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$106+ Cheap flights from Toronto Island (YTZ) to Chicago (CHI)

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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — CHI
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
1 adult, Economy
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Cheap flight deals from Toronto Island to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Toronto Island (YTZ) to Chicago (CHI). 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 agosto 14, 2025.

Round-trip from

$174
(SmartFares)

One-way from

$106
(SmartFares)

Popular in

January

Cheapest in

September

Average price

$175

Good round-trip deal

$174 or less

Good one-way deal

$109 or less
From Toronto Island to Chicago (CHI)
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One-way flight from Toronto Island to Chicago (CHI)
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Highest demand for flights based on searches. 12% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Toronto Island to Chicago (CHI).
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Price to beat on a one-way flight from Toronto Island to Chicago (CHI).
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Find flight deals from Toronto Island to Chicago

Cheapest flights from Toronto Island to Chicago
Explore the most affordable flight options available from Toronto Island to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 14, 2025.

This SmartFares deal was found by Cheapflights users on 8/14. 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.
vie. 10/37:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
mar. 10/75:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/14$174
This SmartFares deal was found by Cheapflights users on 8/12. 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.
mié. 9/103:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
mié. 9/175:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/12$175
This Mytrip deal was found by Cheapflights users on 8/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/23:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
dom. 10/55:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/14$176
This SmartFares deal was found by Cheapflights users on 8/14. 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.
vie. 10/33:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
dom. 10/59:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/14$179
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
vie. 9/193:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
dom. 9/219:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/13$180
This KAYAK deal was found by Cheapflights users on 8/13. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/137:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
jue. 10/165:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/13$182
This FlightHub deal was found by Cheapflights users on 8/14. 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.
sáb. 9/67:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
dom. 9/79:35 amMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/14$183
This SmartFares deal was found by Cheapflights users on 8/13. 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.
jue. 10/167:50 amYTZ - MDW
Nonstop1h 49mPorter Airlines
lun. 10/205:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/13$184
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
vie. 9/193:35 pmYTZ - MDW
Nonstop1h 49mPorter Airlines
lun. 9/225:20 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 8/13$185
This Mytrip deal was found by Cheapflights users on 8/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/210:25 amYTZ - ORD
1 stop5h 30mAir Canada
dom. 10/510:40 amORD - YTZ
1 stop5h 05mAir Canada
Deal found 8/14$199
This Air Canada deal was found by Cheapflights users on 8/14. 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.
mié. 10/2210:25 amYTZ - ORD
1 stop5h 30mAir Canada
jue. 10/238:40 amORD - YTZ
1 stop5h 05mAir Canada
Deal found 8/14$207
This Flightnetwork deal was found by Cheapflights users on 8/13. 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.
sáb. 10/43:25 pmYTZ - ORD
1 stop5h 46mAir Canada
mar. 10/73:35 pmORD - YTZ
1 stop4h 59mAir Canada
Deal found 8/13$209

Cheapflights Fare Finder

 
Customize your flight search to find flights from Toronto Island to Chicago 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 agosto 14, 2025.
Use the filters below to find and compare flights from Toronto Island Airport to Chicago that are best for you.

Fly from

Toronto Island

Fly to

Chicago

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

jue. 9/18

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

dom. 9/28

9:35 am-12:17 pm

Nonstop1h 42m

$174

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

vie. 10/3

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

mar. 10/7

5:20 pm-8:02 pm

Nonstop1h 42m

$174

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

mié. 9/10

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

sáb. 9/20

9:35 am-12:17 pm

Nonstop1h 42m

$174

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

sáb. 9/27

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

sáb. 10/4

9:35 am-12:17 pm

Nonstop1h 42m

$174

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

vie. 9/26

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

lun. 9/29

9:35 am-12:17 pm

Nonstop1h 42m

$174

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

vie. 10/3

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

lun. 10/6

5:20 pm-8:02 pm

Nonstop1h 42m

$174

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

vie. 9/26

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

mar. 9/30

5:20 pm-8:02 pm

Nonstop1h 42m

$175

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

mié. 9/10

3:35 pm-4:24 pm

Nonstop1h 49m

Chicago Midway

mié. 9/17

5:20 pm-8:02 pm

Nonstop1h 42m

$175

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

sáb. 9/13

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

sáb. 9/20

9:35 am-12:17 pm

Nonstop1h 42m

$175

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

vie. 9/12

7:50 am-8:39 am

Nonstop1h 49m

Chicago Midway

vie. 9/19

5:20 pm-8:02 pm

Nonstop1h 42m

$175

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 31 results
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Best time to book a flight from Toronto Island to Chicago

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

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

Currently, August is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago (average of $245). Flying from Toronto Island Airport to Chicago in March 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 YTZ to CHI?

Find hourly flight availability from Toronto Island to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated agosto 14, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 12% on flights from Toronto Island Airport to Chicago by exploring options for tickets at noon.

Weekly flight availability from Toronto Island Airport to Chicago

Explore weekly flight availability from Toronto Island to Chicago. 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 agosto 14, 2025.

The most flights from YTZ to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated agosto 14, 2025.
Read through reviews of airlines operating flights from Toronto Island Airport to Chicago, such as Porter Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
332 reviews

Overall

8.0

Entertainment

7.0

Boarding

8.2

Crew

8.7

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
332 reviews
Porter Airlines
8.0
Very good
332 reviews

Overall

8.0

Entertainment

7.0

Boarding

8.2

Crew

8.7

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

Related info for your journey

Find useful and relevant information for your journey from Toronto Island to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    According to our current data, Porter Airlines ($158), offers the cheapest pricing from Toronto Island Airport to Chicago. Porter Airlines is currently priced 34% below the average price you’ll pay for this route.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago (average of $245). Flying from Toronto Island Airport to Chicago in March 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Toronto Island to Chicago

Discover the top airline that operate flights from Toronto Island to Chicago. 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 agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$158Average$257FlexibilityNo cancel feeOn-time52%

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