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Cheap flights from Chicago to Toronto Island Airport from C$ 96

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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YTZ
3 Aug — 10 Aug1
1 adult

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 29 July 2025.

Round-trip from

C$ 250

One-way from

C$ 96

Popular in

December

Cheapest in

October

Average price

C$ 346

Good round-trip deal

C$ 250 or less

Good one-way deal

C$ 114 or less
Air Transat
  • Air Transat
  • 22/8-31/8
  • Nonstop
  • 3h 30m total
  • Chicago to Toronto
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Air Transat
  • Air Transat
  • 4/9
  • Nonstop
  • 1h 42m total
  • Chicago to Toronto
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Highest demand for flights based on searches. 6% potential increase in price (C$ 32 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 10 potential savings vs. average RT price).
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Average for round-trip flights in July 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 29 July 2025.

Fri 22/89:40 a.m.MDW - YTZ
Nonstop1h 40mMultiple Airlines
Sun 31/88:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 26/7C$ 250
Wed 10/95:20 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Fri 12/97:30 a.m.YTZ - MDW
Nonstop1h 49mAir Transat
Deal found 28/7C$ 252
Sat 16/89:40 a.m.MDW - YTZ
Nonstop1h 40mPorter Airlines
Wed 20/83:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 26/7C$ 255
Thu 23/103:35 p.m.ORD - YTZ
1 stop4h 59mAir Canada
Sun 26/107:20 p.m.YTZ - ORD
2 stops16h 58mAir Canada
Deal found 27/7C$ 270
Wed 10/911:13 a.m.ORD - YTZ
1 stop9h 07mMultiple Airlines
Sat 13/99:10 a.m.YTZ - ORD
2 stops14h 01mMultiple Airlines
Deal found 28/7C$ 465

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 July 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

Fri 22/8

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

Toronto Island

Sun 31/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

C$ 250

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 10/9

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

Nonstop1h 42m

Toronto Island

Fri 12/9

7:30 a.m.-8:19 a.m.

Nonstop1h 49m

C$ 252

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 16/8

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

Toronto Island

Wed 20/8

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

C$ 255

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Thu 23/10

3:35 p.m.-9:34 p.m.

1 stop4h 59m

Toronto Island

Sun 26/10

7:20 p.m.-11:18 a.m.

2 stops16h 58m

C$ 270

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Wed 10/9

11:13 a.m.-9:20 p.m.

1 stop9h 07m

Toronto Island

Sat 13/9

9:10 a.m.-10:11 p.m.

2 stops14h 01m

C$ 465

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 4/9

9:15 a.m.-11:57 a.m.

Nonstop1h 42m

C$ 96

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Mon 8/9

8:40 a.m.-4:45 p.m.

1 stop7h 05m

C$ 100

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 20/8

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

C$ 110

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 9/10

5:56 p.m.-11:40 a.m.

1 stop16h 44m

C$ 181

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Tue 19/8

5:05 a.m.-7:42 p.m.

2 stops13h 37m

C$ 198

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/7

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 29 July 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 16% 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 29 July 2025.

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

Reviews of airlines servicing Toronto Island

Get insights into the airlines that provide service to Toronto Island. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Toronto Island. Reviews last updated 29 July 2025.
Read reviews from past customers who have flown Porter Airlines,Air Transat, andAir Canada from Chicago to Toronto Island Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
317 reviews
Check prices

Comfort

8.0

Crew

8.7

Overall

8.0

Food

7.6

Boarding

8.2

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
317 reviews
Porter Airlines
8.0
Very good
317 reviews
Check prices

Comfort

8.0

Crew

8.7

Overall

8.0

Food

7.6

Boarding

8.2

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Transat
7.7
Good
424 reviews
Porter Airlines
8.0
Very good
317 reviews
Check prices

Comfort

8.0

Crew

8.7

Overall

8.0

Food

7.6

Boarding

8.2

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Canada
7.1
Good
9,826 reviews
Porter Airlines
8.0
Very good
317 reviews
Check prices

Comfort

8.0

Crew

8.7

Overall

8.0

Food

7.6

Boarding

8.2

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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.

  • What are the cheapest airlines flying from Chicago to Toronto Island Airport round-trip?

    Flying on Air Transat is currently your cheapest option to Toronto Island Airport, with prices starting at C$ 252. Additional round-trip tickets that might be worth considering are offered by Porter Airlines and Air Canada, with the lowest prices starting at C$ 255 and C$ 270, respectively. Air Transat is currently priced 31% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Chicago to Toronto Island Airport one-way?

    The cheapest airlines for a one-way flight from Chicago to Toronto Island Airport are Air Transat (C$ 96), Air Canada (C$ 100), and Porter Airlines (C$ 110).

  • 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.

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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.

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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