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Selected fares from Toronto to Chicago

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Route Information for Flights from Toronto to Chicago

Origin Airport IATA Code YYZ
Destination Airport IATA Code ORD
Flight Price $311
Distance 697 km

Toronto (YTO) to Chicago (CHI)

Whaa?! A trip to Chicago! You will definitely need a ticket to Chicago then. We suppose you could ride a bicycle for most of it, but you probably are on a bit of a time crunch. Fortunately, you found us. Hotwire can get you an awesome rate on your flight from YTO to CHI.

How do you get the best deal on a flight from Toronto to Chicago?

We've been doing this for a long time, so we know a few ways to snag the best price on your flight to Chicago. You can pocket that extra cash for more than just getting from point A to point B with a little know-how.

What is the best day of the week to book a flight?

With the right attitude and flexibility, you can fly for less. Below are the cheapest days to fly:

  • Tuesday and Wednesday—You know how most stores are not crowded midweek? Same thing here. So, get on while the getting is good.
  • Thursday and Saturday—Get a head start on that Friday crowd. This also works on your return flight. Shorten your holiday by a day and increase your savings.
  • Monday through Thursday—If you're flying internationally, deals are often available when departing these days.

Can staying the weekend get me a cheaper ticket?

If you stay through the weekend, generally that return ticket to YTO can be cheaper since you'll be leaving earlier in the week. All those business travelers have less flexible itineraries, so that means more savings for you. Of course, we don't want to twist your rubber arm or anything.

Why travel during the off-peak season?

Shoulder or off-peak seasons are when most people aren't flying to certain locations. So when it is cold, most people head to warmer places like the Caribbean, Mexico, Hawaii, etc., just like our feathered friends. But during the summer, you'll find that Europe is really popular. You can usually save on your flight when you avoid flying during the peak seasons.

Is that the lowest price?

There are a lot of others that are longing for an amazing bargain on a flight from Toronto to Chicago. You might miss your opportunity to dial in the time and the flight you wanted.

What is the Hotwire Hot Rate?

The Hotwire Hot Rate is for travelers who have a lot of flexibility in their travel plans. You'll get a great deal on your flight from Toronto (YTO) to Chicago (CHI). After your purchase, you'll get the time and name of the airline, but with a little risk you can get huge savings.

Book today

We're here to help you save some money on your upcoming flight from Toronto to Chicago. Use our guide to help you score that unreal deal. And if you are feeling lucky (and you always will be) book the Hotwire Hot Rate for unbelievable savings. So say "Later" to Toronto and "Hello" to Chicago.

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^Savings based on all package bookings with Flight + Hotel made on Hotwire.com from January 1, 2018 to December 31, 2018 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.