Cheap flights from Toronto to Chicago from $92
This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Toronto to Chicago departing on 5/20. 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
WestJet flights from Toronto to Chicago O'Hare Intl Airport
Our best WestJet 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?
The month of November is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Toronto averaging around $280.
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 $423. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday is the most expensive day to depart from Toronto because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $762.
What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?
Flying to Chicago O'Hare Intl Airport from Toronto in the evening is the least expensive time of day to depart. momondo users have found prices as low as $350 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $691. Of course, these prices can vary depending on the time of year and what airport you fly to.
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 16 weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $302 when searching 16 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 $263 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.
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
What airlines fly to Chicago O'Hare Intl Airport?
Air Canada, American Airlines and United 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 50% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 3 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?
43 flights are operational daily from Toronto to Chicago O'Hare Intl Airport as of April 2025. The most popular departure time for this route is 1:00PM, with 46% 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?
303 flights are operational weekly from Toronto to Chicago O'Hare Intl Airport as of April 2025. The most popular departure day for this route is Tue, with 19% of flights per week taking off 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 446.6 mi between Toronto and Chicago O'Hare Intl. A reasonable flight in good conditions will take 1h 54m.
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 updated daily.
How many operators does momondo search for flights from Toronto to Chicago O'Hare Intl Airport?
There are 3 operators available for flights from Toronto to Chicago O'Hare Intl Airport as of April 2025.
How old do you have to be to fly from Toronto to Chicago O'Hare Intl Airport?
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 O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable 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 14.04% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 12.56%, Embraer 195 E2 with 9.46%, and Airbus A220-300 with 8.60%.
What is the most popular airline from Toronto to Chicago O'Hare Intl Airport?
momondo data reveals that the most frequently booked airline on the route from Toronto to Chicago O'Hare Intl Airport is Air Canada, representing 56% of all bookings. The subsequent popular airlines are American Airlines at 31% and United Airlines at 13%.
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 $202 | Free Cancellation | Rating 7.0 9,240 reviews | |||
| PriceFrom $225 | Free Cancellation | Rating 7.4 8,696 reviews | |||
| PriceFrom $230 | Free Cancellation | Rating 7.2 10,000 reviews |
United Airlines Flights From Toronto to Chicago O'Hare Intl Airport
The lowest priced United Airlines flight from Toronto to Chicago O'Hare Intl Airport from the last 72 hours was $225. Generally, United Airlines has 40 flights on this route every week with an average price of $311. United Airlines is rated 7.4/10 by our users.
American Airlines Flights From Toronto to Chicago O'Hare Intl Airport
The best American Airlines deal for Toronto to Chicago O'Hare Intl Airport flight tickets found on momondo in the last 72 hours was $230, round-trip. It should be noted that an average American Airlines flight deal for this route in this time was higher, at $329 round-trip. American Airlines operates 34 flights out of Toronto into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 10,000 American Airlines reviews by users on momondo have scored the airline at 7.2/10.
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Why should I use momondo to find a flight deal from Toronto to Chicago?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Toronto to Chicago. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Toronto to Chicago with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Toronto to Chicago flights to just show those with flexible booking policies.
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?
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.