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$122+ 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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — CHI
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
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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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$208
(SmartFares)

One-way from

$122
(SmartFares)

Popular in

October

Cheapest in

August

Average price

$168

Good round-trip deal

$188 or less

Good one-way deal

$143 or less
Provider with most accurate pricing for Toronto Island-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Toronto Island-Chicago (CHI) flights.
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From Toronto Island to Chicago (CHI)
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One-way flight from Toronto Island to Chicago (CHI)
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Highest demand for flights based on searches. 3% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Toronto Island to Chicago (CHI).
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Price to beat on a one-way flight from Toronto Island to Chicago (CHI).
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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 September 29, 2025.

This SmartFares deal was found by Cheapflights users on 9/28. 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 11/69:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 11/911:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/28$208
This FlightHub deal was found by Cheapflights users on 9/28. 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.
Fri 11/212:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 11/234:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/28$209
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 11/119:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 11/1811:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/27$210
This Mytrip deal was found by Cheapflights users on 9/27. 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.
Tue 11/49:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 11/911:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/27$214
This FlightHub deal was found by Cheapflights users on 9/26. 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.
Fri 11/79:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 11/104:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/26$217
This Flightnetwork deal was found by Cheapflights users on 9/27. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1110:25 amYTZ - ORD
2 stops10h 35mAir Canada
Tue 11/187:05 amORD - YTZ
1 stop6h 50mAir Canada
Deal found 9/27$226
This SmartFares deal was found by Cheapflights users on 9/28. 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.
Mon 10/279:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 11/34:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/28$227
This Trip.com deal was found by Cheapflights users on 9/28. 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 11/13:30 pmYTZ - ORD
1 stop5h 30mAir Canada
Mon 11/312:50 pmORD - YTZ
1 stop6h 05mAir Canada
Deal found 9/28$235
This Mytrip deal was found by Cheapflights users on 9/28. 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 11/153:30 pmYTZ - ORD
1 stop5h 30mAir Canada
Mon 11/1712:50 pmORD - YTZ
1 stop6h 05mAir Canada
Deal found 9/28$242
This Air Canada deal was found by Cheapflights users on 9/27. 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.
Thu 11/278:30 amYTZ - ORD
1 stop7h 25mAir Canada
Mon 12/112:50 pmORD - YTZ
1 stop6h 05mAir Canada
Deal found 9/27$259
This Air Canada deal was found by Cheapflights users on 9/27. 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 10/255:25 pmYTZ - ORD
1 stop5h 03mAir Canada
Sat 11/13:35 pmORD - YTZ
1 stop5h 00mAir Canada
Deal found 9/27$278
This SmartFares deal was found by Cheapflights users on 9/29. 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 11/138:30 amYTZ - ORD
1 stop7h 25mAir Canada
Thu 11/207:05 amORD - YTZ
1 stop6h 50mAir Canada
Deal found 9/29$284

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 September 29, 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 11/6

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sun 11/9

11:00 am-1:42 pm

Nonstop1h 42m

$211

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 11/5

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Thu 11/20

11:00 am-1:42 pm

Nonstop1h 42m

$213

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 11/12

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Wed 11/19

11:00 am-1:42 pm

Nonstop1h 42m

$214

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 11/5

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sat 11/8

12:45 pm-3:27 pm

Nonstop1h 42m

$214

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 11/13

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Thu 11/20

11:00 am-1:42 pm

Nonstop1h 42m

$215

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 11/7

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Mon 11/10

4:15 pm-6:57 pm

Nonstop1h 42m

$217

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 11/21

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Mon 11/24

4:15 pm-6:57 pm

Nonstop1h 42m

$218

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 11/15

3:30 pm-8:00 pm

1 stop5h 30m

Chicago O'Hare Intl

Mon 11/17

12:50 pm-7:55 pm

1 stop6h 05m

$242

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 10/25

5:25 pm-9:28 pm

1 stop5h 03m

Chicago O'Hare Intl

Sat 11/1

3:35 pm-9:35 pm

1 stop5h 00m

$278

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 11/13

8:30 am-2:55 pm

1 stop7h 25m

Chicago O'Hare Intl

Thu 11/20

7:05 am-2:55 pm

1 stop6h 50m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/29

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 September.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Toronto Island Airport-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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, August is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago (average of $245). Flying from Toronto Island Airport to Chicago in March is currently the most expensive (average of $321). 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 September 29, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 69% on flights from Toronto Island Airport to Chicago by exploring options for tickets at noon.

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 September 29, 2025.

The most flights from YTZ to CHI 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 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 September 29, 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
7.9
Good
371 reviews

Crew

8.6

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
7.9
Good
371 reviews
Porter Airlines
7.9
Good
371 reviews

Crew

8.6

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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 35% 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, August is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago (average of $245). Flying from Toronto Island Airport to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$158Average$258FlexibilityNo cancel feeOn-time52%

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