C$ 184 Find Cheap Flights from Toronto 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 to Illinois departing on 29/11. 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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Cheap Flights from Toronto to Illinois

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Toronto 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 to Illinois

Fri, 5 Dec - Thu, 11 Dec
Porter Airlines Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
C$ 265Porter Airlines
Find Deal
Fri, 21 Nov - Mon, 24 Nov
Porter Airlines Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 271Porter Airlines
Find Deal
Sat, 13 Dec - Thu, 15 Jan
Porter Airlines Logo
11:00 a.m. - 11:50 a.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 272Porter Airlines
Find Deal
Thu, 20 Nov - Mon, 24 Nov
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 275Porter Airlines
Find Deal
Thu, 20 Nov - Wed, 26 Nov
Porter Airlines Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 277Porter Airlines
Find Deal
Thu, 20 Nov - Wed, 26 Nov
Air Canada Logo
8:30 a.m. - 2:55 p.m.YTZ-ORD
7h 25m1 stop
Air Canada Logo
7:05 a.m. - 6:13 p.m.ORD-YTZ
10h 08m2 stops
C$ 281Air Canada
Find Deal
Thu, 15 Jan - Tue, 20 Jan
Air Canada Logo
10:30 a.m. - 2:55 p.m.YTZ-ORD
5h 25m1 stop
Air Canada Logo
12:50 p.m. - 7:55 p.m.ORD-YTZ
6h 05m1 stop
C$ 289Air Canada
Find Deal
Fri, 5 Dec - Mon, 8 Dec
Multiple Airlines Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
Multiple Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 308Multiple Airlines
Find Deal
Thu, 20 Nov - Sun, 23 Nov
Multiple Airlines Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
Multiple Airlines Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
C$ 320Multiple Airlines
Find Deal
Sun, 14 Dec - Sun, 21 Dec
Air Transat Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
Air Transat Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
C$ 359Air Transat
Find Deal
Booking Insights

KAYAK's insights & trends for Toronto to Illinois flights

Get data-powered insights and trends into flights from Toronto 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 C$ 180 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 C$ 180.

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 C$ 412, 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 C$ 237 (return) on average. On the other hand, the most expensive months are October and June, when the average cost of round-trip tickets is C$ 567 and C$ 395 respectively.

Good to know

Low seasonJanuary
Cheapest flightC$ 184
Best time to beat the crowds (12% less expensive on average)
Most popular time to fly and prices are also 31% 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 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 to Illinois.

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

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

  • What is the Hacker Fare option on flights from Toronto 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 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 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 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 morning, when round-trip flights cost C$ 313 on average. Morning departures are around 5% 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 C$ 684.

Top tips for finding cheap flights to Illinois

  • Looking for a cheap flight? 25% of our users found tickets from Toronto to the following destinations at these prices or less: Chicago C$ 199 one-way - C$ 349 round-trip

Reviews of the top airlines flying from Toronto 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 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 387 reviews
7.0Entertainment
8.0Comfort
8.2Boarding
7.6Food
8.6Crew
Airline reviews

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

10.0 ExcellentMike, Oct 2025YYC - YYZ
Read more Porter Airlines reviews

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

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.

Good but need to be better with the flight times.

The staff was great and made the long trip easy peasy!

The free Wi-fi for Aeroplan members was a great touch. The time passed quickly. I found the seats seemed a little closer together than I remember. Not Air Canada's fault, but we were about 20 minutes late landing because the airport was too busy. We had to circle around for a while. The boarding and disembarking went very smoothly.

Extremely turbulent landing. Crew was friendly and plane comfortable. Airport and US pre clearance was understaffed

The airplane is way too tight, you can hardly enter into your row to sit.. more like kids seats than adults.

Wifi was great. Kind air crew and comfortable seating. Also liked the entertainment options.

First message when all on board was that we didnt have a pilot, then they found one, then it was something about the bridge something not working, they will either fix or do manually. Flight of course was leaving late with all the cruise guests worrying about making it to their ship in time. Then only some luggage made it off the ship. Around 15 to 20 people waiting. 45 min later arrived except mine. I asked the rep at the luggage conveyor, he asked me my name. Then said it was not picked up with the first batch so they put it in a room. I was going to take public transport but now worried about time so took a taxi that cost me $65 USD

The flight was very smooth and good. Boarding was fast, but the staff was just decently friendly.

Air Canada flight staff are in contact negotiations and they are less than happy and it show. The process of self checking baggage is less than desirable with lack of support staff to help

A sandwich and a drink would have been better thank a snack bar...

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

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