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$116+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — ORD
Jan 16 — Jan 231
Fri 1/16
Fri 1/23
1 adult, Economy
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Cheap 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 December 17, 2025.

This FlightHub deal was found by Cheapflights users on 12/15. 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 12/309:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 2/111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/15$270
This FlightHub deal was found by Cheapflights users on 12/15. 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
Tue 2/311:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/15$291
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 12/229:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 1/611:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/15$332
This deal was found by Cheapflights users on 12/15. 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 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 12/2211:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/15$345
This Super.com deal was found by Cheapflights users on 12/16. 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.
Mon 12/292:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 1/611:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/16$347
This oojo deal was found by Cheapflights users on 12/15. 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 oojo 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
Mon 2/211:05 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/15$355
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 12/229:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 1/811:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/15$356
This deal was found by Cheapflights users on 12/15. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/199:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 12/234:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/15$358
This deal was found by Cheapflights users on 12/15. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/182:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 12/234:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/15$359
This deal was found by Cheapflights users on 12/15. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/202:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 12/224:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/15$360
This FlightHub deal was found by Cheapflights users on 12/15. 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.
Mon 12/299:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 1/14:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/15$361
This Porter Airlines deal was found by Cheapflights users on 12/15. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/232:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 1/611:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/15$362

Find 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 December 17, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$183
(Trip.com)

One-way from

$116
(Trip.com)

Popular in

December

Cheapest in

July

Average price

$321

Good round-trip deal

$210 or less

Good one-way deal

$117 or less
Provider with most accurate pricing for Toronto (YTO)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Toronto (YTO)-Chicago (CHI) flights.
Search Deals
From Toronto Island to Illinois
Search Deals
One-way flight from Toronto Island to Illinois
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 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 Illinois.
Search Deals
Price to beat on a one-way flight from Toronto Island to Illinois.
Search Deals

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 December 17, 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

Fri 1/16

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Fri 1/23

11:00 am-1:42 pm

Nonstop1h 42m

$185

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 1/29

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Thu 2/5

11:05 am-1:47 pm

Nonstop1h 42m

$186

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 2/20

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Mon 2/23

11:00 am-1:42 pm

Nonstop1h 42m

$187

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 1/25

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Wed 1/28

11:00 am-1:42 pm

Nonstop1h 42m

$200

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 1/15

8:30 am-2:55 pm

1 stop7h 25m

Chicago O'Hare Intl

Sun 1/18

7:15 am-2:55 pm

1 stop6h 40m

$207

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 1/14

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Wed 1/21

11:00 am-1:42 pm

Nonstop1h 42m

$218

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 1/30

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Fri 2/6

11:00 am-1:42 pm

Nonstop1h 42m

$219

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 1/31

3:30 pm-8:10 pm

1 stop5h 40m

Chicago O'Hare Intl

Sat 2/7

12:50 pm-7:55 pm

1 stop6h 05m

$220

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 1/15

8:50 am-2:55 pm

2 stops7h 05m

Chicago O'Hare Intl

Sat 1/17

3:35 pm-9:35 pm

1 stop5h 00m

$228

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 1/14

9:15 am-10:05 am

Nonstop1h 50m

Chicago Midway

Sat 1/17

12:45 pm-3:27 pm

Nonstop1h 42m

$231

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 36 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 December 17, 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 in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 65% 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 December 17, 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
399 reviews

Entertainment

7.0

Boarding

8.2

Overall

8.0

Food

7.6

Crew

8.6

Comfort

7.9

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
399 reviews
Porter Airlines
8.0
Very good
399 reviews

Entertainment

7.0

Boarding

8.2

Overall

8.0

Food

7.6

Crew

8.6

Comfort

7.9

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 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 $185, 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.

  • 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 December 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$158Average$258FlexibilityNo cancel feeOn-time52%

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