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Cheap Flights from Toronto Island to Chicago

Compare Toronto Island to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

Book the best Chicago fare with no extra fees

Flight deals from Toronto Island to Chicago

Looking for a cheap last-minute deal or the best return flight from Toronto Island Airport to Chicago? If you want to travel next month, return fares start from R 3,001. Find the lowest prices on one-way and return tickets right here.
Chicago.R 1,895 per passenger.Departing Sat, 20 Jun.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Sat, 20 Jun, arriving in Chicago Midway.Price includes taxes and charges.From R 1,895, select.
Chicago.R 1,908 per passenger.Departing Wed, 7 Oct.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Wed, 7 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 1,908, select.
Chicago.R 2,005 per passenger.Departing Mon, 9 Nov.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Mon, 9 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,005, select.
Chicago.R 2,009 per passenger.Departing Thu, 10 Sep.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Thu, 10 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,009, select.
Chicago.R 2,031 per passenger.Departing Tue, 26 May.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Tue, 26 May, arriving in Chicago Midway.Price includes taxes and charges.From R 2,031, select.
Chicago.R 2,077 per passenger.Departing Thu, 6 Aug.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Thu, 6 Aug, arriving in Chicago Midway.Price includes taxes and charges.From R 2,077, select.
Chicago.R 2,140 per passenger.Departing Sun, 24 Jan.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Sun, 24 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,140, select.
Chicago.R 2,198 per passenger.Departing Sat, 18 Jul.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Sat, 18 Jul, arriving in Chicago Midway.Price includes taxes and charges.From R 2,198, select.
Chicago.R 2,247 per passenger.Departing Sun, 13 Dec.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Sun, 13 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,247, select.
Chicago.R 2,526 per passenger.Departing Sat, 13 Feb.One-way flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Island on Sat, 13 Feb, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 2,526, select.
Chicago.R 3,123 per passenger.Departing Tue, 23 Mar.One-way flight with Porter Airlines.Outbound direct flight with Porter Airlines departs from Toronto Island on Tue, 23 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 3,123, select.
Chicago.R 3,572 per passenger.Departing Sat, 17 Apr.One-way flight with Air Canada.Outbound direct flight with Air Canada departs from Toronto Island on Sat, 17 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From R 3,572, select.

Find the cheapest month to fly from Toronto Island to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Toronto Island to Chicago flights are currently cheapest in June.
May
from R 2,031
Jun
from R 1,895
Jul
from R 2,198
Aug
from R 2,077
Sep
from R 2,009
Oct
from R 1,908
Nov
from R 2,005
Dec
from R 2,247
Jan
from R 2,140
Feb
from R 2,526
Mar
from R 3,123
Apr
from R 3,572

Direct flights from Toronto Island to Chicago

Alternative Toronto Island to Chicago routes

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

Chicago Midway

14km from central Chicago
ClosestCheapest
from R 1,895
Search flights

Chicago O'Hare International

25km from central Chicago
from R 1,908
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
from R 2,342
Search flights

Toronto to Chicago: Flight information

The things to know before you go.
Cheapest flight foundR 1,895
Cheapest month to flyJune
Average flight time1 hr, 52 mins
Most popular airlineAir Transat
Average flights per week111

Finding cheap flights from Toronto Island 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 Island to Chicago is R 2,883. 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.
1 hour and 52 minutes is the average flight time from Toronto Island to Chicago.
Air Transat, Porter Airlines and Porter Airlines Inc fly direct from Toronto Island to Chicago.
As of May 2026, there are 111 flights per week flying from Toronto Island to Chicago.
The cheapest month to fly from Toronto Island to Chicago is usually May.
If you're flying from Toronto Island Airport, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the centre of Chicago. We've found flights into this airport from R 2,883.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Toronto Island Airport to Chicago on Wednesday, 27 May 2026.
Yes – the average flight time is 1 hour and 52 minutes.
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 May, the average temperature is usually around 13°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, Porter Airlines offers the cheapest flight tickets to Chicago.

Flying from Billy Bishop Toronto City Airport (YTZ) to Chicago: what you need to know

  • The timezone in Chicago is UTC-5. The city is one hour behind Toronto, where Billy Bishop Toronto City Airport is located.

  • Billy Bishop Toronto City Airport (YTZ) to Chicago Midway International Airport (MDW) is the most traveled route, with 13 weekly flights to pick from. If you have things to do before leaving, the last flight from YTZ to MDW is with Porter Airlines at 16:05. Go for the first departure with Porter Airlines at 07:30 if you want to get on your way earlier.

  • Leave plenty of time to make your YTZ to Chicago flight. As a general rule, turn up two hours before international departures and an hour ahead for domestic flights.

  • Be prepared for longer lines in popular months like July. Arriving up to four hours in advance for international flights and two hours for domestic departures is a smart move.

  • Direct Billy Bishop Toronto City Airport to Chicago tickets are available for booking. Chicago Midway International Airport (MDW) is where you'll complete your journey.

  • Porter Airlines is a leading airline that operates direct flights from Billy Bishop Toronto City Airport to Chicago.

  • Travelling from central Toronto to YTZ takes about 40 minutes by public transport. If you drive, ride-share or take a cab, you'll cover the 3 kilometres in 35 minutes or so, depending on traffic conditions.

  • Want an easy start to your journey? Stay near YTZ. Whether you have an early flight from Billy Bishop Toronto City Airport to Chicago or don't want departure day to feel hectic, these hotels are worth a look:

  • Of all flights departing from Billy Bishop Toronto City Airport, 62.09% land on time at their destination.

How to find the cheapest flights from Billy Bishop Toronto City Airport (YTZ) to Chicago

  • The best price we've seen for a one-way Billy Bishop Toronto City Airport to Chicago flight is R 1,895. The cheapest price for a return flight is R 2,883. Keep in mind fares may change due to availability at the time of booking.

  • Book one month before you want to fly. Research on pricing trends suggests this is the ideal window for finding cheap flights from YTZ to Chicago.

  • The best month for scoring cheap Billy Bishop Toronto City Airport to Chicago tickets is May. Use the 'Whole month' tool to compare flight prices, then choose the dates that offer the biggest savings.

  • Stay on top of deals for cheap flights from YTZ to Chicago by creating a Price Alert. You'll receive an email or notification on the app when a new low fare is offered.

  • Select your preferred arrival and departure times, number of stops and airlines with our filters. Then, sort the results for your flight from Billy Bishop Toronto City Airport to Chicago by 'Fastest,' 'Cheapest' or 'Best.'

Airports in Chicago

O'Hare International Airport (ORD)

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

  • Getting to the centre on public transport typically takes 55 minutes.

  • The last thing you want is a lengthy journey to your hotel if you're arriving on a late flight from Billy Bishop Toronto City Airport to Chicago. Book one of these accommodation options near ORD instead:

  • Fast-track your adventure by picking up an O'Hare International Airport rental car. Grab a set of wheels from Routes Car Rentals, Dollar or Budget to explore Chicago and beyond.

  • Lock in the best deal by booking your ride from O'Hare International Airport about four weeks in advance of your flight from YTZ to Chicago.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Central Chicago is about 19 kilometres from Chicago Midway International Airport (MDW). Once your flight from Billy Bishop Toronto City Airport to Chicago has touched down and you've made your way out of the airport, the drive should be around 20 minutes.

  • If you choose to travel on public transport, the journey will take you 45 minutes or so.

  • Hang the 'Do not disturb' sign on your door and unwind at a hotel near MDW. Here are a few options where you can put your feet up after your YTZ to Chicago flight:

  • Forget about public transport timetables or slow-moving cab lines. Pick up a Chicago Midway International Airport rental car and blaze your own trail. Compare rates and availability from Dollar, Hertz and Budget.

  • Avoid paying extra. Booking your ride four weeks before your arrival at MDW can get you a lower rate.

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

Chicago Rockford International Airport (RFD)

  • Set your sights on the city centre after your flight from Billy Bishop Toronto City Airport to Chicago has arrived. Central Chicago is about 137 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 25 minutes to reach by taxi or ride-share.

  • Public transport can get you there in around 4 hours 15 minutes.

  • Book a hotel close to RFD and get from baggage claim to your bed in a snap. Whether you're arriving on a late YTZ to Chicago flight or just want to simplify your travel plans, these accommodation options will have you settling in quickly:

  • Take the guesswork out of the next part of your journey by picking up a Chicago Rockford International Airport rental car. Budget, Alamo and National make getting on the road effortless.

  • If you're looking for a certain make or model, booking early gives you a better shot at getting your first choice. Book your ride from RFD a few weeks ahead of your flight from Billy Bishop Toronto City Airport to Chicago.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

Best time to go to Chicago

  • Before locking in your flights from Billy Bishop Toronto City Airport to Chicago, consider which time of year is best for you. Peak season in Chicago offers a lively atmosphere and plenty to do, while the off-season means you'll get better deals on hotels and smaller crowds.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC (59ºF) and 29ºC (84ºF). Book your Billy Bishop Toronto City Airport to Chicago flight ticket then if you enjoy this type of weather.

  • Look for cheap tickets from YTZ 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

Explore more of United States

  • Chicago is easy to fall in love with, but there are so many other corners of United States just waiting to be discovered. About 451 kilometres south-east of Chicago, a trip to Columbus will keep you busy. Start with attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Around 257 kilometres south-east of Chicago, Indianapolis is another essential stop in United States. No visit is complete without checking out 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.