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YTZ - CHI

$106 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 5/4. 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

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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Cheap Flights from Toronto Island to Chicago

 
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.

Recent round-trip flight deals from Toronto Island to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Toronto Island to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
9:40 am - 12:22 pmMDW-YTZ
1h 42mnonstop
$170Porter Airlines
Find Deal
Thu, May 22 - Mon, May 26
Porter Airlines Logo
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
5:50 pm - 8:32 pmMDW-YTZ
1h 42mnonstop
$171Porter Airlines
Find Deal
Sun, Apr 27 - Mon, May 5
Porter Airlines Logo
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$172Porter Airlines
Find Deal
Wed, Apr 23 - Sun, Apr 27
Porter Airlines Logo
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$173Porter Airlines
Find Deal
Thu, Apr 24 - Sun, Apr 27
Air Canada Logo
8:25 am - 2:55 pmYTZ-ORD
7h 30m1 stop
Air Canada Logo
7:19 am - 2:50 pmORD-YTZ
6h 31m1 stop
$198Air Canada
Find Deal
Tue, Jun 10 - Wed, Jun 11
Air Canada Logo
7:25 am - 11:32 amYTZ-ORD
5h 07m1 stop
Air Canada Logo
1:55 pm - 9:35 pmORD-YTZ
6h 40m1 stop
$199Air Canada
Find Deal
Thu, May 1 - Thu, May 8
Air Transat Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
Air Transat Logo
9:40 am - 12:22 pmMDW-YTZ
1h 42mnonstop
$207Air Transat
Find Deal
Thu, May 1 - Thu, May 8
Logo
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
Logo
9:40 am - 12:22 pmMDW-YTZ
1h 42mnonstop
$216
Find Deal
Wed, Apr 30 - Wed, May 7
Logo
9:30 am - 10:20 amYTZ-MDW
1h 50mnonstop
Logo
9:40 am - 12:22 pmMDW-YTZ
1h 42mnonstop
$217
Find Deal
Wed, Apr 30 - Wed, May 7
Air Transat Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
Air Transat Logo
9:40 am - 12:22 pmMDW-YTZ
1h 42mnonstop
$219Air Transat
Find Deal
Thu, Jun 5 - Wed, Jun 11

Expert advice for your flight from Toronto Island to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
YTZ

YTZ offers free Wi-Fi throughout, ideal for checking emails or booking a taxi before departure.

Read more about YTZby James March
MDW

The CTA Orange Line offers a direct route from MDW to downtown Chicago in about 25-30 minutes.

Read more about MDWby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
James March

James March

Expert on YTZ

James March

James March

For UK-based James March, nothing beats the thrill and chaos of arriving in a new city for the first time, and he tries to put that feeling into his writing and inspire others to travel too. From Birmingham to Blackpool and Leicester to Liverpool, James has reviewed hotels, written narratives and created guides for those who love to travel.

Read more

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Toronto Island Airport to Chicago.
Our data shows that the cheapest route for a return flight from Toronto Island Airport to Chicago cost $129 and was between Toronto Island Airport (YTZ) and Chicago Midway Airport (MDW). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $129.

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 April, where tickets cost $227 (return) on average. On the other hand, the most expensive months are January and September, where the average cost of round-trip tickets is $341 and $336 respectively.
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Good to know

Low season

January

High season

May

Cheapest flight

$106
Best time to beat the crowds but there is an average 24% increase in price.
Most popular time to fly and prices are also 15% 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 $106 for a one-way ticket and $170 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, and American Airlines 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.

See more FAQs

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 $119 or less one-way and $180 or less round-trip.

Prefer to fly 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
See more direct flights

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.
7.9
Porter AirlinesOverall score based on 279 reviews
8.7Crew
7.6Food
6.9Entertainment
8.0Comfort
8.2Boarding
Airline reviews

Overall very good... staff were friendly and helpful. boarding was good for the most part, but a little hard to get our carry-on bags on there.... I think people should be directed to keep their coats and small bags with them until all the carry-ons are loaded, and then, if there is space, they can put their small bags and coats up top.. makes it much easier to put baggage up. i loved the internet feature, but the entertainment was not there unless you have your own Netflix or similar platform. My chair did not recline, which was very annoying, and the arms won't go up near the isle, which makes it tough to get in and out of the seat.

8.0 ExcellentJendan, Mar 2025SFO - YYZ
Read more Porter Airlines reviews

Overall very good... staff were friendly and helpful. boarding was good for the most part, but a little hard to get our carry-on bags on there.... I think people should be directed to keep their coats and small bags with them until all the carry-ons are loaded, and then, if there is space, they can put their small bags and coats up top.. makes it much easier to put baggage up. i loved the internet feature, but the entertainment was not there unless you have your own Netflix or similar platform. My chair did not recline, which was very annoying, and the arms won't go up near the isle, which makes it tough to get in and out of the seat.

Staff were excellant. Only snacks served. Some turbulence so we were offered Free beer or wine.

The staff is always great. Just the fact that our flight was the only one delayed from Halifax when all other carries were still flying. It happen a year ago out of Toronto as well. All others were flying but our flight got cancelled 1 hr before the time of departure.

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

Awesome, the whole way through. Thank you, this is the new Canadian Airline benchmark.

We were given a complimentary seat upgrade which was so unexpected but so lovely!

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

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

Information on your arrival and departure airports

Toronto Island (YTZ)

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