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$131+ Cheap flights from Toronto Island (YTZ) to Illinois

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 11/25. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — ORD
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Toronto Island to Illinois

Keep the following information in mind while searching for Toronto Island to Illinois flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$185
(Kiwi.com)

One-way from

$131
(FlightHub)

Popular in

October

Cheapest in

July

Average price

$296

Good round-trip deal

$333 or less

Good one-way deal

$189 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago (CHI) flights.
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From Toronto Island to Illinois
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One-way flight from Toronto Island to Illinois
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Highest demand for flights based on searches. 5% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Toronto Island to Illinois.
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Price to beat on a one-way flight from Toronto Island to Illinois.
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Find flight deals from Toronto Island to Illinois

Cheapest flights from Toronto Island to Illinois
Explore the most affordable flight options available from Toronto Island to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/239:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Fri 12/1211:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/30$185
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/249:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 12/811:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/30$187
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/179:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 11/2212:45 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/30$188
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/149:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 11/174:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/29$190
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/119:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 12/1411:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/29$193
This FlightHub deal was found by Cheapflights users on 10/28. 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 12/52:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 12/84:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/28$195
This SmartFares deal was found by Cheapflights users on 10/27. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/209:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 11/244:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/27$196
This FlightHub deal was found by Cheapflights users on 10/28. 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.
Thu 11/132:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 11/1811:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/28$197
This FlightHub deal was found by Cheapflights users on 10/30. 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 11/219:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 11/2212:45 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/30$198
This Trip.com deal was found by Cheapflights users on 10/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/242:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 12/111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/29$199
This SmartFares deal was found by Cheapflights users on 10/28. 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.
Fri 11/142:30 pmYTZ - MDW
Nonstop1h 50mAir Transat
Mon 11/174:15 pmMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 10/28$201
This Air Canada deal was found by Cheapflights users on 10/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2510:30 amYTZ - ORD
1 stop5h 25mAir Canada
Fri 11/283:35 pmORD - YTZ
1 stop5h 00mAir Canada
Deal found 10/28$223

Cheapflights Fare Finder

 
Customize your flight search to find flights from Toronto Island to Illinois 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 October 30, 2025.
Use the filters below to find and compare flights from Toronto Island Airport to Illinois that are best for you.

Fly from

Toronto Island

Fly to

Illinois

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 11/22

11:00 am-11:50 am

Nonstop1h 50m

Chicago Midway

Tue 11/25

11:00 am-1:42 pm

Nonstop1h 42m

$197

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 11/24

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Mon 12/1

11:00 am-1:42 pm

Nonstop1h 42m

$199

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 11/28

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Fri 12/5

4:15 pm-6:57 pm

Nonstop1h 42m

$201

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 12/5

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Mon 12/8

4:15 pm-6:57 pm

Nonstop1h 42m

$210

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 12/4

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Sun 12/7

11:00 am-1:42 pm

Nonstop1h 42m

$213

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 11/19

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Fri 11/21

4:15 pm-6:57 pm

Nonstop1h 42m

$215

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 11/21

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sat 11/22

12:45 pm-3:27 pm

Nonstop1h 42m

$215

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 11/14

2:30 pm-3:20 pm

Nonstop1h 50m

Chicago Midway

Sat 12/6

12:45 pm-3:27 pm

Nonstop1h 42m

$215

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 11/22

11:00 am-11:50 am

Nonstop1h 50m

Chicago Midway

Mon 11/24

4:15 pm-6:57 pm

Nonstop1h 42m

$221

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 2/24

6:45 am-11:06 am

1 stop5h 21m

Chicago O'Hare Intl

Sat 2/28

12:50 pm-7:55 pm

1 stop6h 05m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 46 results
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Best time to book a flight from Toronto Island to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois 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 Illinois

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

Currently, June is the cheapest month in which you can book a flight from Toronto Island Airport to Illinois (average of $83). Flying from Toronto Island Airport to Illinois 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 IL?

Find hourly flight availability from Toronto Island to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

One of the essential ways to save on airfare from Toronto Island Airport to Illinois is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 27% on airfare.

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated October 30, 2025.
Peruse reviews from past customers who have flown with Porter Airlines from Toronto Island Airport to Illinois to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
384 reviews

Comfort

8.0

Boarding

8.2

Food

7.6

Overall

8.0

Entertainment

7.0

Crew

8.6

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
8.0
Very good
384 reviews
Porter Airlines
8.0
Very good
384 reviews

Comfort

8.0

Boarding

8.2

Food

7.6

Overall

8.0

Entertainment

7.0

Crew

8.6

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 Illinois. 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 Illinois?

    For as low as $197, Porter Airlines can have you in Illinois from Toronto Island Airport in 1h 50m. There are 442 mi between Toronto Island Airport and Illinois. This flight may include one or multiple stops.

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

    To fly one-way, consider booking your trip with Porter Airlines, which is currently one of the cheapest options available, starting at $133. Air Canada flights start at $134 while deals on Air Transat start at $137 one-way.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Toronto Island to Illinois 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 Illinois?

    Currently, June is the cheapest month in which you can book a flight from Toronto Island Airport to Illinois (average of $83). Flying from Toronto Island Airport to Illinois 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

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Alternative routes for Toronto Island to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Toronto Island to Illinois

Discover the top airline that operate flights from Toronto Island to Illinois. 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$158Average$231FlexibilityNo cancel feeOn-time52%

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