departures

Toronto Pearson Intl to Chicago O'Hare Intl

Monday