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$124+ 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 4/20. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — CHI
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$197
(Trip.com)

One-way from

$124
(Cheapflightsfares)

Popular in

January

Cheapest in

December

Average price

$288

Good round-trip deal

$170 or less

Good one-way deal

$119 or less
Provider with most accurate pricing for Toronto Island-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Toronto Island-Chicago (CHI) flights.
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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. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 28, 2025.

This Trip.com deal was found by Cheapflights users on 3/27. 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.
Sat 4/1911:10 amYTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 4/205:35 pmMDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 3/27$197
This Flightnetwork deal was found by Cheapflights users on 3/27. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/68:25 amYTZ - ORD
1 stop7h 26mAir Canada
Thu 7/103:35 pmORD - YTZ
1 stop4h 56mAir Canada
Deal found 3/27$206
This Booking.com deal was found by Cheapflights users on 3/27. 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.
Tue 4/299:30 amYTZ - MDW
Nonstop1h 50mAir Transat
Sat 5/39:40 amMDW - YTZ
Nonstop1h 42mAir Transat
Deal found 3/27$223
This Trip.com deal was found by Cheapflights users on 3/27. 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.
Thu 4/109:30 amYTZ - MDW
Nonstop1h 50mMultiple Airlines
Thu 4/1711:15 amMDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 3/27$279
This Mytrip deal was found by Cheapflights users on 3/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1312:50 pmYTZ - ORD
1 stop19h 37mMultiple Airlines
Tue 5/209:08 pmORD - YTZ
1 stop23h 12mMultiple Airlines
Deal found 3/27$293

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 March 28, 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

Sat 4/19

11:10 am-12:00 pm

Nonstop1h 50m

Chicago Midway

Sun 4/20

5:35 pm-8:17 pm

Nonstop1h 42m

$197

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sun 7/6

8:25 am-2:51 pm

1 stop7h 26m

Chicago O'Hare Intl

Thu 7/10

3:35 pm-9:31 pm

1 stop4h 56m

$206

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 4/29

9:30 am-10:20 am

Nonstop1h 50m

Chicago Midway

Sat 5/3

9:40 am-12:22 pm

Nonstop1h 42m

$223

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 4/10

9:30 am-10:20 am

Nonstop1h 50m

Chicago Midway

Thu 4/17

11:15 am-1:57 pm

Nonstop1h 42m

$279

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 5/13

12:50 pm-7:27 am

1 stop19h 37m

Chicago O'Hare Intl

Tue 5/20

9:08 pm-9:20 pm

1 stop23h 12m

$293

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 4/20

9:30 am-10:20 am

Nonstop1h 50m

$124

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Mon 5/12

3:25 pm-8:12 pm

1 stop5h 47m

$131

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 5/12

4:05 pm-4:54 pm

Nonstop1h 49m

$135

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 5/6

9:45 am-7:27 am

1 stop22h 42m

$158

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 6/23

8:45 am-7:31 pm

1 stop11h 46m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/28

Compare providers for flights from Toronto Island to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Toronto Island to Chicago in March.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Toronto Island Airport-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Toronto Island Airport-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Toronto Island Airport-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Toronto Island Airport-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Toronto Island Airport-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 $323). 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 March 28, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 5% on flights from Toronto Island Airport to Chicago by exploring options for tickets in the afternoon.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 March 28, 2025.
Read reviews from past customers who have flown Porter Airlines, Air Transat and Air Canada from Toronto to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
7.9
Good
276 reviews

Comfort

8.0

Crew

8.7

Food

7.6

Boarding

8.2

Entertainment

6.9

Overall

7.9

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Porter Airlines
7.9
Good
276 reviews
Porter Airlines
7.9
Good
276 reviews

Comfort

8.0

Crew

8.7

Food

7.6

Boarding

8.2

Entertainment

6.9

Overall

7.9

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Air Transat
7.8
Good
381 reviews
Porter Airlines
7.9
Good
276 reviews

Comfort

8.0

Crew

8.7

Food

7.6

Boarding

8.2

Entertainment

6.9

Overall

7.9

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Air Canada
7.0
Good
8,981 reviews
Porter Airlines
7.9
Good
276 reviews

Comfort

8.0

Crew

8.7

Food

7.6

Boarding

8.2

Entertainment

6.9

Overall

7.9

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

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 are the cheapest airlines flying from Toronto Island Airport to Chicago round-trip?

    According to our current data, Porter Airlines ($197), Air Canada ($206), and Air Transat ($223) offers the cheapest pricing from Toronto Island Airport to Chicago. Porter Airlines is currently priced 28% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Toronto Island Airport to Chicago one-way?

    For one-way options, check prices for Porter Airlines. According to our data, you can fly for as low as $124. Users have also found prices from $131 and $135 on Air Canada and Air Transat, respectively.

  • 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 $323). 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 Toronto Island Airport?

Book flights to Toronto Island Airport if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top 2 airlines flying from Toronto Island to Chicago

Discover the top 2 airlines 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$157Average$290FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$170Average$258FlexibilityNo cancel feeOn-time52%
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