C$ 185 Find Cheap Flights from Toronto to Illinois – Compare and Save

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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?

The cheapest ticket to Illinois from Toronto Island Airport found in the last 5 days was to Chicago, at C$ 237 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 5 days was C$ 237.

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

The cheapest time of day to fly to Illinois is generally in the afternoon, when round-trip flights cost C$ 328 on average. Morning departures are around 4% 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$ 540.

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

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 C$ 398 on average.

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

The cheapest month for flights from Toronto Island Airport to Illinois is January, when tickets cost C$ 309 (return) on average. On the other hand, the most expensive months are May and October, when the average cost of round-trip tickets is C$ 487 and C$ 409 respectively.

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

If you are looking for a flight deal from Toronto to Illinois, look for departures on Fridays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Illinois, Thursday is the cheapest day to fly and Friday is the most expensive.

Good to know

Low season

February

Cheapest flight

C$ 185
Best time to beat the crowds (22% less expensive on average)
Most popular time to fly and prices are also 8% lower on average.
Flight from Toronto Island to Chicago O'Hare 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.

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$ 286 one-way - C$ 293 round-trip; Chicago C$ 199 one-way - C$ 383 round-trip

Reviews of the top airlines flying from Toronto to Illinois

 
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 458 reviews
6.9Entertainment
8.2Boarding
8.0Comfort
7.6Food
8.6Crew
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
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.

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

flight was delayed 6 hours for weather, then cancelled because of the crash in toronto, but none of the links to cancel or rebook my flights are working

They charge 5 dollars for plastic headphones for a flight of 1 hour! Seats are awful. Service is terrible.

Everything was seamless. I would have appreciated knowing there would not be any real food available for purchase in advance. Otherwise a great experience. Thank you!

I was mostly pleased. My greatest disappointment was with respect to the timely update to the estimated departure and arrival times. It was especially sad that the arrival time was not updated online once we were in flight so as to allow my wife to arrive on time to the airport. She was not happy.

Seats weren't comfortable, could have used more let room

Flight was delayed more than 120 min. I had carry on bag but the airplane was full and they had to get it checked in. I had to wait for the small carry on bag at the airport carousel

Flight was delayed 3 hrs, one of the flt attendants was rude to me & I was forced to pay for a middle seat.

Ontime boarding. Almost 1 hour take off delay. We could have boarded slightly later since the pilots were in traffic

This was the first AC flight in a long time that we experienced no delays or frustrations. The gate attendant was extremely polite and accommodating to my husband who has Parkinson’s disease which made boarding extremely stress free. Flight departed ON TIME and was a smooth ride. If only all my AC experiences could be like this.

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

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