YTZ - CHI

$116 Find Cheap Flights from Toronto Island to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Toronto Island to Chicago departing on 1/18. 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 Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Chicago, 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 Toronto to Chicago, 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
$183
Overall average: $204
Porter Airlines
Thu 1/15Sun 1/18
YTZ - MDW • Non-stop
Cheapest one-way
$116
Typical prices: $215-$262
Porter Airlines
Sun 1/18
YTZ - MDW • Non-stop
Top airlines
Porter Airlines
Cheapest • from $185 (round-trip)
Porter Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
YTZ-MDW
Cheapest • 71% average savings
YTZ-MDW
Most popular
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 32% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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 Chicago!
Flight Deals
Booking Insights
Flight Deals

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

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

Thu, Jan 15 - Sun, Jan 18
Porter Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
4:15 pm - 6:57 pm
MDW
-
YTZ
1h 42mnonstop
$183Porter Airlines
Fri, Jan 16 - Fri, Jan 23
Porter Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
$185Porter Airlines
Sun, Jan 25 - Mon, Jan 26
Porter Airlines Logo
2:30 pm - 3:20 pm
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
$186Porter Airlines
Fri, Jan 16 - Fri, Jan 23
Porter Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:05 am - 1:47 pm
MDW
-
YTZ
1h 42mnonstop
$187Porter Airlines
Thu, Jan 15 - Thu, Jan 29
Porter Airlines Logo
9:20 am - 10:10 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:05 am - 1:47 pm
MDW
-
YTZ
1h 42mnonstop
$191Porter Airlines
Thu, Jan 29 - Thu, Feb 5
Multiple Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
Multiple Airlines Logo
11:05 am - 1:47 pm
MDW
-
YTZ
1h 42mnonstop
$196Multiple Airlines
Sat, Jan 31 - Sat, Feb 7
Air Canada Logo
3:30 pm - 8:10 pm
YTZ
-
ORD
5h 40m1 stop
Air Canada Logo
12:50 pm - 7:55 pm
ORD
-
YTZ
6h 05m1 stop
$198Air Canada
Sat, Jan 24 - Sun, Jan 25
Porter Airlines Logo
11:00 am - 11:50 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
$198Porter Airlines
Fri, Jan 16 - Sun, Jan 18
Air Canada Logo
8:30 am - 2:55 pm
YTZ
-
ORD
7h 25m1 stop
Air Canada Logo
7:15 am - 2:55 pm
ORD
-
YTZ
6h 40m1 stop
$199Air Canada
Thu, Jan 15 - Sun, Jan 18
Air Canada Logo
8:30 am - 2:55 pm
YTZ
-
ORD
7h 25m1 stop
Air Canada Logo
7:15 am - 2:55 pm
ORD
-
YTZ
6h 40m1 stop
$207Air Canada
Booking Insights

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

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

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

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

The cheapest return flight from Toronto Island Airport to Chicago costs $120 on the route between Toronto Island Airport (YTZ) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 71% cheaper than other Toronto Island Airport-Chicago routes. It is also the most popular route.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Toronto Island Airport to Chicago, 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 Toronto Island Airport to Chicago is August, where tickets cost $168 (return) on average. On the other hand, the most expensive months are October and December, where the average cost of round-trip tickets is $396 and $282 respectively.

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

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 $264, prices are generally cheapest when you fly direct.

Good to know

Low seasonOctober
Cheapest flight$116
Best time to beat the crowds but there is an average 60% increase in price.
Most popular time to fly and prices are also 32% lower on average.
Flight from Toronto Island to Chicago Midway Airport

When to book flights from Toronto Island to Chicago

Are your dates flexible? Find out the best times to travel from Toronto Island to Chicago 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 Toronto Island to Chicago flights

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

    In the last 3 days, the lowest price for a flight from Toronto Island Airport to Chicago was $116 for a one-way ticket and $183 for a round-trip.

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

    A passport is required to fly from Toronto Island to Chicago.

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

    When flying out of Toronto Island you will be using Toronto Island. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

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

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

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

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

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

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

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

    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 Toronto Island to Chicago.

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

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

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

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

    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 Chicago from Toronto Island 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 Toronto Island Airport to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $117 or less one-way and $210 or less round-trip.

Prefer to fly direct from Toronto Island to Chicago?

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

Direct departures

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

Direct returns

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

Reviews of the top airline flying from Toronto Island to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Toronto to Chicago. 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 Toronto Island to Chicago? 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 399 reviews
7.0Entertainment
7.9Comfort
7.6Food
8.6Crew
8.2Boarding
Airline reviews

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

6.0 GoodAnonymous, Dec 2025
YUL - YTZ
Read more Porter Airlines reviews

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

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

Organization and the adjusted times but the snacks could be of a bigger portion

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

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

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

The flight was fine see earlier note for the problem

All good the seats a little tight and no I pad screen

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

Information on your arrival and departure airports