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Cheap flights from Toronto Island Airport to Chicago from C$ 185

YTZ — CHI
1 Oct — 8 Oct1
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

Sun 11/101:45 p.m. -
Nonstop1h 50m
Wed 14/103:20 p.m. -
Nonstop1h 40m
Deal found 27/8C$ 284
Thu 1/1010:45 a.m. -
1 stop5h 07m
Sun 4/107:25 a.m. -
Nonstop1h 53m
Deal found 27/8C$ 284
Fri 25/910:10 a.m. -
Nonstop1h 50m
Fri 25/93:20 p.m. -
Nonstop1h 40m
Deal found 28/8C$ 286
Thu 24/910:45 a.m. -
1 stop5h 07m
Sun 27/97:25 a.m. -
Nonstop1h 42m
Deal found 30/8C$ 286
Tue 6/101:45 p.m. -
Nonstop1h 50m
Fri 9/103:20 p.m. -
Nonstop1h 40m
Deal found 27/8C$ 287
Thu 17/99:30 a.m. -
1 stop6h 22m
Sun 20/97:25 a.m. -
Nonstop1h 42m
Deal found 27/8C$ 287
Sat 26/912:15 p.m. -
Nonstop2h 06m
Sat 3/108:45 a.m. -
1 stop6h 05m
Deal found 27/8C$ 289
Sat 19/912:15 p.m. -
Nonstop2h 06m
Sat 3/102:00 p.m. -
Nonstop1h 42m
Deal found 27/8C$ 293
Tue 22/912:15 p.m. -
Nonstop2h 06m
Sat 26/98:45 a.m. -
1 stop6h 05m
Deal found 28/8C$ 294
Fri 18/97:35 p.m. -
Nonstop2h 06m
Mon 21/97:25 a.m. -
Nonstop1h 42m
Deal found 27/8C$ 296
Mon 21/910:10 a.m. -
Nonstop1h 50m
Sun 27/911:45 a.m. -
Nonstop1h 40m
Deal found 28/8C$ 297
Fri 25/912:15 p.m. -
Nonstop2h 06m
Mon 28/97:25 a.m. -
Nonstop1h 42m
Deal found 31/8C$ 297

Find flight deals from Toronto Island to Chicago

Round-trip from

C$ 283

One-way from

C$ 185

Popular in

April

Cheapest in

January

Average price

C$ 379

Good round-trip deal

C$ 293 or less

Good one-way deal

C$ 199 or less
Porter Airlines
  • Porter Airlines
  • 13/10-16/10
  • Nonstop
  • 3h 30m total
  • Toronto to Chicago
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Air Canada
  • Air Canada
  • 23/9
  • 1 total stop
  • 5h 07m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 24% potential increase in price (C$ 183 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease (C$ 28 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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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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Cheapflights Fare Finder

 
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 Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 29/9

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

Nonstop1h 50m

Chicago Midway

Sat 3/10

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

Nonstop1h 40m

C$ 318

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Wed 23/9

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

Nonstop1h 50m

Chicago Midway

Thu 24/9

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

Nonstop1h 40m

C$ 321

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 17/9

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

Nonstop1h 50m

Chicago Midway

Mon 21/9

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

Nonstop1h 40m

C$ 321

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 28/9

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

Nonstop1h 50m

Chicago Midway

Mon 5/10

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

Nonstop1h 40m

C$ 355

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Thu 15/10

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

Nonstop1h 50m

Chicago Midway

Thu 22/10

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

Nonstop1h 40m

C$ 371

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 20/10

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

Nonstop1h 50m

Chicago Midway

Fri 23/10

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

Nonstop1h 40m

C$ 372

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 18/9

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

Nonstop1h 50m

Chicago Midway

Tue 29/9

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

Nonstop1h 40m

C$ 375

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sat 10/10

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

Nonstop1h 50m

Chicago Midway

Tue 20/10

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

Nonstop1h 40m

C$ 409

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Fri 25/9

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

Nonstop2h 06m

Chicago O'Hare Intl

Mon 28/9

12:55 p.m.-6:51 p.m.

1 stop4h 56m

C$ 414

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sun 27/9

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

Nonstop1h 50m

Chicago Midway

Thu 1/10

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

Nonstop1h 40m

C$ 418

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/8

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

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, January is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago (average of C$ 309). 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?

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 48% versus a flight in the evening.

Weekly flight availability from Toronto Island Airport to Chicago

The most flights from YTZ to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (2 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$ 350 and C$ 387 in October.
The cheapest round-trip price found within the last 5 days was C$ 283 on Porter Airlines (13 Oct-16 Oct).

How often are flights from Toronto to Chicago delayed?

About 14% of weekly flights between Toronto and Chicago have experienced delays in the past year, with the average delay time being 104 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 Monday 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 14% of flights being delayed.

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

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

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
458 reviews
Check prices

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.6

Entertainment

6.9

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
458 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.6

Entertainment

6.9

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
11,566 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.6

Entertainment

6.9

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

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

    Porter Airlines, United Airlines, and Air Canada 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 67% 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$ 343, our data shows the cheapest flight currently is C$ 177. 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, January is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago (average of C$ 309). 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

Top 2 airlines flying from Toronto Island to Chicago

AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 134AverageC$ 501FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 220AverageC$ 340FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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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.

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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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