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Toronto Island

$81+ Cheap flights from Chicago (CHI) to Toronto Island (YTZ)

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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YTZ
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Chicago to Toronto Island

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Toronto Island (YTZ). 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 17, 2025.

Round-trip from

$230
(Kiwi.com)

One-way from

$81
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$234

Good round-trip deal

$196 or less

Good one-way deal

$88 or less
From Chicago (CHI) to Toronto Island
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One-way flight from Chicago (CHI) to Toronto Island
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Highest demand for flights based on searches. 7% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 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 Chicago (CHI) to Toronto Island.
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Price to beat on a one-way flight from Chicago (CHI) to Toronto Island.
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Find flight deals from Chicago to Toronto Island

Cheapest flights from Chicago to Toronto Island
Explore the most affordable flight options available from Chicago to Toronto Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/159:35 amMDW - YTZ
Nonstop1h 42mMultiple Airlines
Wed 10/2212:00 pmYTZ - MDW
2 stops22h 47mMultiple Airlines
Deal found 9/17$230
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sat 10/189:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 10/207:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/15$244
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/209:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Fri 10/247:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/17$248
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/69:35 amMDW - YTZ
Nonstop1h 42mMultiple Airlines
Tue 10/77:30 pmYTZ - MDW
1 stop4h 55mMultiple Airlines
Deal found 9/15$249
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Wed 10/159:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Thu 10/163:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/15$250
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sat 10/189:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 10/193:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/15$252
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Wed 10/159:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Wed 10/153:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/15$254
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Tue 10/79:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Wed 10/87:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/15$255
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/69:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 10/73:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/15$256
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Sat 10/119:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 10/137:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 9/15$257
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/79:35 amMDW - YTZ
Nonstop1h 42mMultiple Airlines
Tue 10/75:15 pmYTZ - MDW
1 stop7h 10mMultiple Airlines
Deal found 9/16$259
This Flightnetwork deal was found by Cheapflights users on 9/15. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/238:40 amORD - YTZ
1 stop5h 05mAir Canada
Mon 10/273:30 pmYTZ - ORD
1 stop5h 30mAir Canada
Deal found 9/15$288

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Toronto Island 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 17, 2025.
Use the filters below to find and compare flights from Chicago to Toronto Island Airport that are best for you.

Fly from

Chicago

Fly to

Toronto Island

Route

Depart

Return

Price

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 10/23

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Thu 10/30

3:00 pm-11:25 pm

1 stop9h 25m

$246

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 10/15

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Wed 10/22

3:35 pm-4:24 pm

Nonstop1h 49m

$250

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 10/15

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Thu 10/16

3:35 pm-4:24 pm

Nonstop1h 49m

$250

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 10/4

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Tue 10/7

7:30 pm-11:25 pm

1 stop4h 55m

$259

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 10/4

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Tue 10/7

7:50 am-8:39 am

Nonstop1h 49m

$262

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Mon 10/6

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Tue 10/7

7:30 pm-1:38 pm

2 stops19h 08m

$272

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 10/9

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sun 10/12

7:50 am-8:39 am

Nonstop1h 49m

$273

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 10/11

9:35 am-12:17 pm

Nonstop1h 42m

Toronto Island

Sun 10/12

7:50 am-8:39 am

Nonstop1h 49m

$276

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 11/20

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sun 11/23

9:15 am-10:05 am

Nonstop1h 50m

$276

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 10/14

5:20 pm-8:02 pm

Nonstop1h 42m

Toronto Island

Fri 10/17

3:35 pm-4:24 pm

Nonstop1h 49m

$277

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 44 results
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Best time to book a flight from Chicago to Toronto Island

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

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

Currently, February is the cheapest month in which you can book a flight from Chicago to Toronto Island Airport (average of $228). Flying from Chicago to Toronto Island Airport in November 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 CHI to YTZ?

Find hourly flight availability from Chicago to Toronto Island. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Toronto Island Airport in the afternoon. If you’re flexible enough to do this you can expect to save up to 13% on your trip compared to booking a flight in the evening.

Weekly flight availability from Chicago to Toronto Island Airport

Explore weekly flight availability from Chicago to Toronto Island. 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 17, 2025.

The most flights from CHI to YTZ 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 Toronto Island

Get insights into the airlines that provide service to Toronto Island. 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 Toronto Island. Reviews last updated September 17, 2025.
See what other customers who have flown with Porter Airlines from Chicago to Toronto Island Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
7.9
Good
365 reviews

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Crew

8.6

Boarding

8.2

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
365 reviews
Porter Airlines
7.9
Good
365 reviews

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Crew

8.6

Boarding

8.2

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 Chicago to Toronto Island. 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 Chicago to Toronto Island Airport?

    Departing from Chicago to Toronto Island Airport will take you 1h 42m. There are 442 mi between Chicago and Toronto Island Airport. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Flying on Porter Airlines is currently your cheapest option to Toronto Island Airport, with prices starting at $187. Porter Airlines is currently priced 26% below the average price you’ll pay for this route.

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

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Chicago to Toronto Island Airport (average of $228). Flying from Chicago to Toronto Island Airport in November 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

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Chicago to Toronto Island

Discover the top airline that operate flights from Chicago to Toronto Island. 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 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$187Average$257FlexibilityNo cancel feeOn-time52%

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