Cheap flights from Toronto to Chicago from £79
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Toronto to Chicago departing on 14/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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How to get the cheapest flight ticket from Toronto to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Toronto and Chicago?
What is the cheapest month to fly to Chicago?
The cheapest month to fly to Chicago from Toronto is in April. Flight prices, which tend to average around £173, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of April, then book flights to Chicago from Toronto during May instead. Flights to Chicago in May, while not as cheap as those in April, still average around £180.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Monday when prices can be found for as low as £227. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Saturday, with ticket prices averaging around £893.
What is the cheapest time of day to depart on your flight to Chicago?
Flying to Chicago from Toronto in the morning is the least expensive time of day to depart. momondo users have found prices as low as £276 when looking at flights departing in the morning. Flights at midday are often more expensive, with an average ticket price of £863.
What is the cheapest Toronto to Chicago flight route?
Fly from Toronto Island to Chicago Midway for the best Toronto - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Toronto when booking 12 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around £218 when searching 12 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Toronto for as low as £182 on momondo.
What cabin class options are available on Toronto to Chicago flights?
There are 4 cabin classes available to choose from on Toronto to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
How many flights depart from Toronto to Chicago on average per day?
The number of flights available between Toronto and Chicago is 52 per day as of June 2025. The most frequent departure time is 13:00, with 46% of daily flights leaving in the afternoon.
How many flights depart from Toronto to Chicago on average per week?
As of June 2025, 368 flights take off from Toronto and land in Chicago each week. The most common flight departure day for this route is Fri, with 16% of weekly flights taking off on this day.
When to book flights from Toronto to Chicago
Cheap Toronto to Chicago (YTO to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Toronto to Chicago
How far is Toronto to Chicago by plane?
Toronto and Chicago are 435.3 mi apart from one another. 1h 53m is a normal flight duration for this route.
When did momondo last update prices for flights from Toronto to Chicago?
Prices for flights from Toronto to Chicago were last updated today.
How many operators does momondo search for flights from Toronto to Chicago?
As of June 2025, there is 1 operator available to choose from for flights from Toronto to Chicago.
How old do you have to be to fly from Toronto to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Toronto to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Toronto to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Toronto to Chicago is De Havilland (Bombardier) DHC-8-400 Dash 8Q, representing 20.36% of all bookings. The subsequent popular models are Embraer 175 (Enhanced Winglets) at 15.02%, Boeing 737-800 at 12.23%, and Airbus A220-300 at 9.13%.
Best airlines flying from Toronto to Chicago
Compare and see reviews for airlines that fly from Toronto to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom £136 | Free Cancellation | Rating 7.1 9,537 reviews |
Air Canada Flights From Toronto to Chicago
Air Canada flies from Toronto to Chicago around 63 times per week, with 9,537 momondo users rating the airline 7.1/10. The cheapest Air Canada deal from Toronto to Chicago in the last 72 hours was £185 (round-trip), much lower than the average airfare cost of £278 for Air Canada flights on this route.
Why use momondo?
Why should I use momondo to find a flight deal from Toronto to Chicago?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Toronto to Chicago. momondo saves you time and could save you money on your trip.
Can I find flights from Toronto to Chicago with flexible booking policies on momondo?
Flights from Toronto to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Toronto to Chicago?
momondo helps you find the best flight between Toronto and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Toronto to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Toronto are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.