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Cheap Flights from Toronto to Chicago

Top last minute flight deals

Feeling spontaneous? It’s never too late to book a trip. Here’s our pick of the best last minute flights to Chicago...
Estimated lowest prices only. Found in the last 14 days.

Flight information Toronto Pearson International to Chicago

Cheapest return price last month

$299

Direct airlines

7

Flights per week

135

Average flight time, total distance 724 kilometres

1h 41min

Most popular airline last month

Air Canada

Chicago O'Hare International, Chicago Midway and Chicago Rockford

3 airports

Frequently asked questions

There are 3 airports in Chicago: Chicago O'Hare International, Chicago Midway and Chicago Rockford.
The best price found on Skyscanner for a flight from Toronto Pearson International to Chicago is $299. This was found by aggregating across different carriers and is the cheapest price for the whole month.
1h 41min is the average flight time from Toronto Pearson International to Chicago.
There are 7 airlines who fly direct from Toronto Pearson International to Chicago.
There are 135 flights per week flying from Toronto Pearson International to Chicago, as of August.

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Useful information before booking your travel from Toronto to Chicago

Check the travel information panel above to get exact information about:

  • Distance from Chicago to Toronto
  • Flight time from Chicago to Toronto
  • Which airlines provide the cheapest tickets from Toronto to Chicago
  • Which airlines fly direct to Chicago from Toronto.

Know your cabin luggage size and weight restrictions thanks to our guide to hand baggage.

Track your flight status by checking arrival and departure times from Toronto to Chicago

  • Download the Skyscanner App to get live flight tracker updates.
    We’ll keep you posted with the latest schedule information and send you important flight updates for your travel to Chicago from Toronto.

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    FAQ on Flights from Toronto to Chicago

    How far in advance should I book a flight to get the best deal for Toronto to Chicago flights?
    You can use the monthly price chart listed above to book your flights well in advance.
    How can I book cheap Toronto to Chicago flight tickets online?
    Use Skyscanner's flight search above and fill in your travel dates and click on "Search Flights". You can now choose the desired flight to Chicago from the list.
    How Skyscanner is different from online travel agents?
    Skyscanner pulls flight prices from all the major airlines and online travel agents like Expedia, Cheap Flights, Jetstar, Virgin Australia, Tigerair etc. You don’t need to check multiple websites to find the best price. Once you find your flight & click to select, we link you directly to the airline or travel agent. No hidden charges, no added fees.
    Which is the cheapest month to book flights from Toronto to Chicago?
    Check the bar chart at the top to find the cheapest month to fly from Toronto to Chicago. The chart is based on the next 12 months price data we have.
    Should I opt for a travel insurance while flying from of Toronto to Chicago?
    It's always safe and advised to travel with a travel insurance.
    Should I opt for on board food while travelling from Toronto to Chicago?
    Its suggested to opt for on board meals while flying to Chicago.
    What is the check in luggage limit in Toronto to Chicago flights?
    Generally, 15 kg is the allowed baggage limit for an economy class passenger flying from Toronto to Chicago. Its advised to check your baggage limit that is printed on your ticket as it varies from airline to airline.
    What is the hand baggage limit in Toronto to Chicago flights?
    7 to 10 kg is the allowed hand luggage limit while flying from Toronto to Chicago. For most recent updates on the hand luggage weight, contact the airline youa re flying with.
    What is the advantage of doing a web check in while flying from Toronto?
    Web check-in confirms your travel while flying from Toronto and saves your time at the check-in counter.
    How can I change my Toronto to Chicago travel dates after booking?
    Before check-in, the respective flight operator will allow you to change your travel dates. Generally, its chargeable based on the rescheduled date. It is recommended to contact respective airlines to know about the charges.
    How do I subscribe for Skyscanner's price alerts for cheap fares from Toronto to Chicago?
    Use Skyscanner's price alert tool to get notified about cheap fares from Toronto to Chicago.

    Prices shown on this page are estimated lowest prices only. Found in the last 45 days.