CHI - YTZ

$107 Find Cheap Flights from Chicago to Toronto Island

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Toronto Island departing on 11/23. 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 Toronto Island Airport

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

Cheap Flights from Chicago to Toronto Island (CHI-YTZ)

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

Tue, Nov 11 - Tue, Nov 18
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
$225Porter Airlines
Find Deal
Thu, Nov 6 - Sun, Nov 9
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
$226Porter Airlines
Find Deal
Thu, Nov 6 - Sun, Nov 9
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
$227Porter Airlines
Find Deal
Sun, Feb 22 - Tue, Feb 24
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
$234Porter Airlines
Find Deal
Wed, Nov 12 - Wed, Nov 19
Air Canada Logo
7:05 am - 2:55 pmORD-YTZ
6h 50m1 stop
Air Canada Logo
10:30 am - 2:55 pmYTZ-ORD
5h 25m1 stop
$246Air Canada
Find Deal
Sat, Nov 1 - Mon, Nov 3
Air Canada Logo
3:35 pm - 9:35 pmORD-YTZ
5h 00m1 stop
Air Canada Logo
3:30 pm - 8:00 pmYTZ-ORD
5h 30m1 stop
$252Air Canada
Find Deal
Thu, Nov 13 - Thu, Nov 20
Multiple Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
Multiple Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
$262Multiple Airlines
Find Deal
Thu, Nov 6 - Sun, Nov 9
Air Transat Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Air Transat Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
$275Air Transat
Find Deal
Thu, Nov 6 - Sun, Nov 9
Multiple Airlines Logo
6:26 pm - 11:55 amMDW-YTZ
16h 29m2 stops
Multiple Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
$281Multiple Airlines
Find Deal
Thu, Nov 6 - Sun, Nov 9
Air Transat Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
Air Transat Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
$283Air Transat
Find Deal

Everything you should know

Top airlines
Porter Airlines
Cheapest • from $225 (round-trip)
Porter Airlines
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
MDW-YTZ
Cheapest
MDW-YTZ
Most popular
Insights
Insights
Insights
Insights
When to travel
July
Cheapest • 25% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$225
Overall average: $294
Porter Airlines
Tue 11/11Tue 11/18
MDW - YTZ • Non-stop
Cheapest one-way
$107
Overall average: $143
Porter Airlines
Sun 11/23
MDW - YTZ • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Toronto Island!
Booking Insights

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

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

How much is a round-trip flight from Chicago to Toronto Island Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Toronto Island Airport departing in November.

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

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

The cheapest return flight from Chicago to Toronto Island Airport costs $134 on the route between Chicago Midway Airport (MDW) and Toronto Island Airport (YTZ). It is also the most popular route.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Toronto Island Airport, 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 Chicago to Toronto Island Airport is July, where tickets cost $191 (return) on average. On the other hand, the most expensive months are December and May, where the average cost of round-trip tickets is $320 and $314 respectively.

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

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 $251, prices are generally cheapest when you fly direct.

Good to know

Low seasonJanuary
Cheapest flight$107
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Chicago Midway Airport to Toronto Island

When to book flights from Chicago to Toronto Island

Are your dates flexible? Find out the best times to travel from Chicago to Toronto Island based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Toronto Island flights

  • What is the cheapest flight from Chicago to Toronto Island Airport?

    In the last 3 days, the lowest price for a flight from Chicago to Toronto Island Airport was $107 for a one-way ticket and $225 for a round-trip.

  • Do I need a passport to fly between Chicago and Toronto Island?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Chicago and on arrival in Toronto Island.

  • Which airports will I be using when flying from Chicago to Toronto Island?

    On your way to Toronto Island, you’ll fly out from one of these Chicago airports: Chicago Midway or Chicago O'Hare Intl. You’ll be landing at Toronto Island.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Toronto Island?

    American Airlines, Air Canada, and United Airlines offer inflight Wi-Fi service on the Chicago to Toronto Island flight route.

  • Which aircraft models fly most regularly from Chicago to Toronto Island?

    The De Havilland (Bombardier) DHC-8-400 Dash 8Q is the aircraft model that flies most regularly on the Chicago to Toronto Island flight route.

  • On which days can I fly direct from Chicago to Toronto Island?

    There are nonstop flights from Chicago to Toronto Island on a daily basis.

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

    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 Chicago to Toronto Island.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Toronto Island from Chicago 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 Chicago to Toronto Island?

    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 to Toronto Island with an airline and back to Chicago with another airline.

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

    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 to Toronto Island from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago to Toronto Island Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $88 or less one-way and $196 or less round-trip.

Prefer to fly direct from Chicago to Toronto Island?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago to Toronto Island.
Find which airlines fly direct from Chicago to Toronto Island Airport, which days they fly and book direct flights.

Direct departures

Chicago to Toronto Island

Monday

Porter Airlines

Porter Airlines

Tuesday

Porter Airlines

Porter Airlines

Wednesday

Porter Airlines

Porter Airlines

Thursday

Porter Airlines

Porter Airlines

Friday

Porter Airlines

Porter Airlines

Saturday

Porter Airlines

Porter Airlines

Sunday

Porter Airlines

Porter Airlines

See more direct flights

Direct returns

Toronto Island to Chicago

Monday

Porter Airlines

Porter Airlines

Tuesday

Porter Airlines

Porter Airlines

Wednesday

Porter Airlines

Porter Airlines

Thursday

Porter Airlines

Porter Airlines

Friday

Porter Airlines

Porter Airlines

Saturday

Porter Airlines

Porter Airlines

Sunday

Porter Airlines

Porter Airlines

See more direct flights

Reviews of the top airline flying from Chicago to Toronto Island

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Toronto. 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 Chicago to Toronto Island? 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 370 reviews
7.0Entertainment
7.6Food
8.0Comfort
8.2Boarding
8.6Crew
Airline reviews

The flight was half empty yet they charged me $50 for a basic carry on! I saw how passengers of different colors were treated differently.

4.0 OkayAnonymous, Sep 2025LGA - YYZ
Read more Porter Airlines reviews

The flight was half empty yet they charged me $50 for a basic carry on! I saw how passengers of different colors were treated differently.

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

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.

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.

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

Information on your arrival and departure airports

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