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Cheap flights from Toronto Island Airport to Chicago from C$ 181

YTZ — CHI
15 Oct — 22 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

Sat 3/101:45 p.m. -
Nonstop1h 50m
Mon 5/103:20 p.m. -
Nonstop1h 40m
Deal found 11/9C$ 285
Thu 1/1010:45 a.m. -
1 stop5h 07m
Sun 4/108:45 a.m. -
1 stop6h 05m
Deal found 14/9C$ 285
Fri 2/101:45 p.m. -
Nonstop1h 50m
Sun 4/103:20 p.m. -
Nonstop1h 40m
Deal found 9/9C$ 286
Thu 24/910:45 a.m. -
1 stop5h 07m
Thu 1/102:00 p.m. -
Nonstop1h 48m
Deal found 10/9C$ 286
Sun 11/1010:10 a.m. -
Nonstop1h 50m
Wed 14/1011:45 a.m. -
Nonstop1h 40m
Deal found 12/9C$ 288
Fri 25/97:35 p.m. -
Nonstop2h 06m
Sun 27/97:25 a.m. -
Nonstop1h 42m
Deal found 11/9C$ 288
Wed 23/91:45 p.m. -
Nonstop1h 50m
Mon 28/911:45 a.m. -
Nonstop1h 40m
Deal found 9/9C$ 289
Thu 24/97:35 p.m. -
Nonstop2h 06m
Mon 28/97:25 a.m. -
Nonstop1h 42m
Deal found 10/9C$ 289
Wed 23/91:45 p.m. -
Nonstop1h 50m
Sat 26/93:20 p.m. -
Nonstop1h 40m
Deal found 9/9C$ 290
Mon 12/101:45 p.m. -
Nonstop1h 50m
Wed 14/103:20 p.m. -
Nonstop1h 40m
Deal found 11/9C$ 293
Wed 25/114:35 p.m. -
Nonstop2h 05m
Sat 28/116:20 p.m. -
Nonstop1h 46m
Deal found 13/9C$ 295
Tue 6/1012:15 p.m. -
Nonstop2h 10m
Sat 10/108:45 a.m. -
1 stop6h 05m
Deal found 12/9C$ 296

Find flight deals from Toronto Island to Chicago

Round-trip from

C$ 285

One-way from

C$ 181

Popular in

April

Cheapest in

January

Average price

C$ 386

Good round-trip deal

C$ 327 or less

Good one-way deal

C$ 190 or less
Porter Airlines
  • Porter Airlines
  • 3/10-5/10
  • Nonstop
  • 3h 30m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 30/9-31/12
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 24% potential increase in price (C$ 187 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

Thu 1/10

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

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 182

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 29/9

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

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 182

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 20/10

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

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 183

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Fri 16/10

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

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 185

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Sun 18/10

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

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 186

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Sun 13/12

10:35 a.m.-11:40 a.m.

Nonstop2h 05m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 188

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Tue 6/10

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

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 189

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Tue 6/10

12:15 p.m.-1:25 p.m.

Nonstop2h 10m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 193

TorontoChicago

YTZ Toronto Island - ORD Chicago O'Hare Intl

YTZORD

Toronto Island

Tue 13/10

9:30 a.m.-8:12 p.m.

1 stop11h 42m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 210

TorontoChicago

YTZ Toronto Island - MDW Chicago Midway

YTZMDW

Toronto Island

Mon 5/10

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

Nonstop1h 50m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 213

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/9

Showing 1-10 of 41 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$ 304). Flying from Toronto Island Airport to Chicago in May is currently the most expensive (average of C$ 488). 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 Monday, which is when the least amount of flights are scheduled (8 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$ 388 in October.
The cheapest round-trip price found within the last 5 days was C$ 285 on Porter Airlines (3 Oct-5 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
461 reviews
Check prices

Entertainment

6.9

Overall

8.0

Crew

8.6

Food

7.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Porter Airlines
8.0
Very good
461 reviews
Porter Airlines
8.0
Very good
461 reviews
Check prices

Entertainment

6.9

Overall

8.0

Crew

8.6

Food

7.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Air Canada
7.1
Good
11,630 reviews
Porter Airlines
8.0
Very good
461 reviews
Check prices

Entertainment

6.9

Overall

8.0

Crew

8.6

Food

7.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Related info for your journey

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

    Air Canada, Porter Airlines, and United Airlines can get you from Toronto Island Airport to Chicago in just under 1h 50m. Your travel time can differ by up to 8h 37m. The distance from Toronto Island Airport to Chicago is about 711 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • 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 (33%), Jazz (33%) or United Airlines (25%) 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$ 358, our data shows the cheapest flight currently is C$ 173. When looking at the most popular route, (Toronto Island - Chicago O'Hare Intl), you can expect to pay C$ 260 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$ 304). Flying from Toronto Island Airport to Chicago in May is currently the most expensive (average of C$ 488). 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$ 391FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 220AverageC$ 336FlexibilityNo 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.

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

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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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