Cheap flights from Chicago to Toronto from $68
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 9/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Chicago to Toronto
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Air Canada flights from Chicago to Toronto Island Airport
Our best Air Canada deals on Chicago to Toronto Island Airport flight tickets
Porter Airlines flights from Chicago to Toronto Island Airport
Our best Porter Airlines deals on Chicago to Toronto Island Airport flight tickets
See travel insights to Toronto from
How to get the cheapest flight ticket from Chicago to Toronto Island 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 typical price of a round-trip flight between Chicago and Toronto Island Airport?
What is the cheapest month to fly to Toronto Island Airport?
If you aren’t able to travel during the month of January, then book flights to Toronto Island Airport from Chicago during October instead. Flights to Toronto Island Airport in October, while not as cheap as those in January, still average around $239.
What is the cheapest day to depart on your flight to Toronto Island Airport?
The cheapest day to depart on your flight to Toronto Island Airport is on a Thursday when prices can be found for as low as $275. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $377. These prices are subject to change though, so be sure to set up a Price Alert for flights to Toronto Island Airport.
What is the cheapest time of day to depart on your flight to Toronto Island Airport?
Our data shows that the cheapest Chicago to Toronto Island Airport flights are usually those with departure times in the afternoon. Our users have found flights to Toronto Island Airport in the afternoon for as low as $280. In contrast, the most expensive time of day to depart to Toronto Island Airport is in the evening when prices are around $311.
What is the cheapest Chicago to Toronto Island flight route?
Fly from Chicago Midway to Toronto Island for the best Chicago - Toronto Island flight prices
How many flights depart from Chicago to Toronto Island Airport on average per day?
The number of flights available between Chicago and Toronto Island Airport is 4 per day as of June 2025. The most frequent departure time is 9:00AM, with 53% of daily flights leaving at noon.
How many flights depart from Chicago to Toronto Island Airport on average per week?
28 flights are operational weekly from Chicago to Toronto Island Airport as of June 2025. The most popular departure day for this route is Fri, with 21% of flights per week taking off on this day.
When to book flights from Chicago to Toronto Island Airport
Cheap Chicago to Toronto Island Airport (CHI to YTZ) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Toronto Island Airport
How far is Chicago to Toronto Island by plane?
There are 434.2 mi between Chicago and Toronto Island. In terms of flight time, this usually takes a little over 1h 40m.
When did momondo last update prices for flights from Chicago to Toronto Island Airport?
Prices for flights from Chicago to Toronto Island Airport refresh daily.
How many operators does momondo search for flights from Chicago to Toronto Island Airport?
There are 2 operators available for flights from Chicago to Toronto Island Airport as of June 2025.
How old do you have to be to fly from Chicago to Toronto Island 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 Chicago to Toronto Island Airport.
What documentation or ID do you need to fly to Toronto Island Airport?
The travel and health documents required for your trip to Toronto Island Airport 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 Island Airport. 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 Island Airport?
Based on momondo bookings for flights between Chicago and Toronto Island Airport, the leading plane model is De Havilland (Bombardier) DHC-8-400 Dash 8Q, making up 29.83% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 20.68%, Embraer 175 with 9.41%, and Embraer 170 with 7.81%.
What is the most popular airline from Chicago to Toronto Island Airport?
Based on momondo bookings for flights between Chicago and Toronto Island Airport, the leading airline is Porter Airlines, making up 100% of the total bookings.
Best airlines flying from Chicago to Toronto Island Airport
Compare and see reviews for airlines that fly from Chicago to Toronto Island Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $187 | Free Cancellation | Rating 8.0 296 reviews | |||
| PriceFrom $301 | Free Cancellation | Rating 7.1 9,654 reviews |
Porter Airlines Flights From Chicago to Toronto Island Airport
Porter Airlines operates around 14 flights from Chicago to Toronto Island Airport every week. The average price of these flights found in the last 72 hours has been $279, but momondo users have found Porter Airlines deals from Chicago to Toronto Island Airport from as low as $187 round-trip. Porter Airlines has been scored 8.0/10 in 296 reviews.
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Toronto?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Toronto. Millions of users trust and use momondo every year so you are in good hands.
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?
Price alerts on flights to Toronto from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.