Cheap flights from Toronto Pearson Intl Airport to Chicago from $99
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 9/8. 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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United Airlines 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 cheapest month to fly to Chicago?
The month of May is, on average, the cheapest month to fly to Chicago from Toronto Pearson Intl Airport, with most prices found around $253. If you’re not able to fly to Chicago in May, then June is your next best option. Flight prices from Toronto Pearson Intl Airport to Chicago during June average around $262.
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 $381. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Toronto Pearson Intl Airport to Chicago for around $633.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Toronto Pearson Intl Airport to Chicago during this time can be as low as $334. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $575.
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 $296 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 $247 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.
Can stopping save me money on Toronto Pearson Intl Airport to Chicago flights?
No. A direct flight is the cheapest option for a flight between Toronto Pearson Intl Airport to Chicago.
How have Toronto Pearson Intl Airport to Chicago flight prices changed over time?
As of June 2025, prices for Toronto Pearson Intl Airport to Chicago flights are approximately 15% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Toronto Pearson Intl to Chicago?
Air Canada, American Airlines, and United Airlines are the most popular carriers operating from Toronto Pearson Intl to Chicago
What airlines fly to Chicago?
Air Canada, American Airlines and United 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 52% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 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?
The number of flights available between Toronto Pearson Intl Airport and Chicago is 52 per day as of June 2025. The most frequent departure time is 1:00PM, with 47% of daily flights leaving 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 365 per week as of June 2025. The most frequent departure day is Thu, with 16% 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?
The straight-line distance from Toronto Pearson Intl to Chicago is 424.4 mi. Typically, this will take 1h 53m by plane in normal conditions.
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?
There are 3 operators available for flights from Toronto Pearson Intl Airport to Chicago as of June 2025.
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 that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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 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 Pearson Intl Airport to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Toronto Pearson Intl Airport to Chicago is De Havilland (Bombardier) DHC-8-400 Dash 8Q (16.36% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (13.85%), Boeing 737-800 (11.33%), and Airbus A220-300 (8.69%).
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 (63% of total bookings). The next most popular airlines are American Airlines (23%) and United Airlines (14%).
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 $162 | Free Cancellation | Rating 7.1 9,531 reviews | |||
| PriceFrom $165 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom $218 | Free Cancellation | Rating 7.2 10,000 reviews |
United Airlines Flights From Toronto Pearson Intl Airport to Chicago
The lowest priced United Airlines flight from Toronto Pearson Intl Airport to Chicago from the last 72 hours was $165. Generally, United Airlines has 69 flights on this route every week with an average price of $287. United Airlines is rated 7.4/10 by our users.
American Airlines Flights From Toronto Pearson Intl Airport to Chicago
American Airlines (7.2/10 from 10,000 reviews) operates around 27 flights from Toronto Pearson Intl Airport to Chicago in any given week. The average American Airlines airfare for this route is around $318, with deals from around $218 rare but found on momondo. Referenced prices are for round-trip Toronto Pearson Intl Airport to Chicago flight searches in the last 72 hours.
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Why should I use momondo to find a flight deal from Toronto to Chicago?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Toronto to Chicago for you.
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?
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?
Yes momondo offers price alerts on flights to Chicago from Toronto. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.