Cheap flights from Toronto 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 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 to Chicago
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United Airlines flights from Toronto to Chicago
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How to get the cheapest flight ticket from Toronto 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 typical price of a round-trip flight between Toronto and Chicago?
What is the cheapest month to fly to Chicago?
The month of April is, on average, the cheapest month to fly to Chicago from Toronto, with most prices found around $235. If you’re not able to fly to Chicago in April, then May is your next best option. Flight prices from Toronto to Chicago during May average around $244.
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 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 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 to Chicago flight route?
Fly from Toronto Island to Chicago Midway for the best Toronto - 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 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 for as low as $247 on momondo.
What cabin class options are available on Toronto to Chicago flights?
There are 4 cabin classes available to choose from on Toronto 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 to Chicago flights?
No. A direct flight is the cheapest option for a flight between Toronto to Chicago.
How have Toronto to Chicago flight prices changed over time?
As of June 2025, prices for Toronto 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 to Chicago?
Air Canada, Porter Airlines, and American Airlines are the most popular carriers operating from Toronto 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 according to our data. Air Canada is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 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 to Chicago on average per day?
The number of flights available between Toronto and Chicago is 55 per day as of June 2025. The most frequent departure time is 1:00PM, with 46% of daily flights leaving in the afternoon.
How many flights depart from Toronto to Chicago on average per week?
As of June 2025, 391 flights take off from Toronto and land in Chicago each week. The most common flight departure day for this route is Thu, with 16% of weekly flights taking off on this day.
When to book flights from Toronto to Chicago
Cheap Toronto to Chicago (YTO to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Toronto to Chicago
How far is Toronto to Chicago by plane?
There are 435.3 mi between Toronto and Chicago. Flights usually cover this in 1h 49m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Toronto to Chicago?
Prices for flights from Toronto to Chicago are updated daily.
How many operators does momondo search for flights from Toronto to Chicago?
As of June 2025, there are 4 operators available to choose from for flights from Toronto to Chicago.
How old do you have to be to fly from Toronto 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 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 to Chicago?
Based on momondo bookings for flights between Toronto and Chicago, the leading plane model is De Havilland (Bombardier) DHC-8-400 Dash 8Q, making up 20.36% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 15.02%, Boeing 737-800 with 12.23%, and Airbus A220-300 with 9.13%.
What is the most popular airline from Toronto to Chicago?
momondo data reveals that the most frequently booked airline on the route from Toronto to Chicago is Porter Airlines, representing 49% of all bookings. The subsequent popular airlines are Air Canada at 27%, American Airlines at 12%, and United Airlines at 7%.
Best airlines flying from Toronto to Chicago
Compare and see reviews for airlines that fly from Toronto 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 $169 | Free Cancellation | Rating 8.0 288 reviews | |||
| PriceFrom $218 | Free Cancellation | Rating 7.2 10,000 reviews |
Porter Airlines Flights From Toronto to Chicago
Porter Airlines flies from Toronto to Chicago around 13 times per week, with 288 momondo users rating the airline 8.0/10. The cheapest Porter Airlines deal from Toronto to Chicago in the last 72 hours was $169 (round-trip), much lower than the average airfare cost of $252 for Porter Airlines flights on this route.
United Airlines Flights From Toronto to Chicago
United Airlines (7.4/10 from 8,790 reviews) operates around 69 flights from Toronto to Chicago in any given week. The average United Airlines airfare for this route is around $287, with deals from around $165 rare but found on momondo. Referenced prices are for round-trip Toronto to Chicago flight searches in the last 72 hours.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Toronto to Chicago?
It is quick and easy to find Toronto to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.
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 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 Chicago from Toronto.
I’m not ready to book a flight from Toronto to Chicago right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Toronto and alert you when they change.