Cheap Flights from Toronto to Chicago O'Hare International

Compare Toronto to Chicago O'Hare International flight deals

Find the cheapest month or even day of the year to fly to Chicago O'Hare International

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Flight deals from Toronto to Chicago O'Hare International Airport

Looking for a cheap last-minute deal or the best return flight from Toronto to Chicago O'Hare International Airport? If you want to travel next month, return fares start from R 4,319. Find the lowest prices on one-way and return tickets right here.

Chicago.R 1,923 per passenger.Departing Tue, 14 Jul.One-way flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Island on Tue, 14 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,923, select.

Chicago.R 1,999 per passenger.Departing Mon, 7 Sep.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Mon, 7 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,999, select.

Chicago.R 2,056 per passenger.Departing Mon, 8 Jun.One-way flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Island on Mon, 8 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,056, select.

Chicago.R 2,377 per passenger.Departing Mon, 13 Apr.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Toronto Island on Mon, 13 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,377, select.

Chicago.R 2,434 per passenger.Departing Sun, 24 May.One-way flight with Delta.Outbound indirect flight with Delta, departs from Toronto Pearson International on Sun, 24 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,434, select.

Chicago.R 2,634 per passenger.Departing Sun, 31 May.One-way flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Sun, 31 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,634, select.

Chicago.R 2,634 per passenger.Departing Fri, 17 Apr.One-way flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Fri, 17 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,634, select.

Chicago.R 2,692 per passenger.Departing Thu, 15 Oct.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Thu, 15 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,692, select.

Chicago.R 2,742 per passenger.Departing Wed, 23 Dec.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Wed, 23 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,742, select.

Chicago.R 2,924 per passenger.Departing Sun, 8 Nov.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Sun, 8 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,924, select.

Chicago.R 3,000 per passenger.Departing Tue, 25 Aug.One-way flight with American Airlines.Outbound direct flight with American Airlines departs from Toronto Pearson International on Tue, 25 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 3,000, select.

Chicago.R 3,315 per passenger.Departing Mon, 30 Mar.One-way flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Toronto Island on Mon, 30 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 3,315, select.

Chicago.R 4,833 per passenger.Departing Thu, 26 Mar.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Pearson International on Thu, 26 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 4,833, select.

Find the cheapest month to fly from Toronto to Chicago O'Hare International

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Toronto to Chicago O'Hare International flights are currently cheapest in July.

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Direct flights from Toronto to Chicago O'Hare International

Toronto to Chicago O'Hare International: Alternative routes

Compare routes from Toronto to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago O'Hare International.

Toronto to Chicago: Flight information

The things to know before you go.

Cheapest flight found	R 1,923
Cheapest month to fly	July
Average flight time	1 hr, 59 mins
Most popular airline	United
Average flights per week	1,430

Finding cheap flights from Toronto to Chicago O'Hare International: Frequently asked questions

How much are return flights from Toronto to Chicago O'Hare International?

The best price we found for a return flight from Toronto to Chicago O'Hare International is R 3,240. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

How long does it take to fly from Toronto to Chicago O'Hare International?

1 hour and 58 minutes is the average flight time from Toronto to Chicago O'Hare International.

Which airlines fly direct from Toronto to Chicago O'Hare International?

United, Air Canada and British Airways fly direct from Toronto to Chicago O'Hare International.

How many flights are there a week from Toronto to Chicago O'Hare International?

As of March 2026, there are 715 flights per week flying from Toronto to Chicago O'Hare International.

When is the cheapest time to fly from Toronto to Chicago O'Hare International?

The cheapest month to fly from Toronto to Chicago O'Hare International is usually June.

Which upcoming date is cheapest to fly from Toronto to Chicago O'Hare International Airport on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Toronto to Chicago O'Hare International Airport on Monday, 29 June 2026.

Can I get a direct flight from Toronto to Chicago O'Hare International Airport?

Yes – the average flight time is 1 hour and 58 minutes.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Which is the cheapest airline to fly from Toronto to Chicago O'Hare International with?

The cheapest airline that flies to Chicago O'Hare International is Air Canada .

Travelling from Toronto to Chicago O'Hare International Airport (ORD): What you need to know

Toronto is home to two main airports where you can kick off your travels. Explore your options for booking a flight from Toronto to Chicago O'Hare International Airport (ORD) heading out from Toronto Pearson International Airport (YYZ) or Billy Bishop Toronto City Airport (YTZ).
Take a direct Toronto to Chicago O'Hare International Airport flight and you'll be in the air for around 2 hours.
Chicago O'Hare International Airport is located in Chicago. The city runs on the UTC-6 timezone and is one hour behind Toronto.
With 123 direct flights a week between the two airports, Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) is the busiest route. American Airlines operates the earliest flight at 6:15am. If you prefer to get more out of your day before taking off, the last departure from YYZ to ORD is with United Airlines at 9pm.
Arriving two hours before an international flight and one hour ahead of a domestic departure are tried-and-true travel tips. Be at the airport on time to catch your flight from Toronto to ORD.
Travelling during a popular month such as July? School holidays and other high seasons can lead to longer queues and delays at security. Be extra cautious and get there up to four hours before an international flight and two hours before domestic departures.

Airports in Toronto

Toronto Pearson International Airport (YYZ)

You can hop on a direct flight from Toronto to Chicago O'Hare International Airport (ORD) departing from Toronto Pearson International Airport (YYZ).
At YYZ, you can choose from various airlines operating direct flights from Toronto to Chicago O'Hare International Airport, such as:
Most passengers choose to book seats with United between YYZ and ORD.
American Airlines is the most consistent performer for punctuality on this route.
YYZ is about 27 kilometres from central Toronto. If you're ride-sharing, driving or catching a taxi from the centre, it'll take 30 minutes or so to get there, depending on traffic conditions. If you're planning to take public transport, expect the journey time to be around 25 minutes.
Searching for a convenient hotel near Toronto Pearson International Airport? If you've booked an early flight from Toronto to Chicago O'Hare International Airport, these stays will put you conveniently close to check-in:
Of the flights that depart from Toronto Pearson International Airport, 68% arrive on time at their destination.

Billy Bishop Toronto City Airport (YTZ)

Think about setting out from Billy Bishop Toronto City Airport (YTZ). You can book a direct Toronto to Chicago O'Hare International Airport (ORD) plane ticket with departures from here.
From YTZ, direct flights from Toronto to ORD are offered by Air Canada.
On the YTZ to ORD route, Air Canada is the top airline in terms of bookings.
YTZ is around 3 kilometres from central Toronto. It'll take 10 minutes or so to get to the airport driving from the city centre. Public transport takes roughly 20 minutes.
Kick off your holiday early with an additional night away from home. Before catching your Toronto to ORD flight, kick back in one of these hotels close to Billy Bishop Toronto City Airport:
70% of flights leaving Billy Bishop Toronto City Airport arrive according to schedule.

John C. Munro Hamilton International Airport (YHM)

From central Toronto, YHM is around 72 kilometres away. It takes roughly 1 hour 10 minutes to get there by car and 1 hour 50 minutes or so if you use public transport.
Relax in bed for a little longer and still make your Toronto to Chicago O'Hare International Airport flight with plenty of time to spare. These accommodation options near John C. Munro Hamilton International Airport make departure day effortless if you're jetting off early:
Airports have an on-time performance rating that tracks how often flights touch down when they should. At YHM, that figure is 68%.

About Chicago O'Hare International Airport (ORD)

If you have a late flight from Toronto to Chicago O'Hare International Airport, few things top the convenience of staying near the terminal. Pick up your luggage at baggage claim and then be showered and resting not long after at one of these options near ORD:
Booking your ride around four weeks ahead of your Toronto to Chicago O'Hare International Airport flight can help you lock in a great deal.
ORD is located at 10000 West O'Hare.

Getting from Chicago O'Hare International Airport (ORD) to central Chicago

Central Chicago is around 27 kilometres from Chicago O'Hare International Airport and takes about 30 minutes to reach by car. Explore your options for getting into the city, whether that's with a taxi, car hire or ride-share.
If you're taking public transport, expect a journey of around 45 minutes.

How to find the cheapest flights from Toronto to Chicago O'Hare International Airport (ORD)

R 1,923 is currently the best price for a one-way ticket from Toronto to Chicago O'Hare International Airport. Return flights start at R 3,225. These prices may change depending on availability and demand.
To find cheap flights from Toronto to ORD, book ahead. Airlines tend to offer lower prices when tickets are first released.
The 'Whole month' tool will show you the cheapest Toronto to Chicago O'Hare International Airport tickets across every month. It's a good way to snap up a bargain if your dates are flexible.
Save time looking for cheap plane tickets from Toronto to ORD by creating a Price Alert. We'll send you an email or push notification on the app when a lower fare pops up.
Find a cheap flight from Toronto to Chicago O'Hare International Airport by using filters. Select your preferred duration, number of stops and airlines, then sort the results by 'Cheapest' for the best deals.

The best time to fly from Toronto to Chicago O'Hare International Airport (ORD)

It's time to work out when to book your flight from Toronto to Chicago O'Hare International Airport (ORD). July is when most people visit Chicago. If you're all about a more relaxed kind of trip, go in January.
When booking your Toronto to ORD plane ticket, consider what kind of weather works for you. July is the warmest month in Chicago, with temperatures ranging from 16ºC (61ºF) to 28ºC (82ºF).
If you like cooler conditions, search for a cheap ticket from Toronto to Chicago O'Hare International Airport in January when temperatures are between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

Once you've booked your flight from Toronto to Chicago O'Hare International Airport, find a hotel that keeps you close to what you want to see. Make one of these accommodation options your base for exploring Chicago:
Millennium Park and Art Institute of Chicago are a couple of major attractions to add to your Chicago travel itinerary. Continue your sightseeing adventures at Willis Tower.

Explore more of the United States

Chicago has plenty going for it, but there are so many other parts of the United States just waiting to be explored. About 290 kilometres southeast of Chicago, a visit to Indianapolis will fill your itinerary to the brim. Don't miss top attractions like Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.
Milwaukee is another must-experience destination in the United States and is around 121 kilometres north of Chicago. No trip is complete without visiting Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo.