190 € Cheap Flights from Toronto Pearson International to Chicago

Compare Toronto Pearson International to Chicago flight deals

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Flight deals from Toronto Pearson International to Chicago

Looking for a cheap last-minute deal or the best return flight from Toronto Pearson International Airport to Chicago? If you want to travel next month, return fares start from 217 €. Find the lowest prices on one-way and return tickets right here.

Chicago.190 € per passenger.Departing Thu, 3 Sep, returning Mon, 7 Sep.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Thu, 3 Sep, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Mon, 7 Sep, arriving in Toronto Pearson International.Price includes taxes and charges.From 190 €, select.

Chicago.190 € per passenger.Departing Wed, 24 Jun, returning Sun, 28 Jun.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Wed, 24 Jun, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Sun, 28 Jun, arriving in Toronto Pearson International.Price includes taxes and charges.From 190 €, select.

Chicago.206 € per passenger.Departing Mon, 13 Jul, returning Thu, 24 Sep.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Mon, 13 Jul, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Thu, 24 Sep, arriving in Toronto Pearson International.Price includes taxes and charges.From 206 €, select.

Chicago.206 € per passenger.Departing Sat, 29 Aug, returning Wed, 2 Sep.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Sat, 29 Aug, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Wed, 2 Sep, arriving in Toronto Pearson International.Price includes taxes and charges.From 206 €, select.

Chicago.207 € per passenger.Departing Tue, 23 Jun, returning Wed, 1 Jul.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Tue, 23 Jun, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Wed, 1 Jul, arriving in Toronto Pearson International.Price includes taxes and charges.From 207 €, select.

Chicago.207 € per passenger.Departing Tue, 30 Jun, returning Mon, 7 Sep.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Tue, 30 Jun, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Mon, 7 Sep, arriving in Toronto Pearson International.Price includes taxes and charges.From 207 €, select.

Chicago.209 € per passenger.Departing Tue, 29 Sep, returning Thu, 1 Oct.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Tue, 29 Sep, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Thu, 1 Oct, arriving in Toronto Pearson International.Price includes taxes and charges.From 209 €, select.

Chicago.217 € per passenger.Departing Mon, 17 Aug, returning Thu, 20 Aug.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Mon, 17 Aug, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Thu, 20 Aug, arriving in Toronto Pearson International.Price includes taxes and charges.From 217 €, select.

Chicago.217 € per passenger.Departing Fri, 24 Jul, returning Sun, 2 Aug.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Fri, 24 Jul, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Sun, 2 Aug, arriving in Toronto Pearson International.Price includes taxes and charges.From 217 €, select.

Chicago.217 € per passenger.Departing Mon, 6 Jul, returning Thu, 9 Jul.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Mon, 6 Jul, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Thu, 9 Jul, arriving in Toronto Pearson International.Price includes taxes and charges.From 217 €, select.

Chicago.217 € per passenger.Departing Fri, 26 Jun, returning Tue, 4 Aug.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Fri, 26 Jun, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Tue, 4 Aug, arriving in Toronto Pearson International.Price includes taxes and charges.From 217 €, select.

Chicago.221 € per passenger.Departing Wed, 2 Dec, returning Mon, 7 Dec.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Wed, 2 Dec, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Mon, 7 Dec, arriving in Toronto Pearson International.Price includes taxes and charges.From 221 €, select.

Chicago.221 € per passenger.Departing Sun, 18 Oct, returning Mon, 19 Oct.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Sun, 18 Oct, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Mon, 19 Oct, arriving in Toronto Pearson International.Price includes taxes and charges.From 221 €, select.

Chicago.221 € per passenger.Departing Mon, 19 Oct, returning Tue, 17 Nov.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Mon, 19 Oct, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Tue, 17 Nov, arriving in Toronto Pearson International.Price includes taxes and charges.From 221 €, select.

Chicago.221 € per passenger.Departing Sun, 1 Nov, returning Tue, 3 Nov.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Sun, 1 Nov, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Tue, 3 Nov, arriving in Toronto Pearson International.Price includes taxes and charges.From 221 €, select.

Chicago.222 € per passenger.Departing Sun, 6 Sep, returning Tue, 10 Nov.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Sun, 6 Sep, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Tue, 10 Nov, arriving in Toronto Pearson International.Price includes taxes and charges.From 222 €, select.

Find the cheapest month to fly from Toronto Pearson International to Chicago

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

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Direct flights from Toronto Pearson International to Chicago

Alternative Toronto Pearson International to Chicago routes

Looking for the cheapest, fastest or easiest route from Toronto Pearson International to Chicago? You could fly into the following airports instead.

Toronto to Chicago: Flight information

The things to know before you go.

Cheapest flight found	190 €
Cheapest month to fly	June
Average flight time	2 hrs, 3 mins
Most popular airline	United
Average flights per week	707

Finding cheap flights from Toronto Pearson International to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.

How much are return flights from Toronto Pearson International to Chicago?

The best price we found for a return flight from Toronto Pearson International to Chicago is 190 €. 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 Pearson International to Chicago?

2 hours and 3 minutes is the average flight time from Toronto Pearson International to Chicago.

Which airlines fly direct from Toronto Pearson International to Chicago?

United, Air Canada and British Airways fly direct from Toronto Pearson International to Chicago.

How many flights are there a week from Toronto Pearson International to Chicago?

As of June 2026, there are 707 flights per week flying from Toronto Pearson International to Chicago.

When is the cheapest time to fly from Toronto Pearson International to Chicago?

The cheapest month to fly from Toronto Pearson International to Chicago is usually June.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Toronto Pearson International Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from 190 €.

Which upcoming date is cheapest to fly from Toronto Pearson International Airport to Chicago on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Toronto Pearson International Airport to Chicago on Wednesday, 24 June 2026.

Can I get a direct flight from Toronto Pearson International Airport to Chicago?

Yes – the average flight time is 2 hours and 3 minutes.

How can I get the best flight deal from Toronto Pearson International Airport to Chicago?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

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.

What’s the weather like in Chicago?

In June, the average temperature is usually around 19°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.

Which is the cheapest airline to fly from Toronto Pearson International Airport to Chicago with?

Currently, Air Canada offers the cheapest flight tickets to Chicago.

Travelling from Toronto Pearson International Airport (YYZ) to Chicago: what you need to know

Hop on a direct flight from Toronto Pearson International Airport to Chicago and you'll be travelling for an average of 1 hour 45 minutes.
Chicago is one hour behind Toronto, where Toronto Pearson International Airport is located. Chicago runs on the UTC-6 timezone.
With 123 flights a week between the two airports, Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) is the most popular route. American Airlines operates the earliest flight at 06:15. If you're eager to get more out of your day before jetting off, the last flight from YYZ to ORD is with United Airlines at 21:00.
To avoid missing your YYZ to Chicago flight, allow plenty of time for things like check-in and baggage drop. Arriving two hours ahead of international departures and an hour before domestic flights is the general rule.
During popular months like July, it's wise to get to the airport even earlier. Plan to arrive two hours before a domestic departure and four hours ahead for an international flight when you fly during peak periods in general.
Direct Toronto Pearson International Airport to Chicago tickets are available for booking. Chicago O'Hare International Airport (ORD) will be your arrival point.
You'll find a variety of airlines that operate direct flights from Toronto Pearson International Airport to Chicago, including:
Located around 19 kilometres from central Toronto, YYZ can be reached in about 30 minutes by car (depending on traffic). The journey on public transport will take roughly 25 minutes.
Have an early flight from Toronto Pearson International Airport to Chicago? Avoid the hassle of rushing to the terminal (and get some extra shut-eye) by choosing one of these hotels close to YYZ:
Of all flights leaving Toronto Pearson International Airport, 68% land on time at their destination.

How to find the cheapest flights from Toronto Pearson International Airport (YYZ) to Chicago

118 € is currently the lowest price for a one-way Toronto Pearson International Airport to Chicago flight. Return plane tickets start at 190 €. These prices may change depending on availability and demand.
Booking in advance is often the key to locking in a cheap flight from YYZ to Chicago. Flight prices rise as demand increases, so the nearer you get to departure, the more expensive your ticket may be.
The 'Whole month' tool will show you the cheapest tickets from Toronto Pearson International Airport to Chicago throughout the entire month. It's a great way to snap up a bargain if your trip dates are flexible.
Save time looking for cheap flights from YYZ to Chicago by creating a Price Alert. You'll receive an email or notification on the app when a new low fare is offered.
Tailor your flights with filters. Choose your preferred departure and arrival times, airlines and total journey duration. You can also sort results by 'Fastest,' 'Best' or 'Cheapest' flights from Toronto Pearson International Airport to Chicago.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

Chicago O'Hare International Airport (ORD) is around 27 kilometres from central Chicago. If you're opting for a ride-share or a taxi, the drive takes roughly 30 minutes.
When travelling by public transport, expect a journey time of around 45 minutes.
Think about booking a hotel near ORD if you have a late flight from Toronto Pearson International Airport to Chicago. Select one of these options and make your arrival easier:
Lock in the best possible rate by booking your vehicle from Chicago O'Hare International Airport around four weeks in advance of your flight from YYZ to Chicago.
ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

The centre of Chicago is about 16 kilometres from Chicago Midway International Airport (MDW). Once your flight from Toronto Pearson International Airport to Chicago has landed and you've made your way out of the airport, expect a drive of around 25 minutes.
If you travel by public transport, you'll reach the centre in 30 minutes or so.
There are some comfortable places to rest your head close to MDW. Kick back and get cosy after your YYZ to Chicago flight at any of these well-located options:
Get first dibs on the best options. Reserving your ride from MDW four weeks in advance often means lower prices and a greater range of vehicles.
You'll find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Chicago Rockford International Airport (RFD) is about 145 kilometres from central Chicago. It takes about 1 hour 40 minutes to reach the city centre in a ride-share or taxi once you've hopped off your flight from Toronto Pearson International Airport to Chicago.
Public transport will take you there in around 2 hours.
If you don't want to make the journey to the centre, head for a hotel near RFD. Settle in at one of these options after your YYZ to Chicago flight:
If you're hoping for a particular model or make, booking early increases your chances of snagging what you want. Secure your ride from RFD at least a couple of weeks ahead of your flight from Toronto Pearson International Airport to Chicago.
Chicago Rockford International Airport is located at 2 Airport Cir.

Best time to go to Chicago

It's time to pick your trip dates for your flight from Toronto Pearson International Airport to Chicago. July is the busiest month for a trip to Chicago. If you want a quieter vibe, go in January.
Book a Toronto Pearson International Airport to Chicago plane ticket with a departure in July if you're eager to visit the city during its warmest month. You can expect temperatures to range from 16ºC (61ºF) to 28ºC (82ºF).
Look for cheap tickets from YYZ to Chicago in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

When it comes to searching for somewhere to lay your head, you'll find the most popular stays in Chicago right here. Explore these options once you've booked your flight from Toronto Pearson International Airport to Chicago:
All great holidays should include a little sightseeing. Art Institute of Chicago, Millennium Park and Willis Tower are attractions you won't want to skip in Chicago.

Explore more of the United States

Columbus is just one of the many cities in the United States waiting to be explored after you've seen Chicago. Around 451 kilometres away to the southeast, its best attractions include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.
If there's time to check out another side of the United States, head for Indianapolis, about 257 kilometres southeast of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are among its highlights.