$119 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 1/20. 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, 0 bags

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

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

Thu, Jan 22 - Thu, Jan 29
Porter Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
$174Porter Airlines
Tue, Jan 20 - Tue, Jan 27
Porter Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:05 am - 1:47 pm
MDW
-
YTZ
1h 42mnonstop
$177Porter Airlines
Thu, Jan 22 - Sun, Jan 25
Porter Airlines Logo
9:20 am - 10:10 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
4:15 pm - 6:57 pm
MDW
-
YTZ
1h 42mnonstop
$178Porter Airlines
Thu, Jan 22 - Thu, Jan 29
Porter Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:05 am - 1:47 pm
MDW
-
YTZ
1h 42mnonstop
$179Porter Airlines
Fri, Feb 20 - Mon, Feb 23
Porter Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
$180Porter Airlines
Thu, Jan 29 - Sun, Feb 1
Porter Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
$182Porter Airlines
Thu, Jan 29 - Sun, Feb 1
Multiple Airlines Logo
9:20 am - 10:10 am
YTZ
-
MDW
1h 50mnonstop
Multiple Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
$189Multiple Airlines
Fri, Jan 16 - Sun, Jan 18
Air Canada Logo
8:30 am - 2:55 pm
YTZ
-
ORD
7h 25m1 stop
Air Canada Logo
7:15 am - 2:55 pm
ORD
-
YTZ
6h 40m1 stop
$209Air Canada
Wed, Jan 21 - Wed, Jan 28
Air Canada Logo
12:30 pm - 8:10 pm
YTZ
-
ORD
8h 40m1 stop
Air Canada Logo
7:15 am - 2:55 pm
ORD
-
YTZ
6h 40m1 stop
$246Air Canada
Tue, Jan 20 - Tue, Jan 27
Air Canada Logo
12:30 pm - 6:51 pm
YTZ
-
ORD
7h 21m1 stop
Air Canada Logo
1:55 pm - 9:28 pm
ORD
-
YTZ
6h 33m1 stop
$266Air Canada
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 $109 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 $109.

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.

No, with an average price for the route of $264, prices are generally cheapest when you fly direct.

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 August, when tickets cost $168 (return) on average. On the other hand, the most expensive months are October and December, when the average cost of round-trip tickets is $396 and $282 respectively.

Find deals

Good to know

Low seasonOctober
Cheapest flight$119
Best time to beat the crowds but there is an average 62% increase in price.
Most popular time to fly and prices are also 32% 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 $236 on average. Morning departures are around 14% more expensive than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the morning, 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 $116 one-way - $183 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 397 reviews
7.6Food
8.0Comfort
8.6Crew
7.0Entertainment
8.2Boarding
Airline reviews

3.5 hr delay for a 1 hr work flight. No information as to why the delay until 20 mins before boarding.

4.0 OkayAnonymous, Dec 2025
YTZ - YUL
Read more Porter Airlines reviews

3.5 hr delay for a 1 hr work flight. No information as to why the delay until 20 mins before boarding.

Organization and the adjusted times but the snacks could be of a bigger portion

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

This flight to St. Johns was really good. Boarding was a breeze. We left spot on time. Seats were actually pretty good. Recliner further than I expected. Three more flights to go we will see if this is the status quo for Porter.👍

I was not happy with AirfareAssist, the agency that kayak advised me would be handling my booking. I was advised by porter airlines that I had been overcharged for the Basic express , a option that I had asked airfare assist to help arrange after I realized that the basic fare I had chosen with porter did not include a carryon. At each checkin porter advised I had been overcharged for this . They advised that money would be refunded to my credit card, however, this is not likely to happen as it is not my name and credit card that appeared on the porter invoice, but that of another individual/agent. When airfare assist was arranging the basic express with porter on my behalf, they asked me to confirm that I agreed to pay $263 USD for this. I did agree, as I was advised this was needed to proceed. When I checked the invoice on the porter website and saw that it was not my name and credit card on the invoice, I was advised that this was how airfareassist processed the payment. The Porter invoice indicated a billed amount of $126USD I will not use Kayak or their designated AirfareAssist again

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

The flight was fine see earlier note for the problem

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

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

Information on your arrival and departure airports

Toronto Island (YTZ)