Cheap Flights from Toronto to Chicago from S$ 146

Frequently Asked Questions

• Which airlines offer the cheapest flights from Toronto to Chicago?

  Based on Trip.com data, Air Canada offers Cheapest nonstop one-way flights from S$ 146 (for example, YTZ–ORD on Fri, Nov 27). For a Cheapest nonstop return flight, Air Canada offers fares from S$ 240, departing on Sun, Nov 29 and returning on Tue, Dec 1.

• Which airlines offer direct flights from Toronto to Chicago?

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

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

  It takes about 2 hours 7 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 from Toronto to Chicago each week?

  On average, 159 direct flights operate each week between Toronto and Chicago. See below the schedules of the main airlines serving this route:
  Air Canada: S/M/T/W/T/F/S – AC8547 (departure at 12:12)

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

  Here are some tips for finding the best flight deals from Toronto to Chicago on Trip.com:
  · Be flexible with your travel dates. The cheapest flight is currently on Fri, Nov 27, with one-way fares from just S$ 146.
  · Compare airlines. American Airlines currently offers the lowest fares on this route.
  · Set up a price alert to track fare changes without searching every day.
  · Check Trip.com regularly for flight deals and available promo codes.
  · Avoid peak season or book early. January is generally the busiest month for travel to Chicago.
  · Get exclusive promo codes on the Trip.com app.

• When is the best time to book a flight from Toronto to Chicago to get the best price?

  The cheapest month to book a flight from Toronto to Chicago is usually September, when demand is lower.

• Which upcoming date is the cheapest for flights from Toronto to Chicago?

  After crunching the numbers on our October flight calendar, it's currently cheapest to fly from Toronto to Chicago on October 21, 2026 with Porter Airlines, with prices starting at S$ 224.

• Which airports should you choose for flights from Toronto to Chicago?

  Flights to Chicago can arrive at: O'Hare International Airport (ORD), Chicago Midway International Airport (MDW) and Chicago Rockford International Airport (RFD). The most common route connects Toronto Pearson International Airport and O'Hare International Airport (YYZ–ORD).

• What is the time difference between Toronto and Chicago?

  The time difference between Chicago and Toronto is 1h.

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

  Tickets can only be changed or cancelled 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 S$ 330. 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 S$ 496. 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 traveller details and complete payment to receive your confirmation.

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

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