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Cheap Flights from Toronto (YYZ) to Chicago (CHIA)

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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 to Chicago? Find the lowest prices on one-way and return tickets right here.
Chicago.$206 per passenger.Departing Thu, 18 Sep, returning Sun, 21 Sep.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Toronto Pearson International on Thu, 18 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Sun, 21 Sep, arriving in Toronto Pearson International.Price includes taxes and charges.From $206, select.
Chicago.$209 per passenger.Departing Thu, 11 Dec, returning Thu, 11 Dec.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Toronto Pearson International on Thu, 11 Dec, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Thu, 11 Dec, arriving in Toronto Pearson International.Price includes taxes and charges.From $209, select.
Chicago.$219 per passenger.Departing Sat, 16 Aug, returning Sat, 23 Aug.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Toronto Pearson International on Sat, 16 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Sat, 23 Aug, arriving in Toronto Pearson International.Price includes taxes and charges.From $219, select.
Chicago.$221 per passenger.Departing Thu, 18 Sep, returning Sun, 21 Sep.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Thu, 18 Sep, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Sun, 21 Sep, arriving in Toronto Pearson International.Price includes taxes and charges.From $221, select.
Chicago.$225 per passenger.Departing Sat, 1 Nov, returning Sat, 8 Nov.Return flight with United.Outbound direct flight with United departs from Toronto Pearson International on Sat, 1 Nov, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sat, 8 Nov, arriving in Toronto Pearson International.Price includes taxes and charges.From $225, select.
Chicago.$227 per passenger.Departing Thu, 11 Dec, returning Thu, 11 Dec.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Thu, 11 Dec, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Thu, 11 Dec, arriving in Toronto Pearson International.Price includes taxes and charges.From $227, select.
Chicago.$234 per passenger.Departing Thu, 16 Oct, returning Wed, 22 Oct.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Thu, 16 Oct, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Wed, 22 Oct, arriving in Toronto Pearson International.Price includes taxes and charges.From $234, select.
Chicago.$235 per passenger.Departing Sat, 25 Oct, returning Sat, 1 Nov.Return flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Pearson International on Sat, 25 Oct, arriving in Chicago O'Hare International.Inbound direct flight with Air Canada departs from Chicago O'Hare International on Sat, 1 Nov, arriving in Toronto Pearson International.Price includes taxes and charges.From $235, 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 September.
Jul
from $295
Aug
from $219
Sep
from $206
Oct
from $234
Nov
from $225
Dec
from $209
Jan
from $281
Feb
from $281
Mar
Find prices
Apr
Find prices
May
from $520
Jun
Find prices

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$206
Cheapest month to flySeptember
Average flight time2 hrs
Most popular airlineUnited
Average flights per week538

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

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Toronto Pearson International to Chicago is $206. 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.
2 hours is the average flight time from Toronto Pearson International to Chicago.
United, Air Canada and Republic Airways fly direct from Toronto Pearson International to Chicago.
As of July 2025, there are 538 flights per week flying from Toronto Pearson International to Chicago.
The cheapest month to fly from Toronto Pearson International to Chicago is usually September.
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 $206.
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 Thursday, 18 September 2025.
Yes – the average flight time is 2 hours.
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.
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.
In July, the average temperature is usually around 22°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.
Currently, Air Canada offers the cheapest flight tickets to Chicago.

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

  • Expect to be in the air for 1 hour 45 minutes. That's the average duration of a direct flight from Pearson International Airport to Chicago.

  • The timezone in Chicago is UTC-5. The city is one hour behind Toronto, where Pearson International Airport is located.

  • Pearson International Airport (YYZ) to O'Hare International Airport (ORD) is the most traveled route, with 116 weekly departures to pick from. If you have things to do before heading off, the last flight from YYZ to ORD is with United Airlines at 21:00. Go for the first departure operated by American Airlines at 06:15 if you want to fly out earlier.

  • To avoid rushing for your YYZ to Chicago flight, leave plenty of time to check in and find your gate. Turning up two hours ahead of international departures and an hour before domestic flights is the standard rule.

  • Longer lines at check-in and security are more likely if you're heading away during high season, so give yourself even more breathing space. A good general rule for peak times? Arrive up to four hours ahead for international flights and two hours for domestic departures.

  • Direct Pearson International Airport to Chicago tickets are available for booking. O'Hare International Airport (ORD) is where you'll complete your journey.

  • Leading airlines that offer direct flights from Pearson International Airport to Chicago include:

  • The journey from central Toronto to YYZ takes about 50 minutes by public transport. If you ride-share, drive or get a cab, you'll cover the 19 kilometres in 25 minutes or so, depending on traffic.

  • Planning to catch an early flight from Pearson International Airport to Chicago? Avoid the stress of rushing to the terminal (and get some extra shut-eye) by choosing one of these hotels close to YYZ:

  • 63.97% of flights leaving from Pearson International Airport land at their destination on time.

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

  • The lowest price we've seen for a one-way Pearson International Airport to Chicago flight is $126. The cheapest price for a return flight is $206. Bear in mind fares can change due to demand at the time of booking.

  • To pick up cheap flights from YYZ to Chicago, reserve your journey one month before your planned departure.

  • The best month for picking up cheap Pearson International Airport to Chicago tickets is May. Use the 'Whole month' tool to compare prices, then select the dates that offer the lowest fares.

  • 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 lower fare pops up.

  • Find an affordable flight from Pearson International Airport to Chicago with the help of our filters. Select your ideal times, airlines and number of stops, then sort the results by 'Cheapest' to see the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) to central Chicago takes about 35 minutes to reach by car. The centre is roughly 40 kilometres away.

  • When travelling by public transport, expect a journey time of around 55 minutes.

  • The last thing you need is a lengthy journey to your hotel if you're getting in late on a flight from Pearson International Airport to Chicago. Reserve one of these accommodation options near ORD instead:

  • Go wherever you want, whenever you want with an O'Hare International Airport rental car. Book your wheels from Routes Car Rentals, Dollar or Budget and find adventure across Chicago and beyond.

  • Get the best deal by reserving your vehicle from O'Hare International Airport around four weeks before your flight from YYZ to Chicago.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • After your flight from Pearson International Airport to Chicago has touched down, you can reach the city centre in around 20 minutes by car. Central Chicago is roughly 19 kilometres from Chicago Midway International Airport (MDW).

  • If you're catching public transport, it'll take about 45 minutes.

  • After stepping off your YYZ to Chicago flight, kick back at a hotel close to MDW. These are some comfortable options that'll help you sink into relaxation mode:

  • The quickest way to get to where you're going is with a Chicago Midway International Airport rental car. Grab a set of wheels from Dollar, Hertz or Budget and set off in the blink of an eye.

  • Avoid last-minute price surges. Reserving your ride four weeks before your arrival at MDW will help you save.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Step off your flight from Pearson International Airport to Chicago and go straight to your hotel or start sightseeing right away. Central Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and usually takes 1 hour 25 minutes to reach by car.

  • Public transport will take you there in around 4 hours 15 minutes.

  • Enjoy a more relaxed start to your trip by choosing a hotel near RFD after your YYZ to Chicago flight. Take a load off after a long travel day or simply give yourself time to settle into a new destination at:

  • Whether you're after a budget-friendly compact for a solo adventure or a roomy SUV to fit the whole crew comfortably, you'll find the ideal Chicago Rockford International Airport rental car for your needs. Check out the types of wheels available from names such as Budget, Alamo and National.

  • If you're looking for a certain type of vehicle, booking early gives you a better shot at getting exactly what you want. Book your ride from RFD a few weeks ahead of your flight from Pearson International Airport to Chicago.

  • The address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

  • Travel to Chicago in high season if you like a lively atmosphere, but remember that prices are usually higher. Alternatively, book flights from Pearson International Airport to Chicago in the off-season when prices are cheaper and crowds are smaller.

  • Book a Pearson International Airport to Chicago flight ticket with a departure in July if you want to explore the city during its warmest month. You can expect temperatures to range from 15ºC (59ºF) to 29ºC (84ºF).

  • Look for cheap tickets from YYZ to Chicago in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

Explore more of United States

  • Chicago has plenty to offer, but there are so many other corners of United States just waiting to be discovered. About 451 kilometres south-east of Chicago, a visit to Columbus will keep you on the go. Start with leading sights like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another must-experience destination in United States and is around 257 kilometres south-east of Chicago. No journey is complete without visiting The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from Toronto to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.