CHI - YTZ

$106 Find Cheap Flights from Chicago to Toronto Island - Compare and Save

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 7/15. 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$227
Porter Airlines
Fri 10/2Sat 10/3
ORD - YTZ • Non-stop
Cheapest one-way
$106
Typical prices: $106-$128
Porter Airlines
Wed 7/15
MDW - YTZ • Non-stop
Top airlines
Cheapest • from $227 (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 41m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 2% 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 • 66% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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, Oct 2 - Sat, Oct 3
Porter Airlines Logo
7:00 am - 9:40 am
ORD
-
YTZ
1h 40mnonstop
Porter Airlines Logo
1:40 pm - 2:35 pm
YTZ
-
ORD
1h 55mnonstop
$227Porter Airlines
Thu, Jul 16 - Sun, Jul 19
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
$228Porter Airlines
Thu, Sep 24 - Sun, Sep 27
Porter Airlines Logo
7:00 am - 9:40 am
ORD
-
YTZ
1h 40mnonstop
Porter Airlines Logo
10:05 am - 11:00 am
YTZ
-
ORD
1h 55mnonstop
$228Porter Airlines
Wed, Jul 22 - Wed, Jul 29
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
$229Porter Airlines
Sun, Jul 12 - Thu, Jul 16
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
$230Porter Airlines
Wed, Oct 14 - Mon, Oct 19
Porter Airlines Logo
7:00 am - 9:40 am
ORD
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:40 pm - 9:35 pm
YTZ
-
ORD
1h 55mnonstop
$230Porter Airlines
Fri, Jul 17 - Sun, Jul 19
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
$231Porter Airlines
Thu, Jul 16 - Mon, Jul 20
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
$232Porter Airlines
Fri, Oct 2 - Sun, Oct 4
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
$232Porter Airlines
Fri, Oct 9 - Sat, Oct 10
Multiple Airlines Logo
7:25 am - 10:07 am
ORD
-
YTZ
1h 42mnonstop
Multiple Airlines Logo
1:40 pm - 2:35 pm
YTZ
-
ORD
1h 55mnonstop
$234Multiple 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 October.

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 $198 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, 2% 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 Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Tuesday is the most expensive day to fly from Chicago to Toronto Island. For your return ticket, we recommend flying on a Thursday and avoiding Mondays 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 May, where the average cost of round-trip tickets is $232 and $223 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$106
Best time to beat the crowds with an average 49% drop in price.
Most popular time to fly with an average 27% 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 5 days, the lowest price for a flight from Chicago to Toronto Island Airport was $106 for a one-way ticket and $227 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, Porter Airlines, 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.

  • 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 $115 or less one-way and $250 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 440 reviews
8.2Boarding
6.9Entertainment
8.0Comfort
8.6Crew
7.5Food
Airline reviews

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..

6.0 GoodHarsh, Apr 2026
JFK - YYZ
Read more Porter Airlines reviews

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..

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.

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.

Flight was delayed over 2 hours, then landed at a different airport!

Porter was excellent. Boarding was a breeze. The seats were a little uncomfortably but the overall trip was excellent.

Wish we had music during take off and landing like the last flight

Porter is what Westjet used to be. Staff were great

Flight was supposed to be at 3 didn’t fly out until 6:30

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

Information on your arrival and departure airports