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Cheap flights from Toronto Island Airport to Chicago from C$ 148

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 21/7. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — CHI
17 Jun — 24 Jun1
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 12 June 2025.

Round-trip from

C$ 220

One-way from

C$ 148

Popular in

January

Cheapest in

April

Average price

C$ 383

Good round-trip deal

C$ 228 or less

Good one-way deal

C$ 165 or less
Porter Airlines
  • Porter Airlines
  • 26/6-29/6
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 21/7
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 5% potential increase in price (C$ 29 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 15 potential savings vs. average RT price).
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Average for round-trip flights in June 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 12 June 2025.

Thu 26/67:55 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 29/69:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 12/6C$ 220
Sat 30/87:55 a.m.YTZ - MDW
Nonstop1h 50mAir Transat
Fri 12/99:15 a.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 11/6C$ 254
Mon 18/87:55 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Tue 19/85:20 p.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 11/6C$ 280
Sat 4/1010:25 a.m.YTZ - ORD
1 stop5h 30mAir Canada
Wed 15/108:40 a.m.ORD - YTZ
1 stop5h 05mAir Canada
Deal found 12/6C$ 283
Sat 28/65:15 p.m.YTZ - ORD
1 stop14h 22mMultiple Airlines
Wed 2/79:28 p.m.ORD - YTZ
1 stop10h 02mMultiple Airlines
Deal found 12/6C$ 457

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 12 June 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 26/6

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

Nonstop1h 50m

Chicago Midway

Sun 29/6

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

Nonstop1h 42m

C$ 220

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 26/6

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

Nonstop1h 50m

Chicago Midway

Mon 30/6

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

Nonstop1h 40m

C$ 261

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 18/8

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

Nonstop1h 50m

Chicago Midway

Tue 19/8

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

Nonstop1h 42m

C$ 280

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 4/10

10:25 a.m.-2:55 p.m.

1 stop5h 30m

Chicago O'Hare Intl

Wed 15/10

10:40 a.m.-4:45 p.m.

1 stop5h 05m

C$ 283

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 28/6

5:15 p.m.-6:37 a.m.

1 stop14h 22m

Chicago O'Hare Intl

Wed 2/7

9:28 p.m.-8:30 a.m.

1 stop10h 02m

C$ 457

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Mon 21/7

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

Nonstop1h 50m

C$ 148

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 4/7

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

Nonstop1h 49m

C$ 154

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 23/8

3:25 p.m.-8:16 p.m.

1 stop5h 51m

C$ 160

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 1/7

5:15 p.m.-6:37 a.m.

1 stop14h 22m

C$ 232

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 4/7

8:45 a.m.-5:34 p.m.

1 stop9h 49m

C$ 247

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

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 12 June 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 11% versus a flight in the evening.

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 12 June 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).

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 12 June 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
288 reviews
Check prices

Food

7.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.1

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
288 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.1

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Transat
7.8
Good
396 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.1

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Canada
7.1
Good
9,531 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.1

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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$ 220), Air Transat (C$ 254), and Air Canada (C$ 283) offers the cheapest pricing from Toronto Island Airport to Chicago. Users have found that Porter Airlines is 38% 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$ 148 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 Transat and Air Canada, with prices starting from C$ 156 and C$ 160, 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$ 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 12 June 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 237AverageC$ 342FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 303AverageC$ 421FlexibilityNo 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?

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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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