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Cheap flights from Toronto Island Airport to Chicago from C$ 183

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 25/11. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — CHI
29 Nov — 6 Dec1
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 30 October 2025.

Fri 5/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 8/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 29/10C$ 261
Fri 14/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 17/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 29/10C$ 265
Thu 11/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 14/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 29/10C$ 270
Thu 20/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 24/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 27/10C$ 274
Thu 13/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 18/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 28/10C$ 275
Mon 24/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 1/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 29/10C$ 278
Fri 14/112:30 p.m.YTZ - MDW
Nonstop1h 50mAir Transat
Mon 17/114:15 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 28/10C$ 281
Thu 13/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 16/1111:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 29/10C$ 286
Sat 6/1211:00 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 8/124:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 29/10C$ 288
Fri 5/122:30 p.m.YTZ - MDW
Nonstop1h 50mAir Transat
Mon 8/124:15 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 28/10C$ 293
Tue 25/1110:30 a.m.YTZ - ORD
1 stop5h 25mAir Canada
Fri 28/113:35 p.m.ORD - YTZ
1 stop5h 00mAir Canada
Deal found 28/10C$ 311
Sat 22/1110:30 a.m.YTZ - ORD
1 stop5h 25mAir Canada
Tue 25/117:05 a.m.ORD - YTZ
1 stop6h 50mAir Canada
Deal found 30/10C$ 313

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 30 October 2025.

Round-trip from

C$ 258

One-way from

C$ 183

Popular in

October

Cheapest in

August

Average price

C$ 561

Good round-trip deal

C$ 347 or less

Good one-way deal

C$ 197 or less
Porter Airlines
  • Porter Airlines
  • 23/11-12/12
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 25/11
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (C$ 70 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 October 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 30 October 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

Fri 14/11

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

Nonstop1h 50m

Chicago Midway

Mon 17/11

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

Nonstop1h 42m

C$ 265

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 14/11

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

Nonstop1h 50m

Chicago Midway

Tue 18/11

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

Nonstop1h 42m

C$ 275

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 24/11

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

Nonstop1h 50m

Chicago Midway

Mon 1/12

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

Nonstop1h 42m

C$ 278

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 13/1

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

Nonstop1h 50m

Chicago Midway

Tue 20/1

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

Nonstop1h 42m

C$ 278

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 28/11

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

Nonstop1h 50m

Chicago Midway

Fri 5/12

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

Nonstop1h 42m

C$ 281

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 13/11

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

Nonstop1h 50m

Chicago Midway

Sun 16/11

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

Nonstop1h 42m

C$ 286

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 5/12

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

Nonstop1h 50m

Chicago Midway

Mon 8/12

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

Nonstop1h 42m

C$ 293

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 4/12

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

Nonstop1h 50m

Chicago Midway

Sun 7/12

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

Nonstop1h 42m

C$ 297

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 14/11

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

Nonstop1h 50m

Chicago Midway

Wed 3/12

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

Nonstop1h 42m

C$ 300

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 19/11

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

Nonstop1h 50m

Chicago Midway

Fri 21/11

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

Nonstop1h 42m

C$ 300

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/10

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, June is the cheapest month in which you can book a flight from Toronto Island Airport to Chicago (average of C$ 116). Flying from Toronto Island Airport to Chicago in February is currently the most expensive (average of C$ 321). 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 30 October 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 35% versus a flight in the evening.

How much does it cost to fly round-trip from Toronto Island Airport to Chicago?

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 30 October 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
384 reviews
Check prices

Comfort

8.0

Entertainment

7.0

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

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
8.0
Very good
384 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Comfort

8.0

Entertainment

7.0

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

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 50m. Your travel time can differ by up to 3h 20m. 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$ 198), and Air Canada (C$ 309) 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$ 116). Flying from Toronto Island Airport to Chicago in February is currently the most expensive (average of C$ 321). 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 30 October 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 198AverageC$ 290FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 309AverageC$ 447FlexibilityNo 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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