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CHI - YTZ

Find cheap flights from Chicago to Toronto Island from $97

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 5/8. 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
0 bags
Sat 5/18
Sat 5/25

Search hundreds of travel sites at once for deals on flights to Toronto Island

 
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
In the last 7 days travelers have searched 44,471,296 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
5:15 pm - 7:57 pmMDW-YTZ
1h 42mnonstop
8:50 pm - 9:37 pmYTZ-MDW
1h 47mnonstop
$217Porter Airlines
Find Deal
Thu, May 9 - Sun, May 12
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
3:30 pm - 4:17 pmYTZ-MDW
1h 47mnonstop
$218Porter Airlines
Find Deal
Wed, May 8 - Fri, May 10
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
10:30 am - 11:17 amYTZ-MDW
1h 47mnonstop
$219Porter Airlines
Find Deal
Wed, May 8 - Sun, May 12
5:15 pm - 7:57 pmMDW-YTZ
1h 42mnonstop
10:30 am - 11:17 amYTZ-MDW
1h 47mnonstop
$226Porter Airlines
Find Deal
Fri, May 24 - Sun, May 26
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
8:50 pm - 9:37 pmYTZ-MDW
1h 47mnonstop
$228Porter Airlines
Find Deal
Thu, May 23 - Thu, May 30
11:05 am - 1:47 pmMDW-YTZ
1h 42mnonstop
8:50 pm - 9:37 pmYTZ-MDW
1h 47mnonstop
$229Porter Airlines
Find Deal
Wed, May 29 - Fri, Jun 7
5:09 pm - 9:35 amORD-YTZ
15h 26m1 stop
11:00 am - 9:46 pmYTZ-ORD
11h 46m1 stop
Tue, May 7 - Tue, May 14
10:55 am - 5:49 pmORD-YTZ
5h 54m1 stop
8:20 am - 2:41 pmYTZ-ORD
7h 21m1 stop
$300Air Canada
Find Deal
Sat, May 18 - Sat, May 25
10:55 am - 5:49 pmORD-YTZ
5h 54m1 stop
10:20 am - 2:41 pmYTZ-ORD
5h 21m1 stop
$316Air Canada
Find Deal
Sun, May 19 - Tue, May 21
8:45 am - 2:49 pmORD-YTZ
5h 04m1 stop
10:20 am - 2:41 pmYTZ-ORD
5h 21m1 stop
$342Air Canada
Find Deal
Tue, May 7 - Wed, May 8

Flights from Chicago to Toronto Island - Travel Insights & Trends

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.

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

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Chicago to Toronto Island Airport.
Our data shows that the cheapest route for a one-way flight from Chicago to Toronto Island Airport cost $106 and was between Chicago Midway Airport and Toronto Island Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $232.

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

The average price of all flights from Chicago to Toronto Island Airport clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Chicago to Toronto Island, look for departures on Sundays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Toronto Island, Thursday is the cheapest day to fly and Tuesday is the most expensive.

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 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 February, where tickets cost $225 on average. On the other hand, the most expensive months are May and June, where the average cost of tickets is $490 and $452 respectively.

How far in advance should I book a flight from Chicago to Toronto Island Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago to Toronto Island Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago to Toronto Island Airport, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 14 days before departure.

Which airlines provide the cheapest flights from Chicago to Toronto Island?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the cheapest one-way ticket from Chicago to Toronto Island found on KAYAK was with Porter Airlines for $97. Porter Airlines proposed a round-trip connection from $217 and Air Canada from $300.

Which airlines fly non-stop between Chicago and Toronto Island Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago to Toronto Island Airport.
There is just one airline that flies from Chicago to Toronto Island Airport direct and that is Porter Airlines. The best one-way deal found from Porter Airlines for the route is $203.

How many flights are there between Chicago and Toronto Island Airport per day?

Each day, there are between 2 and 3 nonstop flights that take off from Chicago and land in Toronto Island Airport, with an average flight time of 1h 42m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 20 flights. The most frequent day of departure is Thursday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Chicago and Toronto Island Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Chicago to Toronto Island take?

A direct flight to Toronto Island will take on average 1h 42m to travel the 434 miles flying distance from Chicago.

What’s the earliest departure time from Chicago to Toronto Island?

Early birds can take the earliest flight from Chicago at 8:00 am and will be landing in Toronto Island Airport at 10:42 am.

What’s the latest departure time from Chicago to Toronto Island?

If you prefer to fly at night, the latest flight from Chicago to Toronto Island Airport jets off at 5:15 pm and lands at 7:57 pm.

Good to know

Low season

October

High season

July

Cheapest flight

$97
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 11% 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 $97 for a one-way ticket and $217 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?

    All the following airlines offer inflight Wi-Fi service on the Chicago to Toronto Island flight route: Air Canada, American Airlines, United Airlines, Breeze Airways, Delta, and British Airways.

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

    The Embraer 175 (Enhanced Winglets) 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.

See more FAQs

Top tips for finding a cheap flight from Chicago to Toronto

  • Looking for a cheap flight? 25% of our users found flights on this route for $125 or less one-way and $259 or less round-trip.

Prefer to fly non-stop from Chicago to Toronto Island?

Find which airlines fly direct from Chicago to Toronto Island, which days they fly and book direct flights.

Nonstop 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

Nonstop 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
See more direct flights

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.
7.4
Porter AirlinesOverall score based on 439 reviews
7.6boarding
8.2crew
7.4food
7.5comfort
6.6entertainment
Airline reviews

Crew is ok. They offered food n drinks. Had difficulty connecting to wifi on board.

8.0 ExcellentAnonymous, Apr 2024LAX - YYZ
Read more about Porter Airlines reviews

Crew is ok. They offered food n drinks. Had difficulty connecting to wifi on board.

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

Great. Porter is very efficient, welcoming, and organized. I fly Porter often.

Flight was smooth and comfortable. The crew were exceptional. Amanda, Nichole and Hershel were attentive to our every need. So friendly. My daughter and I were surprised at quality of service. Loved the double row seating. Snacks were delicious. We would definitely fly with Porter again. Flight PD 670 SFO to YYZ Thank you so much for the best flight experience we have had

The E195-E2 is a great aircraft! Leather seats, lots of legroom and SO quiet! The flight crew is terrific!

Check in was slow because of passenger ahead in Reserve line. Seats were somewhat uncomfortable.

Delayed by 2.5 hours. This happened previously on my flight from YOW to YVR on Dec. 26.2023. This is a terrible airline. The reason was there was lack of ground crew. This is a known event. AVOID PORTER AIRLINES IF YOU CAN. There is a reason half the plane was empty.

Flight delayed 6 hr. Looking for compensation and will claim for it.allow US people to fix to avoid huge delay having a canadian tech to fix it.

I didn’t make my flight due to poor weather and I had an accident driving there. I tried to get my money back or even credit and nothing. I have an entire flight both to Florida and back that I paid for and no one will give me any money back. I know this isn’t just Porter and it’s 3rd party- however airlines should allow these companies to take money for things they don’t get. I’m so upset. Who can afford a full flight they never take?

Flight Ottawa to Toronto canceled and no crew was available to direct me on what to do. I opened a file and I wait to be compensated.

Book cheap flights from Chicago to Toronto

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Toronto found on KAYAK in the last 72 hours.
5/8Wed
nonstopPorter Airlines
1h 42mMDW-YTZ
$97
5/12Sun
nonstopPorter Airlines
1h 42mMDW-YTZ
$98
5/8Wed
nonstopPorter Airlines
1h 42mMDW-YTZ
$99
5/8Wed
nonstopPorter Airlines
1h 42mMDW-YTZ
$102
5/8Wed
1 stop
9h 01mORD-YTZ
$119
5/14Tue
1 stop
15h 16mORD-YTZ
$137
5/18Sat
1 stopAir Canada
5h 54mORD-YTZ
$138
5/8Wed
2 stopsAir Canada
9h 49mORD-YTZ
$144
7/12Fri
nonstopAPG Airlines
1h 42mMDW-YTZ
$421
5/3Fri
nonstopFLYGTA Airlines
2h 30mMDW-YTZ
$7,722

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Last minute flights from Chicago to Toronto Island

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Toronto that are departing in the next 10 days.
4/23Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
4/26Fri
nonstopPorter Airlines
1h 47mYTZ-MDW
$396
4/20Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
4/30Tue
nonstopPorter Airlines
1h 47mYTZ-MDW
$415
4/23Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
4/23Tue
nonstopPorter Airlines
1h 47mYTZ-MDW
$418
4/22Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
4/29Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$444
4/20Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
4/29Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
$449
4/20Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
4/27Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
$455
4/22Mon
multi-stop
23h 21mORD-YTZ
5/14Tue
multi-stop
10h 45mYTZ-ORD
$555
4/21Sun
multi-stopAir Canada
5h 17mORD-YTZ
4/24Wed
multi-stopAir Canada
5h 16mYTZ-ORD
$591
4/20Sat
multi-stopAir Canada
6h 56mORD-YTZ
4/23Tue
multi-stopAir Canada
7h 11mYTZ-ORD
$630
4/20Sat
multi-stopAir Canada
8h 41mORD-YTZ
4/23Tue
multi-stopAir Canada
7h 11mYTZ-ORD
$639

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Flights to Toronto Island

Destination:

Toronto Island (YTZ)Canada

Return flight deals:

Toronto Island - Chicago

Cabin classes:

$307
$232