$135 Find Cheap Flights from Toronto Island to Illinois - Compare and Save

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 7/26. 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.
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1 adult, Economy, 0 bags

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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

Mon, Sep 14 - Wed, Sep 16
Porter Airlines Logo
8:40 pm - 9:35 pm
YTZ
-
ORD
1h 55mnonstop
Porter Airlines Logo
7:00 am - 9:40 am
ORD
-
YTZ
1h 40mnonstop
$203Porter Airlines
Thu, Sep 24 - Tue, Sep 29
Porter Airlines Logo
1:40 pm - 2:35 pm
YTZ
-
ORD
1h 55mnonstop
Porter Airlines Logo
7:00 am - 9:40 am
ORD
-
YTZ
1h 40mnonstop
$204Porter Airlines
Tue, Jul 14 - Thu, Jul 16
Porter Airlines Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
10:25 am - 1:05 pm
MDW
-
YTZ
1h 40mnonstop
$205Porter Airlines
Sat, Sep 5 - Sun, Sep 6
Porter Airlines Logo
10:05 am - 11:00 am
YTZ
-
ORD
1h 55mnonstop
Porter Airlines Logo
11:45 am - 2:25 pm
ORD
-
YTZ
1h 40mnonstop
$205Porter Airlines
Thu, Jul 16 - Sun, Jul 19
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
$206Porter Airlines
Thu, Sep 3 - Tue, Sep 8
Porter Airlines Logo
10:05 am - 11:00 am
YTZ
-
ORD
1h 55mnonstop
Porter Airlines Logo
3:20 pm - 6:00 pm
ORD
-
YTZ
1h 40mnonstop
$206Porter Airlines
Thu, Jul 16 - Sun, Jul 19
Air Canada Logo
12:15 pm - 1:19 pm
YTZ
-
ORD
2h 04mnonstop
Air Canada Logo
7:25 am - 10:07 am
ORD
-
YTZ
1h 42mnonstop
$207Air Canada
Fri, Jul 31 - Tue, Aug 4
Porter Airlines Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
3:15 pm - 5:55 pm
MDW
-
YTZ
1h 40mnonstop
$207Porter Airlines
Wed, Jul 15 - Tue, Jul 21
Porter Airlines Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
$208Porter Airlines
Fri, Sep 11 - Tue, Sep 29
Air Canada Logo
12:15 pm - 1:19 pm
YTZ
-
ORD
2h 04mnonstop
Air Canada Logo
8:45 am - 3:50 pm
ORD
-
YTZ
6h 05m
1 stop
$210Air 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 5 days was to Chicago, at $141 round-trip. The most popular route is from Toronto Island Airport (YTZ) to Chicago O'Hare Intl Airport (ORD), and the cheapest round-trip airline ticket found on this route in the last 5 days was $196.

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

The average price for all round-trip flights from Toronto Island Airport to Illinois depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Illinois is generally in the morning, when round-trip flights cost $287 on average. Morning departures are around 13% cheaper 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 $369.

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 $262, 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 $80 (return) on average. On the other hand, the most expensive months are March and November, when the average cost of round-trip tickets is $189 and $180 respectively.

What’s the cheapest day of the week to fly from Toronto Island to Illinois?

The average price of all round-trip flights from Toronto Island Airport to Illinois clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Illinois on a Thursday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Toronto Island to Illinois. For your return ticket, we recommend flying on a Friday and avoiding Tuesdays for the best deals.

Find deals

Good to know

Low seasonFebruary
Cheapest flight$135
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 46% 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.

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 $133 one-way - $217 round-trip; Chicago $148 one-way - $253 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.
7.9
Porter AirlinesOverall score based on 442 reviews
7.5Food
7.9Comfort
8.6Crew
6.9Entertainment
8.2Boarding
Airline reviews

It was okay. Had a thing with the front desk, she had me repack my suitcases to have them be under the weight restrictions, but then the other one was overweight, she argued with me about it when there were tons of people in line. Wasn’t great.

6.0 GoodJen, Jan 2026
YTZ - BOS
Read more Porter Airlines reviews

It was okay. Had a thing with the front desk, she had me repack my suitcases to have them be under the weight restrictions, but then the other one was overweight, she argued with me about it when there were tons of people in line. Wasn’t great.

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

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.

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.

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10 Tips for people flying porter from Boston. The airline doesn’t have inflight entertainment No TV No WIFI. Bring your entertainment with you.

Nothing to like about porter. Flight cancelled. No flight back to Boston for 2 days. No hotel accommodation. Terrible. Never again by porter.

Porter is the airline that does care. All trips with Porter have been smooth and relaxing. The extras are the customer appreciation. The others just don’t do that.

The flight was delayed for more than 2 hrs. The plane was changed and staff couldn’t count people so we had to wait even longer while waiting for take off.

Communication at the gate was adequate. Boarding was orderly. Seats are decent, with a reasonable amount of leg room. Flight was only 1.5 hours, so only a modest snack service (short bread cookie or small bag of chips) and a drink (coffee, tea, soda, cup of beer or wine). Exiting the plane was also orderly. Overall the flight was fine and the price reasonable.

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

Information on your arrival and departure airports

Toronto Island (YTZ)