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Cheap flights from Toronto Island Airport to Chicago from C$ 170

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 29/4. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — CHI
16 Apr — 23 Apr1
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 17 March 2026.

Thu 30/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Fri 1/53:20 p.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 17/3C$ 270
Sun 24/58:50 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 28/510:25 a.m.
MDW
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 16/3C$ 272
Sat 4/411:20 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 7/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 17/3C$ 274
Tue 7/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Wed 8/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 16/3C$ 275
Fri 10/42:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 20/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 16/3C$ 277
Wed 8/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 12/44:05 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 15/3C$ 278
Thu 23/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Thu 30/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 13/3C$ 279
Thu 9/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Tue 14/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 16/3C$ 281
Sat 12/91:40 p.m.
YTZ
-
ORD
Nonstop1h 55m
Porter Airlines
Sun 13/93:20 p.m.
ORD
-
YTZ
Nonstop1h 40m
Porter Airlines
Deal found 16/3C$ 281
Fri 10/42:30 p.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sun 12/44:05 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 16/3C$ 282
Tue 7/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Sat 11/412:55 p.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 13/3C$ 283
Thu 23/49:25 a.m.
YTZ
-
MDW
Nonstop1h 50m
Porter Airlines
Mon 27/411:00 a.m.
MDW
-
YTZ
Nonstop1h 42m
Porter Airlines
Deal found 12/3C$ 285

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 17 March 2026.

Round-trip from

C$ 266

One-way from

C$ 170

Popular in

October

Cheapest in

August

Average price

C$ 374

Good round-trip deal

C$ 278 or less
Porter Airlines
  • Porter Airlines
  • 2/9-7/9
  • Nonstop
  • 3h 35m total
  • Toronto to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 29/4
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 1% potential increase in price (C$ 6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip 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 17 March 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 - MDW

YTZMDW

Toronto Island

Tue 28/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

Chicago Midway

Wed 29/4

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 307

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 12/5

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

Nonstop1h 50m

Chicago Midway

Fri 15/5

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

Nonstop1h 40m

C$ 320

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 4/4

11:20 a.m.-12:10 p.m.

Nonstop1h 50m

Chicago Midway

Mon 6/4

4:05 p.m.-6:47 p.m.

Nonstop1h 42m

C$ 322
Quickest round-trip

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 5/5

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

Nonstop1h 50m

Chicago Midway

Sat 9/5

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

Nonstop1h 40m

C$ 324

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 24/4

2:30 p.m.-3:20 p.m.

Nonstop1h 50m

Chicago Midway

Fri 1/5

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

Nonstop1h 40m

C$ 330

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 8/6

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

Nonstop1h 50m

Chicago Midway

Wed 10/6

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

Nonstop1h 40m

C$ 340

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 5/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

Chicago Midway

Tue 7/4

11:00 a.m.-1:42 p.m.

Nonstop1h 42m

C$ 345

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 9/4

9:25 a.m.-10:15 a.m.

Nonstop1h 50m

Chicago Midway

Sun 3/5

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

Nonstop1h 40m

C$ 357

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 1/5

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

Nonstop1h 50m

Chicago Midway

Fri 8/5

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

Nonstop1h 40m

C$ 368

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 4/4

6:25 p.m.-12:22 a.m.

1 stop6h 57m

Chicago O'Hare Intl

Mon 6/4

6:01 p.m.-8:03 p.m.

2 stops25h 02m

C$ 448

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/3

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
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 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 17 March 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 in the afternoon, which can drop the price by up to 69% versus a flight in the evening.

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 14 March 2026.

Travelers seeking maximum savings on their Toronto Island Airport to Chicago flight should consider departing on Monday mornings 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.

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 114 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 14% of flights being delayed.

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 17 March 2026.
Check out reviews from past customers who have flown with Porter Airlines 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
424 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Food

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
424 reviews
Porter Airlines
8.0
Very good
424 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Food

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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 Transat, 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 is the cheapest airline to fly from Toronto Island Airport to Chicago round-trip?

    According to our current data, Porter Airlines (C$ 194), offers the cheapest pricing from Toronto Island Airport to Chicago. Users have found that Porter Airlines is 41% cheaper than the other options available to this destination.

  • 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$ 1,164, our data shows the cheapest flight currently is C$ 368. When looking at the most popular route, (Toronto Island - Chicago Midway), you can expect to pay C$ 234 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.

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 17 March 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 194AverageC$ 284FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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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