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Cheap flights from Chicago to Toronto Island Airport from C$ 149

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 21/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YTZ
31 Aug — 7 Sep1
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 1 August 2026.

Wed 2/911:45 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sat 5/91:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 28/7C$ 331
Wed 9/97:25 a.m.
ORD
-
YTZ
Nonstop1h 42m
Air Canada
Wed 16/99:30 a.m.
YTZ
-
ORD
1 stop6h 22m
Air Canada
Deal found 27/7C$ 331
Wed 9/911:45 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Wed 16/910:10 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 28/7C$ 332
Thu 3/93:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Tue 8/91:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 28/7C$ 334
Thu 10/98:45 a.m.
ORD
-
YTZ
1 stop6h 05m
Air Canada
Sun 13/97:35 p.m.
YTZ
-
ORD
Nonstop2h 06m
Air Canada
Deal found 27/7C$ 334
Thu 3/93:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Sun 6/91:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 28/7C$ 335
Fri 11/911:05 a.m.
ORD
-
YTZ
1 stop5h 45m
Air Canada
Fri 18/912:15 p.m.
YTZ
-
ORD
Nonstop2h 06m
Air Canada
Deal found 28/7C$ 335
Mon 24/88:40 a.m.
ORD
-
YTZ
1 stop6h 11m
Air Canada
Thu 27/87:35 p.m.
YTZ
-
ORD
Nonstop2h 06m
Air Canada
Deal found 31/7C$ 336
Wed 2/911:45 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Mon 7/910:10 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 28/7C$ 338
Tue 25/82:00 p.m.
ORD
-
YTZ
Nonstop1h 53m
Air Canada
Sat 29/810:45 a.m.
YTZ
-
ORD
1 stop5h 10m
Air Canada
Deal found 30/7C$ 338
Mon 24/810:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Fri 28/88:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Deal found 29/7C$ 339
Fri 28/82:00 p.m.
ORD
-
YTZ
Nonstop1h 53m
Air Canada
Mon 31/812:15 p.m.
YTZ
-
ORD
Nonstop2h 06m
Air Canada
Deal found 30/7C$ 339

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 1 August 2026.

Round-trip from

C$ 331

One-way from

C$ 149

Popular in

April

Cheapest in

February

Average price

C$ 358

Good round-trip deal

C$ 150 or less

Good one-way deal

C$ 165 or less
Porter Airlines
  • Porter Airlines
  • 2/9-5/9
  • Nonstop
  • 3h 30m total
  • Chicago to Toronto
Search Deals
Porter Airlines
  • Porter Airlines
  • 21/9
  • Nonstop
  • 1h 40m total
  • Chicago to Toronto
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (C$ 92 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 1 August 2026.
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 - YTZ

MDWYTZ

Chicago Midway

Thu 3/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Sun 6/9

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

C$ 335

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 9/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Sun 13/9

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

C$ 343

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 12/9

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

Nonstop1h 40m

Toronto Island

Tue 15/9

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

C$ 343

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 12/9

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

Nonstop1h 40m

Toronto Island

Sat 19/9

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

C$ 343

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 24/8

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

Nonstop1h 40m

Toronto Island

Mon 31/8

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

C$ 358

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 20/8

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

Nonstop1h 40m

Toronto Island

Sun 30/8

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

Nonstop1h 50m

C$ 370

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 28/8

3:15 p.m.-5:55 p.m.

Nonstop1h 40m

Toronto Island

Sun 30/8

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

C$ 372

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 21/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Fri 25/9

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

C$ 405

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 1/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Fri 4/9

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

C$ 409

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 26/8

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

Nonstop1h 40m

Toronto Island

Sat 29/8

1:40 p.m.-10:47 p.m.

2 stops10h 07m

C$ 414

Flights are sorted by cheapest round-trip flights first.

Deals found on 31/7

Showing 1-10 of 38 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
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, February is the cheapest month in which you can book a flight from Chicago to Toronto Island Airport (average of C$ 245). Flying from Chicago to Toronto Island Airport in December is currently the most expensive (average of C$ 604). 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 1 August 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.

Weekly flight availability from Chicago to Toronto Island Airport

Explore weekly flight availability from Chicago to Toronto Island. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 1 August 2026.

The most flights from CHI to YTZ are scheduled on a Friday (8 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

How much does it cost to fly round-trip from Chicago to Toronto Island Airport?

Airfare is typical for this route at the moment.
Chicago to Toronto Island Airport flights typically cost between C$ 313 and C$ 439 in September.
The cheapest round-trip price found within the last 5 days was C$ 331 on Porter Airlines (2 Sep-5 Sep).

How often are flights from Chicago to Toronto delayed?

About 18% of weekly flights between Chicago and Toronto have experienced delays in the past year, with the average delay time being 118 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 15% 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 United Airlines fly from Chicago to Toronto Island Airport in about 1h 40m. The time it takes to get you to your destination can typically vary by up to 3h 20m. There are 711 km between Chicago and Toronto Island Airport. Both multi-stop and direct flights can be found to your destination and back.

  • 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 (32%), Jazz (32%) and United Airlines (32%).

  • 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$ 403. The most popular route, (Chicago O'Hare Intl - Toronto Island), can usually be booked for C$ 254.

  • 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$ 245). Flying from Chicago to Toronto Island Airport in December is currently the most expensive (average of C$ 604). 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.

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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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