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Cheap flights from Toronto Island Airport to Chicago from C$ 176

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 15/4. Fares are subject to change and may not be available on all flights or dates of travel.
YTZ — CHI
31 Mar — 7 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 26 March 2025.

Round-trip from

C$ 282

One-way from

C$ 176

Popular in

January

Cheapest in

December

Average price

C$ 412

Good round-trip deal

C$ 277 or less

Good one-way deal

C$ 215 or less
Porter Airlines
  • Porter Airlines
  • 19/4-20/4
  • Nonstop
  • 3h 32m total
  • Toronto to Chicago
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Porter Airlines
  • Porter Airlines
  • 15/4
  • Nonstop
  • 1h 50m total
  • Toronto to Chicago
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Highest demand for flights based on searches. 0% potential increase in price (C$ 3 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 14 potential savings vs. average RT price).
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Average for round-trip flights in March 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 26 March 2025.

Sat 19/411:10 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Sun 20/411:15 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 25/3C$ 282
Thu 8/53:35 p.m.YTZ - MDW
Nonstop1h 49mAir Transat
Thu 15/55:20 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Deal found 23/3C$ 292
Wed 23/43:50 p.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Wed 30/411:15 a.m.MDW - YTZ
Nonstop1h 42mMultiple Airlines
Deal found 24/3C$ 310
Thu 1/57:25 a.m.YTZ - ORD
1 stop5h 07mAir Canada
Mon 5/58:40 a.m.ORD - YTZ
1 stop5h 10mAir Canada
Deal found 25/3C$ 313
Mon 5/512:00 p.m.YTZ - ORD
2 stops31h 17mMultiple Airlines
Thu 8/59:08 p.m.ORD - YTZ
2 stops21h 19mMultiple Airlines
Deal found 25/3C$ 423

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 26 March 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 19/4

11:10 a.m.-12:00 p.m.

Nonstop1h 50m

Chicago Midway

Sun 20/4

11:15 a.m.-1:57 p.m.

Nonstop1h 42m

C$ 282

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Thu 8/5

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

Nonstop1h 49m

Chicago Midway

Thu 15/5

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

Nonstop1h 42m

C$ 292

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Wed 23/4

3:50 p.m.-4:40 p.m.

Nonstop1h 50m

Chicago Midway

Wed 30/4

11:15 a.m.-1:57 p.m.

Nonstop1h 42m

C$ 310

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Thu 1/5

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

1 stop5h 07m

Chicago O'Hare Intl

Mon 5/5

8:40 a.m.-2:50 p.m.

1 stop5h 10m

C$ 313

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Mon 5/5

12:00 p.m.-6:17 p.m.

2 stops31h 17m

Chicago O'Hare Intl

Thu 8/5

9:08 p.m.-7:27 p.m.

2 stops21h 19m

C$ 423

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 15/4

9:30 a.m.-10:20 a.m.

Nonstop1h 50m

C$ 176

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 20/5

3:25 p.m.-8:12 p.m.

1 stop5h 47m

C$ 177

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 19/4

11:10 a.m.-12:00 p.m.

Nonstop1h 50m

C$ 195

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Tue 15/4

8:55 p.m.-5:51 p.m.

1 stop21h 56m

C$ 240

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Tue 29/4

7:45 p.m.-7:03 a.m.

1 stop12h 18m

C$ 247

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/3

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 26 March 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 6% 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 26 March 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
7.9
Good
276 reviews
Check prices

Crew

8.7

Entertainment

6.9

Overall

7.9

Food

7.6

Comfort

8.0

Boarding

8.2

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
7.9
Good
276 reviews
Porter Airlines
7.9
Good
276 reviews
Check prices

Crew

8.7

Entertainment

6.9

Overall

7.9

Food

7.6

Comfort

8.0

Boarding

8.2

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
381 reviews
Porter Airlines
7.9
Good
276 reviews
Check prices

Crew

8.7

Entertainment

6.9

Overall

7.9

Food

7.6

Comfort

8.0

Boarding

8.2

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
8,960 reviews
Porter Airlines
7.9
Good
276 reviews
Check prices

Crew

8.7

Entertainment

6.9

Overall

7.9

Food

7.6

Comfort

8.0

Boarding

8.2

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$ 282), Air Transat (C$ 292), and Air Canada (C$ 297) offers the cheapest pricing from Toronto Island Airport to Chicago. Users have found that Porter Airlines is 28% 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$ 176 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$ 177 and C$ 195, 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 26 March 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 285AverageC$ 386FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 351AverageC$ 516FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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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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