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Cheap flights from Chicago to Toronto Island Airport from C$ 116

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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YTZ
29 Nov — 6 Dec1
1 adult
1 adult, Economy, 0 bags

Find 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 30 October 2025.

Wed 19/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sat 22/1111:00 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 29/10C$ 263
Fri 5/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 7/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 29/10C$ 267
Wed 12/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Thu 13/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 29/10C$ 270
Thu 13/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 16/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 30/10C$ 271
Sun 16/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Thu 20/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 30/10C$ 276
Fri 21/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Wed 3/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 29/10C$ 288
Fri 14/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 16/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 29/10C$ 296
Thu 20/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Wed 3/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 30/10C$ 300
Sat 29/1112:50 p.m.ORD - YTZ
1 stop6h 05mAir Canada
Sat 6/123:30 p.m.YTZ - ORD
1 stop5h 40mAir Canada
Deal found 30/10C$ 316
Sat 15/117:05 a.m.ORD - YTZ
1 stop6h 50mAir Canada
Tue 18/1110:30 a.m.YTZ - ORD
1 stop5h 25mAir Canada
Deal found 29/10C$ 344
Sat 13/1212:50 p.m.ORD - YTZ
1 stop6h 05mAir Canada
Sat 20/1210:30 a.m.YTZ - ORD
1 stop10h 40mAir Canada
Deal found 29/10C$ 385
Tue 2/127:05 a.m.ORD - YTZ
1 stop9h 50mAir Canada
Thu 4/128:30 a.m.YTZ - ORD
1 stop7h 25mAir Canada
Deal found 30/10C$ 390

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 30 October 2025.

Round-trip from

C$ 263

One-way from

C$ 116

Popular in

October

Cheapest in

July

Average price

C$ 540

Good round-trip deal

C$ 397 or less

Good one-way deal

C$ 261 or less
Porter Airlines
  • Porter Airlines
  • 19/11-22/11
  • Nonstop
  • 3h 32m total
  • Chicago to Toronto
Search Deals
Porter Airlines
  • Porter Airlines
  • 12/12
  • Nonstop
  • 1h 42m total
  • Chicago to Toronto
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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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.
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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 30 October 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

Wed 12/11

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

Toronto Island

Mon 17/11

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

Nonstop1h 50m

C$ 265

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 5/12

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

Nonstop1h 42m

Toronto Island

Sun 7/12

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

Nonstop1h 50m

C$ 265

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 5/3

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

Toronto Island

Sat 7/3

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

Nonstop1h 50m

C$ 268

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 3/3

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

Toronto Island

Sat 7/3

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

Nonstop1h 50m

C$ 268

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 15/3

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

Toronto Island

Thu 19/3

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

Nonstop1h 50m

C$ 271

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 14/11

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

Nonstop1h 42m

Toronto Island

Sun 16/11

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

Nonstop1h 50m

C$ 271

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 15/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

Toronto Island

Tue 20/1

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

Nonstop1h 50m

C$ 278

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 15/1

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

Toronto Island

Fri 16/1

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

Nonstop1h 50m

C$ 278

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 12/11

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

Toronto Island

Wed 19/11

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

Nonstop1h 50m

C$ 279

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 11/3

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

Toronto Island

Sat 14/3

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

Nonstop1h 50m

C$ 281

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/10

Showing 1-10 of 37 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, August is the cheapest month in which you can book a flight from Chicago to Toronto Island Airport (average of C$ 189). Flying from Chicago to Toronto Island Airport in March is currently the most expensive (average of C$ 660). 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 30 October 2025.

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.

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 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$ 189). Flying from Chicago to Toronto Island Airport in March is currently the most expensive (average of C$ 660). 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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