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$133+ Cheap flights from Toronto Island (YTZ) to Chicago (CHI)

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 11/26. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — CHI
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Find flight deals from Toronto Island to Chicago

Cheapest flights from Toronto Island to Chicago
Explore the most affordable flight options available from Toronto Island to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 13, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/189:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 1/54:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/12$186
This Kiwi.com deal was found by Cheapflights users on 11/13. 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 12/249:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 1/54:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/13$188
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/192:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 1/54:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/12$189
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/122:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 12/1511:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/10$191
This Trip.com deal was found by Cheapflights users on 11/12. 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.
Fri 11/282:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 11/304:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/12$194
This FlightHub deal was found by Cheapflights users on 11/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/279:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 11/284:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/12$195
This SmartFares deal was found by Cheapflights users on 11/11. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/279:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 11/304:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/11$196
This Trip.com deal was found by Cheapflights users on 11/13. 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.
Fri 11/282:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 12/211:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/13$198
This FlightHub deal was found by Cheapflights users on 11/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/29:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 12/411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/11$199
This SmartFares deal was found by Cheapflights users on 11/11. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/279:15 amYTZ - MDW
Nonstop1h 50mAir Transat
Sun 11/3011:00 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 11/11$200
This Kiwi.com deal was found by Cheapflights users on 11/13. 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 12/222:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 1/611:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/13$202
This Trip.com deal was found by Cheapflights users on 11/11. 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 12/611:00 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 12/811:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/11$203

Cheap flight deals from Toronto Island to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Toronto Island (YTZ) to Chicago (CHI). 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 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$186
(Kiwi.com)

One-way from

$133
(Air Canada)

Popular in

October

Cheapest in

August

Average price

$249

Good round-trip deal

$286 or less

Good one-way deal

$189 or less
Provider with most accurate pricing for Toronto Island-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Toronto Island-Chicago (CHI) flights.
Search Deals
From Toronto Island to Chicago (CHI)
Search Deals
One-way flight from Toronto Island to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($14 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 Toronto Island to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Toronto Island to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Toronto Island to Chicago 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 13, 2025.
Use the filters below to find and compare flights from Toronto Island Airport to Chicago that are best for you.

Fly from

Toronto Island

Fly to

Chicago

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/18

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Mon 1/5

4:15 pm-6:57 pm

Nonstop1h 42m

$186

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 1/16

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sat 1/17

12:45 pm-3:27 pm

Nonstop1h 42m

$191

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 1/15

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sat 1/17

12:45 pm-3:27 pm

Nonstop1h 42m

$191

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 11/28

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Sun 11/30

4:15 pm-6:57 pm

Nonstop1h 42m

$194

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 1/11

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Tue 1/13

11:00 am-1:42 pm

Nonstop1h 42m

$194

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 1/11

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Wed 1/14

11:00 am-1:42 pm

Nonstop1h 42m

$194

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 11/27

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sat 11/29

12:45 pm-3:27 pm

Nonstop1h 42m

$195

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 11/27

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sun 11/30

4:15 pm-6:57 pm

Nonstop1h 42m

$196

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/18

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Tue 1/6

11:00 am-1:42 pm

Nonstop1h 42m

$198

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 11/28

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Tue 12/2

11:00 am-1:42 pm

Nonstop1h 42m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 41 results
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Compare providers for flights from Toronto Island to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Toronto Island to Chicago in November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Toronto Island Airport-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Toronto Island Airport-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Toronto Island Airport-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Toronto Island Airport-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Toronto Island Airport-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Toronto Island to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Toronto Island 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 Toronto Island Airport to Chicago

What is the cheapest month to book a flight from Toronto Island Airport to Chicago?

Currently, June is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago (average of $83). Flying from Toronto Island Airport to Chicago in December is currently the most expensive (average of $233). 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 YTZ to CHI?

Find hourly flight availability from Toronto Island to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 13, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 27% on flights from Toronto Island Airport to Chicago by exploring options for tickets in the afternoon.

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

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated November 13, 2025.
Read through reviews of airlines operating flights from Toronto Island Airport to Chicago, such as Porter Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
389 reviews

Comfort

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

Crew

8.6

Overall

8.0

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
389 reviews
Porter Airlines
8.0
Very good
389 reviews

Comfort

8.0

Entertainment

7.0

Food

7.6

Boarding

8.2

Crew

8.6

Overall

8.0

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 Toronto Island to Chicago. 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 Toronto Island Airport to Chicago?

    Departing from Toronto Island Airport to Chicago will take you 1h 50m. The distance from Toronto Island Airport to Chicago is about 442 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    According to our current data, Porter Airlines ($158), offers the cheapest pricing from Toronto Island Airport to Chicago. Porter Airlines is currently priced 34% below the average price you’ll pay for this route.

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

    For one-way options, check prices for Air Canada. According to our data, you can fly for as low as $133. Users have also found prices from $135 and $135 on Porter Airlines and Air Transat, respectively.

  • Can I find deals for flights from Toronto Island to Chicago that include hotel bookings?

    Yes. In addition to deals on Toronto Island to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Toronto Island to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Toronto Island to Chicago.

  • Can I find deals for business class flights from Toronto Island to Chicago?

    Yes. Cheapflights offers flight deals from Toronto Island to Chicago 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 Toronto Island Airport to Chicago?

    Currently, June is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago (average of $83). Flying from Toronto Island Airport to Chicago in December is currently the most expensive (average of $233). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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Top airline flying from Toronto Island to Chicago

Discover the top airline that operate flights from Toronto Island to Chicago. 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 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$158Average$231FlexibilityNo cancel feeOn-time52%

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