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Cheap flights from Chicago to Toronto Island Airport from C$ 104

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 30/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YTZ
11 Oct — 18 Oct1
1 adult
1 adult, Economy

Cheap 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 11 September 2025.

Round-trip from

C$ 237

One-way from

C$ 104

Popular in

December

Cheapest in

July

Average price

C$ 378

Good round-trip deal

C$ 266 or less

Good one-way deal

C$ 125 or less
Porter Airlines
  • Porter Airlines
  • 2/10-5/10
  • Nonstop
  • 3h 31m total
  • Chicago to Toronto
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Porter Airlines
  • Porter Airlines
  • 30/9
  • Nonstop
  • 1h 42m total
  • Chicago to Toronto
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Highest demand for flights based on searches. 8% potential increase in price (C$ 47 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 12 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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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Find flight deals from Chicago to Toronto Island

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 11 September 2025.

Thu 2/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 5/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/9C$ 237
Tue 30/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 5/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/9C$ 238
Wed 15/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sat 18/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/9C$ 241
Thu 23/105:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 26/109:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 9/9C$ 245
Wed 29/104:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Wed 5/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 8/9C$ 248
Wed 26/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 30/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 9/9C$ 254
Sun 5/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 7/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/9C$ 263
Sat 11/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 14/103:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/9C$ 270
Wed 22/108:40 a.m.ORD - YTZ
1 stop5h 05mAir Canada
Sat 1/113:30 p.m.YTZ - ORD
1 stop5h 30mAir Canada
Deal found 9/9C$ 309
Tue 30/910:40 a.m.ORD - YTZ
1 stop5h 05mAir Canada
Thu 2/1012:25 p.m.YTZ - ORD
1 stop8h 52mAir Canada
Deal found 9/9C$ 328
Sun 5/1010:40 a.m.ORD - YTZ
1 stop5h 05mMultiple Airlines
Tue 7/1012:00 p.m.YTZ - ORD
2 stops12h 45mMultiple Airlines
Deal found 9/9C$ 346
Thu 23/1010:40 a.m.ORD - YTZ
1 stop5h 05mAir Canada
Sun 26/108:30 p.m.YTZ - ORD
1 stop15h 48mAir Canada
Deal found 9/9C$ 355

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 11 September 2025.
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

Sat 4/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Wed 8/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 237

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 15/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Wed 22/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 240

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 2/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Sun 5/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 240

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 5/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Tue 7/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 263

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 11/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Sat 18/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 263

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 22/11

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

Nonstop1h 42m

Toronto Island

Mon 24/11

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

Nonstop1h 50m

C$ 270

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 14/10

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

Toronto Island

Wed 15/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 270

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 4/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Sun 5/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 276

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 8/10

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

Toronto Island

Sat 18/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 285

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 26/2

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

Nonstop1h 42m

Toronto Island

Fri 27/2

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

Nonstop1h 50m

C$ 294

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 42 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 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 11 September 2025.

One of the essential ways to save on airfare from Chicago to Toronto Island Airport is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 18% on airfare.

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 11 September 2025.

The most flights from CHI to YTZ are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

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 3h 23m. 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, August is the cheapest month in which you can book a flight from Chicago to Toronto Island Airport (average of C$ 216). Flying from Chicago to Toronto Island Airport in November is currently the most expensive (average of C$ 297). 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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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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