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Cheap flights from Chicago to Toronto Island Airport from C$ 121

CHI — YTZ
17 Oct — 24 Oct1
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

Thu 1/103:20 p.m. -
Nonstop1h 40m
Sun 4/1010:10 a.m. -
Nonstop1h 50m
Deal found 15/9C$ 297
Thu 29/1012:20 p.m. -
Nonstop1h 46m
Sun 1/114:35 p.m. -
Nonstop2h 05m
Deal found 15/9C$ 297
Sat 3/1011:45 a.m. -
Nonstop1h 40m
Sun 4/1010:10 a.m. -
Nonstop1h 50m
Deal found 15/9C$ 298
Sun 6/126:20 p.m. -
Nonstop1h 46m
Wed 16/1210:35 a.m. -
Nonstop2h 05m
Deal found 13/9C$ 298
Wed 28/1012:20 p.m. -
Nonstop1h 46m
Sun 1/1110:35 a.m. -
Nonstop2h 05m
Deal found 13/9C$ 300
Fri 20/1112:20 p.m. -
Nonstop1h 46m
Sat 28/114:35 p.m. -
Nonstop2h 05m
Deal found 14/9C$ 301
Sat 10/103:20 p.m. -
Nonstop1h 40m
Tue 13/101:45 p.m. -
Nonstop1h 50m
Deal found 15/9C$ 303
Thu 10/1212:20 p.m. -
Nonstop1h 46m
Sun 13/1210:35 a.m. -
Nonstop2h 05m
Deal found 13/9C$ 303
Fri 9/102:00 p.m. -
Nonstop1h 48m
Tue 13/1012:15 p.m. -
Nonstop2h 10m
Deal found 16/9C$ 304
Wed 14/102:00 p.m. -
Nonstop1h 48m
Fri 16/1012:15 p.m. -
Nonstop2h 10m
Deal found 16/9C$ 305
Thu 1/103:20 p.m. -
Nonstop1h 40m
Mon 5/101:45 p.m. -
Nonstop1h 50m
Deal found 16/9C$ 307
Fri 23/102:00 p.m. -
Nonstop1h 48m
Sun 25/104:35 p.m. -
Nonstop2h 05m
Deal found 15/9C$ 307

Find flight deals from Chicago to Toronto Island

Round-trip from

C$ 297

One-way from

C$ 121

Popular in

April

Cheapest in

February

Average price

C$ 307

Good round-trip deal

C$ 277 or less

Good one-way deal

C$ 140 or less
Porter Airlines
  • Porter Airlines
  • 1/10-4/10
  • Nonstop
  • 3h 30m total
  • Chicago to Toronto
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Porter Airlines
  • Porter Airlines
  • 1/11-31/12
  • Nonstop
  • 1h 46m total
  • Chicago to Toronto
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 85 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease (C$ 39 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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Price to beat on a round-trip flight from Chicago (CHI) to Toronto Island.
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Price to beat on a one-way flight from Chicago (CHI) to Toronto Island.
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Chicago to Toronto Island Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Fri 23/10

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

Toronto Island

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 141

ChicagoToronto

MDW Chicago Midway - YTZ Toronto Island

MDWYTZ

Chicago Midway

Sat 24/10

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

Toronto Island

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 146

ChicagoToronto

ORD Chicago O'Hare Intl - YTZ Toronto Island

ORDYTZ

Chicago O'Hare Intl

Tue 20/10

2:00 p.m.-4:48 p.m.

Nonstop1h 48m

Toronto Island

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 149

ChicagoToronto

ORD Chicago O'Hare Intl - YTZ Toronto Island

ORDYTZ

Chicago O'Hare Intl

Sun 27/9

7:25 a.m.-10:07 a.m.

Nonstop1h 42m

Toronto Island

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 151

ChicagoToronto

ORD Chicago O'Hare Intl - YTZ Toronto Island

ORDYTZ

Chicago O'Hare Intl

Sat 3/10

2:00 p.m.-4:48 p.m.

Nonstop1h 48m

Toronto Island

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 151

ChicagoToronto

ORD Chicago O'Hare Intl - YTZ Toronto Island

ORDYTZ

Chicago O'Hare Intl

Thu 1/10

2:00 p.m.-4:48 p.m.

Nonstop1h 48m

Toronto Island

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 192

ChicagoToronto

ORD Chicago O'Hare Intl - YTZ Toronto Island

ORDYTZ

Chicago O'Hare Intl

Sun 27/9

7:25 a.m.-10:07 a.m.

Nonstop1h 42m

Toronto Island

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 192

ChicagoToronto

ORD Chicago O'Hare Intl - YTZ Toronto Island

ORDYTZ

Chicago O'Hare Intl

Fri 2/10

2:00 p.m.-4:48 p.m.

Nonstop1h 48m

Toronto Island

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 192

ChicagoToronto

ORD Chicago O'Hare Intl - YTZ Toronto Island

ORDYTZ

Chicago O'Hare Intl

Thu 15/10

10:54 a.m.-6:57 p.m.

1 stop7h 03m

Toronto Island

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 206

ChicagoToronto

ORD Chicago O'Hare Intl - YTZ Toronto Island

ORDYTZ

Chicago O'Hare Intl

Tue 20/10

12:55 p.m.-6:57 p.m.

1 stop5h 02m

Toronto Island

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 206

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/9

Showing 1-10 of 39 resultsSorted by cheapest first
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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

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, February is the cheapest month in which you can book a flight from Chicago to Toronto Island Airport (average of C$ 244). Flying from Chicago to Toronto Island Airport in December is currently the most expensive (average of C$ 601). 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?

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.

Weekly flight availability from Chicago to Toronto Island Airport

The most flights from CHI to YTZ are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 on average).

How often are flights from Chicago to Toronto delayed?

About 22% of weekly flights between Chicago and Toronto have experienced delays in the past year, with the average delay time being 117 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 Friday 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 17% of flights being delayed.

Related info for your journey

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

    Airlines like Porter Airlines fly from Chicago to Toronto Island Airport in about 1h 40m. The time it takes to get you to your destination is usually consistent. There are 711 km between Chicago and Toronto Island Airport. Generally, flights for this route are direct.

  • What are the most reliable airlines from Chicago to Toronto Island Airport?

    The top 3 most reliable airlines when flying from Chicago to Toronto Island Airport are Air Canada (48%), Jazz (48%) and United Airlines (48%).

  • What are the cheapest flights from Chicago to Toronto Island Airport?

    The cheapest flight price from Chicago to Toronto Island Airport is C$ 140. On average you can expect to pay C$ 287. The most popular route, (Chicago O'Hare Intl - Toronto Island), can usually be booked for C$ 289.

  • 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, February is the cheapest month in which you can book a flight from Chicago to Toronto Island Airport (average of C$ 244). Flying from Chicago to Toronto Island Airport in December is currently the most expensive (average of C$ 601). 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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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.

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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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