CHI - YTZ

$98 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 6/3. 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
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Everything you should know

Cheapest round-trip
$220
Porter Airlines
Tue 9/1Mon 9/7
ORD - YTZ • Non-stop
Cheapest non-stop
$220
Porter Airlines
Sun 9/13Thu 9/17
ORD - 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 Air Canada and Porter Airlines. Average duration is 1h 40m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 30% average savings
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 86% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to travel
Cheapest • 62% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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!
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

Tue, Sep 1 - Mon, Sep 7
Porter Airlines Logo
3:20 pm - 6:00 pm
ORD
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:40 pm - 9:35 pm
YTZ
-
ORD
1h 55mnonstop
$220Porter Airlines
Wed, Jun 17 - Sun, Jun 21
Porter Airlines Logo
10:15 am - 12:55 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
$222Porter Airlines
Sat, May 30 - Sun, May 31
Porter Airlines Logo
10:30 am - 1:10 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:55 am - 9:45 am
YTZ
-
MDW
1h 50mnonstop
$223Porter Airlines
Tue, Sep 1 - Tue, Sep 1
Porter Airlines Logo
11:45 am - 2:25 pm
ORD
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:40 pm - 9:35 pm
YTZ
-
ORD
1h 55mnonstop
$223Porter Airlines
Thu, Jun 11 - Sat, Jun 13
Porter Airlines Logo
10:15 am - 12:55 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:45 am - 9:35 am
YTZ
-
MDW
1h 50mnonstop
$225Porter Airlines
Thu, Jun 18 - Fri, Jun 19
Air Canada Logo
7:25 am - 10:06 am
ORD
-
YTZ
1h 41mnonstop
Air Canada Logo
7:20 pm - 8:16 pm
YTZ
-
ORD
1h 56mnonstop
$226Air Canada
Sat, May 30 - Sun, May 31
Porter Airlines Logo
10:30 am - 1:10 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
$226Porter Airlines
Wed, May 27 - Sun, May 31
Porter Airlines Logo
10:30 am - 1:10 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
$230Porter Airlines
Sun, May 31 - Tue, Jun 2
Porter Airlines Logo
10:30 am - 1:10 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:45 am - 9:35 am
YTZ
-
MDW
1h 50mnonstop
$231Porter Airlines
Tue, Jun 23 - Tue, Jun 30
Air Canada Logo
2:00 pm - 4:41 pm
ORD
-
YTZ
1h 41mnonstop
Air Canada Logo
7:20 pm - 8:16 pm
YTZ
-
ORD
1h 56mnonstop
$234Air Canada
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 September.

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 $95 on the route between Chicago O'Hare Intl Airport (ORD) and Toronto Island Airport (YTZ). Over the past month, flights between Chicago Midway Airport (MDW) and Toronto Island Airport (YTZ) were, on average, 30% cheaper than other Chicago-Toronto Island Airport routes. This is also the most popular route.

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

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

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

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 March, where tickets cost $58 (return) on average. On the other hand, the most expensive months are November and January, where the average cost of round-trip tickets is $232 and $205 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.

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 $251 on average.

Good to know

Low seasonFebruary
Cheapest flight$98
Best time to beat the crowds with an average 44% drop in price.
Most popular time to fly with an average 38% 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 $98 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, American Airlines, United 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.

  • Which airline alliances offer flights from Chicago to Toronto Island?

    Star Alliance is the only airline alliance operating flights between Chicago and Toronto Island.

  • 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 $132 or less one-way and $226 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

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Tuesday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Wednesday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Thursday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Friday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Saturday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Sunday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

See more direct flights

Direct returns

Toronto Island to Chicago

Monday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Tuesday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Wednesday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Thursday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Friday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Saturday

Air Canada,Porter Airlines

Air Canada,Porter Airlines

Sunday

Air Canada,Porter Airlines

Air Canada,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 436 reviews
7.0Entertainment
8.6Crew
7.6Food
8.0Comfort
8.2Boarding
Airline reviews

The staff was amazing. Best service I’ve had on an aircraft in a long time. Was not particularly happy with the food. Flight was at 10:50 and left home too early for breakfast and wasn’t able to purchase food at airport and felt for sure I could get some breakfast to buy on airplane. Nope as food was served around 11:30 and only one choice left (I was at 22C) so ordered the chicken dish thinking I’m getting a hot meal but cold chicken with rice and carrots etc. I was looking forward to a croissant sandwich and a hot cup of tea. The FA was kind to explain they were serving dinner at that time. She was lovely Other than the disappointment with the food the staff was amazing. On my return flight I will make sure to eat and take some food with me so I’m not hungry or disappointed. This was my second time ever flying Porter and will consider checking them when I next come to visit my daughter. Have to say it again best crew I’ve ever experienced on a flight and I travel quite a bit. Thanks.

10.0 ExcellentAngela, May 2026
YYZ - YVR
Read more Porter Airlines reviews

The staff was amazing. Best service I’ve had on an aircraft in a long time. Was not particularly happy with the food. Flight was at 10:50 and left home too early for breakfast and wasn’t able to purchase food at airport and felt for sure I could get some breakfast to buy on airplane. Nope as food was served around 11:30 and only one choice left (I was at 22C) so ordered the chicken dish thinking I’m getting a hot meal but cold chicken with rice and carrots etc. I was looking forward to a croissant sandwich and a hot cup of tea. The FA was kind to explain they were serving dinner at that time. She was lovely Other than the disappointment with the food the staff was amazing. On my return flight I will make sure to eat and take some food with me so I’m not hungry or disappointed. This was my second time ever flying Porter and will consider checking them when I next come to visit my daughter. Have to say it again best crew I’ve ever experienced on a flight and I travel quite a bit. Thanks.

A few improvements: 1. No signages at the airport that the porter airline was a codeshare and i could check-in at American counter. 2. Crew at the gate said they couldn't change my reward to Alaska - despite that being done previously 3. Despite there being many open seats, i was assigned a seat at the very back near lavatory, last row. Fortunately, the pilot wanted more people moved up so the flight attendants moved me up. It seemed very odd to have been stuck in last row with very few people nearby..

I didn’t receive any help when they messed up and wasn’t honest and the supervisor did absolutely nothing to help me so I had to buy another ticket at $537

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

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

Information on your arrival and departure airports