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Toronto Island

$86+ Cheap flights from Chicago (CHI) to Toronto Island (YTZ)

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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YTZ
Dec 10 — Dec 171
Wed 12/10
Wed 12/17
1 adult, Economy
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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 November 10, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/234:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 11/259:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/9$187
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/284:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 12/12:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/9$192
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 12/29:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/9$196
This Mytrip deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/227:05 amORD - YTZ
1 stop6h 50mAir Canada
Mon 11/248:30 amYTZ - ORD
1 stop7h 25mAir Canada
Deal found 11/8$198
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2511:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Fri 11/282:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/8$202
This Trip.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2212:45 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 11/239:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/8$203
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/234:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Thu 12/42:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/9$204
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 1/69:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/9$205
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 1/59:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/9$207
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/254:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 1/69:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/9$208
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 1/69:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/9$209
This Kiwi.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2311:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 1/69:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 11/9$211

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 November 10, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$187
(Kiwi.com)

One-way from

$86
(Trip.com)

Popular in

October

Cheapest in

July

Average price

$377

Good round-trip deal

$287 or less

Good one-way deal

$210 or less
Provider with most accurate pricing for Chicago (CHI)-Toronto (YTO) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Toronto (YTO) flights.
Search Deals
From Chicago (CHI) to Toronto Island
Search Deals
One-way flight from Chicago (CHI) to Toronto Island
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 2,558,603 searches. Data last updated November 10, 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

Sun 11/23

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Tue 11/25

9:15 am-10:05 am

Nonstop1h 50m

$187

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 11/23

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Fri 11/28

2:30 pm-3:20 pm

Nonstop1h 50m

$187

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 12/2

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sun 12/7

9:15 am-10:05 am

Nonstop1h 50m

$192

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Sat 11/22

7:05 am-2:55 pm

1 stop6h 50m

Toronto Island

Sun 11/23

8:30 am-2:55 pm

1 stop7h 25m

$198

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 2/20

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Wed 2/25

9:15 am-10:05 am

Nonstop1h 50m

$203

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Fri 1/23

3:35 pm-9:35 pm

1 stop5h 00m

Toronto Island

Tue 1/27

10:30 am-2:55 pm

1 stop5h 25m

$204

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 12/31

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Mon 1/5

9:15 am-10:05 am

Nonstop1h 50m

$209

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 11/25

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Fri 11/28

2:30 pm-3:20 pm

Nonstop1h 50m

$210

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 12/30

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Mon 1/5

9:15 am-10:05 am

Nonstop1h 50m

$213

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 12/4

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sun 12/7

9:15 am-10:05 am

Nonstop1h 50m

$220

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/9

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 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 $135). Flying from Chicago to Toronto Island Airport in March is currently the most expensive (average of $473). 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 November 10, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Toronto Island Airport in the morning. If you’re flexible enough to do this you can expect to save up to 56% on your trip compared to booking a flight at noon.

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 November 10, 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).

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 November 10, 2025.
See what other customers who have flown with Porter Airlines from Chicago to Toronto Island Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
388 reviews

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Overall

8.0

Food

7.6

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Porter Airlines
8.0
Very good
388 reviews
Porter Airlines
8.0
Very good
388 reviews

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Overall

8.0

Food

7.6

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

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?

    Departing from Chicago to Toronto Island Airport will take you 1h 42m. There are 442 mi between Chicago and Toronto Island Airport. Both multi-stop and nonstop flights can be found to your destination and back.

  • What is the cheapest airline to fly from Chicago to Toronto Island Airport round-trip?

    Flying on Porter Airlines is currently your cheapest option to Toronto Island Airport, with prices starting at $185. Porter Airlines 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?

    One-way options have recently been found by users for as low as $86 on Porter Airlines. Other airlines that offer cheap prices include Air Canada from $99 and Air Transat from $110 one-way.

  • 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 $135). Flying from Chicago to Toronto Island Airport in March is currently the most expensive (average of $473). 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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Top airline flying from Chicago to Toronto Island

Discover the top airline that operate flights from Chicago to Toronto Island. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 10, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$185Average$234FlexibilityNo cancel feeOn-time52%

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