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YTZ - CHI

$133 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 12/14. 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

Search 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
In the last 7 days travelers have searched 46,646,933 times on KAYAK, and here is why:

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Cheap Flight Deals from Toronto Island to Chicago (YTZ-CHI)

 
These are the cheapest deals for flights from Toronto Island to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. 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

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Toronto Island to Chicago.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$219Porter Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
10:20 am - 11:10 amYTZ-MDW
1h 50mnonstop
5:35 pm - 8:17 pmMDW-YTZ
1h 42mnonstop
$223Porter Airlines
Find Deal
Fri, Dec 13 - Tue, Dec 17
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
12:05 pm - 2:47 pmMDW-YTZ
1h 42mnonstop
$228Porter Airlines
Find Deal
Thu, Dec 12 - Mon, Dec 16
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$230Porter Airlines
Find Deal
Fri, Dec 13 - Sun, Dec 15
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$255Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
9:40 am - 10:30 amYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$261Air Transat
Find Deal
Thu, Dec 12 - Sun, Dec 15
10:25 am - 2:45 pmYTZ-ORD
5h 20m1 stop
2:01 pm - 7:50 pmORD-YTZ
4h 49m1 stop
$261Air Canada
Find Deal
Thu, Dec 12 - Sun, Dec 15
10:25 am - 2:45 pmYTZ-ORD
5h 20m1 stop
11:35 am - 5:50 pmORD-YTZ
5h 15m1 stop
$264Air Canada
Find Deal
Thu, Dec 12 - Tue, Dec 17
3:50 pm - 4:40 pmYTZ-MDW
1h 50mnonstop
11:15 am - 1:57 pmMDW-YTZ
1h 42mnonstop
$334
Find Deal
Wed, Dec 18 - Sun, Jan 5
3:00 pm - 12:34 amYTZ-ORD
10h 34m1 stop
6:37 pm - 8:30 amORD-YTZ
12h 53m1 stop
$338
Find Deal
Mon, Dec 9 - Wed, Dec 11

Flights from Toronto Island to Chicago - Travel Insights & Trends

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 one-way flights from Toronto Island Airport to Chicago.
Our data shows that the cheapest route for a one-way flight from Toronto Island Airport to Chicago cost $134 and was between Toronto Island Airport and Chicago Midway Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $168.

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

The average price of all flights from Toronto Island Airport to Chicago clicked on KAYAK for each day over the last 12 months.
When flying from Toronto Island to Chicago, you should consider leaving on a Saturday and avoid Sundays if you are looking for the best rates. For your return to Toronto Island, you’ll find the best rates on Tuesdays and the most expensive ones on Fridays.

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 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 $239 on average. On the other hand, the most expensive months are November and August, where the average cost of tickets is $307 and $287 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Toronto Island Airport to Chicago, 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 Toronto Island Airport to Chicago, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 124 days before departure.

Good to know

Low season

February

High season

May

Cheapest flight

$133
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 13% 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 $133 for a one-way ticket and $219 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, 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 $149 or less one-way and $233 or less round-trip.

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

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

Nonstop departures

Toronto Island to Chicago

Monday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Tuesday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Wednesday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Thursday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Friday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Saturday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Sunday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

See more direct flights

Nonstop returns

Chicago to Toronto Island

Monday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Tuesday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Wednesday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Thursday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Friday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Saturday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Sunday

Air Transat, Porter Airlines

Air Transat, 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.
7.8
Porter AirlinesOverall score based on 288 reviews
7.9Comfort
8.1Boarding
8.6Crew
6.9Entertainment
7.6Food
Airline reviews

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

10.0 ExcellentJoan, Nov 2024YOW - YYZ
Read more Porter Airlines reviews

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.

Only packaged snacks were served. It was a flight at lunchtime and a hot meal would have been a great.

Reserve check-in was very slow compared to regular check-in. Internet was slow

Lavatories broke with an hour to go. At least we were on time.

Chaotic boarding, but mostly my issues are with Toronto airport

Book cheap flights from Toronto to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Toronto to Chicago found on KAYAK in the last 72 hours.
12/14Sat
nonstopPorter Airlines
1h 50mYTZ-MDW
$133
12/14Sat
nonstopPorter Airlines
1h 50mYTZ-MDW
$136
12/12Thu
nonstopPorter Airlines
1h 50mYTZ-MDW
$138
12/16Mon
nonstopPorter Airlines
1h 50mYTZ-MDW
$141
12/14Sat
1 stopAir Canada
7h 20mYTZ-ORD
$147
2/12Wed
1 stopAir Canada
7h 20mYTZ-ORD
$152
12/11Wed
1 stop
9h 04mYTZ-ORD
$168
1/6Mon
nonstopAir Transat
1h 50mYTZ-MDW
$170
1/29Wed
2 stops
14h 20mYTZ-ORD
$182
12/21Sat
nonstopAir Transat
1h 50mYTZ-MDW
$203

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Last minute flights from Toronto Island to Chicago

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 Toronto to Chicago that are departing in the next 10 days.
11/25Mon
nonstopPorter Airlines
1h 50mYTZ-MDW
12/9Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
$375
11/26Tue
nonstopAir Transat
1h 50mYTZ-MDW
1/16Thu
nonstopAir Transat
1h 42mMDW-YTZ
$379
11/26Tue
nonstopPorter Airlines
1h 50mYTZ-MDW
12/6Fri
nonstopPorter Airlines
1h 42mMDW-YTZ
$400
11/26Tue
nonstopAir Transat
1h 50mYTZ-MDW
12/4Wed
nonstopAir Transat
1h 42mMDW-YTZ
$412
11/26Tue
nonstopPorter Airlines
1h 50mYTZ-MDW
11/28Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
$418
11/26Tue
multi-stopAir Canada
5h 30mYTZ-ORD
12/4Wed
multi-stopAir Canada
5h 43mORD-YTZ
$419
11/23Sat
nonstopPorter Airlines
1h 50mYTZ-MDW
11/30Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
$438
11/26Tue
multi-stopAir Canada
5h 08mYTZ-ORD
12/1Sun
multi-stopAir Canada
5h 43mORD-YTZ
$479
11/25Mon
nonstop
1h 50mYTZ-MDW
11/30Sat
nonstop
1h 42mMDW-YTZ
$498
11/25Mon
nonstop
1h 50mYTZ-MDW
11/29Fri
nonstop
1h 42mMDW-YTZ
$513

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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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