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YTZ - CHI

Find cheap flights from Toronto Island to Chicago from $135

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 6/26. 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
Mon 6/3
Mon 6/10

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 43,693,958 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
8:50 pm - 9:37 pmYTZ-MDW
1h 47mnonstop
5:15 pm - 7:57 pmMDW-YTZ
1h 42mnonstop
$232Porter Airlines
Find Deal
Fri, May 31 - Mon, Jun 3
9:20 am - 10:07 amYTZ-MDW
1h 47mnonstop
8:00 am - 10:42 amMDW-YTZ
1h 42mnonstop
$233Porter Airlines
Find Deal
Wed, May 29 - Tue, Jun 4
8:50 pm - 9:37 pmYTZ-MDW
1h 47mnonstop
12:30 pm - 3:12 pmMDW-YTZ
1h 42mnonstop
$234Porter Airlines
Find Deal
Thu, May 30 - Sat, Jun 8
3:30 pm - 4:17 pmYTZ-MDW
1h 47mnonstop
8:40 am - 11:22 amMDW-YTZ
1h 42mnonstop
$235Porter Airlines
Find Deal
Thu, May 23 - Sun, May 26
9:20 am - 10:07 amYTZ-MDW
1h 47mnonstop
12:30 pm - 3:12 pmMDW-YTZ
1h 42mnonstop
$239Porter Airlines
Find Deal
Wed, May 29 - Sat, Jun 1
9:20 am - 10:07 amYTZ-MDW
1h 47mnonstop
11:05 am - 1:47 pmMDW-YTZ
1h 42mnonstop
$240Porter Airlines
Find Deal
Wed, May 29 - Wed, Jun 5
12:20 pm - 6:33 pmYTZ-ORD
7h 13m1 stop
7:21 am - 2:49 pmORD-YTZ
6h 28m1 stop
$292Air Canada
Find Deal
Sat, May 25 - Mon, May 27
8:40 pm - 10:14 amYTZ-ORD
14h 34m1 stop
5:07 pm - 8:35 amORD-YTZ
14h 28m1 stop
$298
Find Deal
Tue, Jun 11 - Wed, Jun 12
8:20 am - 1:13 pmYTZ-ORD
5h 53m1 stop
7:21 am - 2:49 pmORD-YTZ
6h 28m1 stop
$307Air Canada
Find Deal
Fri, May 24 - Mon, May 27
9:20 am - 12:37 pmYTZ-ORD
4h 17m1 stop
2:00 pm - 8:44 pmORD-YTZ
5h 44m1 stop
$313Air Canada
Find Deal
Fri, Oct 4 - Wed, Oct 9

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 $124 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 $204.

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 Tuesday and avoid Sundays if you are looking for the best rates. For your return to Toronto Island, you’ll find the best rates on Sundays and the most expensive ones on Mondays.

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 January, where tickets cost $231 on average. On the other hand, the most expensive months are July and August, where the average cost of tickets is $339 and $338 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 78 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.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Porter Airlines ($135) and Air Canada ($153). The cheapest round-trip tickets were found on Porter Airlines ($232) and Air Canada ($292).

Which airlines fly non-stop 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 $206.

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 9:00 am and most flights take off in the morning, while the most flights land at Chicago Midway Airport. Each week, there are 20 flights. The most frequent day of departure is Tuesday, 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 are 2 cabin class options for the route. These are Economy and Prem 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?

The duration of a nonstop flight to Chicago from Toronto Island is typically 1h 47m. The journey crosses a distance of 434 miles.

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 8:50 pm and lands at 9:37 pm.

Good to know

Low season

November

High season

December

Cheapest flight

$135
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 10% 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 $135 for a one-way ticket and $232 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, 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 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

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 $133 or less one-way and $219 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

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

Nonstop 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.
7.4
Porter AirlinesOverall score based on 433 reviews
7.5Comfort
7.4Food
6.6Entertainment
8.2Crew
7.6Boarding
Airline reviews

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.

10.0 ExcellentJustin, Apr 2024YVR - YYZ
Read more about Porter Airlines reviews

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.

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

Check in was slow because of passenger ahead in Reserve line. Seats were somewhat uncomfortable.

First time with Porter. Amazing experience overall, will be my airline of choice in North America whenever possible. Liked the quality of food and how it was served but one suggestion- a hot meal on the longer flights, perhaps?

Delayed by 2.5 hours. This happened previously on my flight from YOW to YVR on Dec. 26.2023. This is a terrible airline. The reason was there was lack of ground crew. This is a known event. AVOID PORTER AIRLINES IF YOU CAN. There is a reason half the plane was empty.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10 Tips for people flying porter from Boston. The airline doesn’t have inflight entertainment No TV No WIFI. Bring your entertainment with you.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10

Wasn’t on the flight- again. Bad weather in Halifax and I was in an accident. What a poor experience to have to pay for all this flight and not be on it

I didn’t make my flight due to poor weather and I had an accident driving there. I tried to get my money back or even credit and nothing. I have an entire flight both to Florida and back that I paid for and no one will give me any money back. I know this isn’t just Porter and it’s 3rd party- however airlines should allow these companies to take money for things they don’t get. I’m so upset. Who can afford a full flight they never take?

Flight Ottawa to Toronto canceled and no crew was available to direct me on what to do. I opened a file and I wait to be compensated.

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.
6/26Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
$135
6/1Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
$138
5/24Fri
nonstopPorter Airlines
1h 47mYTZ-MDW
$140
5/28Tue
nonstopPorter Airlines
1h 47mYTZ-MDW
$141
6/1Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
$142
6/4Tue
nonstopPorter Airlines
1h 47mYTZ-MDW
$148
6/4Tue
1 stop
8h 46mYTZ-ORD
$150
6/8Sat
1 stopAir Canada
5h 56mYTZ-ORD
$153
7/2Tue
1 stopAir Canada
5h 20mYTZ-ORD
$160
6/14Fri
1 stopAir Canada
5h 53mYTZ-ORD
$176

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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.
5/9Thu
nonstopPorter Airlines
1h 47mYTZ-MDW
5/19Sun
nonstopPorter Airlines
1h 42mMDW-YTZ
$331
5/6Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
5/31Fri
nonstopPorter Airlines
1h 42mMDW-YTZ
$345
5/7Tue
nonstopPorter Airlines
1h 47mYTZ-MDW
5/13Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
$383
5/8Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
5/13Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
$392
5/9Thu
nonstopPorter Airlines
1h 47mYTZ-MDW
5/16Thu
nonstopPorter Airlines
1h 42mMDW-YTZ
$398
5/6Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
5/14Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
$402
5/6Mon
multi-stopAir Canada
5h 55mYTZ-ORD
5/15Wed
multi-stopAir Canada
6h 29mORD-YTZ
$448
5/9Thu
multi-stopAir Canada
6h 55mYTZ-ORD
5/15Wed
multi-stopAir Canada
6h 29mORD-YTZ
$469
5/7Tue
multi-stopAir Canada
5h 21mYTZ-ORD
5/14Tue
multi-stopAir Canada
5h 46mORD-YTZ
$472
5/7Tue
multi-stop
23h 35mYTZ-ORD
5/12Sun
multi-stop
6h 29mORD-YTZ
$590

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Toronto Island - Chicago Flights

Departure:

Toronto Island (YTZ)Canada

Return flight deals:

Chicago - Toronto Island

Cabin classes:

$204

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