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Cheap flights from Toronto Island Airport to Chicago from C$ 146

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 8/9. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — CHI
19 Aug — 26 Aug1
1 adult

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 14 August 2025.

Round-trip from

C$ 240

One-way from

C$ 146

Popular in

January

Cheapest in

September

Average price

C$ 241

Good round-trip deal

C$ 216 or less

Good one-way deal

C$ 128 or less
Porter Airlines
  • Porter Airlines
  • 5/9-7/9
  • Nonstop
  • 3h 31m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 8/9
  • Nonstop
  • 1h 49m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 12% potential increase in price (C$ 66 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease (C$ 18 potential savings vs. average RT price).
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Average for round-trip flights in August 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 14 August 2025.

Fri 5/93:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 8/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/8C$ 240
Fri 26/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Tue 30/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 14/8C$ 241
Thu 2/107:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 5/109:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/8C$ 243
Wed 3/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Tue 23/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 13/8C$ 247
Fri 19/93:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 21/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 13/8C$ 248
Sat 6/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 7/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/8C$ 250
Wed 3/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Mon 15/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 13/8C$ 251
Sun 7/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Wed 10/95:20 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/8C$ 252
Fri 26/93:35 p.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Sun 26/1011:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/8C$ 254
Thu 30/109:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 4/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/8C$ 255
Thu 2/1010:25 a.m.YTZ - ORD
1 stop5h 30mAir Canada
Sun 5/1010:40 a.m.ORD - YTZ
1 stop5h 05mAir Canada
Deal found 12/8C$ 272
Wed 22/1010:25 a.m.YTZ - ORD
1 stop5h 30mAir Canada
Thu 23/108:40 a.m.ORD - YTZ
1 stop5h 05mAir Canada
Deal found 14/8C$ 285

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 14 August 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

Thu 2/10

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

Nonstop1h 49m

Chicago Midway

Sun 5/10

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 5/9

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

Nonstop1h 49m

Chicago Midway

Mon 8/9

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

Nonstop1h 42m

C$ 240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 5/9

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

Nonstop1h 49m

Chicago Midway

Sun 7/9

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

Nonstop1h 42m

C$ 240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 27/9

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

Nonstop1h 49m

Chicago Midway

Sat 4/10

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

Nonstop1h 42m

C$ 240

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 26/9

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

Nonstop1h 49m

Chicago Midway

Fri 3/10

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

Nonstop1h 42m

C$ 241

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 26/9

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

Nonstop1h 49m

Chicago Midway

Tue 30/9

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 241

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 10/9

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

Nonstop1h 49m

Chicago Midway

Wed 17/9

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 241

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 24/10

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

Nonstop1h 49m

Chicago Midway

Sun 26/10

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

Nonstop1h 42m

C$ 241

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 13/9

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

Nonstop1h 49m

Chicago Midway

Sat 20/9

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

Nonstop1h 42m

C$ 241

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 12/9

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

Nonstop1h 49m

Chicago Midway

Fri 19/9

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

C$ 241

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/8

Showing 1-10 of 33 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$ 352). 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 14 August 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 31% versus a flight in the afternoon.

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 14 August 2025.

The most flights from YTZ to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Saturday, 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 14 August 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
332 reviews
Check prices

Overall

8.0

Entertainment

7.0

Comfort

8.0

Boarding

8.2

Crew

8.7

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
332 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Overall

8.0

Entertainment

7.0

Comfort

8.0

Boarding

8.2

Crew

8.7

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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.

  • What are the cheapest airlines flying from Toronto Island Airport to Chicago round-trip?

    According to our current data, Porter Airlines (C$ 202), and Air Canada (C$ 305) offers the cheapest pricing from Toronto Island Airport to Chicago. Users have found that Porter Airlines is 39% 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$ 352). 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 14 August 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 202AverageC$ 320FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 305AverageC$ 567FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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How does Cheapflights help users find flights from Toronto Island to Chicago?

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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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