Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 164
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 Pearson Intl Airport to Chicago departing on 26/5. 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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Air Canada flights from Toronto Pearson Intl Airport to Chicago
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Delta flights from Toronto Pearson Intl Airport to Chicago
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How to get the cheapest flight ticket from Toronto Pearson Intl Airport 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 Pearson Intl Airport and Chicago?
What is the cheapest month to fly to Chicago?
The month of April is another great option to travel to Chicago, with average flight prices from Toronto Pearson Intl Airport averaging around C$ 391.
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 Friday when prices can be found for as low as C$ 742. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 1,384. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.
What is the cheapest time of day to depart on your flight to Chicago?
In the evening is the cheapest time of day to fly from Toronto Pearson Intl Airport to Chicago when you can find flight prices for as low as C$ 552. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,564 per ticket.
What is the cheapest Toronto Pearson Intl to Chicago flight route?
Fly from Toronto Pearson Intl to Chicago O'Hare Intl for the best Toronto Pearson Intl - 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 Pearson Intl Airport when booking 12 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 421 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 Pearson Intl Airport for as low as C$ 367 on momondo.
What cabin class options are available on Toronto Pearson Intl to Chicago flights?
There are 4 cabin classes available to choose from on Toronto Pearson Intl to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Toronto Pearson Intl to Chicago?
Air Canada, United Airlines, and American Airlines are the most popular carriers operating from Toronto Pearson Intl to Chicago
Which airlines fly to Chicago?
Air Canada, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago from Toronto Pearson Intl Airport according to our data. Air Canada is the first choice among our users, with 71% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Toronto Pearson Intl Airport to Chicago on average per day?
53 flights are operational daily from Toronto Pearson Intl Airport to Chicago as of April 2025. The most popular departure time for this route is 6:00p.m., with 44% of flights per day taking off in the afternoon.
How many flights depart from Toronto Pearson Intl Airport to Chicago on average per week?
The number of flights available between Toronto Pearson Intl Airport and Chicago is 376 per week as of April 2025. The most frequent departure day is Thu, with 15% of weekly flights leaving on this day.
When to book flights from Toronto Pearson Intl Airport to Chicago
Cheap Toronto Pearson Intl Airport to Chicago (YYZ to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Toronto Pearson Intl Airport to Chicago
How far is Toronto Pearson Intl to Chicago by plane?
There are 683.0 km between Toronto Pearson Intl and Chicago. 1h 53m is a normal flight duration for this route.
When did momondo last update prices for flights from Toronto Pearson Intl Airport to Chicago?
Prices for flights from Toronto Pearson Intl Airport to Chicago refresh daily.
How many operators does momondo search for flights from Toronto Pearson Intl Airport to Chicago?
As of April 2025, there are 5 operators available to choose from for flights from Toronto Pearson Intl Airport to Chicago.
How old do you have to be to fly from Toronto Pearson Intl Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Toronto Pearson Intl Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Toronto Pearson Intl Airport to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Toronto Pearson Intl Airport to Chicago is De Havilland (Bombardier) DHC-8-400 Dash 8Q, representing 12.57% of all bookings. The subsequent popular models are Embraer 195 E2 at 11.54%, Embraer 175 (Enhanced Winglets) at 10.36%, and Airbus A220-300 at 9.05%.
What is the most popular airline from Toronto Pearson Intl Airport to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Toronto Pearson Intl Airport to Chicago is Air Canada (72% of total bookings). The next most popular airlines are United Airlines (17%), Porter Airlines (5%), and American Airlines (4%).
Best airlines flying from Toronto Pearson Intl Airport to Chicago
Compare and see reviews for airlines that fly from Toronto Pearson Intl Airport to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom C$ 261 | Free Cancellation | Rating 8.0 281 reviews | |||
| PriceFrom C$ 303 | Free Cancellation | Rating 7.0 9,142 reviews | |||
| PriceFrom C$ 320 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom C$ 332 | Free Cancellation | Rating 7.4 8,667 reviews | |||
| PriceFrom C$ 431 | Free Cancellation | Rating 7.2 2,809 reviews |
United Airlines Flights From Toronto Pearson Intl Airport to Chicago
United Airlines is one of the most popular airlines flying from Toronto Pearson Intl Airport to Chicago, operating 72 flights/week on average for this route. A good United Airlines flight deal for Toronto Pearson Intl Airport to Chicago starts from C$ 239 round-trip, up to an average price of C$ 327. Our users have rated United Airlines at 7.4/10.
American Airlines Flights From Toronto Pearson Intl Airport to Chicago
American Airlines is also a popular choice for this route. American Airlines flight deals for Toronto Pearson Intl Airport to Chicago start from as low as C$ 230 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around C$ 376. American Airlines operates 33 flights to Chicago from Toronto Pearson Intl Airport in an average week. Users have rated it 7.2/10 across 10,000 reviews.
Travelling to a place near Chicago?
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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?
Yes. All flights to Chicago from Toronto on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Toronto to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Toronto.
I’m not ready to book a flight from Toronto to Chicago right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Toronto to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.