Cheap flights from Chicago to Toronto from $59
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Toronto departing on 9/2. 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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United Airlines flights from Chicago to Toronto
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How to get the cheapest flight ticket from Chicago to Toronto
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 Chicago and Toronto?
What is the cheapest month to fly to Toronto?
The month of July is, on average, the cheapest month to fly to Toronto from Chicago, with most prices found around $268. If you are unable to visit Toronto during the month of July, then departing from Chicago during the month April is also very affordable. Most momondo users find prices during this month for around $271.
What is the cheapest day to depart on your flight to Toronto?
On average, the least expensive day to fly to Toronto from Chicago is on a Friday. momondo users have found tickets for Friday departures for as low as $477. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Toronto is Sunday, with ticket prices averaging around $704.
What is the cheapest time of day to depart on your flight to Toronto?
In the morning is the cheapest time of day to fly from Chicago to Toronto when you can find flight prices for as low as $429. Flying to Toronto in the morning is an ideal time because this is during off-peak travel hours. Flights to Toronto are more costly in the afternoon, with an average ticket price of $710. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.
What is the cheapest Chicago to Toronto flight route?
Fly from Chicago Midway to Toronto Island for the best Chicago - Toronto flight prices
How far in advance should I book a flight to Toronto?
You are more likely to see cheaper flights to Toronto from Chicago when booking 16 weeks ahead of your departure date. In general, you can expect to find flights to Toronto for around $318 when searching 16 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Toronto from Chicago for as low as $166 on momondo.
What cabin class options are available on Chicago to Toronto flights?
There are 4 cabin classes available to choose from on Chicago to Toronto 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 Chicago to Toronto flights?
No. A direct flight is the cheapest option for a flight between Chicago to Toronto.
How have Chicago to Toronto flight prices changed over time?
As of June 2025, prices for Chicago to Toronto flights are approximately 43% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Chicago to Toronto?
United Airlines, Porter Airlines, and Air Canada are the most popular carriers operating from Chicago to Toronto
What airlines fly to Toronto?
Air Canada, United Airlines and American Airlines are the top three most popular airlines that fly to Toronto from Chicago according to our data. Air Canada is the first choice among our users, with 40% of people opting to fly with this airline when traveling to Toronto. Keep in mind that there are 4 different airlines that fly to Toronto on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Toronto on average per day?
The number of flights available between Chicago and Toronto is 56 per day as of June 2025. The most frequent departure time is 8:00PM, with 41% of daily flights leaving at noon.
How many flights depart from Chicago to Toronto on average per week?
397 flights are operational weekly from Chicago to Toronto as of June 2025. The most popular departure day for this route is Thu, with 17% of flights per week taking off on this day.
When to book flights from Chicago to Toronto
Cheap Chicago to Toronto (CHI to YTO) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Toronto
How far is Chicago to Toronto by plane?
A flight from Chicago to Toronto will travel around 435.3 mi. Typically, this will take 1h 35m by plane in normal conditions.
When did momondo last update prices for flights from Chicago to Toronto?
Prices for flights from Chicago to Toronto refresh daily.
How many operators does momondo search for flights from Chicago to Toronto?
There are 4 operators available for flights from Chicago to Toronto as of June 2025.
How old do you have to be to fly from Chicago to Toronto?
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 Chicago to Toronto.
What documentation or ID do you need to fly to Toronto?
The travel and health documents required for your trip to Toronto can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Toronto. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Toronto?
Based on momondo bookings for flights between Chicago and Toronto, the leading plane model is De Havilland (Bombardier) DHC-8-400 Dash 8Q, making up 19.82% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 17.41%, Embraer 175 with 6.85%, and Airbus A220-300 with 6.44%.
What is the most popular airline from Chicago to Toronto?
Based on momondo bookings for flights between Chicago and Toronto, the leading airline is Porter Airlines, making up 53% of the total bookings. Other popular airlines include Air Canada with 17%, United Airlines with 15%, and American Airlines with 11%.
Best airlines flying from Chicago to Toronto
Compare and see reviews for airlines that fly from Chicago to Toronto with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $109 | Free Cancellation | Rating 8.0 288 reviews | |||
| PriceFrom $117 | Free Cancellation | Rating 7.1 9,531 reviews | |||
| PriceFrom $136 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom $162 | Free Cancellation | Rating 7.2 10,000 reviews |
Porter Airlines Flights From Chicago to Toronto
Across 13 Porter Airlines flights from Chicago to Toronto this week, the average price was $283, with the best Porter Airlines deals starting from $109 round-trip. 288 users have rated Porter Airlines on momondo, with an average score of 8.0/10.
United Airlines Flights From Chicago to Toronto
$136 is the best United Airlines flight deal from Chicago to Toronto found on momondo over the last 72 hours. The average United Airlines ticket price found was closer to $333, however, with flight time and availability significantly affecting the price. United Airlines (7.4/10 from 8,790 user reviews) flies into Toronto from Chicago 68 times in an average week so prices can vary.
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Toronto?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Toronto from Chicago.
Can I find flights from Chicago to Toronto with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Chicago to Toronto flights to just show those with flexible booking policies.
How can momondo help me find flights from Chicago to Toronto?
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 Toronto from Chicago.
I’m not ready to book a flight from Chicago to Toronto right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Chicago to Toronto now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Toronto and let you know when they change.