CHI - YTZ

$93 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 5/29. 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 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
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

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Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$220
Typical prices: $599-$228
Porter Airlines
Fri 5/15Sun 5/17
MDW - YTZ • Non-stop
Cheapest one-way
$93
Typical prices: $88-$239
Air Transat
Fri 5/29
MDW - YTZ • Non-stop
Top airlines
Cheapest • from $220 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Porter Airlines. Average duration is 1h 42m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 9% average savings
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 86% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Toronto Island!
Flight Deals
Booking Insights
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

Fri, May 15 - Sun, May 17
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:55 am - 9:45 am
YTZ
-
MDW
1h 50mnonstop
$220Porter Airlines
Sat, Jun 20 - Tue, Jun 23
Porter Airlines Logo
10:25 am - 1:05 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
$221Porter Airlines
Sat, Jul 18 - Sun, Jul 26
Air Canada Logo
8:45 am - 3:51 pm
ORD
-
YTZ
6h 06m
1 stop
Air Canada Logo
12:15 pm - 1:10 pm
YTZ
-
ORD
1h 55mnonstop
$222Air Canada
Wed, Apr 15 - Mon, Apr 27
Porter Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
Porter Airlines Logo
9:25 am - 10:15 am
YTZ
-
MDW
1h 50mnonstop
$222Porter Airlines
Wed, May 27 - Mon, Jun 8
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
$223Porter Airlines
Tue, Jun 23 - Wed, Jul 1
Air Canada Logo
2:00 pm - 4:41 pm
ORD
-
YTZ
1h 41mnonstop
Air Canada Logo
12:15 pm - 1:10 pm
YTZ
-
ORD
1h 55mnonstop
$224Air Canada
Wed, Apr 29 - Mon, May 4
Multiple Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
Multiple Airlines Logo
8:55 am - 9:45 am
YTZ
-
MDW
1h 50mnonstop
$224Multiple Airlines
Sat, Jul 25 - Sat, Aug 1
Air Canada Logo
8:45 am - 3:51 pm
ORD
-
YTZ
6h 06m
1 stop
Air Canada Logo
12:15 pm - 1:10 pm
YTZ
-
ORD
1h 55mnonstop
$225Air Canada
Wed, Apr 29 - Mon, May 4
Multiple Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
Multiple Airlines Logo
8:55 am - 9:45 am
YTZ
-
MDW
1h 50mnonstop
$225Multiple Airlines
Fri, Jun 26 - Mon, Jun 29
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
$226Porter Airlines
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 May.

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 $176 on the route between Chicago Midway Airport (MDW) and Toronto Island Airport (YTZ). Over the past month, this route was, on average, 9% cheaper than other Chicago-Toronto Island Airport routes. It is also the most popular route.

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 $236, prices are generally cheapest when you fly direct.

Good to know

Low seasonFebruary
Cheapest flight$93
Best time to beat the crowds with an average 43% drop in price.
Most popular time to fly with an average 42% increase in price.
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 $93 for a one-way ticket and $220 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?

    Air Canada, United Airlines, American Airlines, and Porter 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 $129 or less one-way and $222 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.
8.0
Porter AirlinesOverall score based on 430 reviews
8.6Crew
8.2Boarding
7.0Entertainment
8.0Comfort
7.6Food
Airline reviews

There was No Flight. Both Kayak and Porter refused to honor my booking. I was asked for an additional 1,300 $ CAD to keep the flight. After several emails to both Kayak and Porter I was ignored. I had to cancel my March spring break plans, dog kennel and hotel. I had to re-book another vacation to Nassau in January w Expedia. I had to re-book a new vacation for spring break. Porter and Kayak both blamed each other and would not work together to fix this. Not cool.

2.0 MediocreAnonymous, Mar 2026
NAS - YOW
Read more Porter Airlines reviews

There was No Flight. Both Kayak and Porter refused to honor my booking. I was asked for an additional 1,300 $ CAD to keep the flight. After several emails to both Kayak and Porter I was ignored. I had to cancel my March spring break plans, dog kennel and hotel. I had to re-book another vacation to Nassau in January w Expedia. I had to re-book a new vacation for spring break. Porter and Kayak both blamed each other and would not work together to fix this. Not cool.

Even tho the flight was a bit delayed the team was apologetic. Everyone was friendly and efficient.

The flight was a little delayed but check in was easy and boarding was quick. Luggage was quickly available and everything worked great.

The Flight took off 2hrs late because there was no pilot showing up when the flight was ready to board.. Though the cabin crew was present and had prepared the plane, the FO turned around after 15 min and went away. A crew to fly the plane finally arrived over an hour later and we were able to board 1h30 min later than planned time... until everything was loaded, we left 2h late from the gate. This was a small plane, so don't expect any Entertainment... Wi-Fi access on board would work, but took an awful amount of time to figure out and get it work (I'm an IT person). Flying as VIPorter customer, I was expecting at least some warm meal, but everything served was just cold.. except the coffee maybe. Even in so-called VIPorter seats, space is cramped and trays are so tiny, you can barely setup your food. Flight caught up during the coast-to-coast crossing and was able to recoup about 45 min from the delay.. still arrived very late in Vancouver and had to wait a long time to get our registered bags. Let's see how the return flight will be in a few days..

The flight booking code given by Kayak was not the correct one used by the airline. I had to call to get the correct one. It was never sent to me. Totally unacceptable!

Due to a known technical error that Porter has not fixed in over a year, I was unable to check in the children on my reservation online and had to do it at the airport. Upon check in, there were no seats together, which was an issue as we had young children. The gate agent did manage to seat us together by moving other passengers, which was appreciated, but the other passengers were never informed, leading to confusion and delay upon boarding. The flight was over an hour late; no explanation or apology was ever issued. The bags on Porter take a long time to arrive--over half an hour at Hamilton on my inbound flight, and not much better on my return to Edmonton.

Much roomer than air Canada! Great flight for the price. No complaints

On my e-boarding pass it shows free wifi, yet the plane I was on didn’t have wifi. Please remove false advertising from your website and boarding passes

As a first time flyer with Porter I was happy with the service and comfort of the airline.

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

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

Information on your arrival and departure airports