Cheap flights from Toronto Island Airport 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 Island Airport to Chicago departing on 4/7. 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 Island Airport to Chicago
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Porter Airlines flights from Toronto Island Airport to Chicago
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How to get the cheapest flight ticket from Toronto Island Airport 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 cheapest month to fly to Chicago?
The month of August is another great option to travel to Chicago, with average flight prices from Toronto Island Airport averaging around C$ 310.
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 C$ 680. 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 Tuesday because tickets tend to average around C$ 1,284. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.
What is the cheapest time of day to depart on your flight to Chicago?
In the evening is the cheapest time of day to fly from Toronto Island Airport to Chicago when you can find flight prices for as low as C$ 551. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,456 per ticket.
What is the cheapest Toronto Island to Chicago flight route?
Fly from Toronto Island to Chicago Midway for the best Toronto Island - Chicago flight prices
What cabin class options are available on Toronto Island to Chicago flights?
There are 1 cabin classes available to choose from on Toronto Island 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 Island Airport to Chicago flights?
No. A direct flight is the cheapest option for a flight between Toronto Island Airport to Chicago.
How many flights depart from Toronto Island Airport to Chicago on average per day?
3 flights are operational daily from Toronto Island Airport to Chicago as of June 2025. The most popular departure time for this route is 7:00a.m., with 63% of flights per day taking off at noon.
How many flights depart from Toronto Island Airport to Chicago on average per week?
As of June 2025, 26 flights take off from Toronto Island Airport and land in Chicago each week. The most common flight departure day for this route is Mon, with 15% of weekly flights taking off on this day.
When to book flights from Toronto Island Airport to Chicago
Cheap Toronto Island Airport to Chicago (YTZ to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Toronto Island Airport to Chicago
How far is Toronto Island to Chicago by plane?
The straight-line distance from Toronto Island to Chicago is 698.8 km. A reasonable flight in good conditions will take 1h 49m.
When did momondo last update prices for flights from Toronto Island Airport to Chicago?
Prices for flights from Toronto Island Airport to Chicago were last updated today.
How many operators does momondo search for flights from Toronto Island Airport to Chicago?
The number of operators available for flights from Toronto Island Airport to Chicago is 2 as of June 2025.
How old do you have to be to fly from Toronto Island Airport 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 Island Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago 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. 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 Island Airport to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Toronto Island Airport to Chicago is De Havilland (Bombardier) DHC-8-400 Dash 8Q (31.14% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (18.16%), Boeing 737-800 (14.61%), and Airbus A220-300 (10.21%).
What is the most popular airline from Toronto Island Airport to Chicago?
momondo data reveals that the most frequently booked airline on the route from Toronto Island Airport to Chicago is Porter Airlines, representing 91% of all bookings. The subsequent popular airline is Air Transat at 9%.
Best airlines flying from Toronto Island Airport to Chicago
Compare and see reviews for airlines that fly from Toronto Island Airport to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom C$ 237 | Free Cancellation | Rating 8.0 288 reviews | |||
| PriceFrom C$ 303 | Free Cancellation | Rating 7.1 9,537 reviews |
Porter Airlines Flights From Toronto Island Airport to Chicago
The lowest priced Porter Airlines flight from Toronto Island Airport to Chicago from the last 72 hours was C$ 173. Generally, Porter Airlines has 13 flights on this route every week with an average price of C$ 250. Porter Airlines is rated 8.0/10 by our users.
Travelling 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?
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 Chicago from Toronto.
Can I find flights from Toronto to Chicago with flexible booking policies on momondo?
Flights from Toronto to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
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?
Price alerts on flights to Chicago from Toronto 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.