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Cheap flights from Toronto Island Airport to Chicago from C$ 168

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 20/6. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — CHI
4 May — 11 May1
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 29 April 2025.

Round-trip from

C$ 245

One-way from

C$ 168

Popular in

January

Cheapest in

April

Average price

C$ 317

Good round-trip deal

C$ 264 or less

Good one-way deal

C$ 152 or less
Porter Airlines
  • Porter Airlines
  • 12/7-16/7
  • Nonstop
  • 3h 30m total
  • Toronto to Chicago
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Air Canada
  • Air Canada
  • 20/6
  • 1 total stop
  • 4h 59m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 2% potential increase in price (C$ 10 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 13 potential savings vs. average RT price).
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Average for round-trip flights in April 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 29 April 2025.

Sat 12/77:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 16/79:40 a.m.MDW - YTZ
Nonstop1h 40mPorter Airlines
Deal found 28/4C$ 245
Thu 28/87:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Mon 1/99:15 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 28/4C$ 249
Fri 6/67:25 a.m.YTZ - ORD
1 stop4h 59mAir Canada
Sun 8/62:07 p.m.ORD - YTZ
1 stop6h 28mAir Canada
Deal found 28/4C$ 256
Thu 10/73:35 p.m.YTZ - MDW
Nonstop1h 49mAir Transat
Sun 13/75:20 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 28/4C$ 310
Tue 10/65:15 p.m.YTZ - ORD
1 stop14h 17mMultiple Airlines
Wed 11/69:08 p.m.ORD - YTZ
1 stop11h 22mMultiple Airlines
Deal found 28/4C$ 412

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 29 April 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

Sat 12/7

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

Nonstop1h 50m

Chicago Midway

Wed 16/7

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

C$ 245

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 28/8

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

Nonstop1h 50m

Chicago Midway

Mon 1/9

9:15 a.m.-11:57 a.m.

Nonstop1h 42m

C$ 249

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 6/6

7:25 a.m.-11:24 a.m.

1 stop4h 59m

Chicago O'Hare Intl

Sun 8/6

2:07 p.m.-9:35 p.m.

1 stop6h 28m

C$ 256

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 10/7

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

Nonstop1h 49m

Chicago Midway

Sun 13/7

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

Nonstop1h 42m

C$ 310

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 10/6

5:15 p.m.-6:32 a.m.

1 stop14h 17m

Chicago O'Hare Intl

Wed 11/6

9:08 p.m.-9:30 a.m.

1 stop11h 22m

C$ 412

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Fri 20/6

7:25 a.m.-11:24 a.m.

1 stop4h 59m

C$ 168

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 28/5

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

Nonstop1h 50m

C$ 170

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sun 31/8

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

Nonstop1h 49m

C$ 183

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 3/6

12:00 p.m.-6:32 a.m.

2 stops19h 32m

C$ 205

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 15/5

8:45 a.m.-2:45 p.m.

1 stop7h 00m

C$ 331

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/4

Showing 1-10 of 11 results
1
2

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$ 355). 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 29 April 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 7% versus a flight in the evening.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 29 April 2025.
Peruse reviews from past customers who have flown with Porter Airlines, Air Transat and Air Canada from Toronto 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
285 reviews
Check prices

Boarding

8.2

Comfort

8.1

Food

7.6

Entertainment

7.0

Crew

8.8

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
285 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Boarding

8.2

Comfort

8.1

Food

7.6

Entertainment

7.0

Crew

8.8

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Transat
7.8
Good
385 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Boarding

8.2

Comfort

8.1

Food

7.6

Entertainment

7.0

Crew

8.8

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Canada
7.0
Good
9,240 reviews
Porter Airlines
8.0
Very good
285 reviews
Check prices

Boarding

8.2

Comfort

8.1

Food

7.6

Entertainment

7.0

Crew

8.8

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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$ 245), Air Canada (C$ 256), and Air Transat (C$ 310) offers the cheapest pricing from Toronto Island Airport to Chicago. Users have found that Porter Airlines is 34% 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$ 168 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$ 170 and C$ 218, 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, 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$ 355). 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 29 April 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 268AverageC$ 361FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 307AverageC$ 354FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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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?

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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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