Can I combine different airlines on the same trip?

Of course. We offer you the possibility of booking with more than 400 airlines so that you can find the cheapest fare or the most convenient combination: outbound flight with one airline and return flight with another.

Is lastminute.com a trustworthy travel brand?

In 1998, lastminute.com was one of the first online travel agencies. Currently, we are selling over 380,000 flights per year – and working hard on bringing travellers wherever they want to go.

What options are there if I have to change my flight?

lastminute.com offers flexibility services for purchase at the time of your booking. These services entitle you to change or cancel your flights without handling fee.**Flexibility services are available on selected flights only. Please read our T&Cs for more information.

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How long does a flight take between Toronto and Chicago?

The flight from Toronto to Chicago has a duration of 2h 3m.

What are the cheapest flights from Toronto to Chicago?

The cheapest one-way flight costs £121 flying with Porter Airlines and the cheapest return flight costs £189 with Air Canada.

How many airports are there in the city of Toronto?

Toronto has 3 airport: YTO - All airports, Toronto Pearson International Airport, Billy Bishop Toronto City Airport.

How many airports does Chicago have?

There are 3 airports in Chicago: CHI - All airports, Chicago O'Hare International Airport, Midway International Airport

Which Chicago airport is the most central?

The most central airport is Midway International Airport, 13.6km.

Which airlines have flights from Toronto to Chicago?

There are 4 airlines with flights from Toronto to Chicago; Those that offer lower prices are Porter Airlines (£347), Air Canada (£427).

Schedules of the first and last flight from Toronto to Chicago

The first flight from Toronto to Chicago is at 13:10 and the last flight departs at 14:35.

Cheap flights from Toronto to Chicago

Fly smart, spend less

Flights to Chicago from Toronto

Cheap flights from Toronto to Chicago from £121. Toronto (Canada) - Chicago (United States) return flights from £189. From 01/09/2026 (Tuesday) - 04/09/2026 (Friday). Check for the dates with the lowest prices and find the cheapest rates.

Direct flights from Toronto to Chicago

Book direct flights from Toronto to Chicago for a smooth journey.

01 Sept - 04 Sept • 3 nights

08 Jul - 12 Jul • 4 nights

17 Aug - 20 Aug • 3 nights

01 Sept - 04 Sept • 3 nights

17 Jul - 24 Jul • 7 nights

17 Jul - 24 Jul • 7 nights

Flights from Toronto to Chicago one way

Find one-way flights from Toronto to Chicago at great prices.

21 Aug

03 Aug

03 Aug

24 Aug

03 Aug

03 Aug

Cheapest flights from Toronto to Chicago

Get the cheapest flights from Toronto to Chicago today.

01 Sept - 04 Sept • 3 nights

08 Jul - 12 Jul • 4 nights

17 Aug - 20 Aug • 3 nights

01 Sept - 04 Sept • 3 nights

17 Jul - 24 Jul • 7 nights

08 Jul - 12 Jul • 4 nights

Cheap flights from Toronto Pearson International Airport to Chicago

Find cheap flights from Toronto Pearson International Airport to Chicago now.

08 Jul - 12 Jul • 4 nights

08 Jul - 10 Jul • 2 nights

17 Jul - 24 Jul • 7 nights

17 Aug - 20 Aug • 3 nights

01 Sept - 04 Sept • 3 nights

21 Aug - 23 Aug • 2 nights

Cheap flights from Billy Bishop Toronto City Airport to Chicago

Find cheap flights from Billy Bishop Toronto City Airport to Chicago now.

01 Sept - 04 Sept • 3 nights

08 Jul - 12 Jul • 4 nights

17 Aug - 20 Aug • 3 nights

17 Jul - 24 Jul • 7 nights

18 Jul - 24 Jul • 6 nights

18 Jul - 24 Jul • 6 nights

Toronto to Chicago flight information

DEPARTING FROM:

Billy Bishop Toronto City Airport, more

ARRIVING IN:

Midway International Airport, more

AIRLINES:

Air Canada, American Airlines, Porter Airlines, more

AVG FLIGHT TIME:

2h 3m

More information about flights to Chicago from Toronto

Information about flights from Toronto to Chicago

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Once you have your flight Toronto-Chicago booked you can always use lastminute.com to organise the rest of your trip just the way you want it. lastminute.com allows you to book a hotel, car hire, tours and activities in Chicago.

Looking for low cost flights from Toronto to Chicago ? Then look no further… lastminute.com searches all available flights from Toronto to Chicago from amongst the top low cost and scheduled airlines.

Not only can you use the lastminute.com website to search low cost flights, but we have even preselected some flight offers from Toronto to Chicago for you to save you time.

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FAQs Toronto to Chicago flights

FAQs

Of course. We offer you the possibility of booking with more than 400 airlines so that you can find the cheapest fare or the most convenient combination: outbound flight with one airline and return flight with another.

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