$106 Find Cheap Flights from Toronto Island to Illinois

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Toronto Island to Illinois departing on 9/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Illinois

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Illinois, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Illinois, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Toronto Island to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicagononstop$174
Chicago
Chicagononstop$174

Book Cheap Toronto Island to Illinois Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Toronto Island to Illinois that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Toronto Island to Illinois

Fri, Sep 26 - Sun, Sep 28
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$174Porter Airlines
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Wed, Sep 10 - Wed, Sep 17
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
$175Porter Airlines
Find Deal
Thu, Oct 2 - Sun, Oct 5
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
$176Porter Airlines
Find Deal
Thu, Oct 2 - Sun, Oct 5
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$177Porter Airlines
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Thu, Oct 2 - Sun, Oct 5
Air Canada Logo
10:25 am - 2:55 pmYTZ-ORD
5h 30m1 stop
Air Canada Logo
10:40 am - 4:45 pmORD-YTZ
5h 05m1 stop
$199Air Canada
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Thu, Oct 2 - Sun, Oct 5
Air Canada Logo
8:25 am - 2:55 pmYTZ-ORD
7h 30m1 stop
Air Canada Logo
10:40 am - 4:45 pmORD-YTZ
5h 05m1 stop
$200Air Canada
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Sun, Sep 28 - Sun, Oct 5
Air Transat Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Air Transat Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$211Air Transat
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Fri, Sep 5 - Sun, Sep 7
Air Transat Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Air Transat Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$212Air Transat
Find Deal
Sun, Sep 28 - Sun, Oct 5
Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
$224
Find Deal
Fri, Sep 5 - Mon, Sep 8
Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
$229
Find Deal
Booking Insights

KAYAK's insights & trends for Toronto Island to Illinois flights

Get data-powered insights and trends into flights from Toronto Island to Illinois to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Toronto Island Airport to Illinois flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Illinois from Toronto Island Airport found in the last 72 hours was to Chicago, at $120 round-trip. The most popular route is from Toronto Island Airport (YTZ) to Chicago Midway Airport (MDW), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $120.

Can I save money by flying with a layover from Toronto Island Airport to Illinois?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $331 on average.

What is the cheapest month to fly from Toronto Island Airport to Illinois?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Toronto Island Airport to Illinois, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Toronto Island Airport to Illinois is September, when tickets cost $135 (return) on average. On the other hand, the most expensive months are January and October, when the average cost of round-trip tickets is $341 and $295 respectively.

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Good to know

Low seasonJanuary
Cheapest flight$106
Best time to beat the crowds but there is an average 40% increase in price.
Most popular time to fly and prices are also 45% lower on average.
Flight from Toronto Island to Chicago Midway Airport

FAQs - booking Illinois flights

  • How does KAYAK find such low prices on flights from Toronto Island to Illinois?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Toronto Island to Illinois.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Toronto Island to Illinois?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Toronto Island to Illinois is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Toronto Island to Illinois?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Toronto Island to Illinois with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Toronto Island to Illinois?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Toronto Island to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Illinois?

    The cheapest time of day to fly to Illinois is generally in the evening, when round-trip flights cost $238 on average. Morning departures are around 11% more expensive than evening flights, on average. The most expensive time of day to fly to Illinois is generally at night, which is peak travel time and where the average cost of a ticket is $268.

Top tips for finding cheap flights to Illinois

  • Looking for a cheap flight? 25% of our users found tickets from Toronto Island to the following destinations at these prices or less: Chicago $109 one-way - $174 round-trip

Reviews of the top airline flying from Toronto Island to Illinois

 
See real verified KAYAK customer reviews for airlines flying from Toronto to Illinois. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Toronto Island to Illinois? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Porter AirlinesOverall score based on 332 reviews
8.2Boarding
7.0Entertainment
8.0Comfort
8.7Crew
7.6Food
Airline reviews

There was a 5 hour delay. Missed connection and now an almost 21 hour lay over!

2.0 MediocreKirsten, Aug 2025BOS - YOW
Read more Porter Airlines reviews

There was a 5 hour delay. Missed connection and now an almost 21 hour lay over!

The flight was fine see earlier note for the problem

Three hours on the tarmac with almost zero communication from the cockpit. Not when offered a water in the interim. In my 67 years of flying all over the world the worst experience ever. The plane was half empty, however had to pay for seats to sit next to my girlfriend. Extra to take a carry on. I would never fly Porter again even for free.

All good the seats a little tight and no I pad screen

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

Our flight was cancelled at the last minute for maintenance reasons and we were rebooked on a late flight when we purposefully booked our flight to be home early due to work.

Seemed like an old plane. Very noisy. The seat cushions were so old that the metal bracing of the seats were poking through. There was plenty of leg room though.

Flight was delayed over 2 hours, then landed at a different airport!

The whole experience from check in to deboarding was fantastic.

Just an evening before they canceled my ticket and offered me ticket costing 3 x times more than. I will not fall prey to these scams,Will never book through kayak now. Such a bad experience.

Everything you need to know for your flight from Toronto Island to Illinois

Information on your arrival and departure airports

Toronto Island (YTZ)

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