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Cheap flights from Toronto Island Airport to Chicago from C$ 186

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 24/12. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — CHI
13 Dec — 20 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 13 November 2025.

Thu 18/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 5/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/11C$ 261
Fri 19/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 5/14:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/11C$ 265
Fri 12/122:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 15/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/11C$ 268
Fri 28/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 30/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/11C$ 272
Thu 27/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sat 29/1112:45 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/11C$ 273
Thu 27/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 30/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/11C$ 275
Fri 28/112:30 p.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Tue 2/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 13/11C$ 277
Tue 2/129:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Thu 4/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/11C$ 279
Thu 27/119:15 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Sun 30/1111:00 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 11/11C$ 280
Sat 6/1211:00 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Mon 8/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/11C$ 284
Tue 25/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 3/1211:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/11C$ 286
Tue 25/119:15 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 30/114:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/11C$ 289

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 13 November 2025.

Round-trip from

C$ 261

One-way from

C$ 186

Popular in

October

Cheapest in

August

Average price

C$ 349

Good round-trip deal

C$ 346 or less

Good one-way deal

C$ 197 or less
Porter Airlines
  • Porter Airlines
  • 18/12-5/1
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 24/12
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 29 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 13 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

Fri 1/5

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Mon 4/5

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

Nonstop1h 42m

C$ 265

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 7/1

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

Nonstop1h 50m

Chicago Midway

Wed 14/1

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

Nonstop1h 42m

C$ 272

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 27/11

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

Nonstop1h 50m

Chicago Midway

Sat 29/11

12:45 p.m.-3:27 p.m.

Nonstop1h 42m

C$ 273

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 27/11

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

Nonstop1h 50m

Chicago Midway

Sun 30/11

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

Nonstop1h 42m

C$ 275

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 18/12

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

Nonstop1h 50m

Chicago Midway

Tue 6/1

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

Nonstop1h 42m

C$ 277

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 2/12

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

Nonstop1h 50m

Chicago Midway

Thu 4/12

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

Nonstop1h 42m

C$ 279

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 2/5

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

Nonstop1h 49m

Chicago Midway

Mon 4/5

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

Nonstop1h 42m

C$ 284

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 6/12

11:00 a.m.-11:50 a.m.

Nonstop1h 50m

Chicago Midway

Mon 8/12

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

Nonstop1h 42m

C$ 284

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 25/11

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

Nonstop1h 50m

Chicago Midway

Wed 3/12

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

Nonstop1h 42m

C$ 286

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 17/4

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

Nonstop1h 50m

Chicago Midway

Sun 19/4

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

Nonstop1h 42m

C$ 289

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 40 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 December is currently the most expensive (average of C$ 326). 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 13 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 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 13 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
389 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Porter Airlines
8.0
Very good
389 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Food

7.6

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

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 5h 35m. 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$ 310) 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 airlines to fly from Toronto Island Airport to Chicago one-way?

    C$ 186 is the cheapest one-way deal found within the past few days, from Air Canada. You may also be able to find cheap deals on Porter Airlines and Air Transat, with prices starting from C$ 189 and C$ 189, respectively.

  • 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 December is currently the most expensive (average of C$ 326). 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 13 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 198AverageC$ 291FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 310AverageC$ 449FlexibilityNo 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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