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Cheap flights from Toronto Island Airport to Chicago from C$ 172

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 29/12. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — CHI
21 dec. — 28 dec.1
1 adult
1 adult, Economy, 0 bags

Find 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 21 november 2025.

fre. 5/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
man. 8/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 20/11C$ 253
fre. 19/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
tir. 6/111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 19/11C$ 269
søn. 7/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
ons. 10/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 19/11C$ 279
tir. 2/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
tor. 4/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 19/11C$ 280
fre. 5/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
søn. 7/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 21/11C$ 288
fre. 19/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
tir. 30/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 19/11C$ 294
lør. 20/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
lør. 3/111:05 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/11C$ 297
tor. 11/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
man. 15/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 18/11C$ 298
ons. 24/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
søn. 28/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 19/11C$ 301
søn. 7/128:50 a.m.YTZ - ORD
1 stop5h 01mAir Canada
lør. 13/1212:50 p.m.ORD - YTZ
1 stop6h 05mAir Canada
Deal found 20/11C$ 350
søn. 7/128:50 a.m.YTZ - ORD
1 stop5h 01mAir Canada
man. 8/1210:38 a.m.ORD - YTZ
1 stop5h 17mAir Canada
Deal found 20/11C$ 367
lør. 13/123:30 p.m.YTZ - ORD
1 stop5h 40mAir Canada
søn. 14/127:05 a.m.ORD - YTZ
1 stop8h 50mAir Canada
Deal found 20/11C$ 376

Cheap 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 21 november 2025.

Round-trip from

C$ 252

One-way from

C$ 172

Popular in

October

Cheapest in

August

Average price

C$ 350

Good round-trip deal

C$ 348 or less

Good one-way deal

C$ 198 or less
Porter Airlines
  • Porter Airlines
  • 2/12-5/12
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 29/12
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 60 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 21 november 2025.
Use the filters below to find and compare flights from Toronto Island Airport to Chicago that are best for you.

Fly from

Toronto Island

Fly to

Chicago

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

tir. 23/12

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

Nonstop1h 50m

Chicago Midway

man. 5/1

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

Nonstop1h 42m

C$ 269

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

man. 22/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

man. 5/1

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

Nonstop1h 42m

C$ 269

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

søn. 21/12

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

Nonstop1h 50m

Chicago Midway

man. 5/1

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

Nonstop1h 42m

C$ 269

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

lør. 20/12

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

Nonstop1h 50m

Chicago Midway

man. 5/1

4:15 p.m.-6:57 p.m.

Nonstop1h 42m

C$ 269

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

tor. 25/12

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

Nonstop1h 50m

Chicago Midway

tir. 6/1

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

Nonstop1h 42m

C$ 269

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

ons. 24/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

man. 5/1

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

Nonstop1h 42m

C$ 269

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

tir. 23/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

tir. 6/1

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

Nonstop1h 42m

C$ 269

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

tor. 25/12

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

Nonstop1h 50m

Chicago Midway

man. 5/1

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

Nonstop1h 42m

C$ 269

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

man. 22/12

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

Nonstop1h 50m

Chicago Midway

tir. 6/1

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

Nonstop1h 42m

C$ 269

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

fre. 19/12

9:15 a.m.-10:05 a.m.

Nonstop1h 50m

Chicago Midway

tir. 6/1

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

Nonstop1h 42m

C$ 269

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/11

Showing 1-10 of 38 results
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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, June is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago (average of C$ 117). Flying from Toronto Island Airport to Chicago in December is currently the most expensive (average of C$ 328). 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 21 november 2025.

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 morning, which can drop the price by up to 36% versus a flight in the evening.

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 111 minutes.

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

Historically, flights departing in the evening 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?

Wednesday 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 21 november 2025.
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
393 reviews
Check prices

Entertainment

7.0

Food

7.6

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
8.0
Very good
393 reviews
Porter Airlines
8.0
Very good
393 reviews
Check prices

Entertainment

7.0

Food

7.6

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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 and Air Canada can get you from Toronto Island Airport to Chicago in just under 1h 50m. Your travel time can differ by up to 3h 11m. 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, Porter Airlines (C$ 199), and Air Canada (C$ 312) 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.

  • 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, June is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago (average of C$ 117). Flying from Toronto Island Airport to Chicago in December is currently the most expensive (average of C$ 328). 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 21 november 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 199AverageC$ 293FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 312AverageC$ 451FlexibilityNo cancel feeOn-time67%
Search Air Canada 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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