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Toronto Island

$85+ 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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YTZ
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
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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 October 27, 2025.

This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 12/79:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/27$190
This Trip.com deal was found by Cheapflights users on 10/25. 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 11/1512:45 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 11/172:30 pmYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/25$191
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1311:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 11/169:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/27$192
This Trip.com deal was found by Cheapflights users on 10/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1211:00 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Sat 11/2211:00 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/26$197
This Trip.com deal was found by Cheapflights users on 10/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/104:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 11/119:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/26$198
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Mon 12/89:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/27$214
This SmartFares deal was found by Cheapflights users on 10/25. 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 11/144:15 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 11/189:15 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 10/25$215
This Booking.com deal was found by Cheapflights users on 10/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/212:50 pmORD - YTZ
1 stop6h 05mAir Canada
Wed 12/1010:30 amYTZ - ORD
1 stop5h 25mAir Canada
Deal found 10/26$221
This Flybillet 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 Flybillet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1312:50 pmORD - YTZ
1 stop7h 45mAir Canada
Sat 11/153:30 pmYTZ - ORD
1 stop5h 30mAir Canada
Deal found 10/27$230
This Air Canada deal was found by Cheapflights users on 10/26. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/153:35 pmORD - YTZ
1 stop5h 00mAir Canada
Tue 11/1810:30 amYTZ - ORD
1 stop5h 25mAir Canada
Deal found 10/26$246
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/63:35 pmORD - YTZ
1 stop5h 00mAir Canada
Sun 12/78:50 amYTZ - ORD
1 stop5h 01mAir Canada
Deal found 10/27$256
This Air Canada deal was found by Cheapflights users on 10/26. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/27:05 amORD - YTZ
2 stops10h 08mAir Canada
Tue 12/98:30 amYTZ - ORD
1 stop7h 25mAir Canada
Deal found 10/26$262

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 October 27, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$191
(Trip.com)

One-way from

$85
(Trip.com)

Popular in

October

Cheapest in

July

Average price

$387

Good round-trip deal

$257 or less

Good one-way deal

$186 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.
Search Deals
From Chicago (CHI) to Toronto Island
Search Deals
One-way flight from Chicago (CHI) to Toronto Island
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 27, 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 11/13

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Sun 11/16

9:15 am-10:05 am

Nonstop1h 50m

$192

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 11/15

12:45 pm-3:27 pm

Nonstop1h 42m

Toronto Island

Mon 11/17

9:15 am-10:05 am

Nonstop1h 50m

$197

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 2/20

11:00 am-1:42 pm

Nonstop1h 42m

Toronto Island

Wed 2/25

9:15 am-10:05 am

Nonstop1h 50m

$203

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 3/21

12:45 pm-3:27 pm

Nonstop1h 42m

Toronto Island

Sun 3/22

9:15 am-10:05 am

Nonstop1h 50m

$211

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 11/14

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Sun 11/16

9:15 am-10:05 am

Nonstop1h 50m

$216

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 2/21

12:45 pm-3:27 pm

Nonstop1h 42m

Toronto Island

Sun 2/22

2:30 pm-3:20 pm

Nonstop1h 50m

$217

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 11/20

4:15 pm-6:57 pm

Nonstop1h 42m

Toronto Island

Sun 11/23

2:30 pm-3:20 pm

Nonstop1h 50m

$223

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 12/6

12:45 pm-3:27 pm

Nonstop1h 42m

Toronto Island

Sun 12/7

9:15 am-10:05 am

Nonstop1h 50m

$231

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Fri 2/20

3:35 pm-9:35 pm

1 stop5h 00m

Toronto Island

Wed 2/25

6:45 am-11:06 am

1 stop5h 21m

$246

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Mon 2/9

12:50 pm-7:55 pm

1 stop6h 05m

Toronto Island

Thu 2/12

6:45 am-11:06 am

1 stop5h 21m

$246

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/25

Showing 1-10 of 40 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, August is the cheapest month in which you can book a flight from Chicago to Toronto Island Airport (average of $135). Flying from Chicago to Toronto Island Airport in March is currently the most expensive (average of $473). 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 October 27, 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 30% on your trip compared to booking a flight at noon.

How much does it cost to fly round-trip from Chicago to Toronto Island Airport?

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 October 27, 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
384 reviews

Entertainment

7.0

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.6

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

Entertainment

7.0

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.6

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 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 $185. Porter Airlines is currently priced 29% 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, August is the cheapest month in which you can book a flight from Chicago to Toronto Island Airport (average of $135). Flying from Chicago to Toronto Island Airport in March is currently the most expensive (average of $473). 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 October 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$185Average$234FlexibilityNo cancel feeOn-time52%

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