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Cheap flights from Toronto Island Airport to Chicago from C$ 170

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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — CHI
20 Apr — 27 Apr1
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 15 April 2025.

Round-trip from

C$ 259

One-way from

C$ 170

Popular in

January

Cheapest in

April

Average price

C$ 302

Good round-trip deal

C$ 266 or less

Good one-way deal

C$ 166 or less
Porter Airlines
  • Porter Airlines
  • 15/6-18/6
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 5/5
  • Nonstop
  • 1h 49m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 2% potential increase in price (C$ 13 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 15 April 2025.

Sun 15/67:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Wed 18/65:50 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 15/4C$ 259
Tue 6/510:20 a.m.YTZ - ORD
2 stops10h 52mAir Canada
Tue 13/52:22 p.m.ORD - YTZ
1 stop5h 15mAir Canada
Deal found 15/4C$ 273
Tue 6/53:35 p.m.YTZ - MDW
Nonstop1h 49mAir Transat
Wed 14/59:40 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 14/4C$ 295
Thu 8/53:35 p.m.YTZ - MDW
Nonstop1h 49mMultiple Airlines
Sat 10/59:40 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 14/4C$ 302
Tue 13/57:25 a.m.YTZ - ORD
1 stop5h 07mMultiple Airlines
Tue 20/512:41 p.m.ORD - YTZ
3 stops30h 56mMultiple Airlines
Deal found 15/4C$ 388

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 15 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

Sun 15/6

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

Nonstop1h 50m

Chicago Midway

Wed 18/6

5:50 p.m.-8:32 p.m.

Nonstop1h 42m

C$ 259

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 6/5

10:20 a.m.-8:12 p.m.

2 stops10h 52m

Chicago O'Hare Intl

Tue 13/5

2:22 p.m.-8:37 p.m.

1 stop5h 15m

C$ 273

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 6/5

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

Nonstop1h 49m

Chicago Midway

Wed 14/5

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

C$ 295

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 8/5

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

Nonstop1h 49m

Chicago Midway

Sat 10/5

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

C$ 302

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 13/5

7:25 a.m.-11:32 a.m.

1 stop5h 07m

Chicago O'Hare Intl

Tue 20/5

12:41 p.m.-8:37 p.m.

3 stops30h 56m

C$ 388

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 5/5

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

Nonstop1h 49m

C$ 170

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Wed 21/5

8:50 a.m.-12:03 p.m.

1 stop4h 13m

C$ 172

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 31/5

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

Nonstop1h 50m

C$ 189

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 6/5

6:45 p.m.-7:27 a.m.

1 stop13h 42m

C$ 213

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 30/5

8:45 a.m.-7:43 p.m.

1 stop11h 58m

C$ 217

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/4

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 15 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 15 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
281 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Crew

8.7

Comfort

8.0

Food

7.6

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Porter Airlines
8.0
Very good
281 reviews
Porter Airlines
8.0
Very good
281 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Crew

8.7

Comfort

8.0

Food

7.6

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Air Transat
7.8
Good
385 reviews
Porter Airlines
8.0
Very good
281 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Crew

8.7

Comfort

8.0

Food

7.6

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Air Canada
7.0
Good
9,134 reviews
Porter Airlines
8.0
Very good
281 reviews
Check prices

Overall

8.0

Boarding

8.2

Entertainment

7.0

Crew

8.7

Comfort

8.0

Food

7.6

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

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$ 259), Air Canada (C$ 273), and Air Transat (C$ 295) offers the cheapest pricing from Toronto Island Airport to Chicago. Users have found that Porter Airlines is 30% 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$ 170 is the cheapest one-way deal found within the past few days, from Porter Airlines. You may also be able to find cheap deals on Air Canada and Air Transat, with prices starting from C$ 172 and C$ 181, 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

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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 15 April 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 269AverageC$ 372FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 341AverageC$ 502FlexibilityNo 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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