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Toronto Island

$87+ 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YTZ
ene. 22 — ene. 291
jue. 1/22
jue. 1/29
1 adult, Economy
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Cheap 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 diciembre 23, 2025.

This Trip.com deal was found by Cheapflights users on 12/22. 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.
lun. 12/294:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
lun. 1/129:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/22$383
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
mar. 12/307:20 amORD - YTZ
2 stops13h 43mMultiple Airlines
lun. 1/126:15 pmYTZ - ORD
1 stop5h 27mMultiple Airlines
Deal found 12/22$452
This FlightHub deal was found by Cheapflights users on 12/22. 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.
mié. 12/3111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
lun. 1/129:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/22$464
This FlightHub deal was found by Cheapflights users on 12/21. 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.
mar. 12/304:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
vie. 1/22:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/21$466
This FlightHub deal was found by Cheapflights users on 12/20. 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.
dom. 12/284:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
vie. 1/99:20 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/20$471
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
mar. 12/304:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
mié. 12/319:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/21$479
This FlightHub deal was found by Cheapflights users on 12/21. 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.
mié. 12/3111:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
jue. 1/12:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/21$507
This oojo deal was found by Cheapflights users on 12/22. 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.
mar. 12/304:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
lun. 1/59:20 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/22$516
This FlightHub deal was found by Cheapflights users on 12/22. 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.
lun. 12/2911:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
sáb. 1/39:20 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/22$517
This FlightHub deal was found by Cheapflights users on 12/22. 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.
mar. 12/304:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
sáb. 1/39:20 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/22$526
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
lun. 12/2911:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
jue. 1/12:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 12/22$536
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
lun. 12/294:15 pmMDW - YTZ
Nonstop1h 42mMultiple Airlines
dom. 1/42:05 pmYTZ - MDW
3 stops33h 07mMultiple Airlines
Deal found 12/22$538

Find 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 diciembre 23, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$194
(Porter Airlines)

One-way from

$87
(Super.com)

Popular in

January

Cheapest in

July

Average price

$358

Good round-trip deal

$266 or less

Good one-way deal

$122 or less
Provider with most accurate pricing for Chicago (CHI)-Toronto (YTO) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Toronto (YTO) flights.
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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. 24% potential increase in price ($92 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($21 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 Chicago (CHI) to Toronto Island.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Toronto Island.
Search Deals

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 diciembre 23, 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

jue. 2/19

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

lun. 2/23

9:15 am-10:05 am

Nonstop1h 50m

$194

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

vie. 1/23

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

mar. 1/27

9:20 am-10:10 am

Nonstop1h 50m

$203

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

dom. 1/18

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

dom. 1/25

2:30 pm-3:20 pm

Nonstop1h 50m

$203

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

jue. 1/15

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

lun. 1/19

9:20 am-10:10 am

Nonstop1h 50m

$204

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

lun. 1/26

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

sáb. 1/31

11:00 am-11:50 am

Nonstop1h 50m

$206

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

vie. 1/16

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

dom. 1/18

2:30 pm-3:20 pm

Nonstop1h 50m

$210

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

vie. 1/16

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

mié. 1/21

9:15 am-10:05 am

Nonstop1h 50m

$215

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

jue. 2/5

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

dom. 2/8

7:00 am-7:52 pm

2 stops13h 52m

$223

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

vie. 1/16

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

lun. 1/19

9:20 am-10:10 am

Nonstop1h 50m

$226

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

vie. 1/16

11:05 am-1:47 pm

Nonstop1h 42m

Toronto Island

dom. 1/18

2:30 pm-3:20 pm

Nonstop1h 50m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

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, March is the cheapest month in which you can book a flight from Chicago to Toronto Island Airport (average of $79). Flying from Chicago to Toronto Island Airport in January is currently the most expensive (average of $333). 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 diciembre 23, 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 53% on your trip compared to booking a flight at noon.

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 diciembre 23, 2025.

The most flights from CHI to YTZ 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 Chicago to Toronto delayed?

About 13% of weekly flights between Chicago and Toronto have experienced delays in the past year, with the average delay time being 119 minutes.

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

Over the last year, Porter Airlines have had the lowest number of delays on this route, with just 13% of flights being delayed.

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 diciembre 23, 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
8.0
Very good
399 reviews

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

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

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

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 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 $172. Porter Airlines is currently priced 38% below the average price you’ll pay for this route.

  • What are the cheapest flights from Chicago to Toronto Island Airport?

    The cheapest flight price from Chicago to Toronto Island Airport is $398. On average you can expect to pay $716. The most popular route, (Chicago Midway - Toronto Island), can usually be booked for $149.

  • 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, March is the cheapest month in which you can book a flight from Chicago to Toronto Island Airport (average of $79). Flying from Chicago to Toronto Island Airport in January is currently the most expensive (average of $333). 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 diciembre 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$185Average$230FlexibilityNo cancel feeOn-time52%

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