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Cheap flights from Toronto Island Airport to Chicago from C$ 192

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 17/8. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — CHI
22 Aug — 29 Aug1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Toronto Island to Chicago

Enter your travel dates to find the best prices.

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 23 July 2026.

Sat 19/91:45 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 20/93:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/7C$ 285
Tue 10/114:35 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Fri 13/116:10 p.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 18/7C$ 285
Thu 3/99:30 a.m.
YTZ
-
ORD
1 stop6h 25m
Air Canada
Sun 6/97:25 a.m.
ORD
-
YTZ
Nonstop1h 42m
Air Canada
Deal found 18/7C$ 286
Thu 27/88:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 30/810:20 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 19/7C$ 288
Fri 21/88:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 24/810:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 21/7C$ 289
Tue 1/912:15 p.m.
YTZ
-
ORD
Nonstop2h 06m
Air Canada
Sun 6/97:25 a.m.
ORD
-
YTZ
Nonstop1h 42m
Air Canada
Deal found 19/7C$ 289
Tue 25/88:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 30/911:45 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 21/7C$ 290
Mon 14/97:35 p.m.
YTZ
-
ORD
Nonstop2h 06m
Air Canada
Wed 16/97:25 a.m.
ORD
-
YTZ
Nonstop1h 42m
Air Canada
Deal found 18/7C$ 290
Mon 26/104:35 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Mon 16/1111:45 a.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 18/7C$ 292
Tue 18/88:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Fri 21/810:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 20/7C$ 293
Thu 3/97:35 p.m.
YTZ
-
ORD
Nonstop2h 06m
Air Canada
Tue 8/98:45 a.m.
ORD
-
YTZ
1 stop6h 05m
Air Canada
Deal found 23/7C$ 293
Mon 10/88:55 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 18/83:15 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 18/7C$ 295

Find 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 23 July 2026.

Round-trip from

C$ 285

One-way from

C$ 192

Popular in

April

Cheapest in

September

Average price

C$ 419

Good round-trip deal

C$ 298 or less

Good one-way deal

C$ 180 or less
Porter Airlines
  • Porter Airlines
  • 19/9-20/9
  • Nonstop
  • 3h 30m total
  • Toronto to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 17/8
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 26% potential increase in price (C$ 202 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Toronto Island to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Toronto Island to Chicago (CHI).
Search Deals

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 629,999 searches. Data last updated 23 July 2026.
Use the filters below to find and compare flights from Toronto Island Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 1/10

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Sun 4/10

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 290

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 24/9

12:15 p.m.-1:21 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Sun 27/9

2:00 p.m.-4:42 p.m.

Nonstop1h 42m

C$ 290

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 21/8

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Mon 24/8

3:15 p.m.-5:55 p.m.

Nonstop1h 40m

C$ 303

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 10/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Thu 13/8

3:15 p.m.-5:55 p.m.

Nonstop1h 40m

C$ 309

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 28/8

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Thu 3/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 310

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 19/8

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Wed 26/8

3:15 p.m.-5:55 p.m.

Nonstop1h 40m

C$ 316

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 9/9

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

Chicago Midway

Sun 13/9

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

C$ 321

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 3/9

10:10 a.m.-11:00 a.m.

Nonstop1h 50m

Chicago Midway

Sun 6/9

11:45 a.m.-2:25 p.m.

Nonstop1h 40m

C$ 330

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 10/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Mon 17/8

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

C$ 331

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 10/8

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

Chicago Midway

Sun 16/8

10:20 a.m.-1:00 p.m.

Nonstop1h 40m

C$ 331

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/7

Showing 1-10 of 31 resultsSorted by cheapest first
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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, September is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago (average of C$ 275). Flying from Toronto Island Airport to Chicago in May is currently the most expensive (average of C$ 495). 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 23 July 2026.

When flying from Toronto Island Airport to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 52% versus a flight in the evening.

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 23 July 2026.

The most flights from YTZ to CHI are scheduled on a Tuesday (8 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

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

Airfare is below average for this route at the moment.
Toronto Island Airport to Chicago flights typically cost between C$ 297 and C$ 531 in September.
The cheapest round-trip price found within the last 5 days was C$ 285 on Porter Airlines (19 Sep-20 Sep).

How often are flights from Toronto to Chicago delayed?

About 15% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 110 minutes.

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

Thursday 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 Toronto to Chicago flights?

Over the past year, Porter Airlines has had the lowest number of delays on this route, with just 15% of flights being delayed.

What is the cheapest day to fly from Toronto Island Airport to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Toronto Island to Chicago. Price data was last updated on 18 July 2026.

Travelers seeking maximum savings on their Toronto Island Airport to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 23 July 2026.
Check out reviews from past customers who have flown with Porter Airlines and Air Canada from Toronto Island Airport to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
448 reviews
Check prices

Crew

8.6

Boarding

8.2

Food

7.5

Overall

8.0

Comfort

8.0

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Porter Airlines
8.0
Very good
448 reviews
Porter Airlines
8.0
Very good
448 reviews
Check prices

Crew

8.6

Boarding

8.2

Food

7.5

Overall

8.0

Comfort

8.0

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Air Canada
7.1
Good
11,372 reviews
Porter Airlines
8.0
Very good
448 reviews
Check prices

Crew

8.6

Boarding

8.2

Food

7.5

Overall

8.0

Comfort

8.0

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats

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.

  • How long is the flight from Toronto Island Airport to Chicago?

    Porter Airlines, Air Canada, and United Airlines can get you from Toronto Island Airport to Chicago in just under 1h 50m. Your travel time will be generally consistent. The distance from Toronto Island Airport to Chicago is about 711 km. Most flights are nonstop.

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

    According to our current data, Porter Airlines (C$ 208), offers the cheapest pricing from Toronto Island Airport to Chicago. Users have found that Porter Airlines is 48% cheaper than the other options available to this destination.

  • What are the most reliable airlines from Toronto Island Airport to Chicago?

    Consider United Airlines (24%), Air Canada (22%) or Jazz (22%) when booking your flight. These represent the most reliable airlines when flying from Toronto Island Airport to Chicago.

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

    While on average a flight from Toronto Island Airport to Chicago is generally C$ 363, our data shows the cheapest flight currently is C$ 196. When looking at the most popular route, (Toronto Island - Chicago Midway), you can expect to pay C$ 244 for that flight.

  • 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, September is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago (average of C$ 275). Flying from Toronto Island Airport to Chicago in May is currently the most expensive (average of C$ 495). 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 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 629,999 searches. Data last updated 23 July 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 208AverageC$ 332FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Toronto Island to Chicago?

Cheapflights makes it easy to find Toronto Island to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Toronto Island to Chicago?

Millions of users choose and trust Cheapflights to book the best flight deals from Toronto Island to Chicago for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from Toronto Island to Chicago with no change fees?

Need flexible booking options for your flight to Chicago from Toronto Island? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Toronto Island to Chicago become cheaper?

Yes! Start tracking prices for Toronto Island to Chicago flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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