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$115+ 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — CHI
Jan 25 — Feb 11
Sun 1/25
Sun 2/1
1 adult, Economy
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Cheap 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 December 26, 2025.

This FlightHub deal was found by Cheapflights users on 12/24. 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.
Wed 12/319:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 1/411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/24$319
This FlightHub deal was found by Cheapflights users on 12/23. 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.
Wed 12/319:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 1/34:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/23$337
This Trip.com deal was found by Cheapflights users on 12/24. 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.
Tue 12/309:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 2/84:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/24$415
This Super.com deal was found by Cheapflights users on 12/23. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/269:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 1/34:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/23$472
This Super.com deal was found by Cheapflights users on 12/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/272:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 1/211:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/24$473
This Trip.com deal was found by Cheapflights users on 12/24. 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.
Thu 12/252:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 1/2611:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/24$475
This Justfly.com deal was found by Cheapflights users on 12/25. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/272:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 1/811:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/25$479
This FlightHub deal was found by Cheapflights users on 12/24. 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.
Sun 12/289:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 1/711:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/24$489
This Justfly.com deal was found by Cheapflights users on 12/25. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/289:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 1/44:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/25$493
This Justfly.com deal was found by Cheapflights users on 12/25. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/309:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 1/611:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/25$499
This Air Canada deal was found by Cheapflights users on 12/24. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/243:30 pmYTZ - ORD
1 stop5h 40mAir Canada
Wed 1/71:55 pmORD - YTZ
1 stop6h 33mAir Canada
Deal found 12/24$549
This Air Canada deal was found by Cheapflights users on 12/25. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/278:30 amYTZ - ORD
1 stop7h 25mAir Canada
Thu 1/81:55 pmORD - YTZ
1 stop6h 33mAir Canada
Deal found 12/25$556

Find 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 December 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$180
(Trip.com)

One-way from

$115
(Trip.com)

Popular in

October

Cheapest in

August

Average price

$282

Good round-trip deal

$210 or less

Good one-way deal

$141 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. 9% potential increase in price ($26 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 December 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 December 26, 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

Sun 1/11

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Thu 1/22

11:00 am-1:42 pm

Nonstop1h 42m

$183

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 2/20

9:20 am-10:10 am

Nonstop1h 50m

Chicago Midway

Sun 2/22

4:15 pm-6:57 pm

Nonstop1h 42m

$184

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 2/7

11:00 am-11:50 am

Nonstop1h 50m

Chicago Midway

Sat 2/14

12:50 pm-3:32 pm

Nonstop1h 42m

$186

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 1/28

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Mon 2/2

11:00 am-1:42 pm

Nonstop1h 42m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 1/28

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sun 2/1

4:15 pm-6:57 pm

Nonstop1h 42m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 1/30

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sun 2/1

11:00 am-1:42 pm

Nonstop1h 42m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 1/11

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sat 2/14

12:45 pm-3:27 pm

Nonstop1h 42m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 1/11

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Sun 2/15

4:15 pm-6:57 pm

Nonstop1h 42m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 1/22

9:20 am-10:10 am

Nonstop1h 50m

Chicago Midway

Sun 1/25

4:15 pm-6:57 pm

Nonstop1h 42m

$188

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 1/9

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Mon 1/19

11:00 am-1:42 pm

Nonstop1h 42m

$188

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/24

Showing 1-10 of 36 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 December.
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 February is currently the most expensive (average of $230). 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 December 26, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 61% on flights from Toronto Island Airport to Chicago by exploring options for tickets in the afternoon.

Weekly flight availability from Toronto Island Airport to Chicago

Explore weekly flight availability from Toronto Island to Chicago. 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 December 26, 2025.

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

How often are flights from Toronto to Chicago delayed?

About 14% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 111 minutes.

What is the most punctual flight time for Toronto to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Toronto to Chicago flights?

Over the last year, Porter Airlines have had the lowest number of delays on this route, with just 14% of flights being delayed.

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 December 26, 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
401 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Crew

8.6

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
8.0
Very good
401 reviews
Porter Airlines
8.0
Very good
401 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.0

Crew

8.6

Overall

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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 ($80), offers the cheapest pricing from Toronto Island Airport to Chicago. Porter Airlines is currently priced 67% below the average price you’ll pay for this route.

  • 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 February is currently the most expensive (average of $230). 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
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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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 December 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$158Average$258FlexibilityNo cancel feeOn-time52%

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