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Cheap flights from Chicago to Toronto Island Airport from C$ 118

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YTZ
28 Feb — 7 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Chicago to Toronto Island

Enter your travel dates to find the best prices.

Cheapest flights from Chicago to Toronto Island
Explore the most affordable flight options available from Chicago to Toronto Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 29 January 2026.

Fri 3/44:15 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Mon 6/49:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 27/1C$ 255
Fri 13/37:15 a.m.
ORD
-
YTZ
1 stop6h 10m
Air Canada
Sun 22/310:45 a.m.
YTZ
-
ORD
1 stop5h 10m
Air Canada
Deal found 29/1C$ 255
Sat 14/312:50 p.m.
ORD
-
YTZ
1 stop6h 05m
Air Canada
Sat 21/37:00 a.m.
YTZ
-
ORD
1 stop5h 18m
Air Canada
Deal found 28/1C$ 258
Thu 19/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Sat 21/211:05 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 27/1C$ 261
Sat 4/412:45 p.m.
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Sat 11/411:00 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Deal found 27/1C$ 263
Tue 17/211:05 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Thu 19/29:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 27/1C$ 265
Sat 11/412:45 p.m.
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Sun 12/49:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Deal found 27/1C$ 266
Thu 16/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Sun 19/49:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 27/1C$ 267
Mon 9/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Multiple Airlines
Thu 12/39:15 a.m.
YTZ
-
MDW
Nonstop1h 50m
Multiple Airlines
Deal found 28/1C$ 270
Wed 11/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Wed 13/54:00 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 27/1C$ 272
Tue 19/55:35 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sun 24/58:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 27/1C$ 273
Wed 11/311:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Tue 12/58:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 27/1C$ 274

Find flight deals from Chicago to Toronto Island

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Toronto Island (YTZ). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 29 January 2026.

Round-trip from

C$ 255

One-way from

C$ 118

Popular in

January

Cheapest in

February

Average price

C$ 686

Good round-trip deal

C$ 467 or less

Good one-way deal

C$ 241 or less
Porter Airlines
  • Porter Airlines
  • 3/4-6/4
  • Nonstop
  • 3h 32m total
  • Chicago to Toronto
Search Deals
Air Transat
  • Air Transat
  • 1/3
  • Nonstop
  • 1h 42m total
  • Chicago to Toronto
Search Deals
Highest demand for flights based on searches. 21% potential increase in price (C$ 133 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease (C$ 45 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Toronto Island.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Toronto Island.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Toronto Island that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 29 January 2026.
Use the filters below to find and compare flights from Chicago to Toronto Island Airport that are best for you.

Fly from

Chicago

Fly to

Toronto Island

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 3/4

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

Toronto Island

Mon 6/4

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

C$ 255

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Fri 13/3

7:15 a.m.-2:25 p.m.

1 stop6h 10m

Toronto Island

Sun 22/3

10:45 a.m.-2:55 p.m.

1 stop5h 10m

C$ 255

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Sun 15/3

3:35 p.m.-9:35 p.m.

1 stop5h 00m

Toronto Island

Sun 22/3

10:45 a.m.-2:55 p.m.

1 stop5h 10m

C$ 255

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 8/4

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

Toronto Island

Sat 11/4

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

C$ 265

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 11/4

12:45 p.m.-3:27 p.m.

Nonstop1h 42m

Toronto Island

Sun 12/4

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

C$ 266

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 27/2

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

Toronto Island

Sun 1/3

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

C$ 267

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 29/5

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

Toronto Island

Sun 31/5

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

C$ 267

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 17/2

11:05 a.m.-1:47 p.m.

Nonstop1h 42m

Toronto Island

Thu 19/2

9:20 a.m.-10:10 a.m.

Nonstop1h 50m

C$ 267

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 7/5

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

Toronto Island

Mon 11/5

4:00 p.m.-4:50 p.m.

Nonstop1h 50m

C$ 267

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Sat 14/3

12:50 p.m.-7:55 p.m.

1 stop6h 05m

Toronto Island

Sat 21/3

7:00 a.m.-11:18 a.m.

1 stop5h 18m

C$ 274

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/1

Showing 1-10 of 44 results
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Best time to book a flight from Chicago to Toronto Island

Have a flexible travel schedule? Discover the best time to fly to Toronto Island from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Toronto Island Airport

What is the cheapest month to book a flight from Chicago to Toronto Island Airport?

Currently, March is the cheapest month in which you can book a flight from Chicago to Toronto Island Airport (average of C$ 107). Flying from Chicago to Toronto Island Airport in November is currently the most expensive (average of C$ 392). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to YTZ?

Find hourly flight availability from Chicago to Toronto Island. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 29 January 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Toronto Island Airport as you normally would.

How often are flights from Chicago to Toronto delayed?

About 13% of weekly flights between Chicago and Toronto have experienced delays in the past year, with the average delay time being 124 minutes.

What is the most punctual flight time for Chicago to Toronto flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Thursday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Toronto flights?

Over the past year, Porter Airlines has had the lowest number of delays on this route, with just 13% of flights being delayed.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Toronto Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Toronto Island Airport?

    Airlines like Porter Airlines and Air Canada fly from Chicago to Toronto Island Airport in about 1h 42m. The time it takes to get you to your destination can typically vary by up to 4h 28m. There are 711 km between Chicago and Toronto Island Airport. Both multi-stop and direct flights can be found to your destination and back.

  • Can I find deals for flights from Chicago to Toronto Island that include hotel bookings?

    Yes. In addition to deals on Chicago to Toronto Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Toronto Island?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Toronto Island.

  • Can I find deals for business class flights from Chicago to Toronto Island?

    Yes. Cheapflights offers flight deals from Chicago to Toronto Island by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Toronto Island Airport?

    Currently, March is the cheapest month in which you can book a flight from Chicago to Toronto Island Airport (average of C$ 107). Flying from Chicago to Toronto Island Airport in November is currently the most expensive (average of C$ 392). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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How does Cheapflights help users find flights from Chicago to Toronto Island?

Cheapflights makes it easy to find Chicago to Toronto Island flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Chicago to Toronto Island?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago to Toronto Island.

Can Cheapflights find flights from Chicago to Toronto Island with no change fees?

Certainly. Search results for flights to Toronto Island from Chicago shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Chicago to Toronto Island become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Toronto Island from Chicago today and book when prices fit your budget.

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