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Cheap flights from Toronto Island Airport to Chicago from C$ 183

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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — CHI
15 Sep — 22 Sep1
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 16 August 2026.

Tue 8/91:45 p.m. -
Nonstop1h 50m
Sat 12/93:20 p.m. -
Nonstop1h 40m
Deal found 13/8C$ 280
Fri 25/97:35 p.m. -
Nonstop2h 06m
Sun 27/97:25 a.m. -
Nonstop1h 42m
Deal found 14/8C$ 280
Thu 10/91:45 p.m. -
Nonstop1h 50m
Sun 13/911:45 a.m. -
Nonstop1h 40m
Deal found 15/8C$ 282
Thu 10/912:15 p.m. -
Nonstop2h 06m
Sun 13/97:25 a.m. -
Nonstop1h 42m
Deal found 14/8C$ 282
Mon 7/91:45 p.m. -
Nonstop1h 50m
Thu 10/93:20 p.m. -
Nonstop1h 40m
Deal found 13/8C$ 284
Wed 2/91:45 p.m. -
Nonstop1h 50m
Fri 11/93:20 p.m. -
Nonstop1h 40m
Deal found 13/8C$ 286
Fri 4/910:10 a.m. -
Nonstop1h 50m
Thu 10/93:20 p.m. -
Nonstop1h 40m
Deal found 13/8C$ 287
Thu 24/910:45 a.m. -
1 stop5h 07m
Sun 27/92:00 p.m. -
Nonstop1h 42m
Deal found 12/8C$ 287
Sat 5/91:45 p.m. -
Nonstop1h 50m
Sun 13/93:20 p.m. -
Nonstop1h 40m
Deal found 12/8C$ 289
Sun 6/910:10 a.m. -
Nonstop1h 50m
Sun 13/911:45 a.m. -
Nonstop1h 40m
Deal found 14/8C$ 290
Mon 7/910:10 a.m. -
Nonstop1h 50m
Wed 9/93:20 p.m. -
Nonstop1h 40m
Deal found 16/8C$ 291
Sat 5/910:45 a.m. -
1 stop5h 10m
Thu 17/92:00 p.m. -
Nonstop1h 42m
Deal found 13/8C$ 291

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 16 August 2026.

Round-trip from

C$ 280

One-way from

C$ 183

Popular in

April

Cheapest in

January

Average price

C$ 337

Good round-trip deal

C$ 281 or less

Good one-way deal

C$ 189 or less
Porter Airlines
  • Porter Airlines
  • 8/9-12/9
  • Nonstop
  • 3h 30m total
  • Toronto to Chicago
Search Deals
Air Canada
  • Air Canada
  • 5/9
  • 1 total stop
  • 5h 10m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 25% potential increase in price (C$ 193 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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).
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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 16 August 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

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Wed 2/9

7:35 p.m.-8:41 p.m.

Nonstop2h 06m

Chicago O'Hare Intl

Wed 9/9

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

Nonstop1h 42m

C$ 294

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Fri 18/9

9:30 a.m.-2:52 p.m.

1 stop6h 22m

Chicago O'Hare Intl

Sun 20/9

11:05 a.m.-5:50 p.m.

1 stop5h 45m

C$ 305
Quickest round-trip

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 17/9

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

Nonstop1h 50m

Chicago Midway

Sun 20/9

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

Nonstop1h 40m

C$ 319

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sat 12/9

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

Nonstop1h 50m

Chicago Midway

Sat 12/9

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

Nonstop1h 40m

C$ 319

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sun 6/9

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

Nonstop1h 50m

Chicago Midway

Thu 10/9

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

Nonstop1h 40m

C$ 319

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 2/9

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

Nonstop1h 50m

Chicago Midway

Wed 9/9

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

Nonstop1h 40m

C$ 323

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 25/9

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

Nonstop1h 50m

Chicago Midway

Fri 2/10

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

Nonstop1h 40m

C$ 345

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sun 30/8

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

Chicago Midway

Mon 31/8

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

Nonstop1h 40m

C$ 361

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 8/9

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

Nonstop1h 50m

Chicago Midway

Tue 8/9

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

Nonstop1h 40m

C$ 362

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Wed 30/9

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

Nonstop2h 06m

Chicago O'Hare Intl

Wed 7/10

7:25 a.m.-10:07 a.m.

Nonstop1h 42m

C$ 363

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/8

Showing 1-10 of 40 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$ 297). Flying from Toronto Island Airport to Chicago in May is currently the most expensive (average of C$ 487). 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 16 August 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 49% 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 16 August 2026.

The most flights from YTZ to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Sunday, 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$ 287 and C$ 404 in September.
The cheapest round-trip price found within the last 5 days was C$ 280 on Porter Airlines (8 Sep-12 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 106 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 15 August 2026.

Travelers seeking maximum savings on their Toronto Island Airport to Chicago flight should consider departing on Friday at noon 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 16 August 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
456 reviews
Check prices

Crew

8.6

Comfort

8.0

Entertainment

6.9

Overall

8.0

Boarding

8.2

Food

7.5

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Porter Airlines
8.0
Very good
456 reviews
Porter Airlines
8.0
Very good
456 reviews
Check prices

Crew

8.6

Comfort

8.0

Entertainment

6.9

Overall

8.0

Boarding

8.2

Food

7.5

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Air Canada
7.1
Good
11,481 reviews
Porter Airlines
8.0
Very good
456 reviews
Check prices

Crew

8.6

Comfort

8.0

Entertainment

6.9

Overall

8.0

Boarding

8.2

Food

7.5

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

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?

    Air Canada and Porter 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 are the cheapest airlines flying from Toronto Island Airport to Chicago round-trip?

    According to our current data, Air Canada (C$ 134), and Porter Airlines (C$ 220) offers the cheapest pricing from Toronto Island Airport to Chicago. Users have found that Air Canada is 66% cheaper than the other options available to this destination.

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

    Consider Air Canada (26%), Jazz (26%) or United Airlines (24%) 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$ 316, our data shows the cheapest flight currently is C$ 183. When looking at the most popular route, (Toronto Island - Chicago O'Hare Intl), you can expect to pay C$ 370 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$ 297). Flying from Toronto Island Airport to Chicago in May is currently the most expensive (average of C$ 487). 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 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 629,999 searches. Data last updated 16 August 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 134AverageC$ 501FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 220AverageC$ 334FlexibilityNo 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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