Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights
Airlines

YTZ - CHI

Find cheap flights from Toronto Island to Chicago from C$ 175

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 20/7. 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
jue. 6/6
jue. 13/6

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 42,573,820 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

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
10:45 a.m. - 11:32 a.m.YTZ-MDW
1h 47mdirect
11:05 a.m. - 1:47 p.m.MDW-YTZ
1h 42mdirect
C$ 308Porter Airlines
Find Deal
sáb., 1 jun. - mié., 5 jun.
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$ 309Porter Airlines
Find Deal
mié., 22 may. - sáb., 25 may.
3:30 p.m. - 4:17 p.m.YTZ-MDW
1h 47mdirect
12:15 p.m. - 2:57 p.m.MDW-YTZ
1h 42mdirect
C$ 314Porter Airlines
Find Deal
jue., 23 may. - dom., 26 may.
3:30 p.m. - 4:17 p.m.YTZ-MDW
1h 47mdirect
11:05 a.m. - 1:47 p.m.MDW-YTZ
1h 42mdirect
C$ 317Porter Airlines
Find Deal
lun., 20 may. - mié., 24 jul.
9:20 a.m. - 10:07 a.m.YTZ-MDW
1h 47mdirect
11:25 a.m. - 2:07 p.m.MDW-YTZ
1h 42mdirect
C$ 319Porter Airlines
Find Deal
lun., 27 may. - lun., 3 jun.
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$ 320Porter Airlines
Find Deal
jue., 23 may. - lun., 27 may.
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$ 357Air Canada
Find Deal
lun., 2 sep. - mié., 4 sep.
12:50 p.m. - 9:46 p.m.YTZ-ORD
9h 56m1 stop
11:24 a.m. - 9:15 p.m.ORD-YTZ
8h 51m1 stop
C$ 383
Find Deal
mar., 4 jun. - mar., 11 jun.
8:20 a.m. - 2:41 p.m.YTZ-ORD
7h 21m1 stop
7:21 a.m. - 2:49 p.m.ORD-YTZ
6h 28m1 stop
C$ 388Air Canada
Find Deal
mié., 22 may. - lun., 27 may.
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$ 392Air Canada
Find Deal
mié., 11 sep. - jue., 12 sep.

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$ 283.

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 Fridays 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$ 327 on average. On the other hand, the most expensive months are August and September, where the average cost of tickets is C$ 461 and C$ 459 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 37 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$ 175. KAYAK users also found Toronto Island to Chicago round-trip flights on Porter Airlines from C$ 308 and on Air Canada from C$ 357.

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$ 268.

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 a.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 Wednesday, 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 8:50 pm and lands at 9:37 pm.

Good to know

Low season

January

High season

May

Cheapest flight

C$ 175
Best time to beat the crowds (19% less expensive on average)
Most popular time to fly and prices are also 21% 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$ 128 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, 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$ 175 or less one-way and C$ 314 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 nonstop 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 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.
7.5
Porter AirlinesOverall score based on 424 reviews
8.3Crew
6.7Entertainment
7.5Food
7.6Boarding
7.5Comfort
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.

Flight delayed 6 hr. Looking for compensation and will claim for it.allow US people to fix to avoid huge delay having a canadian tech to fix it.

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?

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.
20/7sáb.
directPorter Airlines
1h 47mYTZ-MDW
C$ 175
21/5mar.
directPorter Airlines
1h 47mYTZ-MDW
C$ 179
27/5lun.
directPorter Airlines
1h 47mYTZ-MDW
C$ 180
14/6vie.
directPorter Airlines
1h 47mYTZ-MDW
C$ 183
3/6lun.
directPorter Airlines
1h 47mYTZ-MDW
C$ 186
9/6dom.
directPorter Airlines
1h 47mYTZ-MDW
C$ 187
8/6sáb.
1 stopAir Canada
5h 56mYTZ-ORD
C$ 200
4/6mar.
1 stopAir Canada
5h 16mYTZ-ORD
C$ 209
12/6mié.
1 stop
11h 52mYTZ-ORD
C$ 211
10/10jue.
1 stopAir Canada
4h 17mYTZ-ORD
C$ 238

Search by stops

Search by airline

Search by price

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.
9/5jue.
directPorter Airlines
1h 47mYTZ-MDW
21/5mar.
directPorter Airlines
1h 42mMDW-YTZ
C$ 484
8/5mié.
directPorter Airlines
1h 47mYTZ-MDW
21/5mar.
directPorter Airlines
1h 42mMDW-YTZ
C$ 526
11/5sáb.
directPorter Airlines
1h 47mYTZ-MDW
28/5mar.
directPorter Airlines
1h 42mMDW-YTZ
C$ 532
9/5jue.
directPorter Airlines
1h 47mYTZ-MDW
14/5mar.
directPorter Airlines
1h 42mMDW-YTZ
C$ 545
10/5vie.
directPorter Airlines
1h 47mYTZ-MDW
13/5lun.
directPorter Airlines
1h 42mMDW-YTZ
C$ 548
10/5vie.
directPorter Airlines
1h 47mYTZ-MDW
13/5lun.
directPorter Airlines
1h 42mMDW-YTZ
C$ 550
11/5sáb.
multi-stopAir Canada
7h 21mYTZ-ORD
18/5sáb.
multi-stopAir Canada
5h 54mORD-YTZ
C$ 617
9/5jue.
multi-stopAir Canada
5h 55mYTZ-ORD
21/5mar.
multi-stopAir Canada
5h 46mORD-YTZ
C$ 630
10/5vie.
multi-stopAir Canada
5h 55mYTZ-ORD
15/5mié.
multi-stopAir Canada
5h 46mORD-YTZ
C$ 647
8/5mié.
multi-stop
15h 07mYTZ-ORD
21/5mar.
multi-stop
21h 05mORD-YTZ
C$ 696

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$ 543
C$ 279

Browse origins:

Browse destinations: