Cheap flights from Toronto Lester B. Pearson International Airport to Chicago

Q: What are the cheapest airlines?

Air Canada, West Jet. These airlines usually offer the cheapest flights from Toronto Lester B. Pearson International Airport to Chicago.

Q: Can I fly direct to Chicago?

Air Canada. You can fly non-stop from Toronto Lester B. Pearson International Airport to Chicago with these airlines.

Q: What airlines fly indirectly?

West Jet. These airlines fly from Toronto Lester B. Pearson International Airport to Chicago, but you’ll have at least one layover.

Q: How long is the flight?

1 hrs 50 mins. This is the shortest flight time from Toronto Lester B. Pearson International Airport to Chicago.

from as little as £231

7 nights in Chicago, departing Toronto Lester B. Pearson International Airport on 28 / Feb / 2025 with Air Canada (price found 2 hours ago)

Subject to availability, prices correct of the last 24 hours

Part of the Emirates Group

Safe & Secure, ATOL Protected

Over 30 Years in Business

Rated 'Excellent' on Trustpilot

Cheap return flights from Toronto Lester B. Pearson International Airport to Chicago

Find the best deals

The Toronto Lester B. Pearson International Airport / Chicago route

All 696 km of it

Cheap flight deals for this route

See what's hot at the moment

Chicago flight facts

What you need to know

What are the cheapest airlines?

Air Canada
West Jet

These airlines usually offer the cheapest flights from Toronto Lester B. Pearson International Airport to Chicago.

Can I fly direct to Chicago?

Air Canada

You can fly non-stop from Toronto Lester B. Pearson International Airport to Chicago with these airlines.

What airlines fly indirectly?

West Jet

These airlines fly from Toronto Lester B. Pearson International Airport to Chicago, but you’ll have at least one layover.

How long is the flight?

1 hrs 50 mins

This is the shortest flight time from Toronto Lester B. Pearson International Airport to Chicago.

Alternative flights from Toronto Lester B. Pearson International Airport

You might find cheaper flights nearby

Chicago Midway Airport from Toronto Lester B. Pearson International Airport

search for price

Find flights

Chicago O'hare International Airport from Toronto Lester B. Pearson International Airport

from £231 pp

Find flights

28 / Feb / 2025 is currently the lowest priced day of the year to fly the Toronto Lester B. Pearson International Airport/Chicago route. There are around 25 flights on any given week from the UK to Chicago and the cheapest month to fly right now is February.

Not suitable? Try running another search or viewing all cheap flight deals.

Key facts about Chicago

Currency

United States dollar

Language

English

Timezone

6 hrs behind GMT

How to get cheap flights from Toronto Lester B. Pearson International Airport to Chicago

Tips and advice from our flight experts

We've gathered all the available flights from Toronto Lester B. Pearson International Airport to Chicago on your chosen dates. Generally, the most popular airlines are Air Canada, West Jet & West Jet. Air Canada is the most popular, but that doesn’t mean they're the best choice for your travel dates.

Normally, Chicago O'hare International Airport is the cheapest airport to fly into Chicago. This isn’t necessarily the case for your chosen dates, but it’s worth bearing in mind. There are 25 flights every week to Chicago, and the flight from Toronto Lester B. Pearson International Airport normally takes about 4 hrs 5 mins.

Chicago has two airports, so you have more than one option. It could also be worth changing Toronto Lester B. Pearson International Airport to include other airports, to see more flights and, possibly, better prices. At the moment, the cheapest flight is £231.

Did you know you can also book your accommodation and car hire with Netflights? We can sort your whole trip to Chicago.