Cheap flights from Toronto Pearson Intl Airport to Chicago from C$ 135
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 8/9. 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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Air Canada flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport
Our best Air Canada deals on Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flight tickets
United Airlines flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport
Our best United Airlines deals on Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flight tickets
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How to get the cheapest flight ticket from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport
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 O'Hare Intl Airport?
What is the cheapest month to fly to Chicago O'Hare Intl Airport?
In general, April is the cheapest month to fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around C$ 346. The month of May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Toronto Pearson Intl Airport averaging around C$ 346.
What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?
The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as C$ 787. This is often the case because there is less demand to fly during this day of the week. When flying out on a Tuesday, the most expensive travel day of the week, you can expect to see flight prices from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport for around C$ 1,313.
What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?
In the evening is the cheapest time of day to fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport when you can find flight prices for as low as C$ 581. Flying to Chicago O'Hare Intl Airport in the evening is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are C$ 1,509 on average. Flights to Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport in the afternoon are generally more expensive because this time of day is more convenient for travellers’ schedules.
What is the cheapest Toronto Pearson Intl to Chicago O'Hare Intl flight route?
Fly from Toronto Pearson Intl to Chicago O'Hare Intl for the best Toronto Pearson Intl - Chicago O'Hare Intl flight prices
How far in advance should I book a flight to Chicago O'Hare Intl Airport?
You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport when booking 12 weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around C$ 405 when searching 12 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport for as low as C$ 338 on momondo.
What cabin class options are available on Toronto Pearson Intl to Chicago O'Hare Intl flights?
There are 4 cabin classes available to choose from on Toronto Pearson Intl to Chicago O'Hare Intl 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 O'Hare Intl?
Air Canada, American Airlines, and United Airlines are the most popular carriers operating from Toronto Pearson Intl to Chicago O'Hare Intl
Which airlines fly to Chicago O'Hare Intl Airport?
Air Canada, United Airlines and American Airlines are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Toronto Pearson Intl Airport according to our data. Air Canada is the first choice among our users, with 75% of people opting to fly with this airline when travelling to Chicago O'Hare Intl Airport. Keep in mind that there are 5 different airlines that fly to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport on average per day?
As of June 2025, there are 55 flights per day flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport. The most common time of day flights depart is 1:00p.m., with 47% of flights taking off in the afternoon.
How many flights depart from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport on average per week?
The number of flights available between Toronto Pearson Intl Airport and Chicago O'Hare Intl Airport is 391 per week as of June 2025. The most frequent departure day is Wed, with 16% of weekly flights leaving on this day.
When to book flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport
Cheap Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport (YYZ to ORD) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport
How far is Toronto Pearson Intl to Chicago O'Hare Intl by plane?
A flight from Toronto Pearson Intl to Chicago O'Hare Intl will travel around 700.9 km. In terms of flight time, this usually takes a little over 1h 53m.
When did momondo last update prices for flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?
Prices for flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport are updated daily.
How many operators does momondo search for flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?
There are 5 operators available for flights from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport as of June 2025.
How old do you have to be to fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, 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 O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The necessary travel and health documents for your Chicago O'Hare Intl Airport 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 Pearson Intl Airport to Chicago O'Hare Intl Airport?
Based on momondo bookings for flights between Toronto Pearson Intl Airport and Chicago O'Hare Intl Airport, the leading plane model is De Havilland (Bombardier) DHC-8-400 Dash 8Q, making up 16.36% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 13.85%, Boeing 737-800 with 11.33%, and Airbus A220-300 with 8.69%.
What is the most popular airline from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport?
momondo data reveals that the most frequently booked airline on the route from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport is Air Canada, representing 74% of all bookings. The subsequent popular airlines are United Airlines at 18%, American Airlines at 5%, and Porter Airlines at 2%.
Best airlines flying from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport
Compare and see reviews for airlines that fly from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom C$ 232 | Free Cancellation | Rating 8.0 288 reviews | |||
| PriceFrom C$ 278 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom C$ 283 | Free Cancellation | Rating 7.1 9,537 reviews | |||
| PriceFrom C$ 302 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom C$ 423 | Free Cancellation | Rating 7.2 2,868 reviews |
United Airlines Flights From Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport
United Airlines flies from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport around 69 times per week, with 8,790 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport in the last 72 hours was C$ 221 (round-trip), much lower than the average airfare cost of C$ 323 for United Airlines flights on this route.
American Airlines Flights From Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport
Another popular option for Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport flights is American Airlines (7.2/10, 10,000 ratings). American Airlines flies from Toronto Pearson Intl Airport to Chicago O'Hare Intl Airport around 27 times per week, with deals starting from C$ 203 round-trip and rising to an average price of around C$ 375.
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Why should I use momondo to find a flight deal from Toronto to Chicago?
Finding the right flight to Chicago from Toronto is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.
Can I find flights from Toronto to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from Toronto with this policy.
How can momondo help me find flights from Toronto to Chicago?
Once you have performed a search for Toronto to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from Toronto to Chicago right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Toronto to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.