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Cheap flights from Toronto Island Airport to Chicago from C$ 187

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 20/10. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — CHI
17 Oct — 24 Oct1
1 adult
1 adult, Economy

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 17 September 2025.

Round-trip from

C$ 322

One-way from

C$ 187

Popular in

October

Cheapest in

September

Average price

C$ 220

Good round-trip deal

C$ 240 or less

Good one-way deal

C$ 210 or less
Porter Airlines
  • Porter Airlines
  • 14/10-22/10
  • 1 total stop
  • 6h 37m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 20/10
  • Nonstop
  • 1h 49m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 8% potential increase in price (C$ 42 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease (C$ 26 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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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Find flight deals from Toronto Island to Chicago

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 September 2025.

Tue 14/107:30 p.m.YTZ - MDW
1 stop4h 55mMultiple Airlines
Wed 22/109:35 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 15/9C$ 322
Sun 12/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Wed 22/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/9C$ 330
Thu 16/103:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 19/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/9C$ 332
Sat 18/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 20/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/9C$ 334
Fri 17/103:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 20/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/9C$ 337
Tue 14/107:30 p.m.YTZ - MDW
1 stop4h 55mMultiple Airlines
Sun 19/109:35 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 15/9C$ 338
Tue 14/105:15 p.m.YTZ - MDW
1 stop7h 10mMultiple Airlines
Tue 21/109:35 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 15/9C$ 340
Tue 14/103:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Thu 16/105:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/9C$ 341
Thu 9/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 12/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 17/9C$ 343
Wed 15/103:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Fri 17/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/9C$ 345
Sat 1/113:30 p.m.YTZ - ORD
1 stop5h 30mAir Canada
Sat 8/113:35 p.m.ORD - YTZ
1 stop5h 00mAir Canada
Deal found 17/9C$ 362
Sat 18/103:25 p.m.YTZ - ORD
1 stop5h 52mAir Canada
Sun 19/108:40 a.m.ORD - YTZ
1 stop5h 05mAir Canada
Deal found 16/9C$ 382

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 September 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

Tue 14/10

7:30 p.m.-11:25 p.m.

1 stop4h 55m

Chicago Midway

Wed 22/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 322

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 14/10

7:30 p.m.-11:25 p.m.

1 stop4h 55m

Chicago Midway

Thu 23/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 322

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 12/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Mon 20/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 330

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 12/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Tue 21/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 330

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 13/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Tue 21/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 330

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 15/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Mon 20/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 330

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 16/10

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Tue 21/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 330

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 12/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Thu 23/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 330

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 14/10

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

Chicago Midway

Mon 20/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 330

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 17/10

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

Chicago Midway

Mon 20/10

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

C$ 337

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/9

Showing 1-10 of 43 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, January is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago (average of C$ 261). Flying from Toronto Island Airport to Chicago in March is currently the most expensive (average of C$ 348). 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 17 September 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 26% 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 17 September 2025.

The most flights from YTZ to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

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 September 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
7.9
Good
365 reviews
Check prices

Boarding

8.2

Comfort

7.9

Crew

8.6

Entertainment

7.0

Food

7.6

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
7.9
Good
365 reviews
Porter Airlines
7.9
Good
365 reviews
Check prices

Boarding

8.2

Comfort

7.9

Crew

8.6

Entertainment

7.0

Food

7.6

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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 49m. Your travel time can differ by up to 3h 41m. 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$ 203), and Air Canada (C$ 305) 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, January is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago (average of C$ 261). Flying from Toronto Island Airport to Chicago in March is currently the most expensive (average of C$ 348). 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 17 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 203AverageC$ 312FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 305AverageC$ 566FlexibilityNo 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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