Cheap flights from Toronto 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 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 to Chicago O'Hare Intl Airport
Our best Air Canada deals on Toronto to Chicago O'Hare Intl Airport flight tickets
United Airlines flights from Toronto to Chicago O'Hare Intl Airport
Our best United Airlines deals on Toronto to Chicago O'Hare Intl Airport flight tickets
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How to get the cheapest flight ticket from Toronto 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 cheapest month to fly to Chicago O'Hare Intl Airport?
In general, May is the cheapest month to fly from Toronto 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$ 360. The month of November is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Toronto averaging around C$ 380.
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 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 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 in the afternoon are generally more expensive because this time of day is more convenient for travellers’ schedules.
What is the cheapest Toronto to Chicago O'Hare Intl flight route?
Fly from Toronto Pearson Intl to Chicago O'Hare Intl for the best Toronto - 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 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 for as low as C$ 338 on momondo.
What cabin class options are available on Toronto to Chicago O'Hare Intl flights?
There are 4 cabin classes available to choose from on Toronto 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.
Can stopping save me money on Toronto to Chicago O'Hare Intl Airport flights?
No. A direct flight is the cheapest option for a flight between Toronto to Chicago O'Hare Intl Airport.
How have Toronto to Chicago O'Hare Intl Airport flight prices changed over time?
As of June 2025, prices for Toronto to Chicago O'Hare Intl Airport flights are approximately 28% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Toronto to Chicago O'Hare Intl?
Air Canada, American Airlines, and United Airlines are the most popular carriers operating from Toronto 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 according to our data. Air Canada is the first choice among our users, with 76% 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 to Chicago O'Hare Intl Airport on average per day?
52 flights are operational daily from Toronto to Chicago O'Hare Intl Airport as of June 2025. The most popular departure time for this route is 1:00p.m., with 47% of flights per day taking off in the afternoon.
How many flights depart from Toronto to Chicago O'Hare Intl Airport on average per week?
The number of flights available between Toronto and Chicago O'Hare Intl Airport 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 to Chicago O'Hare Intl Airport
Cheap Toronto to Chicago O'Hare Intl Airport (YTO to ORD) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Toronto to Chicago O'Hare Intl Airport
How far is Toronto to Chicago O'Hare Intl by plane?
There are 718.7 km between Toronto and Chicago O'Hare Intl. By plane, this route typically takes 1h 53m.
When did momondo last update prices for flights from Toronto to Chicago O'Hare Intl Airport?
Prices for flights from Toronto to Chicago O'Hare Intl Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Toronto to Chicago O'Hare Intl Airport?
There are 5 operators available for flights from Toronto to Chicago O'Hare Intl Airport as of June 2025.
How old do you have to be to fly from Toronto to Chicago O'Hare Intl Airport?
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 to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport. 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 to Chicago O'Hare Intl Airport?
Based on momondo bookings for flights between Toronto 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 to Chicago O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Toronto to Chicago O'Hare Intl Airport is Air Canada (72% of total bookings). The next most popular airlines are United Airlines (19%), American Airlines (5%), and Porter Airlines (3%).
Best airlines flying from Toronto to Chicago O'Hare Intl Airport
Compare and see reviews for airlines that fly from Toronto 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 to Chicago O'Hare Intl Airport
United Airlines is one of the most popular airlines flying from Toronto to Chicago O'Hare Intl Airport, operating 69 flights/week on average for this route. A good United Airlines flight deal for Toronto to Chicago O'Hare Intl Airport starts from C$ 221 round-trip, up to an average price of C$ 323. Our users have rated United Airlines at 7.4/10.
American Airlines Flights From Toronto to Chicago O'Hare Intl Airport
American Airlines is also a popular choice for this route. American Airlines flight deals for Toronto to Chicago O'Hare Intl Airport start from as low as C$ 203 round-trip, depending on your selected dates, with average American Airlines deals seen on momondo around C$ 375. American Airlines operates 27 flights to Chicago O'Hare Intl Airport from Toronto in an average week. Users have rated it 7.2/10 across 10,000 reviews.
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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?
momondo provides multiple filters to help you find the best flight to Chicago from Toronto. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
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.