Cheap Flights from Toronto to Chicago from $108

Frequently Asked Questions

• What are the cheapest flights from Toronto to Chicago (YTO-CHI)?

  Based on Trip.com data, Porter Airlines offers one-way fares as low as $108 on Cheapest nonstop routes (e.g. YTZ to MDW on Thu, Sep 17), while Porter Airlines offers Cheapest nonstop round-trips from $172 departing on Tue, Sep 29 and returning on Thu, Oct 1.

• Which airlines offer direct flights from Toronto to Chicago?

  At the moment, you can catch a nonstop flight from Toronto to Chicago with the following airlines, including: Porter Airlines Air Canada American Airlines United Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.

• How long does it take to fly from Toronto (YTO) to Chicago (CHI) and what is the distance?

  It takes around 2 hours 3 minutes to fly from Toronto (YTO) to Chicago (CHI).

• When is the best time to book flights from Toronto to Chicago?

  By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Toronto to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

• How many flights are there per week from Toronto to Chicago?

  Based on Trip.com data in the past 4 weeks, there is 148 flight per week flying from Toronto to Chicago. You can check the weekly schedule for popular airlines on this route below: Porter Airlines: S/M/T/W/T/F/S -- PD6005 (07:43) American Airlines: S/M/T/W/T/F/S -- AA3524 (07:43) United Airlines: S/M/T/W/T/F/S -- UA8533 (08:34)

• How can I find the best deals on flights from Toronto to Chicago?

  To find best deals on flights from Toronto to Chicago, you can use various tools on Trip.com:
  · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Thu, Sep 17, with one-way flights priced at just $108.
  · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Porter Airlines.
  · Set up price alerts to easily monitor ticket prices without having to check every day.
  · Check Trip.com flight deals and promo codes frequently.
  · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around July.
  · Get exclusive promo codes for Trip.com app users.

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

  The cheapest months to fly from Toronto to Chicago is September, when demand for travel is lower.

• Which upcoming date is cheapest to fly from Toronto to Chicago on?

  After crunching the numbers on our September flight calendar, it's currently cheapest to fly from Toronto to Chicago on September 30, 2026 with Porter Airlines, with prices starting at $102.

• Which airports can I fly into Chicago from Toronto?

  You can arrive at any of the following airports in Chicago: O'Hare International Airport (ORD), Chicago Midway International Airport (MDW), and Chicago Rockford International Airport (RFD). Flights from Billy Bishop Toronto City Airport to Chicago Midway International Airport (YTZ-MDW) are by far the most popular option for this route.

• Is there any time difference between Toronto and Chicago?

  The time difference between Chicago and Toronto is 1h.

• How do I change or cancel my ticket from Toronto to Chicago?

  Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.

• What is the average cost of a one-way flight from Toronto to Chicago?

  Based on Trip.com data for flights departing in the next 30 days, the average one-way fare from Toronto to Chicago is $219. Fares vary by travel date, airline and availability.

• What is the average cost of a round-trip flight from Toronto to Chicago?

  Based on Trip.com data for travel in the next 30 days, the average round-trip fare from Toronto to Chicago is $371. The final price depends on the outbound and return dates, airline and fare conditions.

• How do I book flights from Toronto to Chicago on Trip.com?

  Enter Toronto and Chicago, choose your travel dates and passengers, then compare flights by price, duration and baggage. Select a fare, review the change and cancellation rules, enter traveler details and complete payment to receive your confirmation.

• Are there budget airlines on the Toronto to Chicago route?

  Porter Airlinesare the most popular budget airlines flying from Toronto to Chicago. Check baggage, seat and payment fees before comparing the final price.