Trip.com
>
Cheap Flights
>
United States
>
Illinois
>
Chicago
Hotels in Chicago
>
Flights from Toronto to Chicago

Airlines Flying from Toronto to Chicago

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
Air Canada logo Air Canada Porter Airlines logo Porter Airlines United Airlines logo United Airlines American Airlines logo American Airlines

Flight deals from Toronto to Chicago

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • Round-trip
  • One way

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Flight Information from Toronto to Chicago

Cheapest one-way flight price £58
Cheapest return ticket price £89
Off-season travel month April
Peak season for travel February
Flight distance 701.97km
Average flight time 1 hour 59 minutes
Popular airline Air Transat

Find the best time to fly from Toronto to Chicago

We monitor flight fares to help you find the best deals effortlessly

Cheapest flights
From price
Search
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
  • 8 15
  • 15 22
  • 22 29

  • Jul

    29 6
  • 6 13
  • 13 20
  • 20 27

  • Aug

    27 3
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

FAQ

  • When are flight tickets from Toronto (YTO) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Toronto to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much are flights from Toronto (YTO) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around £189.

  • How long is the flight from Toronto (YTO) to Chicago (CHI)?

    It takes about 1 hour 59 minutes to fly from Toronto (YTO) to Chicago (CHI).

  • What are the most popular airlines that fly from Toronto (YTO) to Chicago (CHI)?

    Airlines with flights from Toronto (YTO) to Chicago (CHI): Alaska Airlines, Air Canada, American Airlines, United Airlines, Qantas Airways and Qatar Airways.

  • How many airports in Chicago (CHI)?

How to find a cheap flight from Toronto to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Toronto to Chicago. Book your flights at the right time and save more.
1
Be flexible with your travel dates to get the cheapest flight from Toronto to Chicago.
Simply tap "Date" on the flight search bar to browse through the calendar and check out airfare from Toronto to Chicago over the next 6 months in 2025. If you're planning to fly within the next three months, it looks like the most affordable option is on Fri, Jul 11, with one-way flights priced at just £66.
2
Compare cheap flight deals from Toronto to Chicago across hundreds of airlines.
With our extensive search, you can compare prices from over 500 airlines to find the cheapest flight tickets from Toronto to Chicago. The cheapest airline for this route is United Airlines.
3
Set up a Price Alert
By setting up a Price Alert for your journey from Toronto to Chicago, you can easily keep an eye on ticket prices without having to check every day.
4
Don't miss out on cheap flight deals and promo codes from Toronto to Chicago.
You can always find the latest offers through Trip.com Deals and Promo Codes for cheap flights. By signing up for a free membership, you'll get access to even more deals for your flights.
5
Book early or wait until the last minute.
It's usually best to book early. Flight tickets are often cheapest when they're first released, typically about a year before the departure date. So, have a look online as soon as the flights you're interested in become available. If you miss the cheapest time, you might still find some good deals as the departure date gets closer.
6
Search for flights on the go.
For the best travel flight booking experience, download the Trip.com app. You can search for cheap flights from Toronto to Chicago and snag some exclusive deals just for you.

More Travel Options

  • Top Routes from Toronto
  • Top Routes to Chicago
  • Popular Airlines