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YTZ - CHI

C$ 178 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 10/8. 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
Thu 15/8
Thu 22/8

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, travellers have searched 49,276,264 times on KAYAK, and here is why:

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
9:20 a.m. - 10:07 a.m.YTZ-MDW
1h 47mdirect
8:00 a.m. - 10:42 a.m.MDW-YTZ
1h 42mdirect
C$ 290Porter Airlines
Find Deal
Tue, 6 Aug - Wed, 14 Aug
8:50 p.m. - 9:37 p.m.YTZ-MDW
1h 47mdirect
8:00 a.m. - 10:42 a.m.MDW-YTZ
1h 42mdirect
C$ 296Porter Airlines
Find Deal
Fri, 9 Aug - Fri, 16 Aug
3:30 p.m. - 4:17 p.m.YTZ-MDW
1h 47mdirect
5:15 p.m. - 7:57 p.m.MDW-YTZ
1h 42mdirect
C$ 298Porter Airlines
Find Deal
Wed, 14 Aug - Wed, 21 Aug
9:20 a.m. - 10:07 a.m.YTZ-MDW
1h 47mdirect
8:00 a.m. - 10:42 a.m.MDW-YTZ
1h 42mdirect
C$ 299Porter Airlines
Find Deal
Wed, 28 Aug - Fri, 30 Aug
9:20 a.m. - 12:42 p.m.YTZ-ORD
4h 22m1 stop
10:55 a.m. - 5:49 p.m.ORD-YTZ
5h 54m1 stop
C$ 331Air Canada
Find Deal
Wed, 11 Sep - Sun, 15 Sep
9:20 a.m. - 12:42 p.m.YTZ-ORD
4h 22m1 stop
2:00 p.m. - 8:44 p.m.ORD-YTZ
5h 44m1 stop
C$ 348Air Canada
Find Deal
Wed, 4 Sep - Tue, 10 Sep
8:50 p.m. - 9:37 p.m.YTZ-MDW
1h 47mdirect
11:05 a.m. - 1:47 p.m.MDW-YTZ
1h 42mdirect
C$ 357Air Transat
Find Deal
Wed, 7 Aug - Tue, 13 Aug
8:50 p.m. - 9:37 p.m.YTZ-MDW
1h 47mdirect
8:00 a.m. - 10:42 a.m.MDW-YTZ
1h 42mdirect
C$ 361Air Transat
Find Deal
Fri, 9 Aug - Sat, 17 Aug
6:45 a.m. - 4:22 p.m.YTZ-ORD
10h 37m2 stops
11:12 a.m. - 9:15 p.m.ORD-YTZ
9h 03m2 stops
C$ 370
Find Deal
Wed, 14 Aug - Wed, 21 Aug
8:50 p.m. - 9:37 p.m.YTZ-MDW
1h 47mdirect
11:05 a.m. - 1:47 p.m.MDW-YTZ
1h 42mdirect
C$ 378
Find Deal
Wed, 31 Jul - Tue, 6 Aug

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 C$ 163 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 C$ 280.

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 Wednesday and avoid Saturdays 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 Thursdays.

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 C$ 326 on average. On the other hand, the most expensive months are September and October, where the average cost of tickets is C$ 455 and C$ 448 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 150 days before departure.

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

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 3 days, Porter Airlines offered the best one-way deal for that route, at C$ 178. KAYAK users also found Toronto Island to Chicago round-trip flights on Porter Airlines from C$ 290 and on Air Canada from C$ 331.

Which airlines fly direct between Toronto Island Airport and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Toronto Island Airport to Chicago.
There is just one airline that flies from Toronto Island Airport to Chicago direct and that is Porter Airlines. The best one-way deal found from Porter Airlines for the route is C$ 269.

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

Each day, there are between 2 and 3 nonstop flights that take off from Toronto Island Airport and land in Chicago, with an average flight time of 1h 47m. The most common departure time is 6:00 p.m. and most flights take off in the evening, while the most flights land at Chicago Midway Airport. Each week, there are 20 flights. The most frequent day of departure is Monday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.

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

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 Toronto Island to Chicago take?

Direct flights cover the 1,125 km separating Toronto Island to Chicago in about 1h 47m.

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

Early birds can take the earliest flight from Toronto Island Airport at 9:20 am and will be landing in Chicago at 10:07 am.

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

If you prefer to fly at night, the latest flight from Toronto Island Airport to Chicago jets off at 9:35 pm and lands at 10:22 pm.

Good to know

Low season

January

High season

May

Cheapest flight

C$ 178
Best time to beat the crowds (12% less expensive on average)
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 C$ 130 for a one-way ticket and C$ 212 for a round-trip.

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

    Toronto Island is served by only 1 airport and there are 2 airports in Chicago. You will leave Toronto Island from Toronto Island and you will be arriving in Chicago 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, American Airlines, and United 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 Boeing 737 MAX 8 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 direct 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 travellers 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

Top tips for finding a cheap flight from Toronto to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 180 or less one-way and C$ 294 or less round-trip.

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

Find which airlines fly direct from Toronto Island 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 nonstop 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 nonstop flights
See more nonstop 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.
7.6
Porter AirlinesOverall score based on 350 reviews
7.8Boarding
8.4Crew
7.5Food
7.7Comfort
6.7Entertainment
Airline reviews

Chaotic boarding, but mostly my issues are with Toronto airport

6.0 GoodArti, Jul. 2024YYZ - YUL
Read more about Porter Airlines reviews

Chaotic boarding, but mostly my issues are with Toronto airport

Flight delayed by half hour, causing rush to get to connecting flight in Toronto Pearson which doesn’t have good flow for managing immigration check and connections.

Service was amazing, and the plane was comfortable even for this long haul. But they could have more movies selections. But they were still a lot to choose from.

Due to mechanical problems it was delayed causing problems the actual flight. Was fune

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

First time with Porter and I can say this is best airline company in Canada. Great service, free WiFi, free snack and drinks (including beer and wine). Seats were super comfy on the Embraer jet and I appreciated the folding try table too. Staff were excellent both legs of the trip.

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

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.
10/8Sat
directPorter Airlines
1h 47mYTZ-MDW
C$ 178
7/8Wed
directPorter Airlines
1h 47mYTZ-MDW
C$ 180
14/8Wed
directPorter Airlines
1h 47mYTZ-MDW
C$ 182
13/9Fri
directPorter Airlines
1h 47mYTZ-MDW
C$ 183
6/8Tue
directAir Transat
1h 47mYTZ-MDW
C$ 205
13/9Fri
1 stopAir Canada
5h 15mYTZ-ORD
C$ 205
23/9Mon
1 stopAir Canada
4h 22mYTZ-ORD
C$ 208
13/8Tue
2 stops
14h 03mYTZ-ORD
C$ 219
7/8Wed
1 stop
12h 14mYTZ-ORD
C$ 224
3/8Sat
directAir Transat
1h 47mYTZ-MDW
C$ 231

Search by stops

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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.
21/7Sun
directPorter Airlines
1h 47mYTZ-MDW
31/8Sat
directPorter Airlines
1h 42mMDW-YTZ
C$ 482
19/7Fri
directPorter Airlines
1h 47mYTZ-MDW
29/7Mon
directPorter Airlines
1h 42mMDW-YTZ
C$ 497
21/7Sun
direct
1h 47mYTZ-MDW
31/8Sat
direct
1h 42mMDW-YTZ
C$ 552
20/7Sat
directPorter Airlines
1h 47mYTZ-MDW
27/7Sat
directPorter Airlines
1h 42mMDW-YTZ
C$ 565
20/7Sat
directPorter Airlines
1h 47mYTZ-MDW
24/7Wed
directPorter Airlines
1h 42mMDW-YTZ
C$ 568
19/7Fri
directPorter Airlines
1h 47mYTZ-MDW
23/7Tue
directPorter Airlines
1h 42mMDW-YTZ
C$ 578
18/7Thu
directPorter Airlines
1h 47mYTZ-MDW
25/7Thu
directPorter Airlines
1h 42mMDW-YTZ
C$ 589
21/7Sun
multi-stopAir Canada
5h 53mYTZ-ORD
31/8Sat
multi-stopAir Canada
5h 44mORD-YTZ
C$ 632
21/7Sun
multi-stopAir Canada
5h 53mYTZ-ORD
23/7Tue
multi-stopAir Canada
4h 54mORD-YTZ
C$ 638
21/7Sun
multi-stopAir Canada
5h 53mYTZ-ORD
28/7Sun
multi-stopAir Canada
5h 49mORD-YTZ
C$ 647

Search by stops

Search by airline

Search by price

Toronto Island - Chicago Flights

Departure:

Toronto Island (YTZ)Canada

Return flight deals:

Chicago - Toronto Island

Cabin classes:

C$ 601
C$ 280