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YTZ - CHI

C$ 194 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 17/11. 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, travellers have searched 46,214,184 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.

Recent one-way flight deals from Toronto Island to Chicago

Only flying one-way? Below are some of the best one-way flight deals from Toronto Island to Chicago found on KAYAK recently.

Recent last-minute flight deals from Toronto Island to Chicago

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Toronto Island to Chicago.

Recent direct flight deals from Toronto Island to Chicago

The latest deals for direct flights from Toronto Island to Chicago so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Toronto Island to Chicago

Find recent round-trip train or bus tickets from Toronto Island to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 311Porter Airlines
Find Deal
Thu, 14 Nov - Sun, 24 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 315Porter Airlines
Find Deal
Mon, 18 Nov - Mon, 25 Nov
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 317Porter Airlines
Find Deal
Thu, 14 Nov - Sun, 17 Nov
11:10 a.m. - 12:00 p.m.YTZ-MDW
1h 50mdirect
12:55 p.m. - 3:37 p.m.MDW-YTZ
1h 42mdirect
C$ 318Porter Airlines
Find Deal
Tue, 14 Jan - Thu, 16 Jan
8:50 a.m. - 12:58 p.m.YTZ-ORD
5h 08m1 stop
2:00 p.m. - 8:43 p.m.ORD-YTZ
5h 43m1 stop
C$ 328Air Canada
Find Deal
Mon, 25 Nov - Wed, 27 Nov
8:50 a.m. - 12:58 p.m.YTZ-ORD
5h 08m1 stop
2:01 p.m. - 7:50 p.m.ORD-YTZ
4h 49m1 stop
C$ 342Air Canada
Find Deal
Thu, 12 Dec - Mon, 16 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 348Air Transat
Find Deal
Thu, 14 Nov - Sun, 17 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 354Air Transat
Find Deal
Thu, 14 Nov - Sun, 17 Nov
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 371
Find Deal
Thu, 14 Nov - Mon, 18 Nov
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 387
Find Deal
Thu, 14 Nov - Sun, 15 Dec
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
C$ 194Porter Airlines
Find Deal
Sun, 17 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
C$ 196Porter Airlines
Find Deal
Tue, 12 Nov
7:45 p.m. - 10:05 a.m.YTZ-ORD
15h 20m1 stop
C$ 196
Find Deal
Mon, 11 Nov
3:25 p.m. - 7:55 p.m.YTZ-ORD
5h 30m1 stop
C$ 200Air Canada
Find Deal
Tue, 12 Nov
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
C$ 200Porter Airlines
Find Deal
Mon, 4 Nov
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
C$ 202Porter Airlines
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Fri, 15 Nov
7:00 a.m. - 10:06 p.m.YTZ-ORD
16h 06m2 stops
C$ 203
Find Deal
Tue, 12 Nov
10:25 a.m. - 2:45 p.m.YTZ-ORD
5h 20m1 stop
C$ 210Air Canada
Find Deal
Wed, 11 Dec
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
C$ 213Air Transat
Find Deal
Wed, 13 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
C$ 214Air Transat
Find Deal
Wed, 13 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
12:55 p.m. - 3:37 p.m.MDW-YTZ
1h 42mdirect
C$ 471Porter Airlines
Find Deal
Sun, 27 Oct - Sat, 30 Nov
10:45 a.m. - 11:32 a.m.YTZ-MDW
1h 47mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 476Porter Airlines
Find Deal
Sat, 26 Oct - Fri, 29 Nov
3:30 p.m. - 4:17 p.m.YTZ-MDW
1h 47mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 525Porter Airlines
Find Deal
Wed, 23 Oct - Mon, 25 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 542Porter Airlines
Find Deal
Sun, 27 Oct - Thu, 31 Oct
10:45 a.m. - 11:32 a.m.YTZ-MDW
1h 47mdirect
12:55 p.m. - 3:37 p.m.MDW-YTZ
1h 42mdirect
C$ 545Porter Airlines
Find Deal
Sat, 26 Oct - Sat, 2 Nov
9:20 a.m. - 10:07 a.m.YTZ-MDW
1h 47mdirect
6:43 p.m. - 10:13 p.m.MDW-YTZ
26h 30m2 stops
C$ 565
Find Deal
Thu, 24 Oct - Mon, 28 Oct
12:20 p.m. - 6:33 p.m.YTZ-ORD
7h 13m1 stop
9:15 a.m. - 6:43 p.m.ORD-YTZ
8h 28m2 stops
C$ 612Air Canada
Find Deal
Sat, 26 Oct - Mon, 28 Oct
3:20 p.m. - 8:10 p.m.YTZ-ORD
5h 50m1 stop
11:35 a.m. - 5:50 p.m.ORD-YTZ
5h 15m1 stop
C$ 624Air Canada
Find Deal
Sat, 26 Oct - Sat, 2 Nov
3:30 p.m. - 4:17 p.m.YTZ-MDW
1h 47mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 654Air Transat
Find Deal
Thu, 24 Oct - Sun, 27 Oct
10:55 a.m. - 2:37 p.m.YTZ-ORD
28h 42m3 stops
8:17 p.m. - 10:13 p.m.ORD-YTZ
24h 56m3 stops
C$ 676
Find Deal
Sun, 27 Oct - Mon, 28 Oct
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 296Porter Airlines
Find Deal
Thu, 14 Nov - Sun, 17 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 297Porter Airlines
Find Deal
Thu, 21 Nov - Sun, 24 Nov
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 299Porter Airlines
Find Deal
Fri, 6 Dec - Sun, 8 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 301Porter Airlines
Find Deal
Thu, 14 Nov - Sun, 17 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
12:05 p.m. - 2:47 p.m.MDW-YTZ
1h 42mdirect
C$ 304Porter Airlines
Find Deal
Fri, 22 Nov - Wed, 4 Dec
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 306Porter Airlines
Find Deal
Thu, 14 Nov - Sun, 17 Nov
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 348Air Transat
Find Deal
Thu, 14 Nov - Sun, 17 Nov
9:30 a.m. - 10:20 a.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 354Air Transat
Find Deal
Thu, 14 Nov - Sun, 17 Nov
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
11:15 a.m. - 1:57 p.m.MDW-YTZ
1h 42mdirect
C$ 355Air Transat
Find Deal
Thu, 14 Nov - Sun, 17 Nov
3:50 p.m. - 4:40 p.m.YTZ-MDW
1h 50mdirect
5:35 p.m. - 8:17 p.m.MDW-YTZ
1h 42mdirect
C$ 371
Find Deal
Thu, 14 Nov - Mon, 18 Nov

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$ 172 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$ 299.

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$ 330 on average. On the other hand, the most expensive months are November and October, where the average cost of tickets is C$ 415 and C$ 408 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

C$ 194
Best time to beat the crowds (7% 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$ 140 for a one-way ticket and C$ 225 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, 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 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

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 C$ 183 or less one-way and C$ 315 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 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.
7.8
Porter AirlinesOverall score based on 294 reviews
6.9Entertainment
7.6Food
8.0Boarding
8.6Crew
7.9Comfort
Airline reviews

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.

4.0 OkayJanna, Oct 2024YTZ - BOS
Read more Porter Airlines reviews

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

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.

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.
17/11Sun
directPorter Airlines
1h 50mYTZ-MDW
C$ 194
12/11Tue
directPorter Airlines
1h 50mYTZ-MDW
C$ 196
11/11Mon
1 stop
15h 20mYTZ-ORD
C$ 196
12/11Tue
1 stopAir Canada
5h 30mYTZ-ORD
C$ 200
4/11Mon
directPorter Airlines
1h 50mYTZ-MDW
C$ 200
15/11Fri
directPorter Airlines
1h 50mYTZ-MDW
C$ 202
12/11Tue
2 stops
16h 06mYTZ-ORD
C$ 203
11/12Wed
1 stopAir Canada
5h 20mYTZ-ORD
C$ 210
13/11Wed
directAir Transat
1h 50mYTZ-MDW
C$ 213
13/11Wed
directAir Transat
1h 50mYTZ-MDW
C$ 214

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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.
27/10Sun
directPorter Airlines
1h 50mYTZ-MDW
30/11Sat
directPorter Airlines
1h 42mMDW-YTZ
C$ 471
26/10Sat
directPorter Airlines
1h 47mYTZ-MDW
29/11Fri
directPorter Airlines
1h 42mMDW-YTZ
C$ 476
23/10Wed
directPorter Airlines
1h 47mYTZ-MDW
25/11Mon
directPorter Airlines
1h 42mMDW-YTZ
C$ 525
27/10Sun
directPorter Airlines
1h 50mYTZ-MDW
31/10Thu
directPorter Airlines
1h 42mMDW-YTZ
C$ 542
26/10Sat
directPorter Airlines
1h 47mYTZ-MDW
2/11Sat
directPorter Airlines
1h 42mMDW-YTZ
C$ 545
24/10Thu
direct
1h 47mYTZ-MDW
28/10Mon
multi-stop
26h 30mMDW-YTZ
C$ 565
26/10Sat
multi-stopAir Canada
7h 13mYTZ-ORD
28/10Mon
multi-stopAir Canada
8h 28mORD-YTZ
C$ 612
26/10Sat
multi-stopAir Canada
5h 50mYTZ-ORD
2/11Sat
multi-stopAir Canada
5h 15mORD-YTZ
C$ 624
24/10Thu
directAir Transat
1h 47mYTZ-MDW
27/10Sun
directAir Transat
1h 42mMDW-YTZ
C$ 654
27/10Sun
multi-stop
28h 42mYTZ-ORD
28/10Mon
multi-stop
24h 56mORD-YTZ
C$ 676

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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)