Flights from Toronto Island to Chicago

Flights tailored to your budget

Selected dates may not give results due to COVID-19. We suggest you change the dates.
Multi-city Round trip One way
Round trip
One way
Multi-city
From
No results match your search criteria
To
No results match your search criteria
{{ weekDay }}
Dates
{{ panel.label }}
Looking for a one-way flight?

Flexible dates can save you money

Explore nearby dates to find lower fares

{{ fromDate | dateToLongNamedDate }}
?
Flexible dates
Depart {{ flexibleFromDateLabel }}
{{ option.label }}
?
Return {{ flexibleToDateLabel }}
{{ option.label }}
Passengers / Class
Number of passengers
Adults
{{ adults }}
Children
{{ children }}
Infants
{{ infants }}
Class
Economy
Available for Economy only
New Multi-city experience

Discover a new Multi-city search experience from Jetcost, designed to handle more complex itineraries. By continuing, you’ll be taken to a dedicated page powered by Kiwi.com.
How do we get the info you see here? Please note that we offer an online comparison service and that all information and prices regarding services and/or products available on our website are provided by our third-party partners. We do our best to show you up-to-date information, but please note that we are not responsible for the completeness or accuracy of the information published, so please check all conditions carefully on the website of the partner before making a booking. Please check our Terms and Conditions for more details. Read more

Looking for the price of a flight from Toronto Island to Chicago?

There’s no fixed price — fares between Toronto and Chicago can vary a lot by day or time.

Select your dates to check current offers.

It’s often useful to check whether nearby airports offer better fares. Flying during less crowded periods also increases your chances of finding good deals.

Which airports serve Toronto and Chicago?

When planning a trip of about 438 mi, it's a good idea to check flights from surrounding airports too.

  • Airports in Toronto: Toronto is connected to 4 airports - John C. Munro, Kitchener Lake, Lester B. Pearson, Toronto Island Airport.
  • Airports in Chicago: Chicago offers flights from 3 airports - Midway, O'Hare, Rockford.

The closest airport isn’t always the cheapest — it’s worth checking the alternatives too. In some cities, smaller airports offer lower fares than the main ones.

Flights from Toronto - Toronto Island Airport to Chicago

Adjust your flight filters for Toronto Island – Chicago

Jetcost gives you tools to search smarter. Pick your ideal price range, airline, departure time, and flight type — then compare offers from agencies like Expedia, eDreams, and more.

Other popular destinations

Planning a trip to United States? These cities are popular too: Atlanta, Los Angeles, Miami, New York City, Orlando.

Sorting options let you see the most affordable flights first. Some results may include extra fees shown only at checkout — always read carefully to see what’s included.
Frequently Asked Questions

Frequently asked questions about flights from Toronto Island to Chicago.

How much does an airline ticket from Toronto Island to Chicago cost?

Flight prices can vary a lot depending on the period and destination. At the moment, this information is not available for flights from Toronto Island to Chicago.

How far is Toronto from Chicago?

Toronto is about 438 mi from Chicago.

What are the airports in Chicago?

Chicago has 3 airports: Midway, O'Hare, Rockford.

What are the airports in Toronto?

Toronto has 4 airports: John C. Munro, Kitchener Lake, Lester B. Pearson, Toronto Island Airport.

What are the most popular cities in United States?

The most popular cities in United States according to our users' searches are: Atlanta, Los Angeles, Miami, New York City, Orlando.

When should I book a flight from Toronto to Chicago?

The best time to book a flight from Toronto to Chicago is 1 month in advance, while the worst time is 1 week in advance.

What is the cheapest month to fly from Toronto to Chicago?

This information is not available at the moment.

What is the most expensive month to fly from Toronto to Chicago?

This information is not available at the moment.

What is the best day of the week to fly from Toronto to Chicago?

This information is not available at the moment.