Cheap Flights from Toronto Island to Chicago

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Flight deals from Toronto Island to Chicago

Looking for a cheap last-minute deal or the best return flight from Toronto Island to Chicago? Find the lowest prices on one-way and return tickets right here.

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 April.

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.

Toronto to Chicago: Flight information

The things to know before you go.
Cheapest flight foundر.ق.‏ 404
Cheapest month to flyApril
Average flight time1 hr, 50 mins
Most popular airlinePorter Airlines (Canada) Ltd
Average flights per week37

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 ر.ق.‏ 590. 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 50 minutes is the average flight time from Toronto Island to Chicago.
Porter Airlines (Canada) Ltd, Porter Airlines Inc and Air Transat fly direct from Toronto Island to Chicago.
As of March 2025, there are 37 flights per week flying from Toronto Island to Chicago.
The cheapest month to fly from Toronto Island to Chicago is usually April.
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 ر.ق.‏ 590.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Toronto Island Airport to Chicago on Thursday, 10 April 2025.
Yes – the average flight time is 1 hour and 50 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 March, the average temperature is usually around 3°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 (Canada) Ltd offers the cheapest flight tickets to Chicago.

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

  • Chicago is 1 hour behind Toronto, where Billy Bishop Toronto City Airport is located. Chicago operates on the UTC-5 timezone.

  • With 43 flights a week between the two airports, Billy Bishop Toronto City Airport (YTZ) to Chicago Midway International Airport (MDW) is the busiest route. Porter Airlines (Canada) Ltd operates the earliest flight at 09:20. If you prefer to make the most of your day before jetting off, the last flight from YTZ to MDW is with Porter Airlines (Canada) Ltd at 21:35.

  • For hassle-free travel, arrive at the airport two hours ahead of international flights and an hour before domestic departures. This way, you'll have plenty of time to board your flight from YTZ to Chicago.

  • During popular months like July, it's a good idea to get to the airport earlier than normal. Arrive two hours before a domestic departure and four hours ahead of international flights when you travel during peak periods in general.

  • You can book a nonstop flight from Billy Bishop Toronto City Airport to Chicago that lands at Chicago Midway International Airport (MDW).

  • Book your ticket with Porter Airlines (Canada) Ltd. This leading carrier offers direct flights from Billy Bishop Toronto City Airport to Chicago.

  • You don't need a visa for United States if you hold a passport from Canada and are visiting for tourism purposes. Visa and travel documentation requirements are subject to changes or updates. So before locking in your flight tickets from Billy Bishop Toronto City Airport to Chicago, be sure to check with your airline and your destination country's local embassy or consulate for the latest rules.

  • YTZ is about 3 kilometres from central Toronto. If you're catching a cab, driving or ride-sharing from the centre, it'll take you 35 minutes or so to get there, depending on traffic conditions. If you're using public transport, expect the travel time to be around 39 minutes.

  • Looking for a convenient hotel near YTZ? If you're catching an early flight from Billy Bishop Toronto City Airport to Chicago, these stays will put you moments from your departure gate:

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

  • ر.ق.‏ 404 is the best price for a one-way ticket from Billy Bishop Toronto City Airport to Chicago. A return flight starts from ر.ق.‏ 590. These prices may change based on availability.

  • Book 9 months before you want to fly. After looking at the numbers on our calendar, this is how far you'll want to book ahead to secure cheap tickets from YTZ to Chicago.

  • Schedule your trip for May. That's the cheapest month for tickets from Billy Bishop Toronto City Airport to Chicago. If you have flexibility with your dates, use the 'Whole month' tool to see the cheapest price across each month.

  • Sign into your online account or use the app to set up a Price Alert. You'll be notified right away if there's a cheaper deal on this route. It's easy to do, and it'll save you from checking for cheap flight tickets from YTZ to Chicago every day.

  • Use the filters to tailor your flights from Billy Bishop Toronto City Airport to Chicago. Pick your ideal departure and arrival times, number of stops and airlines. Or sort your results by 'Cheapest' to see the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

Chicago Midway International Airport (MDW)

Best time to go to Chicago

  • It's time to pick your travel dates for your flight from Billy Bishop Toronto City Airport to Chicago. August is the busiest month to visit Chicago. If you like a more relaxed vibe, go in February.

  • The warmest month in Chicago is July, with temperatures ranging between 15ºC and 29ºC. Lock in your flights from Billy Bishop Toronto City Airport to Chicago in this month if you enjoy this type of weather.

  • Search for cheap flights from YTZ to Chicago in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC and 3ºC on average.

More about Chicago

  • After booking your flight from Billy Bishop Toronto City Airport to Chicago, think about where to rest your head in this city. Make one of these accommodation options your base for exploring Chicago:

  • There are so many things to discover in this city it can be difficult to know where to start. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are highlights which should feature on any good Chicago itinerary.

Complete your Chicago trip with a car rental

  • We use the same magic that helped you find your cheap flight from Billy Bishop Toronto City Airport to Chicago to track down amazing deals on car rentals. Search for your ride in seconds and easily compare your options. Plus you'll find all the info you need on car rentals in Chicago, from the most popular car type to the best time to book.

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